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10 Days San Francisco Wine Tour & Trekking Holiday

  • San Francisco - Sausalito - Sonoma

Hiking Holiday & Wine Tasting San Francisco

Enjoy a ten-day signature trek vacation, experiencing the best of the San Francisco Bay Area. This vacation takes you to San Francisco and the Golden Gate Bridge to the superb Sonoma estate wineries. Enjoy 6 days of hiking from 6 to 12 miles (10 to 19 kilometers) as well as a morning kayaking adventure with a naturalist guide on beautiful Tomales Bay. Indulge in a privately catered dinner and prepare yourself for a day of walking between winery estates for wine tastings. Each night, stay in premier lodgings, ranging from charming country inns to luxury boutique hotels, and have many opportunities for world-class dining and spa treatments.


  • 6 days of hiking
  • Privately catered dinner
  • Wine sampling at winery estates
  • Visit 7 different parts of the San Francisco Bay Area
  • Morning kayaking adventure with a naturalist guide
  • Premier lodging accommodations
  • 9 nights accommodation
  • 9 days with instruction
  • English
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In the cities, you will stay in luxury boutique hotels. When your trek takes you to the country, you will be in charming country inns with all the amenities one would expect of premier lodging. Wine Country Trekking has chosen lodging that is the best an area has to offer, is always highly rated, and fitting for a first class trek experience. The rooms chosen are the most luxurious offered, often suites with outdoor patios or decks. If you are interested in a lower cost option for a standard room, which may be available in some locations, please contact Wine Country Trekking.

Day 1 - San Francisco

Start your vacation in San Francisco, staying near famous Ghirardelli Square and Fishermans 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. Your personal trail guide will suggest local walks and sights to see.

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 kilometers) with 250 feet (75 meters) 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 town. 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 kilometers) with 2300 feet (700 meters) elevation gain and loss.

Day 4 - Muir Beach to Mount Tamalpais

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. Ascend through fern and redwood canyons to your destination: a romantic inn with beautiful views from every room! Relax on the expansive deck with other hikers comparing hiking and nature notes. You will enjoy a delicious three-course California cuisine dinner right at your mountaintop inn.

Hiking today: 9 miles (14 kilometers) with 2100 feet (640 meters) elevation gain and 1100 feet (335 meters) of elevation loss.

Day 5 - Mount Tamalpais to Olema/Point Reyes

A transport will leave you at Limantour Beach, in Point Reyes National Seashore. Hike along the beach, and 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 a real treat - fresh organic and artisan foods from famous West Marin dairies and farms prepared in an award winning local restaurant.

Hiking today: 9 miles (14 kilometers) with 1300 feet (400 meters) elevation gain and 1100 feet (335 meters) 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 is privately catered, including local wines, at your lodging.

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

Day 7 - Tomales Bay kayak trip

Today you will enjoy a guided morning kayak trip on Tomales Bay. A naturalist guide will explain the scenic beauty of the area while you paddle and spot local wild life. Dinner tonight is at a local restaurant.

Hiking today: 1 mile (1.6 kilometers) 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 can visit the authors home and grave, as well as a museum established by his wife. You will hike up into the park enjoying the redwoods, creeks, wildlife, and vistas of Sonoma's Valley of the Moon vineyards. Finish your day with a special tour and tasting at a family owned vineyard estate and winery. Tonight's lodging has a world class reputation as one of the best luxury inns in the U.S. You will relax by the pool, enjoy the Zen spa and walk to one of several wine country restaurants with fabulous food and a wine list to match.

Hiking today: 6 miles (10 kilometers) with 900 feet (270 meters) 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. A short transport will bring you to the first winery estate you will visit today. As the day progresses, you will enjoy delicious reserve wine tastings walking between wineries. At your final tasting, the winemaker/owner will greet and escort you into his estate where you will 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: 4 miles (7 kilometers) walking between winery estates with 300 feet (90 meters) elevation gain and loss.

