Coast to Coast · Spring 2026

Adventure
of a Lifetime

Stewart · Jane · Lara

June 1 – July 14, 2026 · 13 stops · ~5,000 miles · 44 nights across America — from the fog of the Golden Gate to the lights of Manhattan.

The Route

From sea to shining sea

Tap any stop to dive in. Follow the dotted road across the country.

01 · San Francisco02 · Point Arena03 · Lake Tahoe04 · San Diego & La Jolla05 · Santa Monica & Los Angeles06 · Disneyland, Anaheim07 · Las Vegas08 · Grand Canyon09 · Route 6610 · Memphis, Tennessee11 · Nashville, Tennessee12 · Chicago, Illinois13 · New York City
Thirteen Stops

The Journey

San Francisco
STOP · 01
June 1 — Departure DayDay 1 · Depart today
California

San Francisco

"The launch pad. Fog, sourdough, and the open road calling."

Where to stay (if overnighting)

  • Hotel Drisco, Pacific HeightsSplurge

    Boutique Edwardian hotel in a quiet residential neighbourhood. Exceptional service, stunning Bay views. This is old San Francisco money energy — refined, quiet, beautiful.

  • The Phoenix HotelMid

    Rock and roll motel in the Tenderloin with a pool and serious attitude. Every band that played SF stayed here. Fun, eccentric, and surprisingly good value.

  • HI San Francisco Fisherman's WharfBudget

    Set inside a historic fort with actual Bay views. One of the best-located hostels in America — private rooms available.

Where to eat

  • Tartine ManufactoryEssential

    The most celebrated bakery in America. Go morning of departure — country bread, croissants, morning buns. Queue outside at 8am. Worth every minute.

  • Swan Oyster Depot

    No-frills counter serving the freshest clam chowder and Dungeness crab since 1912. Cash only. Queue outside. An SF institution you cannot skip.

  • Zuni Café

    The whole roasted chicken (for two, 45 min wait) is possibly the best chicken dish in America. Book lunch before you leave the city.

  • Mission Chinese Food

    Wildly creative, slightly unhinged Chinese-American food in the Mission. The salt cod fried rice and kung pao pastrami are iconic. Dinner the night before you leave.

Before you drive north

  • Battery Spencer, Marin HeadlandsBest GG Photo

    Cross the Golden Gate and immediately pull into the Headlands. The view back to the bridge with SF skyline is the best photograph you'll ever take. Go at sunrise for empty roads.

  • Lands End Trail

    Clifftop trail on the far west of the city — ruins of the Sutro Baths, wave-battered rocks, Golden Gate in the distance. 45 minutes of pure wildness inside a city.

  • Ferry Building Marketplace

    Saturday farmers market is the best in California. Grab supplies for the road — cheese, charcuterie, fruit, artisan everything. A moving pantry for Highway 1.

The Drive North: From the Golden Gate, Hwy 1 opens up almost immediately into jaw-dropping coastal scenery. Point Reyes Station (45 min) is worth a coffee stop — Cowgirl Creamery is here. Then Bodega Bay (Hitchcock's The Birds), then Jenner where the Russian River meets the Pacific. All before you reach Dara.
→ San Francisco to Point Arena via Highway 1 — the slow, magnificent way ~3.5 hrs · 115 miles
Point Arena
STOP · 02
June 1 — Afternoon arrival1 night
California Coast

Point Arena

"Visiting Dara. One of the wildest, most beautiful stretches of the California coast."

Where to stay

  • Coast Guard House Historic InnSplurge

    1901 Life-Saving Station right on the headlands. Arts & Crafts interior, fireplaces, ocean views. Six rooms — romantic, historic, utterly unlike anything else.

  • Wharf Master's InnMid

    Cluster of cottages and rooms on the Arena Cove bluffs. Fantastic ocean views, private and peaceful. Exactly the vibe you want on a road trip night stop.

  • Manchester Beach KOABudget

    Glamping tents and cabins right on the beach 20 min south. If the weather's good, sleeping with the sound of the Pacific is unforgettable.

Where to eat

  • Franny's Cup & SaucerLegendary

    Tiny, eccentric pie and bakery café run by a mother-daughter duo. People drive hours for the pies. The lemon curd tart will change you. Get there early — they sell out.

  • Arena Market & Café

    Worker-owned co-op with brilliant local food, great wine selection from Mendocino coast wineries. The kind of community hub that makes small-town America remarkable.

  • Bones Roadhouse BBQ

    Proper smoked BBQ in what feels like the end of the world. Ribs, brisket, cold beer, ocean air. Ideal dinner with Dara.

See & Do

  • Point Arena LighthouseMust See

    115 feet tall, 145 steps, built in 1908 after the 1906 earthquake destroyed the original. The views from the top are staggering. You can stay overnight in the lighthouse keeper's cottages.

  • Stornetta Public Lands Tide Pools

    BLM land with sea arches, sea stacks, puffins, harbor seals. Wild and completely uncrowded. Go at low tide — check the tide tables the morning you arrive.

  • Point Arena Cove / Pier

    Watch fishing boats come in. Local abalone divers sometimes sell their catch here. The cove at sunset turns pink and gold — one of those moments you'll remember forever.

→ Point Arena inland to Hwy 101 north, then east on I-80 / Hwy 50 to Tahoe ~3.5 hrs to South Lake Tahoe
Lake Tahoe
STOP · 03
June 2–42 nights
California / Nevada

Lake Tahoe

"The Sierra Nevada's jewel. The clearest water you will ever see."

Where to stay

  • Edgewood Tahoe ResortSplurge

    Directly on the lake on the Nevada side. Lodge-style luxury — stone fireplaces, lake-view suites, infinity pool over the water. One of the finest resort hotels in America.

