American Experiences: Discover San Francisco and Wine Country

Road trip through Northern California

Zip across the Golden Gate Bridge along beautiful coastline as you discover the charm of California’s cultural hub. Enjoy phenomenal local wines and stunning vineyard landscapes while venturing through Napa and Sonoma.



per person


Each American Experiences trip is designed for you to craft and customize your own adventure. Pick your own date, add or remove nights, upgrade your car, reverse cities, add on activities, and more. Our team of adventure experts has curated suggestions to make your trip incredible and our team is standing by to assist you in creating your incredible adventure.

While crafting your road trip, be assured that your package includes centrally-located hotels, a Hertz car rental, breakfast daily, free hotel WiFi, and an adventure all your own.

*Above pricing quoted is per person, land, and air from Boston.

Suggested Itinerary

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Day 1: Arrive in San Francisco

Cable cars, the Golden Gate Bridge, the Transamerica Pyramid — San Francisco is a travelogue of iconic images. There's so much to see so don't wait to start exploring! After arriving and driving to your hotel, head out to Fisherman's Wharf  to check out its museums, restaurants, and to peruse local shops. Make sure to look for Boudin sourdough bread for which the city is well known in the baking world. After you've loaded up on local food, keep an eye out for all the barking sea lions on Pier 39! If you're up for some local exploration, join a North Beach Pub tour to meet everyone from hardened fishermen to karaoke kings in this eclectic neighborhood.

Day 2: San Francisco

Script your own adventure with a multitude of options to choose from! You may opt to discover the city on an urban hiking tour through iconic neighborhoods and get your heart racing with a trek up Nob Hill. After working up an appetite, enjoy a well deserved lunch on a Chinatown Culinary Walking tour that showcases hard-to-find herbs and produce, tea, dim sum and more. Looking for something a little more hardcore? Visit Alcatraz, which was once a maximum security federal penitentiary. After, consider making your way back to the hotel on a cable car! However you spend the day, plan to end up at Ocean Beach to watch the sun set.

Day 3: San Francisco to Wine Country

A West Coast road trip isn't complete without a drive over the Golden Gate Bridge! Enjoy the views as you cross the historic bridge en route to Napa and Sonoma where lush vineyards await. Upon arrival, you'll find wineries of all kinds —whether it's an impressive castle, modern architectural wonder or small family-run shop, you’ll be warmly greeted by the local owners and sommeliers eager to explain their craft. Take your time and travel unscripted. Check into your hotel and relax or pick one of the many award-winning restaurants to enjoy dinner paired with a local Chardonnay or Cabernet Sauvignon perhaps.

Day 4: Wine Country

Much of the great attraction of being in "wine country" is having the opportunity to simply relax and enjoy where you are. The area is chock full of incredible experiences, should you wish to delve in. Hop aboard the Napa Valley Wine train for a delicious meal as you roll through Northern California. Hone your craft during a private cooking class, or discover local flavors on a walking foodie tour. Wine not your thing? Join a behind the scenes brewery tour in Sonoma. The adventure is yours!

Day 5: Farewell

For your last day in Wine Country, an incredible way to end your adventure is a hot air balloon ride. Watch the day break over beautiful vineyards and expansive estates beneath you. Return to San Francisco today for the end of your great adventure.

Add-On Adventures

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Union Square, Nob Hill, and Chinatown Urban Hiking Tour

Discover more of San Francisco on an urban hiking tour through must-see neighborhoods: Union Square, Nob Hill, and Chinatown. Get a workout as you take in Nob Hill landmarks such as Grace Cathedral and the Fairmont Hotel, and visit the Cable Car Museum and the Fortune Cookie Factory. Learn about the Gold Rush, the Beat Generation, hippies in the 1960's, and more, before concluding in Union Square.
$54 per person

The Essential SF Night Bike Tour

Explore local San Francisco after dark on this extra delicious & memorable night tour featuring: the city’s coolest ‘hoods & landmarks, best pizza, dazzling light displays, most fun to ride back roads, and so much more. This is San Francisco’s only night tour by bike, exploring SF’s best city lights, views, food, and drinks in the most fun way possible. This extra-cool, active adventure will be full of new discoveries for longtime locals and is perfect for visitors seeking a memorable way to experience all SF has to offer and make the most of their time here. Don’t miss out on this unique way to learn, eat, and uncover the real, local SF & its special hidden gems!
$74 per person

Chinatown Culinary Walking Tour

Stroll the narrow streets and back alleys of San Francisco's Chinatown on this small-group walking tour. Stop by shops selling authentic Chinese crafts and pottery, as well as hard-to-find herbs and produce. A variety of tastings add up to a full lunch, including tea, fortune cookies, dim sum, and other treats. Listen to guided commentary and ask plenty of questions as you explore.
$63 per person