Day 10 - Trek conclusion

Your wine country trek comes to an end.

  • A guided morning kayak trip on Tomales Bay
  • Ascend Mount Vision with its stunning views of Tomales Bay and descend into the coastal village of Inverness on Tomales Bay
  • Ascend through fern and redwood canyons
  • Descend into Muir Woods National Monument enjoying the ancient and magical redwood forest
  • Hike across the beautiful coastal hills in the Golden Gate National Recreation Area to the village of Muir Beach
  • Hike along the beach of Point Reyes National Seashore into the National Park and continue to the small historic town of Olema
  • Hike onto Mount Tamalpais taking in the dramatic views of the Pacific Ocean
  • Hike up into the Jack London State Historic Park enjoying the redwoods, creeks, wildlife, and vistas of Sonomas Valley of the Moon vineyards
  • Take a short walk to the gorgeous Point Reyes National Seashore Park
  • Take a special tour and tasting at a family owned vineyard estate and winery in the Sonoma Valley
  • Take a transport to the famous Jack London State Historic Park
  • Walk along the San Francisco waterfront, across the majestic Golden Gate Bridge and into the historic village of Sausalito

Your wine and hiking tour takes you to many different places across the San Francisco Bay Area.

Jack London State Historic Park

The park contains the cottage residence where Jack London wrote books, short stories, articles and letters while he oversaw various agricultural enterprises. After Londons death, his wife, Charmian, continued to live in the cottage until her death in 1955. It was her wish that the ranch be preserved in memory of Jack London and his work. There is a museum in The House of Happy Walls, which Mrs. London built in a redwood grove. Todays traveler can explore the historical sites and hike miles into the 1,400-acre gorgeous park.

Muir Woods and Mount Tamalpais

Mount Tamalpais State Park, which surrounds Muir Woods, is a beautiful park with sweeping hillsides cloaked with chaparral covered ridges, grassland, and oak woodlands. Deep canyons filled with solemn redwood groves intersect these ridges and slopes to create a diverse environment for a wide array of plant and animal species. This area was inhabited by the Coast Miwok Indians prior to the arrival of the Europeans in the 1700s.

Point Reyes National Seashore and Tomales Bay

The cultural history of Point Reyes reaches back some 5,000 years to the Coast Miwok Indians who were the first human inhabitants of the Peninsula. Over 120 known village sites exist within the park. According to many experts, Sir Francis Drake landed here in 1579, the first European explorer to do so.

In response to the many shipwrecks in the treacherous coastal waters, key lighthouse and lifesaving stations were established by the United States government in the late 1800s and early 1900s. In the early 1800s, Mexican land grantees established ranchos. They were followed by a wave of American agricultural operations, which continue to this day in the seashores pastoral zone.

Today the landscape is still very rural and agricultural. The cows dotting the hillsides produce milk that makes some of the best artisan cheeses in the United States. Renowned for its organic farming, West Marin, where Point Reyes is located, has been a model for the world - in 2006 Prince Charles of England made a stop to study the farming. Tomales Bay itself is the best oyster producer in California with restaurants vying for the sweet shellfish.

Point Reyes National Seashore hosts many trails for hiking, biking, and horseback riding with sweeping views of both Tomales Bay and the magnificent Pacific Ocean. The coves and beaches are full of vibrant tidal life and seals can be viewed from the cliffs. The towns of Olema, Inverness, Point Reyes, and Marshall maintain a rustic Western charm, it is easy to visualize the wild west of the Gold Rush of 1849 when you see the wooden buildings.

San Francisco

San Francisco has a relatively young history, just like the state of California. It was inhabited by the Ohlone Indians prior to European discovery of California in the 1500s, and the Golden Gate (San Francisco Bay) in 1769. The Spaniards were the first European occupants, and called the city Yerba Buena.

