Napa Valley & San Fran Weekend: Wine, Food & Rolling Hills




Itinerary
Ever wondered what it feels like to spend a day in one of the most iconic wine regions in the world? This trip is all about Napa Valley, where rolling vineyards, legendary wineries, and perfectly crafted tastings set the scene.
Everything revolves around wine country, but it’s colored by the energy of San Francisco, the gateway that gives this experience its unique balance. One moment we’re in the city, surrounded by iconic views and a buzzing food scene, the next we’re among the vineyards, where time slows down and every glass tells a story.
In Napa Valley we connect, not just with wine, but with the place itself: the landscapes, the atmosphere, and the shared moments that turn a simple tasting into something more. It’s about enjoying the rhythm of the day, moving from one winery to another, and letting the experience unfold naturally.
Back in San Francisco, the journey continues between waterfront views, hidden corners, and experiences that add a different flavor to the trip.
A short escape with a clear soul: Napa Valley at its core, with San Francisco giving it character.


Welcome to San Francisco
1 night: San Francisco
First vibes, first connections
We arrive in San Francisco, the starting point of our journey and the gateway to California’s wine country. After check-in, we head out for a first exploration of the city, walking through its streets, taking in the views, and getting a feel for the unique atmosphere that makes San Francisco so iconic.
In the evening, we kick things off properly with a welcome drink paired with food tastings, the perfect moment to break the ice and connect with the group. This is where the trip really begins: new faces, shared stories, and the first toast to the days ahead.
San Francisco sets the tone, Napa Valley is calling.

Into California’s wine country: Napa Valley
1 night: San Francisco
A day among vineyards and flavors
Today we leave the city behind and head into Napa Valley, the heart of this journey and one of the most iconic wine regions in the world. As the landscape changes, vineyards start to take over, setting the scene for a day dedicated to wine, flavors, and shared moments.
We spend the day immersed in the atmosphere of wine country, moving between selected wineries, tasting different labels, and enjoying the slower rhythm that defines Napa Valley. It’s not just about the wine, but about the experience itself: the views, the stories behind each glass, and the feeling of being exactly where we’re meant to be.
This is the moment where the group truly connects, surrounded by vineyards and a setting that makes everything feel effortless.
We return to San Francisco in the afternoon, with a different pace and a few more stories to share.

One last taste of the city
Free time and optional experiences
We wake up in San Francisco with one last day to enjoy the city at our own pace. After a day in Napa Valley, today is about getting back into the rhythm of the city, exploring, wandering, and taking in the atmosphere one last time.
Some of us might visit iconic spots, while others may go for something different, like a wine cruise on the bay, a visit to Alcatraz Island, or simply discovering hidden corners around the city. The plan is simple: follow the mood of the group and make the most of these final hours together.
It’s the perfect moment to slow down, share a last drink, and wrap up the experience with new connections and great memories.
What's included
- 2 nights in accommodation in San Francisco in shared rooms
- Winery wine tasting experience in Napa Valley
- Welcome drink with food tastings in San Francisco
- Round-trip transportation between San Francisco and Napa Valley at Day 2
Group Leader services
Medical and baggage insurance - (coverage limits by destination country/region - €10,000 Italy, €20,000 Europe, €30,000 World, €50,000 USA/Canada)
What's not included
- Food and beverages when not specified
- All the extras you'll be able to fit in your backpack
- Anything not mentioned in the "What's included" section
Optional activities
Please see below extra optional activities that you can experience during your trip. Your Group Leader will be happy to assist with organizing these activities for the group. Availability may vary depending on location and group preferences. Please note these activities are provided by third party suppliers and liability rests exclusively with these third party suppliers.
Cocktail class in a local distillery - approx. USD90
Wine tasting cruise on the bay - approx. USD120
Alcatraz experience including ferry and entrance to Alcatraz Island - approx. USD130
Additional info
Activities may be operated on a private or shared basis, depending on the group size. Activities on Day 3 are subject to supplier availability.
The accommodations will be in the San Francisco area, in hotels with shared rooms. Some accommodations may require local taxes to be paid directly on site
- Info on private roomsShow all details
Why WeRoad
Small groups, on average 11 people
Move or change your trip for free up to 31 days before departure
Book with $ 0. Pay the $ 100 deposit only once the trip is confirmed
The Group Leaders
Find your flight
For this trip, we recommend arriving and departing from these airports.
This is a WeRoadX
A trip designed and created entirely by an experienced WeRoad Travel Group Leader.
This is a trip designed and created entirely by an experienced WeRoad Travel Group Leader. They organise the whole trip: from defining the itinerary to selecting accommodation and on-site experiences. On the WeRoad website you can book the trip and manage it in MyWeRoad, just like any other WeRoad.








