Some proposals are perfectly planned. Some are perfectly surprising. And then there are those that fall beautifully in between—like John and Lindsey’s unforgettable engagement at Pride Mountain Winery, a hidden gem nestled high in the mountains where Sonoma and Napa Valley meet.

This wasn't just any romantic getaway. It was a milestone six years in the making, planned across state lines, with both of their families secretly flying in to be part of the moment. And while John tried to keep it a surprise, Lindsey’s instincts kicked in just enough to make the moment even sweeter.

From Virginia Tech to Vineyards: John & Lindsey’s Story

John and Lindsey first met on Tinder while attending Virginia Tech. Lindsey was a freshman, and John was a junior—and from their very first date, something just clicked.

“I knew he was the one because I could always be myself around him,” Lindsey shared. “I never got tired of spending time together. He constantly makes me laugh and has always been incredibly thoughtful.”

Six years later, after navigating college, jobs, and long-distance life (a year and a half apart between San Diego and the East Coast), they were ready to take the next step. All that was missing was the perfect plan—and John had one in the works.

A Picture-Perfect Proposal at Pride Mountain Winery

Lindsey had visited Napa Valley once before with her mom and sister and fell in love with the rolling hills, golden light, and peaceful vineyard energy. She always wanted to go back—and John remembered.

“I was suspicious because he wanted to go to Napa so bad,” Lindsey laughed. “But John doesn’t even like wine! He was very insistent on going that specific weekend. That’s when I started to wonder…”

The setting he chose was nothing short of stunning. Pride Mountain Vineyards, located at an elevation of 2,100 feet, offers panoramic views, lush vineyards, stone cellars, and quiet, tucked-away spots perfect for intimate moments. John led Lindsey along a pathway surrounded by vines, and just as they reached the top of the hill, he got down on one knee and asked her to marry him.

What she didn’t see coming? Both of their families had flown in and were quietly watching the entire proposal from a nearby picnic area, hidden from view until the big moment. When Lindsey said yes, her joyful tears quickly turned to shock and laughter as parents and siblings ran toward them, cheering and celebrating.

Why Pride Mountain Winery is a Top Proposal Spot in Napa/Sonoma

As a proposal photographer, I’ve captured love stories all over Northern California—but Pride Mountain Winery is truly special. Here’s why it’s one of my favorite proposal locations in wine country:

1. Incredible Views

Located on the Napa/Sonoma County line, the elevation gives you breathtaking panoramic views in every direction. Whether you're surrounded by fog in the morning or golden light at sunset, it feels like you're on top of the world.

2. Intimate Picnic Areas

Many wineries offer tastings, but not all have private, shaded picnic areas with space to gather family or enjoy a post-proposal celebration. Pride offers both charm and flexibility for those meaningful extra moments.

3. Romantic Atmosphere

The stone buildings, vine-covered trails, and warm, rustic ambiance make it feel like a fairytale. It’s ideal for couples who want a blend of natural beauty and timeless charm.

4. Staff That Goes Above and Beyond

Coordinating a surprise proposal—especially one involving family and timing—is no small feat. The staff at Pride is incredibly professional, discreet, and warm, making sure everything runs smoothly behind the scenes.

5. Versatile Backdrops for Photos

From quiet vineyards and mountain views to ancient oak trees and cellar pathways, every corner of Pride offers a different look for stunning proposal photos.

The Moment After: What Came Next

With the proposal done and the family surprises revealed, the group popped some bubbly and shared in the joy of the moment. For Lindsey, that was the highlight.

“The best part was having our families there,” she said. “I had no idea everyone had flown all the way to California just for this. It made everything so much more meaningful.”

As for what’s next? “We don’t have a wedding date or venue yet,” she shared. “We’re still deciding where we want to live and just excited to finally be in the same place. After being long-distance, we’re looking forward to doing everyday life together.”

Proposal Planning Advice: What NOT to Do if You Want to Keep It a Surprise

John’s proposal was beautiful—and though Lindsey had her suspicions, the moment was still full of joy and surprise. If you’re planning your own proposal and hoping to keep your partner guessing, here are a few gentle tips to avoid tipping them off:

🚫 Don’t suddenly act too romantic

If your partner knows you're not into wine, don’t push too hard for a weekend in Napa without a solid reason.

🚫 Don’t ignore the details

A sudden change in wardrobe, excessive phone-checking, or nervous energy can be giveaways. Try to stay calm and consistent.

🚫 Don’t plan without a cover story

Make sure your alibi holds up—especially if you’re coordinating hidden guests or a photographer (that’s me!).

🚫 Don’t underestimate your partner’s intuition

If they know you well, they might sense something. That’s okay! Focus on the emotion of the moment, not the element of surprise.

Final Thoughts

John and Lindsey’s proposal at Pride Mountain Winery was a beautiful reminder that love is worth celebrating in big, thoughtful ways—and that even if your partner kind of sees it coming, the joy of the moment can still take their breath away.

Whether you're planning a surprise proposal or dreaming up the perfect spot in Napa or Sonoma wine country, Pride Mountain Winery offers a stunning setting that feels private, intentional, and romantic. And if you’re looking for someone to capture the moment with timeless, joyful photos—I’d be honored to help.

Let’s Create Your Dream Proposal
Thinking about proposing in wine country? I help couples plan and photograph unforgettable proposals all across Sonoma and Napa.
📸 Reach out here to start planning, or view my Proposal Photography Guide to see the most romantic places to pop the question.