  • The Landing Resort & SpaSplurge

    South Lake Tahoe boutique hotel with private beach and pier. Rooms facing the lake are extraordinary. Good spa for recovery days.

  • Basecamp HotelMid

    Fun, adventure-themed boutique motel in South Lake. Outdoor fire pits, cool design, social vibe. Great for a road trip group.

  • Camp Richardson ResortBudget

    Historic lakeside resort with cabins, beach access, and the famous Beacon Bar & Grill on the water. Affordable and atmospheric.

Where to eat

  • Edgewood RestaurantSplurge

    Floor-to-ceiling windows, the lake right there. California-refined menu. Have the sunset dinner here — it's a proper special occasion meal.

  • Beacon Bar & Grill

    Right on the lake, open-air deck. Famous "Rum Runner" cocktail. Excellent fish tacos and burgers. The vibe is perfect — casual lakeside paradise.

  • Sprouts Café

    South Lake health-focused breakfast and lunch spot. Incredible açaí bowls, grain salads, and wraps. Perfect post-hike fuel.

  • Kalani's at Lake Tahoe

    Hawaiian fusion dinner spot — unexpected and excellent. The Kona kampachi and miso black cod are outstanding.

Must See & Do

  • Emerald Bay & VikingsholmDon't Miss

    The most photographed spot in California. Hike down (steep!) to Vikingsholm Castle — a 1929 Scandinavian-style mansion. Kayak through the bay past Fannette Island.

  • Sand Harbor State Park

    Nevada side — crystal clear water over massive granite boulders. Lake Tahoe Shakespeare Festival performs here in July. Bring picnic, arrive before 9am in summer.

  • Tahoe Rim Trail section

    The 165-mile trail circles the lake at elevation. Do the Tahoe Meadows section near Incline Village for 2-3 hours of stunning high alpine walking.

  • Heavenly Gondola (no skiing needed)

    Take the cable car up for panoramic views of the entire lake and Nevada desert. Top restaurant for lunch with jaw-dropping views. Runs in summer.

Hidden Gem: D.L. Bliss State Park on the west shore has the most beautiful secluded beaches on the lake — Rubicon Beach and Calawee Cove. Arrive at 7am or queue for parking. The water is so clear you can see 70 feet down. Bring snorkelling masks.
→ Tahoe → Sacramento → Hwy 99 or I-5 south to San Diego. Optional: Big Sur / Carmel detour on Hwy 1 (add 3hrs, worth it) ~7–8 hrs direct
San Diego & La Jolla
STOP · 04
June 5–72 nights
California

San Diego & La Jolla

"America's finest city. Perfect weather, sea lions, craft beer, and the most beautiful coastline in the continental US."

Where to stay

  • La Valencia Hotel, La JollaSplurge

    "The Pink Lady" — 1926 Mediterranean-style landmark perched above La Jolla Cove. Rooftop pool, ocean views, old-money California glamour. Absolute classic.

  • Hotel del CoronadoLegendary

    1888 Victorian beachfront resort on Coronado Island. Marilyn Monroe filmed Some Like It Hot here. The white beach is extraordinary. Take the ferry from Downtown San Diego.

  • Kimpton Hotel PalomarMid

    Boutique hotel in the Gaslamp Quarter downtown — central, stylish, excellent rooftop pool and bar. Walk everywhere from here.

  • USA Hostels San DiegoBudget

    Consistently rated best hostel in San Diego — private rooms available, central Gaslamp location, rooftop parties most nights.

Where to eat

  • George's at the CoveLa Jolla Icon

    Three-level restaurant above La Jolla Cove — rooftop terrace is the spot for sunset dinner. California cuisine at its finest. Book the terrace weeks ahead.

  • Lucha Libre Gourmet Taco ShopEssential

    Wrestling-themed taco shop, voted best in the city for years. The Surfin' California burrito (fries inside) is life-changing. $10 and worth every cent.

  • Ironside Fish & Oyster

    Little Italy — stunning converted warehouse, raw bar, incredible fish and chips, craft cocktails. The best fish restaurant in San Diego.

  • Carnitas' Snack Shack

    North Park neighbourhood — epic pork-focused street food. Triple Threat pork sandwich (pork belly + pulled pork + egg) is insane. Outdoor seating, cold beer.

  • Extraordinary Desserts

    Pastry chef Karen Krasne creates the most beautiful cakes and desserts you've ever seen. Go for tea and something outrageous in Little Italy.

See & Do

  • La Jolla Cove at low tideDo This

    Arrive 7–8am. Wild sea lions right on the rocks. Snorkelling in the ecological reserve — leopard sharks in July, fish everywhere. The Children's Pool has the largest seal colony.

  • Balboa Park

    1,200-acre urban park housing 17 museums, the San Diego Zoo, botanical gardens, and the gorgeous Spanish Colonial architecture of El Prado. Full day minimum.

  • Torrey Pines State Reserve

    Cliffside trails above one of the last old-growth torrey pine forests, dropping to pristine beach. Sunrise here is extraordinary.

  • Coronado Beach

    Consistently rated America's #1 beach. White silver sand, Hotel Del backdrop, wide open, rarely crowded. Take the ferry from downtown — it's part of the experience.

  • Cabrillo National Monument

    Point Loma — tide pools, whale migration corridor, and the best 360° view of San Diego Harbour, the bay, and Coronado. Sunset here is spectacular.

