14-Day Luxurious Adventure Road Trip in San Francisco and Beyond

Day 1: Arrive in San Francisco

San Francisco, USA

10:00AM

Check-in at The St. Regis San Francisco

Begin your luxurious adventure by checking into one of San Francisco's finest hotels.
Directly upon arrival at the airport, head to your accommodation.
USD500, 1 hour

12:00PM

Lunch at The Rotunda

Enjoy a sophisticated lunch with a stunning view of the city.
A 5-minute walk from your hotel.
USD50, 1.5 hours

2:00PM

Explore Golden Gate Park

Stroll through this sprawling park filled with gardens, museums, and scenic views.
Drive 15 minutes from The Rotunda.
Free, 3 hours

5:00PM

Visit the California Academy of Sciences

Discover fascinating exhibits including an aquarium and planetarium.
Located within Golden Gate Park, a short walk away.
USD40, 2 hours

7:30PM

Dinner at Gary Danko

Savor a Michelin-starred dinner in an intimate setting.
15 minutes’ drive from the Academy.
USD150, 2.5 hours
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Day 2: San Francisco Sightseeing

San Francisco, USA

8:00AM

Breakfast at Mama's on Washington Square

A must-visit for a delightful breakfast experience cafe with homemade dishes.
Drive 15 minutes from the hotel.
USD30, 1 hour

9:30AM

Visit Alcatraz Island

Take a ferry ride to this historic prison and learn its intriguing history.
Head to Pier 33 for the ferry, 15 minutes' drive.
USD40, 4 hours with ferry ride

2:00PM

Lunch at The Fog Harbor Fish House

Enjoy fresh seafood with a view of the Bay and Alcatraz.
Return to Pier 39 for this restaurant, a 10-minute walk.
USD45, 1.5 hours

4:00PM

Walk along the San Francisco Embarcadero

Take a leisurely stroll with picturesque waterfront views.
Bike rental available near Pier 39 for added fun.
USD20, 2 hours

6:30PM

Dinner at Boulevard

Dine on innovative cuisine with seasonal ingredients in a Victorian setting.
10 minutes’ drive from Embarcadero.
USD100, 2 hours
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Day 3: Stunning Vineyards

Napa Valley, USA

8:00AM

Breakfast at your hotel

Start with a rich breakfast at The St. Regis prior to your journey.
Dine at the hotel restaurant.
Included in stay, 1 hour

9:00AM

Drive to Napa Valley

Enjoy the scenic route teasing the vineyards ahead.
Drive 1.5 hours (approx. 70 miles) from San Francisco.
Varies, 1.5 hours

10:30AM

Wine tasting at Domaine Carneros

Indulge in exquisite sparkling wines with a view.
Located just 10 minutes from the hotel.
USD40, 1.5 hours

12:30PM

Lunch at Farmstead at Long Meadow Ranch

Enjoy farm-to-table dining in a rustic atmosphere.
A 15-minute drive from Domaine Carneros.
USD50, 1.5 hours

2:00PM

Explore and shop at Oxbow Public Market

Visit local vendors and pick up gourmet treats.
10 minutes away from Farmstead.
Free to explore, 2 hours

4:30PM

Winery Tour at Robert Mondavi Winery

Experience a behind-the-scenes tour and tasting.
Drive 20 minutes from Oxbow.
USD70, 2 hours

7:00PM

Dinner at The French Laundry

An unforgettable dining experience at a world-renowned restaurant.
Drive 15 minutes from the winery.
USD350, 3 hours
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Day 4: More Vineyards

Napa Valley, USA

8:00AM

Breakfast at your accommodation

Enjoy a leisurely morning and breakfast at your vineyard hotel.
Enjoy the hotel breakfast.
Included in stay, 1 hour

9:30AM

Hot Air Balloon ride

Experience stunning aerial views of the vineyards at sunrise.
Arranged through local providers close to your hotel.
USD250, 3 hours

