Planes, Trains and Automobiles: 10 Fun and Unique Ways to Explore California Wine Country

Planes, trains and automobiles are just the start. There are also hot air balloons, vintage cable cars, a 14-person party bike, and more.

Without a doubt, Wine Country is one of the world’s most breathtaking regions to travel through, whether you are looking for a romantic escape, a relaxing retreat or seeking thrills.

The area abounds with diverse landscapes and places to explore, as well as a plethora of ways to get there. Planes, trains and automobiles are just the start. There are also hot air balloons, horseback riding, replica vintage cable cars and a variety of other modes of transport that capture the imagination.

They say it’s not the destination, but the journey that matters. We’ve compiled a list of ways to get around Wine Country that make both the journey and the destination a true delight. Read on and click through the above gallery for inspiration.


With its origins in the 19th century, train travel conjures up the romance of the past, but investments in new technology also make it a vision for an environmentally friendly future. Romantics, commuters and day trippers alike can enjoy a ride on the rails on the Napa Valley Wine Train or the SMART train.

Traveling through the heart of Wine Country, the Napa Valley Wine Train features a variety of leisurely journeys in vintage Pullman rail cars that include multi-course gourmet meals, sparkling wine and afternoon tea, as well as stops for tastings and photo opportunities at vineyards along the way. Travelers can cap off their experience with a stay at the Napa Valley Railway Inn, eight steam-era railcars converted into finely appointed hotel guest rooms in downtown Yountville.

For a more modern take on the rail experience, the SMART train is an excellent way to travel in Sonoma County or south to Marin County. The line’s stops in Santa Rosa are close to attractions that include the Charles M. Schulz Museum, shopping at Whistlestop Antiques and Hot Couture Vintage Fashion or a stay at Hotel La Rose by Railroad Square; the Cotati station is a short walk from a meal or snack at Oliver’s Market, Acme Burger and Red Bird Bakery; the Petaluma station brings travelers right up to cultural venue the Petaluma Arts Center, while the city’s downtown restaurants and music venues are only a 10-minute walk away.

Afternoon tea on the Napa Valley Wine Train. (Courtesy of Napa Valley Wine Train)
Afternoon tea on the Napa Valley Wine Train. (Courtesy of Napa Valley Wine Train)


There is nothing like getting a bird’s eye view of Wine Country’s varied topography and natural beauty. Based in Sonoma, Obsidian Wine Co. provides wine-related excursions including a de Havilland DHC-2 Beavers seaplane flight that takes off in Sausalito with an overfly of the Golden Gate Bridge before heading over the Mayacamas Mountains and making a water landing onto Clear Lake. (Food & Wine magazine recently named Obsidian’s Seaplane Wine Flight one of  “the most extreme wine tastings around the world”.)

If you want to experience aviation history while you feel the rush of air and adrenaline, you can book a ride on a 1941 open cockpit biplane through Vintage Aircraft Co. in Sonoma. The Boeing PT-17 Stearman, which now takes passengers for joyrides above Wine Country and beyond, was used as a training plane for cadets prior to and during World War II.


If you have ever dreamed of driving a classic sports car or luxury vehicle through the rolling hills of Wine Country, your dreams may not be so far from coming true.

This fall, the Four Seasons Napa Valley in Calistoga created a weeklong curated driving and sightseeing itinerary that allowed guests to drive their own car or choose from iconic sports cars such as the Aston Martin DB11, silver and neon green Lamborghini Huracan Spyder or cherry-red Ferrari 488 GTB.

The next iteration of the Napa Valley 750 Road Rally, a five-day event that brings together more than two dozen owners of vintage race cars (such as a 1958 Porsche Speedster or 1955 Lancia Aurelia B24 Spider) for a local road tour, takes place May 5-10.

The event’s organizers have created a one-day 125-mile road tour route of Sonoma County for anyone to enjoy. Sites such as Vinity and Turo make it possible to rent the dream car you most desire for a local spin, from a Bentley R Type to a Porsche 911L to a Pontiac Firebird 400 Convertible.