Local Secret: Ocean Beach is the anti-La Jolla — hippie surf town, Newport Ave antique shops, Newport Pier bars, the Wednesday farmers market. Grab fish tacos at South Beach Bar & Grille right on the pier and watch the surfers at sunset.
→ San Diego north on I-5 to Santa Monica — cruise Pacific Coast Highway (Hwy 1) from Malibu ~2.5 hrs · 125 miles
Santa Monica & Los Angeles
STOP · 05
June 7–92 nights
California

Santa Monica & Los Angeles

"The end of Route 66. The beginning of the LA dream. This city contains multitudes."

Where to stay

  • Shutters on the BeachDream Hotel

    Literally on the sand in Santa Monica. White-shingled New England beach house look, impeccable rooms, beds you'll want to live in forever. The best beach hotel in LA.

  • The LINE Hotel, KoreatownCool

    Roy Choi-designed hotel in a converted 1964 building. Incredible rooftop pool, great restaurants, genuinely hip without being insufferable. Central to everything.

  • Venice Beach Suites & HotelCharacter

    Quirky studios right in Venice Beach. Kitchen facilities for self-catering, surf vibes, steps from the boardwalk. Great for soaking up the Venice atmosphere.

  • Samesun Venice BeachBudget

    Hostel right on the boardwalk. Private rooms available. Rooftop deck with ocean views. The location is unbeatable for the price.

Where to eat

  • GjustaVenice Legend

    The most celebrated deli/bakery in LA. Smoked fish, house-cured meats, incredible pastries. Arrive early for the morning rush. Sunday here is a religion.

  • Reservation almost impossible to get but worth trying. Italian-ish, whole animal, spectacular pasta, stunning industrial space. If you get a table, go.

  • Grand Central Market Downtown

    Century-old food hall with 30+ vendors. Eggslut, Sticky Rice, Berlin Currywurst, Lula's Tamales. Lunch here is an event. Go weekday to avoid weekend crowds.

  • n/naka, PalmsOnce in a Lifetime

    Chef Niki Nakayama's kaiseki restaurant — 13-course Japanese omakase. Featured in Chef's Table. Book 2 months ahead if you want to try. Worth every dollar.

  • Rossoblu

    Downtown — Northern Italian done perfectly. The tagliatelle bolognese and wood-fired lamb are extraordinary. Great Italian wine list.

  • Howlin' Ray's, Chinatown

    Nashville hot chicken in LA. Queue is brutal but moves fast. The "Howlin'" level heat is genuinely dangerous. Start at "Country" if you're not a masochist.

See & Do

  • Getty CentreFree Entry

    Free gallery (parking $20), Richard Meier's travertine building is one of America's finest. Impressionist collection, Monet, Cézanne. Gardens designed by Robert Irwin. Views of the entire city.

  • Griffith Observatory at Sunset

    Park below and hike up (45 min) or drive. Observatory is free. The Hollywood Sign view and the city stretching to the ocean at golden hour is the quintessential LA moment.

  • Venice Beach Canals (the quiet ones)

    Two blocks from the boardwalk chaos — actual canals with bridges, ducks, and beautiful houses. Completely peaceful. A secret neighbourhood that surprises everyone.

  • The Last Bookstore, Downtown

    Two floors of magnificent chaos — an art installation inside a bookshop. The spiral tunnel made of books alone is worth it. Spend an afternoon here.

  • Mulholland Drive

    Drive the ridge from Laurel Canyon to the 405. The panoramic view of the San Fernando Valley on one side and LA basin on the other is extraordinary.

Day Trip: Malibu is 30 minutes north on PCH. Nobu Malibu for lunch on the water (book ahead), then Zuma Beach for the afternoon. The drive back at sunset with the Pacific turning gold to your left is one of the great drives in America.
→ Santa Monica south on I-405 / I-5 to Anaheim — 45 mins without traffic ~30 miles · Book Disney in advance
Disneyland, Anaheim
STOP · 06
June 9–112 nights
California

Disneyland, Anaheim

"The original. Walt's park. Two days is the magic number."

Where to stay

  • Disney's Grand Californian HotelOn Property

    Arts & Crafts lodge-style hotel with a private entrance directly into California Adventure. Nightly campfire storytelling, Craftsman architecture, three pools. You feel the magic before you enter the parks.

  • Anaheim Majestic Garden HotelOff-Property

    10 min walk from the parks, free shuttle, proper resort feel at half the on-property price. Pool, garden, surprisingly lovely for the price.

  • Residence Inn AnaheimPractical

    Suite-style rooms with kitchen — great for three people sharing. Free breakfast included. Walking distance to the parks.

Inside the Parks

  • Star Wars: Galaxy's EdgeUnmissable

    Build your own lightsaber at Savi's Workshop ($250 but extraordinary). Drink blue or green milk at Oga's Cantina. Millennium Falcon: Smugglers Run — everyone gets a role.

  • Buy Lightning Lane Multi Pass

    Buy the day before on the app. Book your first ride the second the park opens (midnight in the app). You'll ride everything before noon without queueing.

  • Indiana Jones Adventure, Haunted Mansion, Pirates of the Caribbean, Space Mountain. Stay for World of Color show in California Adventure at 9pm.

  • Guardians of the Galaxy: Mission Breakout, Radiator Springs Racers (Cars Land is stunning), Incredicoaster. Then Galaxy's Edge all afternoon.

  • Carthay Circle RestaurantBest Park Dining

    Sit-down restaurant in a gorgeous 1920s-replica building. Actually excellent food — not typical park dining. The Monte Cristo sandwich is famous. Book well ahead.

