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Planning a Romantic Weekend in San Diego

Updated: Feb 15, 2022

Lately, lounging on the couch, bingeing Netflix over takeout, is the new norm. It may be time to plan a weekend in San Diego with your significant other. With award winning wines, beautiful hotels, a booming food scene – San Diego is the perfect place for a much needed romantic getaway!

In sharing our passion for all things San Diego, we’ve compiled a list of our top experiences for couples to stay, eat, and sip, to help you plan your romantic getaway. While we are only scratching the surface here, there are many other AMAZING options in the stay, sip, and eat categories, these are just a couple of our many favorites. Your memorable romantic experience is waiting in San Diego.

Where to Stay

Italian Villa in San Pasqual-Escondido, CA

Your Italian Vacation awaits! This stunning Tuscan home boasts amazing hilltop views on over 5 acres with a private gate, vineyard, and avocado grove. Home was completely updated in July of 2020 & is maintained to the highest standards. Conveniently located within minutes of San Diego Safari Park, Eagle Crest and Vineyard Golf Courses, Stone Brewing, The Escondido wine trail, local hiking trails, Westfield North County - it's the perfect place to stay to enjoy the many small production wineries of San Diego.

Insider Tip:

This beautiful Italian villa is a 5-10 minute drive to some of the best wineries in San Diego within the Highland Valley. Purchase a bottle from a few of the neighboring wineries and enjoy on one of 4 decks with amazing views.

Cheval Winery

2919 Hill Valley Drive, Escondido CA

Not only does Cheval have a winery, they have 2 Airbnb experiences to choose from! You have a choice between the following:

Luxury Villa

Vineyard Casita

Talk about an experience! Cheval is an exclusive, modern winery located in Escondido. The estate includes vineyards, champion show horses, along with Vacation Villas, available to rent. All of these really create quite the luxury experience. Both of these luxury options are on the winery estate - which is home to beautiful vineyards, and some farm friends. Visit with the champion show horses, goats and Thelma and Louise the Alpacas - The winery is here for you to explore.

Insider Tip:

With names like “Cash” and “Simply Vane” some of their wines are inspired by one of their blue ribbon winning horses. Like their horses, Cheval Winery has some real show stoppers – my favorite being Bullet, their Cabernet Franc.

Where to Sip

Hungry Hawk Vineyards & Winery

3255 Summit Drive, Escondido CA 92025

Located in the San Pasqual Valley, this Husband and Wife owned winery offers beautiful views and award winning wines. Hungry Hawk Vineyards and Winery has over 15 varietals grown on the estate. Included in those, is their Cab Franc. A beautiful medium-bodied, dry red with aromas of black cherry and dark fruits. NOT TO BE MISSED!

Insider Tip:

Get a behind the scenes look with a tour of their vineyard and production facility, led by the winemaker or owner, while tasting wines along the way. A tour of 2 + tasting is $150, with each additional person $50. Make sure to call and make a reservation.

Old Survey Vineyards

16850 Old Survey Rd. Escondido 92025

Taste full-bodied red wines at small family owned Old Survey Vineyards. Overlooking the San Pasqual Valley, their beautiful patio boasts breathtaking views and is the perfect way to end your perfect day with a bottle of Barbera and a sunset. Located off the beaten path, this hidden gem is a must see.

Insider Tip:

I will let you in on a secret (I don’t know how secret), but sweet Rosie is known to whip up some refreshing sangria on the weekends. Made with their amazing wine, fruit, and a lot of love - it’s so enjoyable on a warm summer day on the mountain! Additionally, they have a community grill you can use - grab some meat and grill up something delicious to pair their their show-stopping wine!

Sunrise Vineyards

16620 Highland Valley Road Ramona, CA

Sunrise Vineyards is a beautiful setting overlooking the rolling hills of Ramona. Located between Speckled Rock, and Three Hills Winery, Sunrise Vineyards is a husband and wife venture, first planting their vines in 2014. Having been open for about 4 months now, plan to visit this charming winery. All the wines I tried were delightful, my favorite being S & M (75% Mourvedre, 25% Syrah), which was a medium bodied wine with blueberry and hints of vanilla.

Where to Eat

Cordiano Winery

15732 Highland Valley Rd Escondido, CA

Originally from Italy, husband and wife duo, Gerardo and Rosa opened Cordiano Winery in 2008, after many years of owning authentic Italian restaurants in New York, and Louisiana. Another winery with spectacular views and impressive wine, Cordiano also has a kitchen! From charcuterie boards to Pizza and Pasta, this homemade cuisine is perfectly paired with their robust wine offerings. Cordiano Winery is about enjoying life to its fullest and sharing that experience with friends, both new and old.

Bernardo Winery

13330 Paseo Del Verano Norte San Diego, CA

Bernardo Winery is a family owned winery, and home to historic antique wine making facilities. Guests can stroll through the charming grounds, visiting the village shops while sipping their various wine options. While walking around the grounds, one can work up quite the appetite.

While the tasting room offers great fare to share at the table, their Kitchen menu is much more extensive. Featuring their BW Reserve Wine List and a seasonal elevated menu incorporating locally sourced and estate grown ingredients created by Executive Chef Yakub and his team, the food is delicious! The menu boasts Sicilian/Old Californian focused food with handcrafted pastas, sauces, and traditional rustic pizza - all celebrating Bernardo Winery's long culinary history.

Insider Tip:

Located amongst the Village Shops on the Winery estate, The Bernardo Winery Sweet Shoppe features chocolates, candies, and nuts. Stop by with your wine from the tasting room to pair with their beautiful chocolate samples.


We always recommend having a driver when wine tasting in San Diego. Many of these wineries are located on winding country roads.

While there is Uber and Lyft in San Diego County, given the limited coverage in the San Diego wine country, it can be difficult to request a ride after each winery, there will be a lot of waiting around, and the costs add up.

To enhance your San Diego wine country visit, we recommend booking a wine tour company to help you make the most of your time and make this a memorable experience. Depending on the wine tour company, and what’s included, you will find prices varying from $85 - $200+ per person.

All Things Considered

Now that you have a small glimpse into the many experiences that await you in San Diego - now is the time to get planning your romantic getaway.

Hidden City Wine Tours includes trip planning and customization from start to finish, safe and private luxury transportation, and a memorable day. We provide more than just transportation, but an entire experience for a group of up to 6 guests.

Your Private Wine Experience Awaits...

Contact Hidden City Tours on our Contact Us page to book your San Diego wine tasting trip today.

Tour Highlights Include:

Professional Concierge Service

Full Itinerary Planning - we make all reservations

Safe, Spacious & Comfortable Luxury Mercedes Van

Friendly Tour Guides - 5 Star Customer Service

Complimentary Bottled Water

Dog-Friendly - must be friendly and on a leash

Deli Lunch/Charcuterie available upon request

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