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Self-Guided Walking : North America

California: The Wine Country

Easy to Moderate Terrain: 4-7 Miles Daily

California: The Wine Country

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 overlooking 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.


Tour Highlights:
  • 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.
Tour Only

6 days, 5 nights

FROM $1,998 USD

per person, double occupancy



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  • Generous inclusions: all breakfasts, many meals, and luggage transfers.
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  • We take care of our solo travelers.
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Itinerary & Accommodations

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Day 1

Arrival at St. Helena

Your adventure begins in sophisticated St. Helena, a charming town in the heart of the Napa Valley. After settling into your centrally located hotel, get acquainted with the area’s shops, galleries, and wine-tasting rooms, relax at your hotel’s pool and spa, or visit the culinary marketplace at Greystone, the castle-like former Christian Brothers monastery.

Accommodation: Southbridge Napa Valley, St. Helena

Ideally located in the heart of historical St. Helena, this welcoming hotel boasts spacious rooms with vaulted ceilings and fireplaces, small “Juliet” balconies overlooking the courtyard, spa, or hillsides, and classic décor and furnishings. A full-service spa and fitness center is on site. Within walking distance of the town’s many shops, restaurants, and cafés, the hotel also offers complimentary car service to its sister property, The Restaurant at Meadowood (reservations required)—recipient of three Michelin stars (one of only two restaurants with this rating west of Chicago!).

Day 2

Bothe-Napa Valley State Park to Schramsberg Vineyards

Today’s walk winds from beautiful Bale Grist Mill State Historic Park into Bothe State Park, a large natural area encompassing stands of coastal redwood, Douglas fir, madrone, and oak chaparral. Following a creekside picnic, partake in a tour and tasting at Schramsberg Vineyards before shuttling back to St. Helena.

Accommodation: Southbridge Napa Valley, St. Helena

Ideally located in the heart of historical St. Helena, this welcoming hotel boasts spacious rooms with vaulted ceilings and fireplaces, small “Juliet” balconies overlooking the courtyard, spa, or hillsides, and classic décor and furnishings. A full-service spa and fitness center is on site. Within walking distance of the town’s many shops, restaurants, and cafés, the hotel also offers complimentary car service to its sister property, The Restaurant at Meadowood (reservations required)—recipient of three Michelin stars (one of only two restaurants with this rating west of Chicago!).

Day 3

Sonoma overlook to Sebastiani Winery

Transfer this morning to historic Sonoma, whose vast central plaza is home to the northernmost of California’s 21 Spanish missions. This afternoon’s loop on the Overlook Trail affords spectacular views of the entire Sonoma Valley. Descend to the historical Sebastiani Winery for a wine and local artisan cheese tasting before returning to your inn, a block from Sonoma’s plaza.

Accommodation: Cottage Inn & Spa, Sonoma

In the heart of Sonoma’s walkable downtown, this luxurious bed and breakfast offers spacious individually decorated rooms and suites with tiled bathrooms and French doors. Capturing wine country’s elegant, California-casual feel, inviting patios and public spaces feature unique artwork and antiques, with a perfect atmosphere to relax and perhaps enjoy a bottle of wine from one of the eight wineries which are within walking distance. A range of body treatments are available at the on-site massage room and Zen garden. Complimentary bicycles are at your disposal with a town bike path a block away. A breakfast basket is delivered to your room daily.

Day 4

Bartholomew Park to Buena Vista Winery

Stroll through Bartholomew Park’s lovely manicured grounds and vineyards to a 19th-century villa founded by exiled heirs to the Habsburg throne. Later, enjoy a picnic hamper and wine tasting among the beautiful stone walls of historic Buena Vista Winery. Your return walk leads past the heritage homes of Sonoma’s elegant East Side, leaving time to explore the plaza’s shops or relax by the pool.

Accommodation: Cottage Inn & Spa, Sonoma

In the heart of Sonoma’s walkable downtown, this luxurious bed and breakfast offers spacious individually decorated rooms and suites with tiled bathrooms and French doors. Capturing wine country’s elegant, California-casual feel, inviting patios and public spaces feature unique artwork and antiques, with a perfect atmosphere to relax and perhaps enjoy a bottle of wine from one of the eight wineries which are within walking distance. A range of body treatments are available at the on-site massage room and Zen garden. Complimentary bicycles are at your disposal with a town bike path a block away. A breakfast basket is delivered to your room daily.

Day 5

Jack London State Park to Benziger Family Winery

Enjoy fine views of the Sonoma Valley as you walk through historic Jack London State Park, visiting a 2000-year-old ancient redwood tree and the cottage where the author wrote several of his famous novels. After a tour and tasting at the Benziger Family Winery, return to appreciate your hotel’s tranquil gardens, swimming pool, and riverside hammocks.

Accommodation: The Gaige House, Glen Ellen

With the feel of a sophisticated home, this inn invites relaxation in its fireside public rooms and tranquil grounds and gardens, with an outdoor swimming pool and hot tub. Guest rooms are contemporary with Asian-inspired accents and furnishings, muted colors and fabrics. Included are a bountiful breakfast in the dining room, an evening wine and cheese reception in the sitting room, and fresh-baked cookies and refreshments throughout the day. Spa treatments are offered in-room, in the spa loft, or in a private outdoor cabana. In the heart of Sonoma wine country, Glen Ellen is at the intersection of vineyards, hiking trails, and state and historical parks and gardens.

Day 6

Departure from Glen Ellen

After breakfast, depart at your leisure.

Download Full Itinerary
Download Full Itinerary
Day 1

Arrival at St. Helena

Your adventure begins in sophisticated St. Helena, a charming town in the heart of the Napa Valley. After settling into your centrally located hotel, get acquainted with the area’s shops, galleries, and wine-tasting rooms, relax at your hotel’s pool and spa, or visit the culinary marketplace at Greystone, the castle-like former Christian Brothers monastery.