San Francisco Combo: Ferry Building Food Tour and Alcatraz

Tour San Francisco's Ferry Building Marketplace with a culinary expert guide and sample many products from artisan and local food purveyors. Then visit the former maximum-security prison, Alcatraz, to shed light on the history-packed location during this full-day excursion in San Francisco.
$152 per person

Teas, Temples & Beatniks

Come explore where east meets west, fortunes are told with more sincerity than your average cookie, and the legends of masters live on. Between the Beatniks of North Beach and San Francisco’s iconic Chinatown, it'll give you a taste of teas, temples, and culture, all with a local flare.
$66 per person

North Beach Pub

From Beatniks to Blues masters, drunken sailors, hardened fishermen, and karaoke kings, North Beach is full of colorful, local identities and fanciful folk heroes. Find out about them over an Anchor Steam ale on this San Francisco tour that will get you talking.
$58 per person

Small-Group Wine-Tasting Tour through Napa Valley

Discover Napa Valley at a relaxed pace on a 6.5-hour small-group tour. Comfortable transportation collects you from your hotel and carries your group to four distinct wineries, where you can enjoy tastings at your own expense. Listen to live commentary and ask questions at any time. Your experience also includes a complimentary picnic lunch, complete with cheese plate, at a charming winery.
$120 per person

Half-Day Napa Valley Bike + Wine Tour

Experience the beauty of Napa Valley on a guided bike tour with stops at two local wineries for tastings. Your tour will finish in the early afternoon, leaving you free to explore Napa further on your own. Ride with an informative guide, proceeding at a relaxed pace.
$135 per person

Sonoma County Brewery Tour Including Behind-the-Scenes Access

There's more to Sonoma County than just wine, so if you're more of a barley and hops fan than a grape lover, get an insider look at three regional breweries on this behind-the-scenes tour. With a guide, you'll enjoy tastings and learn about the brewing process at locations such as Lagunitas Brewing Company in Petaluma, Stumptown Brewing Company in Guerneville, Bear Republic Brewing Company in Healdsburg, or others, depending on the day of your tour. Lunch is included.
$103 per person

Napa Valley Wine Train with Gourmet Lunch

Roll through Northern California’s famous wine country on the renowned Napa Valley Wine Train. Pass charming towns like Rutherford and St. Helena, and soak up the scenery of rolling hills, vineyards, and estates through large picture windows. Explore the restored vintage train cars, and then take a seat for a gourmet lunch or dinner freshly prepared by the train’s acclaimed on-board restaurant.
$165 per person

Private California Cooking Class in the Heart of Napa Valley

Enjoy a private and authentic cooking class and home-cooked meal with your host Ray. This is a perfect experience for anyone looking to connect with local culture over food. Ray has been cooking professionally since he was 16 years old. He has traveled the world, cooking, tasting and learning as he goes, which has resulted in a vast repertoire of recipes and techniques from nearly every cuisine imaginable. Now semi-retired, Ray feeds his passion for hospitality and cooking by hosting guests at his home. His annual 'Pig and Pinot' party attracts 200 guests, and his friends know they can stop in anytime for a delicious meal, lingering in his backyard over an excellent bottle of wine. Ray can cook it all - Thai, Chinese, French, Indian, delicate patisserie, Italian, but his favorite way to eat is seasonal, unpretentious family-style dishes inspired by the bounty of ingredients available in California's Napa Valley. Join him at his rustic home for a memorable culinary experience in Napa.
$77 per person

Napa Valley Hot-Air-Balloon Ride with Sparkling Wine Toast

Experience Napa Valley's world-famous wine country from the air on a sunrise hot-air-balloon ride. Start the day off right with coffee and pastries and then climb into a comfortable basket to take to the skies as day breaks across the valley. Enjoy a bird’s-eye perspective of rolling hills, expansive vineyards, and elegant estates during your flight. Once back on solid ground enjoy a sparkling wine toast with your pilot.
$219 per person

Downtown Napa Food and Wine Tour

Explore Napa’s legendary food and wine on a 3-hour gourmet walking tour through downtown. Get an insider’s perspective on the culinary scene as you stroll the 1-mile (1.6-km) route alongside a local, foodie guide, and pause at a series of seven boutiques, cafés and restaurants. Learn about California’s terroir from a local olive oil maker, taste fine, handmade chocolates and visit an elegant collective of vintners. Enjoy the leisurely, strolling meal with a small group of fellow foodies, and experience the flavors of California wine country.
$101 per person


American Experiences: Discover San Francisco and Wine Country



Unscripted experiences, insider access and authentic local flavors

Our team of travel specialists and local contacts have curated some of the best, most exclusive and authentic experiences, restaurants and accommodations to truly immerse yourself in a way that wouldn't be possible in larger groups or just on your own.

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