San Francisco to the Wine Country Self-Guided Hiking Holiday

Experience the best of San Francisco on this self-guided inn-to-inn 10-day Wine Country hiking holiday in California.


Enjoy our signature ten day trek vacation where you will experience the best of the San Francisco Bay Area. This vacation takes you to San Francisco, the , Sausalito, Muir Woods National Monument, Point Reyes National Seashore, pristine Tomales Bay, Jack London State Historic Park in Glen Ellen, and superb Sonoma Valley Wine Country estate wineries. This trek is a fantastic walking holiday that has everything you could wish for!

The San Francisco to the Wine Country self-guided hiking holiday in California includes 6 days of hiking from 7 to 12 miles (11 to 19 km). You may schedule a morning kayaking paddle on Tomales Bay. A day of walking between winery estates for wine tastings is included. Each night you will stay in premier lodging, ranging from charming country inns to luxury boutique hotels, and have many opportunities for world class dining and spa treatments.

This self-guided trek is a complete vacation package that brings together fabulous hiking, lodging, food, and wine, allowing you to “Experience Luxury on Foot”. Uniquely designed in the European style of hiking village to village, this trek is accomplished on foot with very few transfers necessary.

The San Francisco to the Wine Country hiking holiday in California is self-guided, meaning that you travel with your own family or friends, not with a tour of strangers. We provide you with a complete itinerary, including custom maps and detailed trail notes, and arrange all of the lodging for you. You have the confidence of knowing that everything is taken care of and the freedom to manage your own time. Our in-depth local knowledge makes our maps and step by step trail notes invaluable assets on your trek. Our custom maps chart your course on well marked trails that accommodate all levels of hikers.

We arrange luggage transport between inns and provide details on how to obtain a packed lunch for the trail. This allows you to enjoy your hike each day with just a simple day pack for your Trail Guide and lunch. At a leisurely pace the daily hikes can be completed in 5 to 7 hours.

Price Includes

  • Premier Lodging
  • Breakfasts
  • Wine Tastings
  • All taxes, fees, and tips, including park fees
  • Detailed Trail Guide with custom maps and trail notes for each day
  • Luggage transfer between lodgings
  • Transportation to the trailhead (on the few days it may be needed)
  • Local assistance phone number
  • Restaurant listings
  • Local area information package and Planning Guide

Price Excludes

  1. Dinners and Lunches
  2. Pre and post trek airport transfers

What to expect

Itinerary for the San Francisco to the Wine Country Self-Guided Hiking Holiday

Day 1: San Francisco
Start your vacation in San Francisco, staying near famous Ghirardelli Square and Fisherman’s Wharf. Enjoy the ambiance of this beautiful city strolling along the waterfront or riding on an historic cable car. Lodge in a luxury boutique hotel and you may choose to dine at a world class restaurant, recognized by both Michelin and Wine Spectator.

Hiking today: No planned hikes. If you are arriving early, let us know, and we will include the trail guide for a great walking tour of San Francisco, the Barbary Coast Trail.

Day 2: San Francisco to Sausalito
Walk along the San Francisco waterfront, across the majestic Golden Gate Bridge, and into the historic village of Sausalito. Along the way enjoy splendid views of the City and Bay of San Francisco, including Alcatraz and Angel Islands. Your boutique hotel and spa is on the waterfront in Sausalito, where you can enjoy the artists’ studios, cafes, and restaurants of this charming town.

Hiking today: 9 miles (14 km) with 250 feet (75m) elevation gain and loss.

Day 3: Sausalito to Muir Beach
Hike across the beautiful coastal hills in the Golden Gate National Recreation Area to the village of Muir Beach. Enjoy spectacular views of the rugged Pacific Ocean and the San Francisco skyline. Take time to relax on the sandy beach when you arrive in the village. Tonight’s lodging is a classic English Tudor Inn with an elegant salon for guests and a Pub reminiscent of Stratford-on-Avon where you’ll enjoy classic pub fare paired with excellent local and international wines and beers.

Hiking today: 9 miles (14 km) with 2300 feet (700 m) elevation gain and loss.

Day 4: Muir Beach to Mill Valley
Hike onto Mount Tamalpais taking in the dramatic views of the Pacific Ocean. Descend into Muir Woods National Monument enjoying the ancient and magical redwood forest. Then hike/run part of the Dipsea Trail, where the famed Dipsea Race is run. Finish in the charming town of Mill Valley, and enjoy dinner at one of the excellent Mill Valley restaurants.

Hiking today: 10 miles (16 km) with 2000 feet (610 m) of elevation gain and 1900 feet (580 m) of elevation loss.

Day 5: Mill Valley to Olema/Point Reyes
A transport will leave you at Limantour Beach, in Point Reyes National Seashore. Hike along the beach, then up into the National Park. Finish your hike in the small historic town of Olema. A rustic yet luxurious lodge welcomes you with expansive lawns and lazy Adirondack chairs to rest after a day of hiking. Tonight’s dinner is at a sophisticated roadside tavern, serving fresh organic and artisan foods from West Marin dairies and farms.

Hiking today: 9 miles (14 km) with 1300 feet (400 m) elevation gain and 1100 feet (335 m) elevation loss.

Day 6: Olema/Point Reyes to Inverness
A short walk from the lodge takes you into the gorgeous Point Reyes National Seashore Park. Ascend Mt. Vision with its stunning views of Tomales Bay, the Pacific Ocean and the distant Farallone Islands, then descend into the coastal village of Inverness on Tomales Bay. Your lodging is on the water with astounding privacy and views. Dinner tonight can be at an oyster bar with fresh seafood and local fare.

Hiking today: 12 miles (19 km) with 2100 feet (640 m) elevation gain and loss.

Day 7: Tomales Bay
Today you can enjoy a morning kayak trip on Tomales Bay. A naturalist guide is available to explain the scenic beauty of the area while you paddle and spot local wild life. Or you can relax on the shores of Tomales Bay, one of the cleanest bays in California. Dinner tonight is at a local restaurant.

Hiking today: 1 mile (1.6 km) each way walking to and from the kayak launch.

Day 8: Inverness to Glen Ellen
Move from the seashore to the land of vineyards today. A transport will pick you up and take you to the famous Jack London State Historic Park where you will take a hike to see the “Grandmother Tree”, an 1,800+ year old redwood tree. You can also visit the author’s home, as well as the museum established by his wife. After a hike through the park, finish your day with a special tour and tasting at a vineyard estate and winery. Tonight’s lodging has a world class reputation as one of the best luxury inns in the U.S. You’ll relax by the pool, enjoy a spa treatment if you wish, and walk to one of several wine country restaurants.

Hiking today: 7 miles (11 km) with 900 feet (270 m) elevation gain and loss.

Day 9: Glen Ellen Winery Walk
The final day of your trip is an immersion into the wonderful world of Sonoma Valley wines. Enjoy a morning walk from your inn to the first winery estate for a reserve tasting with a food pairing. As the day progresses, you will enjoy delicious reserve wine tastings walking between wineries. Often your final tasting is with the winemaker/owner who will greet and escort you into his estate where you’ll enjoy his cult status Pinot Noirs. A short walk back to your inn lets you relax before another lovely wine country restaurant dinner.

Hiking today: 8 miles (13 km) walking between winery estates with 500 feet (150 m) elevation gain and loss.

Day 10: Trek Conclusion
Your San Francisco to the Wine Country hiking holiday in California comes to an end.


San Francisco to the Wine Country Self-Guided Hiking Holiday: From $3,200 to $6,300 for 10 days

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$3,200 to 6,300 10 days
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