Insider Move: Rope drop (be at the gate 45 mins before opening). Hit your top 2-3 rides with zero queue in the first 90 minutes, then use Lightning Lane for the rest. By 2pm the queues are brutal — take a hotel break and come back at 7pm for the evening magic.
→ Anaheim northeast on I-15 to Las Vegas. Stop at Barstow Station (Route 66 kitsch) and Baker (world's tallest thermometer, tragically famous) ~4 hrs · 270 miles
Las Vegas
STOP · 07
June 11–143 nights
Nevada

Las Vegas

"The most American thing on Earth. Surrender to it completely."

Where to stay

  • The Venetian / PalazzoBest Value Luxury

    All-suite hotel — every room is a 650sq ft suite. Enormous beds, deep soaking tubs, excellent pools. The gondola canal is absurd and wonderful. Often cheaper than you'd expect.

  • Wynn Las VegasBest Overall

    Steve Wynn's masterpiece — genuinely the most luxurious hotel on the Strip. Botanical garden, incredible pool, the best casino design in Vegas.

  • Cosmopolitan of Las VegasCoolest Vibe

    The hippest hotel on the Strip — excellent restaurants (including secret pizza place on Floor 14), three pools, the Chandelier Bar is spectacular.

  • Circa Resort (Downtown)Alternative

    Downtown Fremont Street — Vegas's older, grittier, more interesting neighbourhood. Stadium swim pool, adults-only hotel. Escape the Strip energy.

Where to eat

  • é by José AndrésWorld Class

    8-seat secret restaurant inside Jaleo at the Cosmopolitan. 20-course avant-garde tasting menu by the man who fed Puerto Rico. Book months ahead. A once-in-a-decade meal.

  • Joël RobuchonLegendary

    L'Atelier de Joël Robuchon at MGM — the late master's best restaurant outside Paris. The black truffle tart and langoustine ravioli are extraordinary.

  • Secret Pizza (Cosmopolitan, Floor 14)

    No signage. Take the escalator up to Floor 14, follow the hallway. New York-style pizza by the slice, $5, hidden from tourists. The best thing in Vegas that nobody knows about.

  • Other Mama (off-Strip)

    Japanese-influenced oyster bar on Paradise Road. Where Vegas locals eat when they want great food without the show. The omakase sushi counter is exceptional.

  • Bouchon at The Venetian

    Thomas Keller's French brasserie. The weekend brunch is legendary — croque madame, eggs Benedict, perfect pastries. Join the queue.

Beyond the Casino

  • MSG SphereNew Wonder

    The 160,000 sq ft LED sphere on the east end of the Strip. Darren Aronofsky's "Postcard from Earth" film experience is jaw-dropping — book tickets online. Unlike anything.

  • Bellagio Fountains at Night

    Every 15-30 minutes, 1,000 fountains choreographed to music rise eight storeys high. Free, 9pm-midnight. Stand at the railing — not across the street. You'll cry slightly.

  • Valley of Fire State Park (Day Trip)

    45 minutes north. Ancient red sandstone formations on fire at sunset. Wave formations, petroglyphs, complete Mars-scape. June sunrise here before it gets hot.

  • Cirque du Soleil "O" at Bellagio Essential ShowEssential Show

    Set entirely on/in/around a 1.5 million-gallon pool. Water-based acrobatics that seem physically impossible. Book mid-price seats — view is better than front row. 90 minutes of wonder.

  • Atomic Museum (Fremont)

    America's only museum dedicated to the nuclear age. Fascinating, sobering, unexpected. Nevada's nuclear test history is extraordinary and little-known.

Vegas Strategy: Stay up late, sleep till noon — that's the Vegas way. Book your show and one special dinner before you arrive. Everything else can be spontaneous. Keep $100 for gambling — set a limit, have fun with it, don't chase losses. The Strip walk at 2am is an experience unlike anywhere on Earth.
→ Las Vegas east on US-93 to Kingman AZ, then north on AZ-64 to Grand Canyon South Rim ~4.5 hrs · 280 miles
Grand Canyon
STOP · 08
June 14–162 nights
Arizona

Grand Canyon

"Nothing in two decades of travel will have prepared you. Nothing."

Where to stay

  • El Tovar Lodge On the RimOn the Rim

    Built in 1905, steps from the South Rim. Theodore Roosevelt, Albert Einstein, and every US president have stayed here. Canyon-view rooms are extraordinary. Book 6 months ahead.

  • Bright Angel Lodge On the RimOn the Rim

    Historic 1935 lodge by Mary Colter right at the trailhead. Rim Cabins have canyon views from bed. More affordable than El Tovar, equally atmospheric.

  • The Grand Hotel, Tusayan 7 min from Rim7 min from Rim

    If rim lodges are full (they often are), Tusayan village 7 miles south. The Grand Hotel is the best here — pool, good restaurant, easy early morning rim access.

Where to eat

  • El Tovar Dining Room HistoricHistoric

    Canyon views, 1905 dark timber interior, white tablecloths. Dinner reservation essential — book when you book the lodge. The bison tenderloin is excellent.

  • Bright Angel Restaurant

    Classic American diner inside Bright Angel Lodge. Pre-hike breakfast here is a tradition — enormous portions, canyon views, strong coffee.

  • Canyon Village Market & Deli

    Stock up for hike lunches here. Sandwiches, trail mix, electrolyte drinks. The only sensible option for day-hike nutrition.

Canyon Experiences

  • Mather Point Sunrise 4:30am Wake-Up4:30am Wake-Up

    The canyon changes colour as light enters it — orange, then red, then gold. The silence before the tourist crowds arrive is profound. Set your alarm for 4:30am. You will not regret it.

  • South Kaibab Trail — Ooh Aah Point

    1.8 miles return, steep but achievable. The first true canyon perspective hike. 360° canyon views — completely different from the rim. Start at first light, before heat arrives.

