Walking among green and golden grapevines as morning sunlight chases away the mist, you’ll see what makes Napa Valley and Sonoma so special.

With a picnic basket of local specialties, you’ll experience the full glory of wine country: towering redwoods, remnants of historic frontier towns, renowned vineyards, modern tasting rooms, and charming art galleries. Walk the Overlook Trail, with its scenic views of Sonoma County and the distant sapphire-blue San Pablo Bay. Wander the gardens of the Buena Vista Winery—the oldest in the region—before reaching Jack London State Park. Stay in an elegant hotel with full-service spa, a contemporary property just off historic Sonoma Plaza, and a sophisticated inn with Asian-inspired accents—all within walking distance of some of the world’s finest restaurants. Along the way, don’t forget the wine: at the end of each day of walking, you are rewarded with a visit and tasting at one of the region’s most iconic wineries.


  • Enjoy daily wine tastings, including an indulgent sampling of Benziger Family Winery's vintages paired with a tour of their vineyards.
  • Stay in the charming Gaige House, a boutique hotel in the heart of Sonoma, which boasts fireside public rooms, tranquil gardens, and easy access to wineries and hiking trails.
  • Savor a picnic basket of local specialties at Buena Vista Winery, the oldest vineyard in the entire region.
  • Explore Bothe-Napa Valley State Park, a beautiful landscape of oak and redwood chaparral laced by burbling creeks.
On all Self-Guided Adventures you can count on...
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A local representative available 24/7.
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Detailed maps & route notes featuring turn-by-turn directions and places of interest.
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Delicious meals—many are included.
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Scheduled taxi transfers to bring you to and from each day’s walks.
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Gracious accommodations that are a clean, comfortable home away from home.
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Experts to handle all the details, including moving your luggage between hotels while you’re out exploring.
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Access to a Self-Guided Flight Concierge—ask our knowledgeable team to find flights that sync with your planned trip.


Mon, Apr 1 to Sat, Nov 30 - 2019

Show Itinerary:

Your tour starts in the Napa Valley and the historical town of St. Helena. The heart of this wine-making county, St. Helena has a small-town feel, with a sophisticated side befitting its place in American wine-making history. Your hotel is within walking distance of the town’s many enticing shops and galleries, wine-tasting rooms, coffee shops, and bakeries. Just over a mile from your hotel is Greystone, the castle-like former Christian Brothers Monastery that now houses one of the Culinary Institute of America’s campuses. In addition to restaurants and a café, it has a fully stocked culinary marketplace shop with a flavor bar for food and olive oil tastings. After getting acquainted with the town, you may choose to relax in your hotel’s pool and spa before enjoying one of the many nearby fine restaurants.

Overnight in St. Helena

3.7 miles or 5.3 miles, easy to moderate, 600-ft. elevation gain and 300-ft. elevation loss

Today’s walk takes you on trails through state parks and on to the famous Schramsberg Vineyards. Your first priority, of course, is to pick up your packed lunch from a local purveyor. A transfer takes you to beautiful Bale Grist Mill State Historic Park and the Bothe State Park, a large natural area encompassing stands of coastal redwood trees along its valley floors, as well as Douglas fir and madrone. The trail starts at the Bale Grist Mill State Historic Park, which is the site of a protected grist mill, dating from the mid-19th century and used for grinding wheat and corn into flour into the early 1900s (milling demonstrations on Saturdays and Sundays). The path then winds into Bothe State Park. Making your way through oak and redwood chaparral, you find a perfect picnic spot along the banks of a creek. The trail finally leads you to the back gate of Schramsberg Vineyards, in time for a tour of their cellars and tasting of their excellent sparkling wines. Transportation is provided from the vineyard back to your hotel in St. Helena.

Overnight in St. Helena

4.6 miles, easy to moderate, 500-ft. elevation gain and loss

This morning, you leave the Napa Valley and travel by private transfer about 45 minutes to the heart of the Sonoma Valley—the historical Sonoma Plaza in the center of the town, where you can purchase delicacies for your picnic lunch. The site of the northernmost of California’s 21 missions, and the last to be constructed in 1823, in the 19th century this town (or pueblo) was a fascinating interface of native tribes, Mexican rule, Russian settlement, and American immigrants. A National Historic Landmark, the vast eight-acre plaza was designed as the focal point of the original Mexican “Pueblo de Sonoma.” Your walk begins and ends here, as you start out on the Overlook Trail—which, as its name describes, overlooks the entire Sonoma Valley all the way to San Pablo Bay, the northernmost tidal estuary of San Francisco Bay. You can find a perfect spot to enjoy your packed lunch on the Overlook before you descend into the valley and walk to Pangloss Cellars whose wines are a celebration of Sonoma and the diversity of grape varietals for which Sonoma is known. Pangloss winemaker, Erich Bradley, takes an Old World and minimalist approach, using only hand-picked and hand-sorted grapes, open-top fermenters, and French oak barrels. His goal is to craft small batches of elegant and accessible wines that above all exhibit balance and complexity. Your immersive Cellar tasting, hosted in one of the stone-walled enclaves, is tailored to you and accompanied by local artisan cheeses and charcuterie plate. From here, it’s just a short stroll back to your perfectly situated inn just a block from Sonoma Plaza.