12:00PM

Lunch at Brix Restaurant & Gardens

Delight in local flavors with beautiful gardens.
Drive 20 minutes from the balloon landing site.
USD40, 1.5 hours

2:00PM

Tour and tasting at Chateau Montelena

Discover this historic winery with great wines.
About a 25-minute drive from Brix.
USD50, 2 hours

4:30PM

Explore the quaint town of Yountville

Take some time to browse boutiques or enjoy a coffee.
A 10-minute drive from Chateau Montelena.
Free to shop, 1.5 hours

7:00PM

Dinner at Ad Hoc

Enjoy Thomas Keller’s casual yet upscale dining concept.
5-minute drive from Yountville.
USD60, 2 hours
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Day 5: Nature Escape

Point Reyes National Seashore, USA

8:00AM

Breakfast at your hotel

Have your last breakfast at the vineyard before embarking on your journey.
In hotel dining area.
Included in stay, 1 hour

9:00AM

Drive to Point Reyes National Seashore

Take a scenic drive through the beautiful California landscape.
A 1.5-hour drive (approx. 45 miles).
Varies, 1.5 hours

10:30AM

Visit the Point Reyes Lighthouse

Explore this historic landmark with stunning ocean views.
Drive 25 minutes from the park entrance.
Free, 1 hour

12:00PM

Picnic Lunch

Pack your own picnic lunch to enjoy at one of the beautiful viewpoints.
Bring from local vendors in Point Reyes Station.
USD20, 1 hour

1:00PM

Hiking Trails

Enjoy hiking along a scenic trail – the Tomales Point Trail is highly recommended.
Return to the entrance of the park.
Free, 2.5 hours

4:00PM

Visit Drakes Beach

Unwind at this beautiful beach with astonishing views.
A 20-minute drive from the park trails.
Free, 2 hours

6:30PM

Dinner at Saltwater

Savor fresh seafood right on the waters of Point Reyes.
Approximately 30 minutes from Drakes Beach.
USD80, 2 hours
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Day 6: Artistic Coastal Town

Carmel-by-the-Sea, USA

8:00AM

Breakfast at your hotel

Enjoy breakfast at your accommodations in Point Reyes before leaving.
In hotel dining area.
Included in stay, 1 hour

9:00AM

Drive to Carmel-by-the-Sea

Experience the picturesque route along the coastal highway.
A scenic drive lasting around 2 hours.
Varies, 2 hours

11:30AM

Explore Carmel Mission Basilica

Visit this historic mission with beautiful gardens.
Just a short drive and well-marked.
USD10, 1 hour

1:00PM

Lunch at Casanova

Dine on a taste of France in a charming setting.
Around a 5-minute drive from the mission.
USD50, 2 hours

3:00PM

Walk along Carmel Beach

Enjoy the beautiful beach and stunning sunset if you time it right.
5 minutes’ drive from the restaurant.
Free, 1.5 hours

5:00PM

Visit Point Lobos State Natural Reserve

Take a scenic hike along the coastal cliffs.
10 minutes drive from the beach.
USD10, 2.5 hours

8:00PM

Dinner at Aubergine

Conclude your day with an exquisite dining experience at the hotel.
At Hotel Carmel.
USD120, 2 hours
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Day 7: Explore Big Sur

Big Sur, USA

8:00AM

Breakfast at your hotel

Enjoy breakfast at your lovely hotel in Carmel.
In hotel dining area.
Included in stay, 1 hour

9:00AM

Drive to Big Sur

Set out early to enjoy the scenic beauty along the Pacific Coast Highway.
A drive of about 30 minutes to the heart of Big Sur.
Varies, 30 minutes

10:00AM

Visit McWay Falls

Marvel at the stunning waterfall that cascades into the Pacific Ocean.
Located about 20 minutes from your starting point.
Free, 1 hour

12:00PM

Lunch at Nepenthe

Enjoy breathtaking views and fresh local fare.
A short 10-minute drive from McWay Falls.
USD50, 2 hours