It was the discovery of gold in California in 1848 that brought rapid growth to the city. In 1906, most of the buildings in the city were lost to an earthquake with a magnitude of 8.5 on the Richter scale, and a subsequent fire. In 1937, the Golden Gate Bridge was opened, at the time the longest suspension bridge in the world with a span length of 4,200 feet, 1,280 meters.

San Francisco has always been very ethnically and culturally diverse, which is the source of much of its charm. There are world-class restaurants serving food of every nationality in neighborhoods with rich cultural heritages, such as Chinatown and North Beach, also called Little Italy.

Because the western United States is large and was settled relatively recently, San Francisco adjoins many unique and beautiful natural lands that have not been developed. It sits between the majestic Pacific Ocean to the west, beautiful San Francisco Bay to the east, with the Sierra Nevada mountains and Lake Tahoe only three hours further east, the Napa and Sonoma Wine Country to the north, and Silicon Valley and the coastal communities of Monterey and Carmel to the south.


Named by a Spanish explorer for the little willows (saucelitos) growing along its shores, Sausalito was settled in the early 1800s by sailors, whalers, and shipbuilders. Today, you can stroll along the water and watch the sea lions cavort, rest in the plaza and listen to the splashing fountain, soak up the ambiance in the many open-air cafes, browse through the unique boutiques, and check out the marinas. There are many well-groomed hiking and biking trails, as well as easy access to Muir Woods and Mt Tamalpais.Sausalito hosts a thriving artist community, so its not surprising that the town sports several world-class art galleries and is the home of the number 1 outdoor fine-art fair in the nation.


Native American tribes inhabited Sonoma Valley long before the Spanish influence began. The tribes included the Miwok, Pomos, and Wintuns who found the fertile valley a perfect place to live with fish in the creeks, wildlife in the hills and rushes for intricate basket weaving.

The Mission San Francisco Solano de Sonoma was founded on July 4, 1823 under the direction of Padre Altimira. It is the last and most northern of the famous 21 Franciscan missions along the California coast. In 1836, General Mariano Vallejo laid out a grid for an 8-acre Plaza adjacent to the Mission turning the area from a mission town to a Mexican style pueblo. Today the Plaza is lined with charming shops, popular restaurants, cheese vendors, and wine bars - all surrounding the wonderful old adobe buildings Vallejo built.

Your Wine Country Trekking tour includes all breakfasts and lunches for the entire trip. Dinner is only included on day 5 of your journey. Wine Country Trekking knows that their trekkers are passionate about food and want the ability to select their own menu items and restaurants where dining options are available. Wine Country Trekking provides descriptions and reviews of local restaurants and makes reservations for you.

  • Dine at a world-class restaurant
  • Enjoy a Zen spa treatment
  • Enjoy the artists studios, cafes and restaurants in Sausalito
  • Relax by the pool
  • Walk to several wine country restaurants
  • 1 dinner
  • 6 days hiking activities of 4 to 12 miles (7 to 19 kilometers) with elevation gain up to 2300 feet (700 meters)
  • 9 nights accommodation
  • All taxes, fees and tips
  • Any necessary transfers during the trek
  • Assistance with restaurant and spa reservations
  • Breakfasts and lunches
  • Custom maps and trail notes
  • Kayak trip
  • Local area information package
  • Luggage transfers
  • Planning guide
  • Privately catered beach dinner
  • Wine tastings
  • 8 dinners
  • Airfare
  • Health insurance
  • Pre- and post-trek airport transfers
  • Travel expenses
  • Travel insurance

Arrival by airplane

Airport shuttles are available for most of Wine Country Trekking treks. The planning guide will have more information on airport transfer options, which are not included in the trek price.


  • Review by Share Duggan

    "We had an amazing time on our trip, organized by Wine Country Trekking. We opted for the Runners' Trek, and ran through picturesque state and regional parks in the mornings, visited beautiful wineries in the afternoons, and stayed at luxurious inns overnight. Thank you, thank you, thank you!"