For centuries before the advent of planes, trains and automobiles, the quickest way to travel over land was on horseback at a gallop. But these days it’s okay to saunter along riding high in the saddle, enjoying scenery and paths not accessible by mechanized transport.

Bartholomew Estate Vineyards and Winery in Sonoma offers a 45-minute ride on horseback through its historic estate guided by Sonoma Valley Trail Rides. The experience includes a bottle of Bartholomew Estate wine to take home.

Triple Creek Horse Outfit in Glen Ellen provides a variety of riding trail options at Jack London State Historic Park, allowing guests to explore different areas of the park from rides that last an hour to combo rides that take place over the course of two days. Riders can commune with the writing legacy and life of “Sailor on Horseback” Jack London, taking in the views of the author’s prized Beauty Ranch while passing through the many natural features that captured his imagination.

Triple Creek Horse Outfit in Glen Ellen provides a variety of riding trail options at Jack London State Historic Park. (Triple Creek Horse Outfit)
Wine Country Balloons
Enjoy scenic flights over Sonoma County with Wine Country Balloons. (Courtesy of Wine Country Balloons)

Hot air balloons

If you’d like to travel at a more leisurely pace, floating above it all, there are plenty of options. Calling its rides “A Nature Walk in the Sky,” Wine Country Balloons says it has flown everyone from chef Gordon Ramsey to musician Dave Matthews, and customers are invited to take part in the set up and inflation process. Wine Country Balloons, established over 40 years ago, is the oldest continuously operated balloon company in Sonoma County. Based out of Yountville, the family-run Napa Valley Aloft’s ballooning history also stretches back to the 1970s. Napa Valley Balloons starts the day with a pre-flight pastry from Bouchon Bakery in Yountville and offers packages that include wine tasting and bike experiences.

Vintage cable cars

If you only think of the city when you think of cable cars, you might just think again after visiting Wine Country. The Sonoma Valley Wine Trolley, designed to look like an 1890s San Francisco cable car, takes riders on a six-hour tour from Sonoma Plaza that includes guided private wine tasting experiences.

The Napa Valley Wine Trolley has two distinct six to seven hour tour routes travelers can choose from to ride on a replica San Francisco cable car on wheels: The Napa Valley Classic wine tour focuses on South Napa and the Up Valley Castle Tour visits wineries in North Nap, including the Castello Di Amorosa.


Flat-bottomed boats traversing the canals of Venice might first come to mind when you hear the word gondola. However, Sterling Vineyards in Napa features the kind of gondola you are most likely to see when climbing the Alps.

Thought to be the only winery in the world with an aerial gondola, Sterling’s tram provides 360-degree views up a tree-covered hill to the winery. After the gondola ride, travelers can have a self-guided wine tasting, learn about the art and science of winemaking and enjoy a seated tasting of a reserve wine paired with a cheese board on a terrace overlooking the Napa Valley as part of Sterling’s The Tour and Terrace Experience.

Sonoma Wedding Photographer
Sonoma Wedding Photographer

Volkswagen bus

If you are not interested in another run of the mill chartered bus tour, you just might want to check out West Wine Tours’ fleet of classic VW buses which embarks on tours in Sonoma and Napa. You can book just a seat or an entire six-seat or eight-seat bus for groups. Tours include stops at local wineries (wine tasting fees not included) or you can create your own custom itinerary if you book an entire bus. A picnic lunch is included in every itinerary.

14-person party bike

Those who like to get some exercise while socializing, sightseeing and imbibing might want to take a ride on one of Bike Healdsburg’s two basic tours. The Just The Seat Tour features a bar crawl of three stops in Healdsburg, while the All-Inclusive Tour features three unique wine tastings and small bites.


For the pure adventure seekers, there are few experiences that can match the thrill of jumping out of a plane, free falling in the sky before pulling open your parachute and gliding down to earth. NorCal Skydiving caters to those interested in taking a tandem skydive or receiving instruction to be able to make a solo jump.