2:00PM

Explore Pfeiffer Beach

Discover the purple sand on this hidden gem beach.
20 minutes drive from Nepenthe.
USD15, 2 hours

5:00PM

Visit Big Sur River Inn

Relax at this rustic inn along the river.
Driving back towards your starting point.
Free, 1.5 hours

7:00PM

Dinner at Post Ranch Inn

Indulge in Michelin-starred cuisine with dramatic ocean views.
Just a quick drive from Big Sur River Inn.
USD200, 2.5 hours
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Day 8: Santa Cruz Adventure

Santa Cruz, USA

8:00AM

Breakfast at your hotel

Relish a delicious breakfast at the inn near Big Sur.
In hotel dining area.
Included in stay, 1 hour

9:00AM

Drive to Santa Cruz

Enjoy the scenic coastal drive, which takes approximately 1 hour.
A drive of about 30 miles.
Varies, 1 hour

10:30AM

Visit the Santa Cruz Beach Boardwalk

Experience the fun rides and games at this iconic location.
15 minutes drive from your hotel.
Varies depending on rides, 3 hours

1:30PM

Lunch at The Picnic Basket

Enjoy a fresh, local meal in a laid-back spot.
Just a short walk from the Boardwalk.
USD20, 1 hour

3:00PM

Explore Natural Bridges State Beach

Wander through this unique beach with natural rock formations.
A 15-minute drive from the restaurant.
Free, 2 hours

5:30PM

Visit Santa Cruz Wharf

Take a stroll or enjoy snacks at this vibrant waterfront.
Drive back to the wharf area.
Free, 1.5 hours

7:30PM

Dinner at Laili

Dine on Mediterranean cuisine with fresh ingredients.
A 15-minute drive from the wharf.
USD50, 2 hours
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Day 9: Hollywood Glamour

Los Angeles, USA

7:00AM

Breakfast at your hotel

Enjoy a leisurely breakfast before the drive to LA.
In hotel dining area.
Included in stay, 1 hour

8:00AM

Drive to Los Angeles

Head south towards the glamour of Hollywood.
A drive lasting approx. 5 hours.
Varies, 5 hours

1:00PM

Lunch at the Farmers Market

Taste various culinary offerings from local vendors.
Drive 10 minutes from your hotel.
USD20, 1.5 hours

3:00PM

Visit the Hollywood Sign

Take a short hike to get an iconic view of the sign.
30 minutes drive from Farmers Market.
Free, 2 hours

5:30PM

Explore The Getty Center

Admire art pieces and stunning architecture.
A 30-minute drive from the sign.
Free, 2 hours

8:00PM

Dinner at Spago

Indulge in elegant Californian cuisine at a renowned restaurant.
15 minutes from The Getty Center.
USD150, 2 hours
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Day 10: Explore Los Angeles

Los Angeles, USA

8:00AM

Breakfast at hotel

Enjoy a hearty breakfast before heading out.
At your Los Angeles hotel.
Included in stay, 1 hour

9:30AM

Visit Santa Monica Pier

Experience the iconic pier and sandy beach.
35 minutes drive from your hotel.
Free, 1.5 hours

11:30AM

Explore Venice Beach

Stroll down the boardwalk and take in the colorful atmosphere.
15 minutes drive from Santa Monica.
Free, 1.5 hours

1:00PM

Lunch at Guelaguetza

Savor authentic Oaxacan cuisine in a casual setting.
About 30 minutes from Venice.
USD30, 1.5 hours

3:00PM

Tour of the Hollywood Walk of Fame

Take photos with the stars and enjoy the culture.
Back towards Hollywood, about 20 minutes drive.
Free, 2 hours

5:30PM

Dinner at The Bazaar by José Andrés

Enjoy a fusion of Spanish and American flavors.
A 20-minute drive from the Walk of Fame.
USD70, 2 hours
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Day 11: Beachside Bliss