  • Rim Trail Walk (all day)

    13 miles rim-to-rim, flat, multiple viewpoints — Mather, Yavapai, Mohave, Hopi. Take the free shuttle back. Sunset from Hopi or Mohave Point is world-famous.

  • Stargazing from Yavapai Point

    International Dark Sky Park — no light pollution. The Milky Way visible from 9pm June-July. Yavapai Geology Museum hosts free ranger stargazing talks.

  • IMAX Theatre, Tusayan

    The Grand Canyon IMAX film gives geological and cultural context before you see the real thing. Worth seeing the night you arrive.

June Heat Reality: Canyon temperatures 20-25°F hotter than the rim. June midday at the bottom is 110°F+. Hike to Cedar Ridge max (3 miles RT) and turn back. Carry 3 litres per person. The ranger rule: "if you reach the canyon floor in June, you are in a life-threatening situation by 10am without water." Dramatic but true.
→ St Louis or Springfield MO → Memphis TN via I-55. The Mississippi River crossing is dramatic. ~5 hrs from St Louis · 280 miles
Route 66
STOP · 09
June 16–19 — RollingRolling stops
AZ → NM → TX → OK

Route 66

"Arizona → New Mexico → Texas → Oklahoma. The Mother Road. America's greatest highway."

Essential Stops — Arizona & New Mexico

  • Williams, AZ — The Last TownStay Here

    The last town bypassed by I-40. Red Garter B&B in an 1897 bordello building. Rod's Steak House since 1946. Walking the original main street feels like time travel.

  • Standin' on the Corner, Winslow AZ

    The Eagles "Take It Easy" corner with the mural and flatbed Ford. Tiny town, enormous charm. The La Posada Hotel nearby is one of the great Harvey Houses — have lunch.

  • Petrified Forest National Park

    Ancient wood turned to crystal over 200 million years. Straddles Rt 66/I-40 — free with America the Beautiful pass. The painted desert section at dawn is unearthly.

  • Route 66 through Gallup, NM

    Native American trading capital — El Rancho Hotel (1937, where John Wayne and every Western star stayed). Buy Navajo jewelry direct from artists on the sidewalk.

  • Blue Hole, Santa Rosa NM

    A perfect circular natural pool, 80ft wide, 80°F constant temperature. Crystal clear turquoise water. Completely free. One of the great swimming holes in America.

Texas, Oklahoma & Missouri

  • Cadillac Ranch, Amarillo TXDo This

    Stanley Marsh's 1974 art installation — 10 Cadillacs buried nose-first. Bring spray paint (buy in Amarillo). Everyone tags them. Photo at sunrise when the light turns them gold.

  • Big Texan Steak Ranch, Amarillo

    72oz steak free if you eat it in 1hr. Don't attempt it. Do watch someone attempt it. Ridiculous, kitsch, and genuinely entertaining. Great steaks at normal sizes too.

  • Wigwam Village Motel, Holbrook AZ

    Sleep in a concrete wigwam. National Historic Landmark. $80 a night. Completely wonderful and absurd. Book ahead — they fill up.

  • Bob Dylan Center, Tulsa OKWorld Class

    Opened 2022. Every notebook, manuscript, film, and recording from Dylan's archive. Even non-fans will be stunned. Stay overnight in Tulsa — Brady Arts District for dinner.

  • Chain of Rocks Bridge, St Louis MO

    Walk the original Route 66 bridge over the Mississippi — closed to cars, pedestrians only. The river views and the fact you're literally walking Route 66 history is extraordinary.

  • Gateway Arch, St Louis

    630 feet of stainless steel. Take the tram to the top — tiny windows, heart-in-mouth views. The Museum of Westward Expansion underneath is genuinely excellent.

The Route 66 App: Download the "Route 66" app before you leave. GPS-triggered alerts for every historic stop, diner, neon sign, and roadside oddity. It knows when you're approaching a ghost town or a 1950s drive-in. Essential companion.
→ Memphis east on I-40 to Nashville — straightforward, pretty drive through Tennessee countryside ~3.5 hrs · 212 miles
Memphis, Tennessee
STOP · 10
June 19–212 nights
Tennessee

Memphis, Tennessee

"Where the blues were born. Where rock and roll exploded. Where BBQ is a religion."

Where to stay

  • The Peabody Memphis The HotelThe Hotel

    The grand dame of the South. 1925 Italian Renaissance hotel where ducks march through the lobby twice daily. The rooftop bar and the lobby bar are Memphis institutions. Stay here.

  • Big Cypress Lodge UniqueUnique

    Inside Bass Pro Shops at the Pyramid — yes, really. Treetop cabins and lodge rooms inside a massive glass pyramid. Swimming pool, bowling, fishing. Utterly bizarre. Brilliantly fun.

  • Moxy Memphis Downtown HipHip

    Converted 1924 building, great bar, walkable to Beale Street. Fun design, solid value. The rooftop has views over Downtown.

Memphis Eats

  • Central BBQBest BBQ

    Dry rub ribs, pulled pork, smoked turkey — the real Memphis deal. Multiple locations, the Midtown one is the best. The nachos topped with pulled pork are absurdly good.

  • Gus's World Famous Fried ChickenEssential

    The most important fried chicken in America. Spicy crust, impeccably juicy, $12 a plate. Queue outside on a plastic chair. Worth every minute. Cash preferred.

  • Alcenia's in North Memphis

    Ms Betty Joyce's soul food — fried catfish, smothered pork chops, sweet potato pie. Locals only, almost no tourist footfall. This is real Memphis cooking. Go for lunch.

