Falling in Love in San Diego

Fall is the perfect time to visit “America’s Finest City”. The warm weather sticks around, but the city is less crowded, making it a perfect time for couples to enjoy a vacation. Whether it’s your first getaway together or you’re celebrating a milestone anniversary, here are some of our favorite autumn date ideas for a romantic getaway San Diego style.

Date Night at Humphreys (on-site)

(Photo: @backstagelivesd)

Our intimate lounge and venue Backstage LIVE hosts a wide range of live performances, and is perfect for a fun date night. Sip on local brews or handcrafted cocktails from our in-house mixologists while enjoying the show and taking in the waterfront views. Upcoming shows include: Jack Tempchin & Mrs. Henry (Oct. 13), Skrewball Comedy Night with Mal Hall (Oct. 17), Glen Fisher Jazz Band (Oct. 25), and many more! 

2241 Shelter Island Dr, San Diego, CA 92106


Catch a Show at Humphreys Concerts By the Bay

(Photo: @humphreysshows)

Imagine dancing under the stars next to the sparkling waters of our private marins, all just steps away from your room. Plan the perfect date night by catching one of the last shows of our 2022 concert season at Humphreys Concerts by the Bay. Our outdoor concert venue has hosted some of the biggest names and continues to have a star-packed 2022 season. Upcoming shows include: Big Wild (Oct. 12), Willie Nelson and Family (Oct. 18 & 19) and Oingo Boingo (Oct. 29). Check out the calendar for a full list, and explore our Dinner Show Packages for unbeatable offers!

2241 Shelter Island Dr, San Diego, CA 92106 


Enjoy a Romantic Beachside Dinner (on-site) 

Head to Humphreys SoCAL Dining & Music for a delicious meal prepared by our talented Executive Chef Tom Connolly. Enjoy fresh, locally sourced seafood, steaks, and creative SoCal-inspired cuisine. Not only will you be treated to delicious food, but the views of the marina are unbeatable! Whether you’re catching a show after or simply want to soak in the views, you’re sure to have a beautiful time without ever leaving the hotel. 


Explore San Diego’s Speakeasies 

(Photo: @falseidoltiki)

The perfect date spot can be hard to find, especially when the entrance itself is hidden. So why not head to the hush-hush hideaway bars of San Diego to sip your libations in secret? Nearly a century after the repeal of the Great Depression-era prohibition culture that gave rise to these surreptitious saloons, the appeal of the mysterious keeps them alive. From tropical cocktails to vintage spirits, our favorite speakeasies have it all. So put on your best getup and enjoy a night out on the town with your favorite partner in crime. 


Gondola Cruise (16 miles away)

(Photo: @thegondolacompany)

No need to go to Venice, Italy to embark on a gondola ride. Not when you can stay right here in San Diego and rent one from Gondola Company! Friendly gondoliers, a peaceful ride through the Coronado Cays, and beverages and chocolates available to purchase make this an unforgettable and romantic experience. The gondola rides are perfect for celebrating an anniversary or even proposing! With rides available all day long, you can choose the perfect time for you and your amore. 


Hot Air Balloon Ride (24 miles away)

(Photo: @compassballoons)

Enjoy a once-in-a-lifetime hot air balloon ride over San Diego! Embark on the sunset tour with Compass Balloons to get a bird’s eye view of the city and coastline. Cruise through stunning canyons and over exclusive golf courses. Nothing is more romantic than enjoying these amazing things while sipping champagne with your loved one. 


Apple Picking And Autumn Ambience in Julian (60 miles away) 

(Photo: @julianfarmandorchard)

Enjoy a scenic fall drive to Julian, California where you’ll find orchards and cideries aplenty! Pick apples, berries, sunflowers, and wildflowers at Julian Farm and Orchard. The stunning views and seasonal activities make it a perfect day trip date idea. For the animal lovers, the orchard features a petting zoo full of friendly farm animals! Stop by Calico Cidery for delicious fresh cider best enjoyed under the oak and apple trees. 


No matter your favorite types of activities, San Diego has something for everyone and every couple! Spend your fall with us at Humphreys Half Moon Inn to make the most of your Southern California vacation. Explore our offers and reserve your room today!