San Diego, USA

8:00AM

Breakfast at hotel

Enjoy breakfast before the drive south to San Diego.
At your Los Angeles hotel.
Included in stay, 1 hour

9:00AM

Drive to San Diego

Enjoy a coastal drive along the beautiful California coast.
Travel time of about 2 hours.
Varies, 2 hours

11:30AM

Visit Balboa Park

Explore this expansive park filled with gardens and museums.
Drive 10 minutes from your hotel.
Free to explore, 2 hours

1:30PM

Lunch at The Prado

Savor delicious Californian cuisine in this beautiful setting.
Just a short walk in Balboa Park.
USD40, 1.5 hours

3:00PM

Explore San Diego Zoo

Witness an incredible variety of wildlife in one of the best zoos globally.
Located inside Balboa Park.
USD70, 3 hours

6:30PM

Dinner at The Fish Market

Enjoy fresh seafood with panoramic views of the bay.
A 10-minute drive from the zoo.
USD70, 2 hours
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Day 12: San Diego Charm

San Diego, USA

8:00AM

Breakfast at hotel

Start your day with breakfast at your San Diego hotel.
In hotel dining area.
Included in stay, 1 hour

9:00AM

Visit Coronado Island

Take a ferry ride and explore this picturesque island.
Board ferry at Downtown San Diego.
USD10, 2.5 hours

12:00PM

Lunch at Hotel Del Coronado

Enjoy a lovely meal at one of California's most iconic hotels.
Short walk from the ferry landing.
USD70, 1.5 hours

2:00PM

Relax at Coronado Beach

Spend a few hours enjoying the sun and sandy beach.
Directly across from the hotel.
Free, 3 hours

5:30PM

Dinner at George's at the Cove

Dine with sweeping ocean views and elegant cuisine.
A ferry ride back and then a short drive.
USD80, 2 hours
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Day 13: Desert Retreat

Palm Springs, USA

8:00AM

Breakfast at hotel

Enjoy a leisurely breakfast before the drive to Palm Springs.
At your San Diego hotel.
Included in stay, 1 hour

9:00AM

Drive to Palm Springs

Travel towards the desert via scenic routes.
A drive lasting approximately 2 hours.
Varies, 2 hours

11:30AM

Visit the Palm Springs Aerial Tramway

Experience breathtaking views from the aerial tram.
A short drive from your arrival point.
USD28, 2 hours

2:00PM

Lunch at Spencer's

Dine al fresco with stunning views of the mountains.
Close to the tramway station.
USD50, 1.5 hours

3:30PM

Relax by the pool at your hotel

Unwind and soak in the desert sun.
Return to your luxury hotel.
Free, 2.5 hours

6:30PM

Dinner at Workshop Kitchen + Bar

Enjoy farm to table dining in a stylish setting.
15-minute drive from your hotel.
USD80, 2 hours
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Day 14: Return Home

San Francisco, USA

8:00AM

Breakfast at hotel

Savor a final breakfast in Palm Springs.
At your hotel.
Included in stay, 1 hour

9:00AM

Drive back to San Francisco

Reflect on an amazing road trip back to the city.
A drive of about 2 hours.
Varies, 2 hours

11:00AM

Check-in at The St. Regis San Francisco

Return to your luxurious hotel for some relaxation.
5-minute drive from your destination.
USD500, 1 hour

1:00PM

Lunch at Quince

Celebrate your final day in San Francisco with a Michelin-starred lunch.
A short drive from your hotel.
USD120, 2 hours

3:00PM

Free Time for Last Explorations

Explore any remaining sights or last-minute shopping.
Flexible based on your interests.
Varies, 2 hours

6:00PM

Dinner at The Cliff House

Enjoy your farewell meal with breathtaking ocean views.
Drive to the coast, around 25 minutes.
USD100, 2 hours

9:00PM

Depart for Home

Reflect on your luxurious Californian road trip as you head to the airport.
Return your rental vehicle and check-in.
Varies, 1 hour
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