  • Hog & Hominy

    James Beard-nominated Italian-Southern fusion. The pizza with slow-roasted pork shoulder is remarkable. Great cocktails, creative wine list. Memphis's best upscale dining.

  • Wiseacre Brewing Co.

    Best local brewery — the Tiny Bomb pilsner is perfect in June heat. Food trucks outside on weekends. Memphis's Midtown neighbourhood is your base for this.

Memphis Culture

  • Graceland Book AheadBook Ahead

    Elvis's home — genuinely extraordinary. The Jungle Room, the Meditation Garden where he's buried, the pink Cadillac collection. Get the "Elvis: The Entertainer" package. Book a time slot online.

  • National Civil Rights MuseumEssential

    Built around the Lorraine Motel where Dr. King was assassinated April 4, 1968. The most powerful museum in America. Two hours minimum — take your time. Deeply moving.

  • Stax Museum of American Soul Music

    Where Otis Redding, Booker T & the MGs, and Isaac Hayes made their records. A replica of the original studio, Isaac Hayes's gold-plated Cadillac, listening stations for everything recorded here.

  • Beale Street at Night

    Open container laws — walk with a drink. Live blues at every bar, no cover charge. B.B. King's Blues Club, rum boogie Café, Blues City Café. Start at one end and work your way down.

  • Sun Studio

    Where Elvis, Johnny Cash, Jerry Lee Lewis, and Roy Orbison all recorded. The original studio is still intact. Tour runs hourly and is genuinely spine-tingling.

Peabody Duck March: Every morning at 11am, five Mallard ducks ride the elevator from their penthouse suite, walk the red carpet to the lobby fountain, and spend the day swimming. At 5pm they march back. It's been happening since 1933. Everyone watching the first time gets the same look of confused delight.
→ Nashville north on I-65 to Louisville KY (stop for bourbon!), then I-65 to Chicago. Or Nashville → Cincinnati → Chicago on I-71. Both scenic. ~5 hrs direct to Chicago · 470 miles
Nashville, Tennessee
STOP · 11
June 21–232 nights
Tennessee

Nashville, Tennessee

"Music City. Cowboy boots optional. Hot chicken mandatory. Live music: inescapable."

Where to stay

  • Graduate NashvilleBest Location

    Directly on Broadway, rooftop bar with views over the honky-tonk strip and the Cumberland River. The rooftop Founders Room is one of the best bars in Nashville.

  • The Joseph, a Luxury Collection HotelBest Hotel

    2021 opening — the best hotel in Nashville by some margin. Art collection throughout, extraordinary bar, remarkable service. On 4th Avenue, walking distance everywhere.

  • Thompson NashvilleCool

    The Tune rooftop bar here is the most sought-after perch in Nashville for sunset. Great pool, the 1 Hotel inspired design, excellent restaurant below.

  • Noelle Nashville BoutiqueBoutique

    1930 art deco building, rooftop pool, independent boutique feel amid the big hotel openings. Intimate, well-designed, excellent location.

Nashville Eats

  • Hattie B's Hot Chicken The OriginalThe Original

    The Nashville institution. Start at "Mild" — "Hot" is genuinely painful, "Shut the Cluck Up!!!" is medical emergency territory. Queue down the block but moves fast. The pickle and coleslaw cool you down.

  • The Loveless Cafe

    15 miles out on Hwy 100 — the most beloved Southern cooking restaurant in the state. Biscuits made from a 70-year recipe, country ham, fried chicken. Pilgrimage-worthy.

  • Henrietta Red

    James Beard-nominated raw bar and Southern-coastal cooking in Germantown. The oysters and the gulf shrimp are outstanding. Nashville's finest restaurant full stop.

  • Arnold's Country Kitchen

    Meat-and-three cafeteria — the lunch institution since 1983. $12 gets you a protein plus three sides. The turnip greens and cornbread are transcendent. Line out the door, moves fast.

  • Butcher & Bee

    Middle Eastern-influenced eclectic menu in the Nations neighbourhood. The whipped feta is life-changing. Outstanding cocktails. Great for a relaxed dinner away from Broadway.

Nashville Beyond Broadway

  • Ryman Auditorium Sacred GroundSacred Ground

    The Mother Church of Country Music. Check for shows — seeing any act here is extraordinary. The day tour ($30) is excellent — stand on the stage where Hank Williams, Patsy Cline, and Johnny Cash performed.

  • Broadway Honky-Tonks (Free Music)

    Tootsies Orchid Lounge (opened 1960), Robert's Western World (best traditional country), Layla's, the Stage. No cover charge anywhere. Live music starts at 10am. Start at one end and drift.

  • East Nashville Neighbourhood

    The creative, less touristy side — 5 Points for bars and restaurants, Shelby Park for morning runs along the Cumberland. The Five Points Pizza and Dino's diner are neighbourhood staples.

  • The "I Believe in Nashville" Mural

    12 South neighbourhood — the mural everyone photographs. The whole street is excellent — Imogene + Willie denim, Draper James (Reese Witherspoon's store), great coffee at Frothy Monkey.

  • Cheekwood Estate & Gardens

    55-acre botanical garden in a 1929 estate. Summer Blooms in June — wildflowers, sculpture trail, Japanese garden. The mansion interior tour is excellent.

Chicago, Illinois
STOP · 12
June 23–263 nights
Illinois

Chicago, Illinois

"Architecture, deep dish, jazz, the blues, The Bean, the lake. A proper city."

Where to stay

  • The Langham ChicagoBest Hotel

    In the former IBM Building designed by Mies van der Rohe. River views from the rooms, the best pool in the city, extraordinary afternoon tea. Serious luxury in a landmark building.

