5
Moderate
Activities
  • 3 days self-guided hiking
Accommodation
  • 4 nights boutique hotels

Price

5 daysfrom

$USD

Overview

Trip code: NSSG

Trip highlights


  • Hike to Sonoma ridgelines with sweeping valley views
  • Explore historic Sonoma Plaza and enjoy a reserve wine tasting
  • Wander through vineyards and quiet redwood groves
  • Tour a sparkling wine cave and taste world-class bubbly in Napa
  • Stay in charming boutique hotels, with seamless luggage transfers

Experience the best of California Wine Country on this five-day self-guided trek, combining rolling vineyards, historic towns, and scenic forest trails. Hike through peaceful redwoods and oak groves, climb to sweeping valley overlooks, and follow trails that wind past charming wineries and historic landmarks. Stay in boutique hotels in Sonoma and Napa, each offering easy access to local dining, shops, and the unique character of these towns. From sun-dappled forest paths to lively tasting rooms, this adventure blends outdoor exploration, rich history, and world-class wine into an unforgettable experience.


Itinerary

Arrive in San Francisco and settle into a comfortable, perfectly situated accommodation near Ghirardelli Square and Fisherman’s Wharf. Your stay offers a relaxed coastal feel and easy access to nearby dining and neighborhood highlights. Depending on your arrival time, your app includes everything you need for a self-guided walk along the Barbary Coast Trail, a 3.8-mile route marked by bronze medallions that trace San Francisco’s Gold Rush past. Along the way, you’ll discover historic landmarks, hidden alleys, and scenic viewpoints that bring the city’s colorful history to life, with the option to hop on San Francisco’s iconic cable car at points along the route to shorten or extend your walk as desired. __________________________________________________________________________________________________________________________ • Overnight - 4-star accommodation near Ghirardelli Square and Fisherman’s Wharf • Hiking: 3.8 mi / 6.1 km, Elevation gain/loss: minimal

Meals:  Nil

Start your morning with a nourishing breakfast at the hotel and then shuttle to Sonoma Plaza. Drop your luggage at your charming historic lodging, then pick up a picnic lunch from a local gourmet favorite. Set out on a hike through rolling hills to a sweeping overlook, winding back through quiet, storied paths that hint at the area’s rich history. Finish your hike with a thoughtfully arranged wine tasting on the plaza, and enjoy the many nearby shops and cafes at your leisure. __________________________________________________________________________________________________________________________ • Overnight: 4-star accommodation in Sonoma • Hiking: 5 mi / 8 km, Elevation gain/loss: 500 ft / 150 m • Vehicle Transfer: 1 hour

Meals:  B

Today you will walk through the stately east side of Sonoma. Wander among redwoods, oaks, and vineyards as you climb to ridge tops revealing sweeping views of the valley below. Your trail climbs steadily toward a ridgeline, opening to wide, sunlit views across the valley. The descent carries you through vineyard-lined paths to a tasting at California’s oldest winery, beautifully restored and steeped in history. Your day concludes back on the Sonoma Plaza, steps from your lodging, with time to unwind before settling in for a well-earned wine country dinner. __________________________________________________________________________________________________________________________ • Overnight: 4-star accommodation in Sonoma • Hiking: 7 mi / 11 km, Elevation gain/loss: 500 ft / 150 m

Meals:  B

After a scenic morning shuttle, arrive at the Bale Grist Mill and Bothe-Napa Valley State Park. Your hike meanders through quiet redwood and oak forest before reaching a world-famous winery, where sparkling wines are crafted using the Méthode Champenoise. This technique gives Champagne and other high-quality sparkling wines their fine, persistent bubbles and layered flavors, from crisp green apple to creamy brioche notes. After a guided cave tour and tasting, you’ll be transferred to a Calistoga resort known for its natural hot springs. Consider booking a spa treatment, such as the town’s signature mud bath, and reserve ahead to secure your preferred time. You can also explore the charming downtown before enjoying dinner at one of the area’s excellent restaurants. __________________________________________________________________________________________________________________________ • Overnight: 4-star accommodation in Calistoga • Hiking: 5 mi / 8 km, Elevation gain: 1,100 ft / 225 m, loss: 600 ft / 185 m • Vehicle Transfer: 1 hour

Meals:  B

After a leisurely morning and perhaps a visit to one of the many great local coffee shops, head out to your next adventure. __________________________________________________________________________________________________________________________

Meals:  B


Inclusions

  • 4 nights in boutique hotels
  • 3 breakfasts
  • 3 wine tastings
  • Navigation app with maps, trip information and recommendations
  • Luggage transfers (1 piece per person, not exceeding 45lbs./20kg)
  • Transfers as indicated in the itinerary
  • Emergency hotline

  • Travel to and from San Francisco
  • Travel to first hotel and from last hotel
  • Guide (this is a self-guided tour)
  • Drinks, snacks, lunches, and dinners 
  • Unscheduled transfers
  • Insurance of any kind

Suitability

Moderate

5

Moderate. Self-guided hiking requires individuals to use problem solving skills, be adaptable and have a keen eye. It is recommended that you are comfortable map reading, referring to route notes and that you have a good sense of direction (or are willing to work on improving this!). This hike is best suited for travelers with a moderate level of fitness who enjoy walking for several hours a day. Daily hikes range from 4 to 7 miles (6.5–11 km) on varied terrain, including vineyard paths, forest trails, and quiet town streets. Daily elevation gain and loss ranges from 500 to 1,100 feet (150–335 m), offering a satisfying challenge without technical difficulty. Most days are at a steady pace, with plenty of chances to pause, enjoy the scenery, and explore the local towns.


Departure dates

Available for Saturday, Sunday and Monday starts from March through mid-November

Want to organise a customised tour?

School groups, friends, family trips, corporate events or just tailoring a trip to suit your own needs - learn how you can tailor your own Customised Tour.

Priceper person from

$USD

* All prices subject to applicable taxes

Options & Supplements*
  • Napa and Sonoma SG - Single SupplementUSD$2100
* Prices listed are per person. All prices subject to applicable taxes.

Trip reviews


Why travel with us

Our Expertise

Everyone who works with us, from our office staff, ground staff and guides is the ‘’real deal’’. Our team is comprised of actual hikers and cyclists who have explored or live in the region in which you will be traveling. Our entire network is highly-specialised in active travel.

Great Value

Quality services at the best price make our active trips great value for money. Having essential items included like National Park fees, accommodations, most meals, bikes for cycling trips, maps and support for peace of mind. Our inclusions allow you to better budget for your big adventure.

Innovative Itineraries

We look beyond the horizon to find new and exciting adventures. We’re passionate about shaping the next generation of outdoor travel in North America, and constantly seek different ways, routes and alternatives to exceed our clients’ dreams.

Eco Friendly

We are committed to responsible travel and true sustainability, formed when the company was established, and in the face of a multitude of threats to the environment, our commitment is stronger than ever. We aim to "leave no trace" in both an environmental and cultural sense.