Celebrating an anniversary on a long weekend in Napa Valley felt like the perfect blend of romance and indulgence — where each glass of wine told a story and every vineyard offered a new memory. We decided on Napa because the last (and only) time we were there together, I was pregnant with Chloe and couldn’t really enjoy the wine. We decided on President’s Day Weekend in February because it’s the closest to our anniversary, we had childcare available, and it tied into a bank holiday. February in Napa can have chilly temps, and the vines are naked, but the wine drinking was just as good. Summertime is when the vines are growing and in the fall is when harvest happens, so you can plan your trip around those!

I used this website to book most of our tastings. There were a few that I booked directly, and a couple that we walked into.

We flew into San Francisco and picked up a rental car. After stopping for lunch at Hillstone (our favorite), we headed into the heart of wine country. The drive to Napa (a little over an hour long) set the tone — winding roads, rolling hills, and that first breath of vineyard air that makes you instantly relax.

We stayed at the Andaz Napa, a very cute boutique hotel in the heart of Downtown Napa. Our room, a great size with a separate seating area and fireplace, was ready when we arrived. The hotel’s receptionist and concierge were really helpful and gave us some great suggestions. There is a parking garage behind the hotel where we were able to park the car free of charge. Every afternoon, there was a wine tasting with a representative from a different vineyard, and each evening there was live music in the lobby. The hotel does have a restaurant, but we didn’t check it out.

Our first evening, we went to a tasting at Alpha Omega Collective, which was a short walk from our hotel.  From there we finished the evening with dinner at Bottega, a perfect finale — rustic Italian dishes paired with local wines. The pasta dishes were so fresh and light – I would definitely recommend trying at least one of their pastas. We also really enjoyed the shaved Brussels sprouts appetizer.

A Day of Icons and Hidden Gems

Valentine’s Day started with breakfast at Winston’s Café before diving into a full day of wine. The bagels here were the best we have ever had. We enjoyed Winston’s so much that we ended up here for breakfast every day of our trip!

Caymus greeted us with its signature warmth and iconic Cabernet Sauvignon. Far Niente followed, where manicured gardens and elegant wines created a serene atmosphere.

Lunch at Gott’s Roadside was a fun, casual interlude — juicy burgers and crispy fries savored under the California sun. Don’t sleep on the milkshakes!

The afternoon took us to Hall Wines, where art and wine danced together. This was followed by a tour and tasting at Castello Di Amorosa — a medieval-inspired castle that felt like stepping into another world. Of all the places we visited, the wine here was my least favorite. The tour is cool, and this place is fashioned like a medieval castle, but if you don’t like Italian-style wine, this will probably not be your kind of winery. This was also the busiest of all the places we went to.

Before dinner, we visited RH Wine Vault, tucked away and intimate, the perfect prelude to our evening at Mustard’s. With its hearty dishes and lively ambiance, it was a dinner to remember. I would highly recommend the pork chop, which is their most famous dish.

Off the Beaten Path

Saturday led us to hidden treasures. Seavey Vineyards, a working farm, welcomed us with open arms — the kind of place where time slows, and each sip feels deeply rooted in the land. Of all the wineries we visited during our weekend in Napa Valley, this was my favorite. It felt off the beaten path and just really special.

Porter Family Vineyards followed, its stunning wine caves offering a cozy, romantic setting as we explored their beautiful varietals. I loved that they didn’t have a traditional tasting room. We really enjoyed spending some time in the caves.

One mistake we made was not having lunch on this day – I would not recommend doing this. We were given the recommendation to stop at Oakville Grocery, so I would try that!

Dinner at Oenotri closed the day with comforting Italian fare — wood-fired pizza and tender meatballs, making for a relaxed, laughter-filled evening.

A Perfect Farewell for Our Weekend in Napa Valley

We started our Sunday off with Mass and then took a little drive. We didn’t have any wineries booked for the morning so we decided to just stop in at places we came across and wanted to see. Though Chimney Rock and Stag’s Leap were fully booked, we still enjoyed a splash of wine and time to wander their beautiful grounds.

Lunch at R+D Kitchen brought fresh flavors and easy conversation before one last tasting at Artesa. Perched on a hill with panoramic views, it was the perfect place to toast to love and an unforgettable weekend. We actually came here the last time we came to Napa and we wanted to repeat it, since the tasting room is very cool and we liked the wine.

We ended our night with dinner at Cole’s Chop House — a classic steakhouse where every bite felt like a celebration.

On Monday morning, we had breakfast, checked out of our hotel, and drove in to San Francisco. We stopped at the Golden Gate Bridge before taking a quick drive through the city and heading to the airport.

This anniversary trip wasn’t just about the wine — though every pour was exceptional — it was about pausing, reconnecting, and savoring the simple joys. Napa Valley gave us more than tastings and tours; it gifted us moments of togetherness, laughter, and love, all wrapped in the beauty of its rolling vineyards.

If you’re looking for other couples trip options, check out these posts:

• Nashville
• Palm Springs & Joshua Tree
• Minneapolis
• Fall Foliage Trip/Vermont
• Bourbon Trail 
• Virgin Voyages

xoxo