  • Ace Hotel ChicagoCool

    Fulton Market District — Chicago's most interesting neighbourhood for food. The hotel's Longman & Eagle restaurant is legendary. The vibe is artists and food people.

  • Virgin Hotels Chicago FunFun

    Loop location, rooftop pool, great restaurant (Miss Ricky's). The rooms are cleverly designed with dressing room and bathroom separate from the sleeping area — smart for three people sharing.

  • HI Chicago HostelBest Budget

    Loop location, private rooms available, lake views from some rooms. Organised tours every evening, rooftop access. Consistently rated best hostel in the Midwest.

Chicago Eats

  • Lou Malnati's Deep Dish The OriginalThe Original

    The best deep dish in the city — butter crust, chunky tomato sauce on top, cheese on the bottom (yes, really). The Magnificent Mile location. 45-minute wait for the pie — order immediately.

  • Smyth + The LoyalistWorld Class

    Two-Michelin-star Smyth upstairs (book months ahead), and the brilliant burger at The Loyalist bar below. The Loyalist smash burger is ranked among America's finest.

  • Publican, Fulton Market

    Large communal tables, whole animal cooking, extraordinary oyster selection, Belgian beer list. Sunday brunch here is the greatest meal in Chicago. Book ahead.

  • Dove's Luncheonette

    Tex-Mex soul food in Wicker Park. Counter seating, incredible enchiladas, the best margaritas in the city. Johnny Cash on the jukebox. Arrive when they open.

  • Chicago French Market

    Ogilvie Station — indoor market with 30+ vendors. The crepes from Crepe Bistro, cheese from Murray's, coffee from 4 Letter Word. Great quick lunch before an afternoon exploring.

Chicago Must-Do

  • Architecture River CruiseBest Thing in Chicago

    Chicago Architecture Centre's 90-minute boat tour — the most concentrated architecture education available anywhere. 50+ buildings explained by expert docents. Book online the night before.

  • Millennium Park & The Bean

    Cloud Gate by Anish Kapoor — walk underneath it at 7am before crowds. Jay Pritzker Pavilion for free summer concerts. Crown Fountain is brilliant for children (of all ages).

  • Art Institute of Chicago

    Second largest art museum in the US. Seurat's Sunday Afternoon on the Island of La Grande Jatte, Nighthawks by Hopper, American Gothic by Grant Wood. Half a day minimum.

  • Green Mill Jazz Club, UptownLegendary

    1907 supper club — Al Capone's booth still marked. Sunday night Stomping Steele (11pm onwards) is the best jazz in America. Go late, go twice.

  • Wicker Park & Bucktown

    The real Chicago — Damen Avenue for independent shops, Cafe Mustache and Violet Hour for cocktails, Reckless Records for vinyl. The Violet Hour is one of America's great cocktail bars.

  • Chicago Riverwalk

    Bars and restaurants extending 1.25 miles along the Chicago River. City Winery has a river terrace. Summer evening here with an Architecture Cruise is perfect.

  • Fly ✈️ 2hrs2hrs

    ORD or MDW to JFK/LGA/EWR. Multiple airlines, often $80-150. Easiest but ends the road trip feeling abruptly. Book 3 weeks ahead.

  • Amtrak Lake Shore Limited 🚂Best Experience

    Overnight train — departs Chicago Union Station ~3pm, arrives Penn Station NYC ~9am next day. Private sleeper roomettes available (~$150-250 extra). Dinner in the dining car, lake views through Ohio, wake up in New York. Romantic and unforgettable.

  • Drive Yourself 🚗Epic Ending

    I-90 east — two days via Cleveland and Pittsburgh. Stops: Rock and Roll Hall of Fame in Cleveland (essential), Pittsburgh's incredible bridges and Strip District. Arrive NYC via I-78 through NJ — Manhattan skyline approach unforgettable.

New York City
STOP · 13
June 30 — July 1414 nights
New York

New York City

"Fourteen days. The greatest city on Earth. You've earned it."

Splurge — Best Hotels

  • The Nomad Hotel, Flatiron Top PickTop Pick

    1903 beaux arts building, the most beautiful lobby in New York. NoMad Restaurant is world-renowned. Flatiron location is perfect — walking distance to everything. The library bar is heaven.

  • Aman New York, Fifth Avenue

    The Crown Building on 5th & 57th — 22 floors, 83 rooms, the most expensive hotel in New York. The spa is 25,000 sq ft. For a truly extraordinary two-night splurge.

  • Wythe Hotel, Williamsburg Brooklyn

    Converted 1901 cooperage. Brooklyn base — Manhattan views from every room, rooftop bar, Lilia restaurant next door. A different NYC experience, 10 min from Manhattan by subway.

Mid-Range — Great Value

  • The Standard High Line, Meatpacking SceneScene

    Straddling the High Line with rooms facing the Hudson. The Biergarten below is one of NYC's best outdoor bars. Meatpacking District puts you near Chelsea, West Village, and the Whitney.

  • Pod Hotels (Various) SmartSmart Budget

    Pod 51 (Midtown), Pod Times Square, Pod Brooklyn — cleverly designed compact rooms, excellent locations, rooftop bars. For two weeks, save money here and spend it on experiences.

  • The Jane Hotel, West Village

    Titanic survivors were brought here in 1912. Tiny cabin-style rooms — maritime aesthetic, incredibly characterful. The Grand Ballroom nightclub is extraordinary.

Must See

  • Brooklyn Bridge Walk at DawnDay 1

    Cross from Brooklyn to Manhattan at 6am. The light on the suspension cables, the skyline ahead of you, the East River below. Walk back by subway. The most iconic view in America.