    Wine Country Trekking Facebook, edited

  • Review by a traveler from United States

    "Net, net, best hike ever, and both Cam and I have taken many, many organized hikes. Yours was fabulous. Loved the restaurants Sir & Star, Glen Ellen Star and Pogglia. They were just outstanding, and to miss them would have been a crime. Loved the two drivers, Kevin and Bridget. Both delightful. I would love to do the hike a second time, and I hope to be able to talk someone into it. Thanks again."

    Wine Country Trekking website, edited

  • Review by three couples from UK, Virginia, USA and New Mexico, USA

    "We would like to say a big thank you for organizing our trek. We had a fantastic time and the holiday exceeded our expectations. We had so many different and wonderful experiences that it's difficult to say what we enjoyed the most. Highlights included seeing a coyote standing a few feet away from us, the mist hanging in the trees in Muir Woods, making it even more magical, seeing dolphins playing in the sea at Limantour Beach, the friendliness of people we met and the variety of places we stayed.The walk over Golden Gate Bridge was a 'must do' experience. Sausalito was charming. Lying in bed at night in Muir Beach and Olema, listening to the coyotes howling was eerie but exciting! Another first for us both was kayaking on Tomales Bay. I was a bit apprehensive, but the guide put us at ease and was competent and friendly. She even took photos with her phone and emailed them to us. There was a mix up over the start time, which meant we had to wait longer than we should have, but the guide offered to stay out over our allotted time (which we did). We saw seals bobbing up in the water a few feet away and pelicans taking off and landing in the water.As for the hotels, I think our favorite for location was Inverness. We woke early both mornings and watched the sunrise over the bay - so beautiful. What a treat too to have dinner cooked for us. The caterer was efficient and friendly; putting us at ease in what for us could have felt a slightly uncomfortable experience. The food was delicious and there was so much of it we had to save some for the next day. Our favorite hotel was in Glen Ellen. The Zen Suite was awesome. I was sorry that we didn't really have enough time to enjoy all the facilities there. Whilst we enjoyed the wine tasting, I think we would have preferred to maybe have just one wine tasting visit or even none at all on our last full day, as for us the hiking and scenery were more important than the wine tasting."

    Wine Country Trekking website, edited

  • Review by a couple from United States

    "Incredible! Beautiful surroundings, off-the-beaten-path hikes (maybe it was the holiday week effect?), great food, amazing wine, helpful, friendly people, we really had a wonderful, wonderful time. We loved the hikes, whether we were going through neighborhoods, on remote-feeling trails, atop mountains, or on the forest floor. We were awed by the beauty and tranquility at every turn. The guide was great - the instructions alongside the maps kept us on course. Only one or two spots were we not entirely sure of but we made the right choice so, no problems. There was one day that the hike was described as challenging. I would suggest adding this warning to the Sausalito to Muir Beach day, too. Maybe include a warning to flatlanders that a gain and loss of 2300 feet is nothing to sneeze at.We enjoyed meeting the Trek folks along the way, Maryellen, Brigid, and our transport to Point Reyes Seashore Lodge (his name escapes me). The meal and wine and cheese that Maryellen provided were outta sight! Brigid was a lot of fun to chat with and it was fun to learn about the area from everyone we talked with. It was also great meeting Mary (and her husband, who had to give us a ride to the hotel after we drank wine with the winemaker past dark!) He was a lot of fun and very interesting and we are looking forward to a wine shipment from him! We really enjoyed meeting him and hearing his take on wine. Oh, and our guide on the kayaking trip was also great!Marin County seems like such a special place. It was inspiring to hear how its cared for and preserved by the folks there. It was just beautiful. The little sliver of moon over the bay in the early morning (we were still on Dallas time, evidently!), that image will stay with me always. I hope well be able to trek with you again sometime; it was truly magical! Many thanks to you and all who contributed to our experience!"

    Wine Country Trekking website, edited

  • Review by a couple from United States

    "We had a great time and very much enjoyed all accommodations and services along the trek. We will be telling our family and friends about Wine Country Trekking."

    Wine Country Trekking website, edited