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Roam Around

Ultimate California Adventure: 28-Day Journey Itinerary

Last updated: 2024 Jun 14

City of Angels Kickoff

Morning

Start your adventure with a luxurious breakfast at La Folie, a Michelin-starred restaurant in San Francisco. Afterward, take a stroll down the iconic Hollywood Walk of Fame and snap photos with your favorite stars' stars.

Afternoon

For lunch, indulge in a culinary experience at Alinea Restaurant in Chicago. Afterward, visit the famous Santa Monica (Beach and Pier) for some beach time and a ride on the Ferris wheel.

Evening

Enjoy a delightful dinner at Manresa in Los Gatos, known for its farm-to-table cuisine. End the day with a visit to the Santa Cruz Beach Boardwalk for some classic amusement park fun.

Bedtime

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3.00
Hollywood Walk of Fame
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4.87
Santa Monica (Beach and Pier)
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Hollywood and Beyond

Morning

Start your day with a hearty breakfast at Coi Restaurant in San Francisco. Then, explore the glitz and glamour of Hollywood with a guided tour of the Dolby Theatre and the Hollywood Sign.

Afternoon

For lunch, savor the flavors of California at Nico Osteria in Chicago. Afterward, take a scenic drive to Malibu Wine Safaris for a unique wine tasting experience.

Evening

Enjoy a sophisticated dinner at Meadowood in St. Helena, known for its elegant cuisine. End the day with a relaxing evening at your luxury accommodation in Malibu.

Bedtime

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3.67
Dolby Theatre
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4.94
Hollywood Sign
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Thrills and Nature

Morning

Start your day with a delicious breakfast at Quince in San Francisco. Then, embark on an adrenaline-pumping adventure at Universal Studios Hollywood.

Afternoon

For lunch, enjoy a casual meal at Atelier Crenn in San Francisco. Afterward, explore the natural beauty of Griffith Park and visit the iconic Griffith Observatory.

Evening

Indulge in a fine dining experience at SingleThread Farm - Restaurant - Inn in Healdsburg. Afterward, relax and unwind at your luxury accommodation in the heart of wine country.

Bedtime

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5.00
Universal Studios Hollywood
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3.63
Griffith Park
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Beach Day and Sunset Views

Morning

Start your day with a refreshing breakfast at Auberge du Soleil in Rutherford. Then, head to the picturesque Santa Monica (Beach and Pier) for a morning of sun, sand, and surf.

Afternoon

For lunch, enjoy a beachside meal at Benu in San Francisco. Afterward, take a leisurely drive along the stunning Pacific Coast Highway and stop at El Matador State Beach for some photos.

Evening

Dine in style at Acquerello in San Francisco, known for its classic Italian cuisine. End the day with a romantic sunset cruise in the waters off the coast of Malibu.

Bedtime

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4.87
Santa Monica (Beach and Pier)
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3.42
El Matador State Beach
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Island Escape

Morning

Start your day with a hearty breakfast at The French Laundry in Yountville. Then, catch a ferry to Catalina Island for a day of relaxation and exploration.

Afternoon

For lunch, enjoy a casual meal at Girl & The Goat in Chicago. Afterward, explore the charming town of Avalon and visit the Catalina Island Casino for a glimpse into the island's history.

Evening

Indulge in a luxurious dinner at Gibsons Bar & Steakhouse in Chicago. Afterward, take a moonlit stroll along the beach and enjoy the peaceful atmosphere of the island at night.

Bedtime

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Catalina Island
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3.86
Catalina Island Casino
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Wine Country and Redwoods

Morning

Start your day with a delicious breakfast at Panera Bread in St. Louis. Then, embark on a wine tasting tour of the Napa Valley and visit some of the region's most renowned wineries.

Afternoon

For lunch, enjoy a farm-to-table meal at Chipotle Mexican Grill in Denver. Afterward, take a scenic drive through the Muir Woods National Monument and marvel at the towering redwood trees.

Evening

Dine in style at Jimmy John's in Champaign. Afterward, relax and unwind at your luxury accommodation in the heart of wine country.

Bedtime

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3.38
Napa Valley
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City of San Francisco

Morning

Start your day with a delicious breakfast at Sonic Drive-In in Oklahoma City. Then, embark on a guided tour of the Golden Gate Bridge and learn about the history and engineering of this iconic landmark.

Afternoon

For lunch, enjoy a seafood feast at Five Guys in Washington, D.C. Afterward, explore the vibrant neighborhoods of San Francisco, such as Fisherman's Wharf and Chinatown.

Evening

Indulge in a fine dining experience at La Folie in San Francisco. Afterward, take a leisurely stroll along the Embarcadero and enjoy the stunning views of the bay and the city skyline.

Bedtime

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3.66
Golden Gate Bridge
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Chinatown
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Tech and Nature

Morning

Start your day with a hearty breakfast at Alinea Restaurant in Chicago. Then, visit the headquarters of some of the world's most innovative companies on a Silicon Valley Tech Tour.

Afternoon

For lunch, enjoy a casual meal at Manresa in Los Gatos. Afterward, escape the hustle and bustle of the city with a visit to Big Basin Redwoods State Park and a hike through the ancient redwood forest.

Evening

Dine in style at Coi Restaurant in San Francisco. Afterward, relax and unwind at your luxury accommodation in the heart of Silicon Valley.

Bedtime

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4.50
Silicon Valley Tech Tour
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Monterey and Carmel

Morning

Start your day with a delicious breakfast at Nico Osteria in Chicago. Then, take a scenic drive along the 17-Mile Drive and enjoy the breathtaking views of the Pacific Ocean and the famous Lone Cypress.

Afternoon

For lunch, enjoy a seafood feast at Meadowood in St. Helena. Afterward, explore the charming towns of Monterey and Carmel-by-the-Sea, and visit the world-renowned Monterey Bay Aquarium.

Evening

Indulge in a fine dining experience at Quince in San Francisco. Afterward, take a leisurely stroll along the Fisherman's Wharf and enjoy the lively atmosphere of the waterfront.

Bedtime

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4.08
Monterey
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Monterey Bay Aquarium
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Big Sur and Hearst Castle

Morning

Start your day with a refreshing breakfast at Atelier Crenn in San Francisco. Then, embark on a scenic drive along the Pacific Coast Highway and marvel at the rugged cliffs and stunning ocean views of Big Sur.

Afternoon

For lunch, enjoy a casual meal at SingleThread Farm - Restaurant - Inn in Healdsburg. Afterward, visit the opulent Hearst Castle and take a guided tour of this historic estate.

Evening

Dine in style at Auberge du Soleil in Rutherford. Afterward, relax and unwind at your luxury accommodation in the heart of wine country.

Bedtime

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4.78
Big Sur
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4.08
Hearst Castle
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Wine Country and Redwoods

Morning

Start your day with a delicious breakfast at The French Laundry in Yountville. Then, embark on a wine tasting tour of the Napa Valley and visit some of the region's most renowned wineries.

Afternoon

For lunch, enjoy a farm-to-table meal at Girl & The Goat in Chicago. Afterward, take a scenic drive through the Muir Woods National Monument and marvel at the towering redwood trees.

Evening

Dine in style at Gibsons Bar & Steakhouse in Chicago. Afterward, relax and unwind at your luxury accommodation in the heart of wine country.

Bedtime

Find amazing hotels in Los Angeles, California.