How to Celebrate Valentine’s Day in San Diego

The options for how to spend the perfect Valentine’s Day in San Diego are endless. From classic date ideas that take you to the most romantic restaurants around the city to more creative activities that bring out your adventurous side, there’s something for everyone to enjoy on the holiday.

If you’re lucky enough to spend the day or evening out in Little Italy, you’re already kicking things off right. Little Italy, San Diego, is one of the city’s most romantic neighborhoods. Use this guide to plan your perfect Valentine’s Day in San Diego in both Little Italy and beyond.

The popular cheese wheel paste at Monello in Little Italy, San Diego
Image credit: Monello Italian Restaurant

Enjoy a Delicious Meal Out

Little Italy is one of San Diego’s best neighborhoods for eating out on the town, so it’s no surprise that you’ll have plenty to choose from when reserving a spot at some very romantic eateries.

Head to the Kettner Exchange for a see-and-be-seen atmosphere and shared plates or upgrade to one of their cabanas for the ultimate rooftop experience. For classic Italian, head to Monello. Their Milanese menu features classic squid ink pasta in a lobster bisque sauce, a dish that’s perfect for indulgent date nights.

If the weather’s nice, book a table at some of San Diego’s best patios in Little Italy. Start with Davanti Enoteca if you’re looking for something a bit livelier this Valentine’s Day. Share a pizza or any one of their house-made pasta dishes for delicious comfort food and some of the best Italian cuisine in the city.

The rooftop pool at Allegro Tower

Enjoy a Romantic Night In

If you don’t want to brave the crowds on Valentine’s Day, a romantic evening in is a great alternative. Cook something delicious and serve it up with a bottle of wine from one of the many beer and wine purveyors in downtown San Diego. 

Bottlecraft Little Italy is a great option if you’re not quite sure what you want, as they always have a knowledgeable staff member on hand to help you make the best choice. 

If you’re lucky enough to live in a luxury apartment with special amenities, take advantage of those perks. Those can include shared community spaces, barbecue stations, and outdoor pools with impressive views. If you’re spending time with friends this Valentine’s Day instead of a date, host them at your apartment and make use of these incredible spaces.

Sailing in the San Diego harbor

Seas the Day

Take advantage of San Diego’s perfect weather and hit the water on one of the many San Diego boating opportunities out there. 

For something truly unique, take a gondola ride with The Gondola Company. The Coronado-based cruise company will take you and your date on a 50-minute ride through the canals of the Coronado Cays. Special Valentine’s Day “Saint Valentino” cruises on the day of the holiday and the weekend before are pricier, but sure to sell out.

Sunsets are always romantic. Plan a sunset cruise on the Bahia Belle or a sunset sailing excursion with San Diego Sailing Tours. Pack a few snacks to enjoy onboard as you take in the breathtaking views.

Glasses of wine

Go Urban Wine Tasting

If you’re looking for a place to have a glass of wine or two this Valentine’s Day, Little Italy is an excellent place to start. Try Pali Wine Co. and their Little Italy outpost for a variety of wine flights and cheese boards. Flights come in 4-6 tastes, including a natural wine flight if you’d like to try a few organic wines.

Carruth Cellars is a popular urban winery in San Diego, and their Little Italy wine garden is a mainstay in the neighborhood. Light snacks round out an extensive wine menu of both flights and wines by the glass. If you’re there on a weekday outside of Valentine’s Day, their happy hour is a generous one.

Strawberry scones at Extraordinary Desserts in San Diego
Image credit: Extraordinary Desserts

Don’t Forget Dessert

Downtown San Diego is the perfect neighborhood to find a variety of delicious dessert options for after that romantic meal. These are special enough that you can make an evening out of just dessert if you please.

Head to Extraordinary Desserts if you’re looking for a wow factor with your sweets. Their Little Italy destination always has picture-perfect options in their display case for you to choose from, or go with any of their fruit tarts if you’re looking for something romantic. 

If you’d like to walk and chat after picking up a scoop, get some gelato at Pappalecco or craft ice cream at Salt & Straw. Take your scoops to the bay for a romantic stroll and the perfect end to your San Diego Valentine’s.

Two white cups of cappucino with love art latte

Celebrate Galentine’s Day

If you want an evening out with your friends, it doesn’t get much better than Galentine’s Day. The day falls on Feb. 13, Sunday Bowl Sunday this year, and it’s a time to celebrate female friendships before couples and Cupid get their day. 

For a casual morning, start your day off at one of the best coffee shops in downtown San Diego. Lofty Coffee Co. or James Coffee Co. are both great options. If brunch is more your speed, head to Queenstown Public House or Farmer’s Table. Both offer options for mimosas and other brunch cocktails to go along with your sweet and savory treats.

Interested in something a bit more adventurous? Try out an aerial yoga class at Mission Beach Yoga or join Club Mud at the Glen Ivy Hot Springs outside of San Diego. 

Choose Your Own Adventure

Living in San Diego’s Little Italy has so much to offer, whether you’re single in the city or coupled up and ready for Valentine’s Day. It’s the perfect neighborhood to find your own favorite place, too, and share that with someone you love. 

Spend time on the Piazza della Famiglia, San Diego’s love letter to similar gathering spaces in Italy. Go on a hunt for Little Italy’s historical markers. Find your favorite Italian eatery among all of the delicious options.

If it’s the neighborhood you’ve fallen in love with, you won’t find a better option than the luxury Allegro Towers. Schedule a visit to see what living in style really looks like and to take advantage of peak walkability in Little Italy.