Accommodation: Southbridge Napa Valley, St. Helena

Ideally located in the heart of historical St. Helena, this welcoming hotel boasts spacious rooms with vaulted ceilings and fireplaces, small “Juliet” balconies overlooking the courtyard, spa, or hillsides, and classic décor and furnishings. A full-service spa and fitness center is on site. Within walking distance of the town’s many shops, restaurants, and cafés, the hotel also offers complimentary car service to its sister property, The Restaurant at Meadowood (reservations required)—recipient of three Michelin stars (one of only two restaurants with this rating west of Chicago!).

Day 2

Bothe-Napa Valley State Park to Schramsberg Vineyards

Today’s walk winds from beautiful Bale Grist Mill State Historic Park into Bothe State Park, a large natural area encompassing stands of coastal redwood, Douglas fir, madrone, and oak chaparral. Following a creekside picnic, partake in a tour and tasting at Schramsberg Vineyards before shuttling back to St. Helena.

Accommodation: Southbridge Napa Valley, St. Helena

Ideally located in the heart of historical St. Helena, this welcoming hotel boasts spacious rooms with vaulted ceilings and fireplaces, small “Juliet” balconies overlooking the courtyard, spa, or hillsides, and classic décor and furnishings. A full-service spa and fitness center is on site. Within walking distance of the town’s many shops, restaurants, and cafés, the hotel also offers complimentary car service to its sister property, The Restaurant at Meadowood (reservations required)—recipient of three Michelin stars (one of only two restaurants with this rating west of Chicago!).

Day 3

Sonoma overlook to Sebastiani Winery

Transfer this morning to historic Sonoma, whose vast central plaza is home to the northernmost of California’s 21 Spanish missions. This afternoon’s loop on the Overlook Trail affords spectacular views of the entire Sonoma Valley. Descend to the historical Sebastiani Winery for a wine and local artisan cheese tasting before returning to your inn, a block from Sonoma’s plaza.

Accommodation: Cottage Inn & Spa, Sonoma

In the heart of Sonoma’s walkable downtown, this luxurious bed and breakfast offers spacious individually decorated rooms and suites with tiled bathrooms and French doors. Capturing wine country’s elegant, California-casual feel, inviting patios and public spaces feature unique artwork and antiques, with a perfect atmosphere to relax and perhaps enjoy a bottle of wine from one of the eight wineries which are within walking distance. A range of body treatments are available at the on-site massage room and Zen garden. Complimentary bicycles are at your disposal with a town bike path a block away. A breakfast basket is delivered to your room daily.

Day 4

Bartholomew Park to Buena Vista Winery

Stroll through Bartholomew Park’s lovely manicured grounds and vineyards to a 19th-century villa founded by exiled heirs to the Habsburg throne. Later, enjoy a picnic hamper and wine tasting among the beautiful stone walls of historic Buena Vista Winery. Your return walk leads past the heritage homes of Sonoma’s elegant East Side, leaving time to explore the plaza’s shops or relax by the pool.

Accommodation: Cottage Inn & Spa, Sonoma

In the heart of Sonoma’s walkable downtown, this luxurious bed and breakfast offers spacious individually decorated rooms and suites with tiled bathrooms and French doors. Capturing wine country’s elegant, California-casual feel, inviting patios and public spaces feature unique artwork and antiques, with a perfect atmosphere to relax and perhaps enjoy a bottle of wine from one of the eight wineries which are within walking distance. A range of body treatments are available at the on-site massage room and Zen garden. Complimentary bicycles are at your disposal with a town bike path a block away. A breakfast basket is delivered to your room daily.

Day 5

Jack London State Park to Benziger Family Winery

Enjoy fine views of the Sonoma Valley as you walk through historic Jack London State Park, visiting a 2000-year-old ancient redwood tree and the cottage where the author wrote several of his famous novels. After a tour and tasting at the Benziger Family Winery, return to appreciate your hotel’s tranquil gardens, swimming pool, and riverside hammocks.

Accommodation: The Gaige House, Glen Ellen

With the feel of a sophisticated home, this inn invites relaxation in its fireside public rooms and tranquil grounds and gardens, with an outdoor swimming pool and hot tub. Guest rooms are contemporary with Asian-inspired accents and furnishings, muted colors and fabrics. Included are a bountiful breakfast in the dining room, an evening wine and cheese reception in the sitting room, and fresh-baked cookies and refreshments throughout the day. Spa treatments are offered in-room, in the spa loft, or in a private outdoor cabana. In the heart of Sonoma wine country, Glen Ellen is at the intersection of vineyards, hiking trails, and state and historical parks and gardens.

Day 6

Departure from Glen Ellen

After breakfast, depart at your leisure.

Download Full Itinerary

Dates & Prices

Seasonal Tour Pricing

2016 Dates Number of Travelers
2 3 4 5 6 Single Supplement
more info
Solo Surcharge
more info
Apr 1 - Nov 30 $2,198 $2,198 $2,198 $2,198 $2,198 $995 $245
*All prices are per person, based on double occupancy.

Seasonal Tour Pricing

2017 Dates Number of Travelers
2 3 4 5 6 Single Supplement
more info
Solo Surcharge
more info
Mar 1 - Mar 30 $1,998 $1,998 $1,998 $1,998 $1,998 $790 $265
Apr 1 - Nov 30 $2,198 $2,198 $2,198 $2,198 $2,198 $1,050 $265
This tour is available daily, on request, from March 1 through November 30, 2017. All prices are per person, based on double occupancy.

Photos

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