Overnight in Sonoma

5-7 miles, easy to moderate, 100-ft.–500 ft. elevation gain and loss

You walk from your hotel this morning to lovely Bartholomew Park, with its manicured grounds and vineyards, and past a reconstructed 19th-century villa. Originally founded by Hungarian immigrants—exiled heirs to the Habsburg throne—in 1861, the vineyard is a microcosm of the region’s boom, bust, and boom wine history: from its start, through the phylloxera blight of the late 1860s, to its 20th-century resurgence and success. Your morning walk ends at Buena Vista Winery—the oldest winery in Sonoma and Napa, founded in 1857 by an eccentric Hungarian count who sought the perfect terroir in the New World. Recently refurbished to its original beauty, the winery’s beautiful old stone walls provide a lovely setting for a Barrel Tour and Tasting. Beginning with a stroll through the beautiful grounds, followed by a journey through the newly renovated Champagne Cellar, you will be taken from 1857 to the present while savoring a flight of Buena Vista current release wines. Next, you will step into the caves of Buena Vista to sample wine thieved directly from a barrel! Afterward, enjoy a wine-country picnic hamper and tasting before making your way back on foot to the Plaza, through the elegant East Side of Sonoma with its heritage homes. You have time this afternoon and evening to enjoy the shops and tasting rooms on the Plaza or to relax at your inn.

Overnight in Sonoma

Please note: Due to the 2017 wildfires in this region, the two-mile network of hiking trails behind Bartholomew Park (which would normally be included on today’s walk) have been closed until further notice. As a result, the walk is currently alongside paved town and country roads to and from Buena Vista Winery.

6 miles, easy to moderate, 900-ft. elevation gain and 850-ft. elevation loss

You depart Sonoma this morning by private transfer to the nearby village of Glen Ellen (just eight miles) where your walk takes you into historical Jack London State Park. Among the vast trail network and early-20th-century buildings, your route winds past oaks to the Ancient Redwood tree, an estimated 1,800–2,000-year-old redwood. En route are views of the “Valley of the Moon,” the writer’s name for the Sonoma Valley. After finding the perfect picnic spot, you can then visit Jack London’s cottage, where he wrote several of his famous novels, and also the location of the “House of Happy Walls”—a museum dedicated to Jack by his wife, Charmian. A short walk down London Ranch Road brings you to the Benziger Family Winery for a vineyard “Tribute Estate Tour” in a small tram—here you taste wines in the vineyard where the grapes are grown. The tour proceeds through the property, where you learn about biodynamic, organic, and sustainable farming methods, and to the barrel storage cave for further exploration. You then conclude the visit at the tasting room to sample the winery’s full range of wines. A short descent of about 1½ miles leads to your hotel, or you can also call for a ride. A welcome glass of wine awaits you, or perhaps a stroll through the tranquil lawn and gardens to the swimming pool or riverside hammocks.

Overnight in Glen Ellen

You are free to depart anytime this morning after a copious breakfast at your inn.


What's Included

Tour Only
Breakfast daily and one lunch (day 4); beverages not included Check
Four winery tours and tastings (days 2, 3, 4, and 5) Check
All accommodations while on tour Check
Local transfers as noted in the itinerary Check
Orientation phone call with a Country Walkers representative Check
Luggage transfers between the hotels Check
Detailed water- and tear-resistant Route Notes and maps Check
24-hour tour-related support provided by Country Walkers’ local partner Check
24-hour travel-related support provided by Allianz Global Assistance Check
The unbeatable and cumulative experience of the Country Walkers staff Check
Morocco: Marrakesh, Foothills of the High Atlas & Essaouira

Dates & Prices

2019 Dates Number of Travelers
2 3 4 5 6 Single Supplement
Solo Surcharge
Apr 1 - Nov 30 $2,498 $2,498 $2,498 $2,498 $2,498 $1,185 $125
This tour is available daily, on request, from March 1 through November 30, 2019. All prices are per person, based on double occupancy.

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