“Fall”-ing in Love in San Diego

Fall is the perfect time to visit San Diego. 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 in “America’s Finest City”.


Date Night Drinks at Humphreys Backstage LIVE 

(Photo: @eathumphreys)

Looking for a fun night out for two? Head to our lounge and venue at Backstage LIVE, which hosts a wide range of live performances perfect for an evening out. Sip on local brews or handcrafted cocktails from our in-house mixologists while enjoying the show and taking in the waterfront views. Our “Drink, Dine and Dance” package includes a whole host of romantic extras you and your sweetie are sure to appreciate, as well — including a stay at our tropical-style resort. So book early for the best available dates!

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 marina, all just steps away from your room. Plan the perfect date night by catching one of the last shows of our 2023 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 schedule. Upcoming shows include: ZZ Top (Oct. 18), Air Supply (Oct. 27). Daryl Hall (Oct. 30) and REO Speedwagon (Nov. 13). 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 

Head to Humphreys SoCAL Dining & Music for a delicious meal prepared by our talented Executive Chef Percy Oani. 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: @thehivelajolla)

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. We recommend checking out one of the city’s newest secret sips at The Hive in La Jolla, itself a beautiful coastal neighborhood perfect for date night. This secret spot offers breathtaking ocean views from within the Beeside Balcony restaurant, and romantic cocktails like the “Bed of Roses” — with hibiscus-infused vodka, rose water, simple syrup and lemon. The Hive also features live music. So put on your best glad rags and enjoy a night out on the town with your favorite partner in crime. 


Relax on a Gondola Cruise 

(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. 


Check Out a Midweek Farmers Market

(Photo: @sd_farmersmarkets)

What better way to spend an afternoon enjoying each other’s company than by strolling hand-in-hand through a farmer’s market? These bountiful bazaars are always especially alive during the harvest season, so you’ll no doubt discover amazing arts and crafts, fresh produce and even gorgeous floral arrangements. The Ocean Beach Farmers Market is particularly popular in the autumn thanks to its proximity to Sunset Cliffs — one of the most picturesque spots to witness the natural fireworks that happen at day’s end on the west coast. So why not grab some provisions, whip up an on-the-fly picnic, and watch the sun slip below the horizon with that special someone? 


Go Apple Picking in Julian

(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! Be sure to stop by Calico Cidery for delicious fresh cider best enjoyed under the oak and apple trees. 


Discover San Diego’s Fall Festival Season

(Photo: @lajollaartandwinefestival)

Fall in San Diego brings a vibrant tapestry of festivals that cater to every taste and interest. The San Diego International Film Festival takes center stage, drawing cinephiles and celebrities alike. It’s a week of cinematic magic, showcasing cutting-edge films and honoring the art of storytelling. Meanwhile, the La Jolla Art & Wine Festival transforms the city into a bustling artistic paradise, where visitors can admire stunning creations from local and national artists while savoring exquisite wines. For a taste of small-town charm, the Escondido Grand Avenue Festival is a must-visit, offering a delightful medley of live music, food vendors, and unique treasures from local artisans. The Borrego Days Desert Festival captivates visitors with stunning desert blooms, dazzling art installations, and a celebration of the region’s rich heritage.


Go Ghost Hunting

(Photo: @hauntedtrailbp)

San Diego’s status as one of the country’s oldest cities means one thing: “spooky season” always brings plenty of creepy attractions and macabre mysteries for the bold to encounter. From over-the-top Halloween celebrations like the Balboa Park Haunted Trail or SeaWorld San Diego’s Howl-O-Scream, to “real” haunted spots like The Whaley House Museum and El Campo Santo Cemetery, there’s no shortage of spine-tingling thrills to be discovered in and around “America’s Finest City.” 


Find Fall Fun at Humphreys

(Photo: @halfmooninn)

On the hunt for autumnal activities? You need look no further than right on-site at Humphreys! Our Live Blues Music Series starts on November 18th, and brings the best of this distinctly American art form to our stage. Our “Aloha in Autumn” package lets you celebrate a “second summer” with us at our island-inspired hotel. And while you’re here, don’t forget to sample our special fall-themed libations, including the Smashing Pumpkin (a blend of Tito’s vodka and Kahlúa with fresh pumpkin spice puree, a splash of cream and a graham cracker rim), and the Harvest Moon Margarita (reposado tequila, fresh lime, apple cider, agave nectar and cinnamon with a sugared rim). 

No matter your favorite date adventures, San Diego has something for everyone! Make the most of your Southern California vacation with us — Explore our special offers and reserve your fall stay for two today!