  • Staten Island Ferry (Free)

    Round trip costs nothing. The Statue of Liberty passes within 200 metres. Manhattan skyline from the water. Sail at sunset — the light on the towers is unforgettable.

  • Top of the Rock, Rockefeller Center

    Better views than Empire State — because you can see the Empire State from here. Book the sunset-to-night combo ticket. The transition from golden to neon blue is extraordinary.

  • Central Park — Whole Day

    Row a boat on the Lake, Bethesda Fountain (Angel of Waters), the Ramble for birding, Shakespeare in the Park (free July tickets via lottery), Conservatory Garden in the northeast corner.

  • MoMA — Modern Art Museum

    Van Gogh's Starry Night, Picasso's Demoiselles d'Avignon, Pollock, Warhol, Cindy Sherman. The redesigned building (2019) is excellent. Friday evenings are free 5:30-9pm.

  • The High Line

    Elevated park on former railroad tracks through Chelsea and West Side. Art installations, wildflower plantings, Hudson views. Walk from Gansevoort to 34th Street — all downhill.

Eat Your Way Through Week 1

  • Absolute Bagels, Upper West SideDay 1 Breakfast

    Water bagels, lox, cream cheese. This is the standard everything else is measured against. The everything bagel with scallion cream cheese will redefine your relationship with the bagel.

  • Le BernardinOnce in a Lifetime

    Eric Ripert's three Michelin star seafood restaurant on 51st. The most technically perfect meal in New York. Book three months ahead. The barely cooked halibut in a shellfish broth is a religious experience.

  • Katz's Delicatessen, Lower East Side

    1888. When Harry Met Sally orgasm scene was filmed here. The pastrami sandwich ($25) is carved to order, piled 4 inches high. You share. It's still too much food. Get the ticket when you enter.

  • Chelsea Market

    Former Nabisco factory — The Lobster Place for extraordinary fresh seafood, Los Tacos No. 1 (best quick tacos in NYC), Creamline for milkshakes. Lunch destination for the High Line walk.

  • Shake Shack, Madison Square Park

    The original location — outdoor, under the trees in the park. The ShackBurger and the custard concrete. Sitting in the park eating this in July sunshine — quintessential New York.

  • Broadway Show Book NowBook Now

    July is peak season — book ahead or use the TKTS booth in Times Square for same-day half-price tickets (go at 10am). For the most money: Hamilton or the currently running smash hit. Ask the concierge what's hot when you arrive.

Hidden Gems & Neighbourhoods

  • DUMBO, Brooklyn at Golden HourBest Photo

    Under the Manhattan Bridge on Washington Street — the bridge frames perfectly against the Manhattan skyline at sunset. The best urban photograph in America. Go 7pm in July.

  • Flushing, Queens — Chinatown

    The most authentic Chinese food outside mainland China. Golden Shopping Mall basement — Xi'an lamb burgers, dumplings for $3, soup dumplings. An entire afternoon. Take the 7 train.

  • The Strand Bookstore, Greenwich Village

    18 miles of books across four floors. The rare book room upstairs, the carts outside (books from $1). Sunday afternoon here — a bookshop that's actually a NYC institution.

  • Governors Island

    Ferry from Lower Manhattan (free weekends before noon) — car-free island with hammock groves, food vendors, art installations, and the best view of Manhattan from distance. A secret city park.

  • The Cloisters, Washington Heights

    Metropolitan Museum's medieval art branch — a reconstructed monastery on a cliff above the Hudson. The Unicorn Tapestries are here. Completely different NYC experience — go on a quiet weekday.

  • Coney Island

    D train to the end of the line. Nathan's Famous hot dogs (since 1916), the Wonder Wheel, the Cyclone wooden roller coaster, the boardwalk. Peak Americana. June/July, weekday — not too crowded.

Week 2 Food & Drink

  • Attaboy, Lower East SideBest Bar

    No menu. No sign on the door. Ring the bell. Tell the bartender what spirits or flavours you like and they make your drink. Tiny, dark, impeccable. Consistently ranked among the world's best bars.

  • Lilia, WilliamsburgBest Pasta

    Missy Robbins's restaurant — mafaldini with pink peppercorn and parmigiano, sheep's milk agnolotti. Possibly the best pasta restaurant in America. Book months ahead or join the walk-in line at 5pm.

  • Russ & Daughters Café, LES

    Fifth generation Jewish appetising shop, opened 1914. The Super Heebster (whitefish salad, wasabi roe, pickled onions on a bagel) will end your search for meaning. Saturday brunch, be early.

  • Balthazar, SoHo

    The great New York brasserie — warm lighting, burgundy banquettes, incredible noise, extraordinary food. The steak frites and the bouillabaisse are perfect. Weekend brunch is exceptional.

  • Joe's Pizza, Greenwich Village

    $3.50 slice, fold it in half New York style. Since 1975. The cheese slice is perfect. This is what pizza is supposed to be. Every other pizza experience is judged against this.

  • Jazz at Village VanguardMonday Nights

    Monday nights — the Vanguard Jazz Orchestra has played every Monday since 1966. $30 + two-drink minimum in the basement. The greatest ongoing jazz event in the world. Book online.

  • July 4th Fireworks 🎆

    Macy's 4th of July Fireworks over the Hudson River — largest fireworks display in America. Best free views: Weehawken NJ waterfront, Riverside Park, any Hudson pier above 59th St. Arrive by 6pm.

  • Dead Rabbit, Financial District

    Irish pub downstairs, craft cocktail bar upstairs, multiple times voted world's best bar. The cocktail menu reads like a novella. The Flip Room upstairs is the best bar room in America.