Seven Day Urban Wine trek San Francisco Bay


Experience the vibrant history of San Francisco, the famous “City by the Bay”, on this seven day urban trek. This vacation allows you to expolore San Francisco, the Golden Gate Bridge, Sausalito, the quaint village of Tiburon, and two famous islands in San Francisco Bay: Angel Island, the “Ellis Island” of the West Coast, and Alcatraz Island, site of the infamous prison known as “The Rock”. This trek is perfect for getting to know San Francisco if you are visiting for the first time, or experiencing its history and famous sights on foot if you are a repeat visitor.

Trek Summary

  • 7 days/6 nights
  • Hiking 4 to 9 miles (6 to 14 km) daily
  • Elevation gain up to 800 feet (250 m)
  • 5 days walking
  • Stay in premier hotels
  • All breakfasts and lunches included
  • Luggage transfers included
  • All taxes, fees, and tips included
  • Detailed maps and trail notes included
  • Ferry and island fees included
  • $1950 per person double occupancy, April-November
  • $1750 per person double occupancy, December-March
  • $3500 single occupancy, April-November
  • $3100 single occupancy, December-March
  • You can start your trek on any Friday, Saturday, Sunday, or Monday

Your Itinerary

Day 1: San Francisco

Start your vacation in the heart of San Francisco, where you will stay on Union Square, a chic shopping and dining mecca, in an historic luxury San Francisco hotel. Enjoy a stroll around Union Square, shopping, riding a cable car, or wine tasting. Tonight you can dine at any one of several nearby Michelin starred world class restaurants.

Hiking today: No planned hikes. Your personal Trail Guide will suggest sights to see.

Day 2: San Francisco, Union Square to Fisherman’s Wharf

Stroll along the streets of San Francisco, the birthplace of the California Gold Rush, following the “Barbary Coast” tour through Downtown, Chinatown, the Italian North Beach neighborhood, and Fisherman’s Wharf. Along the way enjoy lunch in Chinatown or at one of the many classic sidewalk cafes in North Beach. Your lodging is a luxury boutique hotel near Ghirardelli Square and one of the highest rated restaurants in Northern California is just two blocks away.

Hiking today: 4 miles (6 km) with 300 feet (100 m) elevation gain and loss.

Day 3: 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 luxury boutique hotel and spa is on the waterfront in Sausalito, where you can enjoy the artists’ studios, cafes, and restaurants of this charming town. Dinner this evening can be at another Michelin recognized restaurant.

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

Day 4: Sausalito to Tiburon

Follow the San Francisco Bay Trail as you walk around the bay and through its wetlands, home to a wide variety of shorebirds and water fowl. This relatively flat walk hugs the water and takes you through some of the bayside communities of Marin County with views of Angel and Belvedere islands. You end at a waterfront hotel in the quaint village of Tiburon where you will enjoy stunning views back to San Francisco from your room. There are many dining options ranging from elegant to casual with fresh California cuisine.

Hiking today: 9 miles (14 km) with 200 feet (60 m) of elevation gain and loss. Note: This day also has options of hiking either 6 or 11 miles, rather than 9.

Day 5: Angel Island and San Francisco Embarcadero

Catch a ferry right outside your door to Angel Island, where you can explore the treasures of Angel Island State Park. Visit historic sites, including the immigration station, the “Ellis Island” of the west coast. Enjoy breathtaking views of San Francisco, the Golden Gate Bridge, and Mount Tamalpais. Ferry back to Tiburon, and then on to San Francisco, where you will stay in a luxury boutique hotel on the waterfront in the Embarcadero area. This is another dining mecca, with multiple world class restaurants within walking distance of your hotel.

Hiking today: Varies from 2 to 5 miles (3 to 8 km) with 200 to 800 feet (60 to 250 m) of elevation gain and loss, depending on the route you choose on Angel Island.

Day 6: San Francisco and Alcatraz Island

Today is another day on San Francisco Bay. In the morning, visit the Ferry Building right next to your hotel, peruse its year round farmer’s market and small shops, and enjoy lunch. Then walk along the Embarcadero to the Alcatraz Island ferry. Enjoy the ferry ride to the island, seeing where your trek has taken you the last few days. Alcatraz is historic and scenic, and you can spend as much time as you want exploring. Enjoy the excellent self guided audio tour of “The Rock” narrated by actual prisoners and guards from the old prison. After taking the ferry back, return to your hotel and enjoy your final night in San Francisco.

Hiking today: About 3 miles (5 km) total. (1 mile to and from the Alcatraz ferry and 1 mile or so on Alcatraz.) No significant elevation gain or loss.

Day 7: Trek Conclusion

Your Wine Country Trek comes to an end. Let us help you arrange airport transfer or plans to continue your holiday.

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