Walking San Francisco to Wine Country

7 Days & 6 Nights 4.5 Read 2 reviews
  • Sample a variety of wine from the world-renowned Sonoma Valley
  • Visit vibrant San Francisco and immerse yourself in the history of the Barbary Coast
  • Walk through Crissy Field and across the Golden Gate Bridge, an American icon
  • Enjoy comfortable stays in hand-picked accommodations
  • Stroll through the colonial-era plaza of Sonoma, home to California’s oldest winery
Make your way from vibrant San Francisco to the beautiful wine country of Sonoma Valley while tasting a variety of reds, whites, and rosés along the way. Walk through scenic Crissy Field and over the iconic Golden Gate Bridge, and spend some time along the picturesque Pacific Coast. Follow trails through peaceful rolling hills and amongst towering coastal forests, including the famous Dipsea Trail. In the evenings, explore the charming downtown areas and relax in your luxurious accommodations.
This tour is graded as moderate, with daily hikes averaging around 8 miles a day. This tour is perfect for those who want to explore the expanse of the Marin Headlands and Sonoma by foot and with free time to enjoy wine tastings and to explore the cute towns. Hikers should expect walking along dirt trails and varied terrain. Trails are well-signed, maintained, and traveled frequently. Enjoy staying at charming hotels each night.

Tour Type:

Slower Adventures | Slower Adventures


Inn to Inn Walking | Walk from place-to-place changing accommodations each night. Generally staying in B&B’s, inns, and guesthouses.

This trip is suitable for:

Solo Travellers

As a guide, we would suggest that the minimum age of traveler this tour would be suitable for is: 5 Years

Ideal if you have an interest in:

  • Wine

Activity Level & Terrain

The hiking on this trip is moderate, averaging 8-9 miles per day. Your third day of hiking will be the most challenging with about 2,300 ft / 610 m of elevation gained. Once you reach Sonoma the final two walks are shorter, only 5-7 miles, so you have time to enjoy wine tastings in the evening if you wish. 


A detailed guidebook with turn-by-turn instructions will be mailed one month before departure. You will also have 24/7 telephone support from us here at Macs Adventure.

Experience & Fitness

The trails used on this trip are well-established, thoroughly waymarked, and highly traveled. However, conditions vary including mud, rocks, and tree roots. You should be accustomed to hiking for several hours at a time and will enjoy your tour much more if you are well-prepared. Some hiking experience is necessary.


One of the highlights of this tour is the high standard of accommodation. You will stay in carefully selected 3-4* small hotels. Your room will always have an ensuite or private bathroom. A delicious breakfast is also included. 

Twin Rooms

If you would like a room with two separate beds, please let us know, and we will accommodate you wherever possible.  However, many of the hotels and inns we use do not have that option. Almost all have king beds; a few offer only queen beds.  In most cases, if the accommodations do not have rooms with two beds, they can bring in a roll-away bed or a futon for the second person, although this may incur a price supplement. If you choose you can book two separate rooms at these accommodations, but you will need to be prepared to pay more for an extra room. 

Single Rooms

If you require single rooms within your party we will always try and accommodate you subject to availability. A single supplement is payable.


A hearty breakfast is included each morning except in Sonoma. Lunch and dinners are not included so you are free to choose from the surrounding options. Dinner is available either at your accommodation or at nearby restaurants.

  • 6 Nights at hand-selected lodges and hotels
  • 4 Breakfasts (Every morning except in Sonoma)
  • Luggage Transfers
  • Transfer from Mill Valley to Sonoma
  • Detailed pre-departure information pack
  • Detailed Route Notes and Maps
  • 24/7 telephone support
  • Lunches, dinners, drinks, and snacks
  • Travel to San Francisco and from Sonoma
  • Travel insurance
  • Personal equipment
  • 2 Breakfasts in Sonoma
  • Room Upgrades (only where applicable)
  • Additional nights along the route

When To Go

"The coldest winter I ever spent was a summer in San Francisco" 

- Mark Twain

We offer this trip year-round and there are plenty of reasons to go to the Bay Area and wine country in each season based on your goals. Throughout the year the average high temperatures are in the upper 60s Fahrenheit, with lows in the 40s and 50s. As you leave the bay and head towards the Wine region, the weather tends to get warmer. 

In the winter months of Nov - March the average temperature drops a little, with the average high in the upper 50's during the day. These are also the rainest months so always check the weather forecast before starting your hike and carry appropriate equipment! The spring months of April - June are lush, green, and the daily average increases a little to the mid to upper 60's. The summer months of June - Sept are the warmest days, with an average high of the low 70s around San Francisco, but once you reach the Wine region the average highs can reach the mid-80s. September and October see a decrease in summer tourists and the temperatures at this time of year are between the 40s and 60s Fahrenheit, with October tending to be a bit drier and crisper than September.


This trip is available any time of year but can only depart on a Saturday. We suggest booking as far in advance as possible for a better chance of securing your desired dates. 

Weather and Climate

Getting to the Start

Depending on where you are traveling from, there are several options to get to San Francisco. 

The nearest airports are San Francisco International or Oakland International. From either airport, you can catch the BART train to your accommodation in the city. 

Getting from the End

There are several options to get back to the Bay Area after you finish your trip. 

There are several bus services from Sonoma to San Francisco and the surrounding areas with Sonoma County Transit (4 hours) and there is also the new SMART train (3 Hours) that can take you from nearby Santa Rosa to San Francisco. We can also arrange a private transfer to San Francisco after your tour ends. Please enquire with your destination and sales specialist if you are interested in this option. 

Luggage Transfer

Baggage transfer from San Francisco to Sonoma is included in the cost of your holiday. We ask you to limit your luggage to one bag of up to 22 kg / 50lbs per person.


Our pre-departure information pack includes a detailed equipment list on what to take with you. This includes warm and cold weather gear, hiking boots, rain gear, and lots of other specifics. If you have any questions about what to take, we'd be happy to share our own top tips and advice.

Travel Insurance

It is a requirement of booking this tour with Macs Adventure that you have suitable travel insurance that covers you for the activity and emergency evacuation and hospital care.

What personal equipment do I need?
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Day 1 Arrive in San Francisco Day 2 Walk to Sausalito 9 miles / 14 km Day 3: Walk to Muir Beach 9 miles / 14 km Day 4: Walk to Mill Valley 10 miles / 16 km Day 5: Loop Walk in Sonoma 5 miles / 8 km Day 6: Bartholemew Park Loop Walk 7 miles / 11 km Day 7: Onward Travel

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