A Romantic Weekend Getaway In San Diego, Little Italy-Style

Whether you’ve traveled across state lines for a big San Diego trip or you and your significant other just need a staycation weekend, your stay at La Pensione boutique hotel will make you feel relaxed and fall in love all over again.

The Heart of Little Italy, San Diego

The area surrounding La Pensione is made for couple’s weekends and you won’t be able to pack it all in with just one stay, but maybe you’ll keep coming back for more. Start with a stroll up (or down) India Street and check out some of the many boutiques, cafes, and resting piazzas. We’re particularly fond of The Space, located at 2355 India, which features several curated boutiques like James Coffee Co and Walter & George, featuring unique women’s accessories. 

Across the street, check out galleries like Jett or Subtext, then circle down to Kettner to peek at the cool vintage housewares at Architectural Salvage and get inspired by the charming Mexican folk arts at Casa Artelexia. 

The neighborhood’s newest addition, Roma Urban Market, is an 8,900 square-foot marketplace and eatery for locals and visitors alike. Check out the specialty food counters, coffee bar and wine & beer bar, grab-n-go items, and a salad bar. It’s located on the corner of West Beech & Columbia.

One more place to stroll hand-in-hand with your partner: Little Italy Mercato.  If you’re staying with us on a weekend, it’s a must. The year-round Farmers’ Market happens every Saturday from 8:00 a.m. to 2:00 p.m. Over 200 tents line West Cedar Street from Kettner Boulevard to Front Street.

Cocktails, Craft Beer & Cuisine

By now you’re ready for dinner and there are so many amazing restaurants to choose from.  If you’re ready for some exquisite food prepared by renowned Chef Richard Blais, Juniper & Ivy is sure to be a palate pleaser. Expect a journey through multiple courses and food so good you just might cry. Don’t skip the legendary short rib. You want a reservation for this spot and we’re happy to help you make one.

Photo Credit: Juniper and Ivy

After dinner, perhaps it’s time for a stiff cocktail? Little Italy offers many options in this arena, too, from one of San Diego’s oldest bars (The Waterfront) to the hipster meccas (like Craft & Commerce). For a super fun experience, hit the side hostess at Craft & Commerce for your chance to be transported to Tiki Bar heaven at False Idol. Made to be speakeasy-style, the entrance is through a refrigerator and some other hidden doors and is like nothing you’ve seen before.

Get in the Groove

Now you’re at a crossroads…call it a night or experience the night owl lifestyle? Little Italy is capped by two amazing music venues—the 800 capacity Music Box on the south end just across Ash on India and the 225 capacity world-famous Casbah to the north just across Laurel on Kettner. The former features several touring bands throughout the week while the latter offers a diverse slate of indie, punk, acoustic, and rock bands nightly. Once it’s all said and done, you’ve got the comfort of La Pensione to rest your tired head to do it all over again when the sun comes up.