Our Team’s Favorite San Diego Traditions
The holidays in San Diego come with their own kind of magic. Instead of snow-covered streets, we’ve got palm trees, waterfront views, festive lights, and plenty of ways to celebrate the season. Here at Humphreys Half Moon Inn, our Shelter Island location puts us close to some of San Diego’s favorite holiday traditions, including the annual San Diego Bay Parade of Lights!
And while we love sharing our favorite ways to experience San Diego with guests, we figured we’d go straight to the people who know it best: our team!
We asked our Humphreys team to share the holiday traditions, local favorites, and seasonal experiences they look forward to every year. From festive family outings and neighborhood light displays to holiday cocktails and date-night ideas, here’s how we like to celebrate the season in San Diego.
What San Diego tradition makes it officially feel like the holiday season?
For our Director of Finance + Human Resources, Michael, the holidays wouldn’t be complete without a family visit to the iconic Hotel del Coronado.
Every year, Michael and his family head to Coronado to admire the hotel’s Christmas tree, stop by the gift shop to pick out a new ornament, and grab a cup of hot chocolate or coffee. They finish the outing with a walk along Coronado Beach.
It’s one of those traditions that perfectly captures the San Diego holiday season: Christmas trees, family memories, and a little beach time all in one afternoon!
What’s your favorite way to experience the San Diego Bay Parade of Lights?
This one is especially close to home! Our Director of Guest Services, Melissa, recommends experiencing the annual San Diego Bay Parade of Lights right here at Humphreys, as the parade itself kicks off at our location on Shelter Island!
Her ideal holiday evening? Getting cozy in her pajamas, wrapping up in a warm blanket, and enjoying a mug of hot cocoa while watching the decorated boats glide across San Diego Bay.
Insider Tip: Melissa recommends booking one of our Junior Suites early and requesting a second-floor balcony with views of San Diego Bay. Room locations and views are subject to availability, so be sure to check with our team when booking!
Before settling in for the parade, stop by Humphreys Backstage LIVE for a handcrafted cocktail or a bite to eat. Located just across the street from our hotel, it’s a great place to kick off the evening before enjoying the holiday festivities.
The 2026 San Diego Bay Parade of Lights takes place December 13 and 20, with the parade beginning right here at Shelter Island.
Where are the best places to see holiday lights around San Diego?
If you’re looking to see some of San Diego’s best holiday decorations, our team has a couple of favorites worth adding to your list!
Our Senior Sales Manager, Amberly, recommends Christmas Card Lane in Rancho Peñasquitos. Each year, more than 200 homes in the neighborhood decorate their yards with oversized, hand-painted Christmas cards featuring everything from classic holiday characters to superheroes and colorful festive scenes.
Amberly loves that you can explore the neighborhood on foot, take in the decorations, and even find residents selling hot cocoa, candy, and seasonal treats along the way. It’s a fun way to spend an evening with family or friends!
For something a little closer to home, our Director of Sales, Sarah, recommends checking out the decorated boats in our very own Humphreys Marina.
Sarah loves seeing the boats dressed up with holiday lights and decorations throughout the season. With the festive displays reflecting off the water, it’s one of our favorite reminders that you don’t have to venture far from Shelter Island to find a little holiday cheer!
What’s an underrated San Diego holiday experience worth discovering?
Sometimes the best holiday traditions involve getting out of town for the day! Our Director of Facilities, Brad, recommends a trip to the mountain town of Julian when the weather starts to cool down. Located approximately 1 hour and 15 minutes to 1 hour and 30 minutes from San Diego, Julian makes for a wonderful holiday day trip, especially for visitors looking to experience a different side of Southern California.
Brad and his family love the scenic drive into the mountains, taking in the trees and hoping to spot a little snow along the way. Once they arrive, they spend time browsing the local shops, enjoying dinner, and finishing the day with Julian’s famous apple pie.
Insider Tip: For a taste of this local tradition, visitors can stop by Mom’s Pie House, a Julian favorite known for its freshly baked apple pies and sweet treats since 1984. It’s easy to see why people make the drive just for a slice!
If you’re looking for a change of scenery during your San Diego getaway, this is a fun way to trade the waterfront for mountain views, small-town charm, and a slice of something sweet.
What’s one must-do San Diego holiday activity for first-time visitors?
For our Guest Services Agent, Damaryhz, it’s Jungle Bells at the San Diego Zoo!
During the holiday season, the San Diego Zoo transforms into a festive wonderland filled with colorful lights, seasonal entertainment, and activities for the whole family.
Damaryhz especially recommends Santa’s Factory, the Painted Jungle, Rainbow Forest, and Laser Trail, along with the holiday entertainment and Reindeer Games. If you’re visiting San Diego with little ones, this is one holiday outing we’d definitely add to your itinerary! Jungle Bells returns December 19, 2026, through January 3, 2027, excluding December 24, with a special member preview on December 18.
Where’s your favorite place to enjoy a festive holiday cocktail?
For Sarah, it’s hard to beat the holiday atmosphere at the Cutwater Tasting Room in Miramar.
During the holiday season, Cutwater transforms its tasting room into a festive Winter Lodge, complete with seasonal decorations, creative cocktails, and unique holiday experiences.
One of Sarah’s favorite memories is the gondola dining experience from a previous holiday season, where guests could reserve a seat inside a decorated gondola for an extra-special outing.
With seasonal cocktails and festive experiences to discover, it’s a fun spot to raise a glass to the holidays. Cutwater’s Winter Lodge returns in November 2026, with special events and limited dates for gondola dining.
And if you’re looking to enjoy a Cutwater beverage without venturing far, we also offer Cutwater drinks right here at Humphreys Half Moon Inn in our Lobby Pantry! It’s one more way to enjoy a little holiday spirit during your Shelter Island getaway.
What’s your favorite festive date-night activity in San Diego?
If you’re planning a little holiday romance, we’ve got a couple of recommendations from our team!
Sarah recommends ice skating at Liberty Station, just a short drive from our Shelter Island location. Between the festive lights, outdoor skating rink, and plenty of nearby restaurants, it’s an easy way to turn a holiday outing into a full date night. Plus, net proceeds from ticket sales support the Thriving After Cancer Program at Rady Children’s Hospital. The rink returns November 19, 2026, through January 3, 2027.
For something a little different, our Conference Service Coordinator, Annie, recommends the Candlelight Concerts around Balboa Park. Annie especially loves the romantic atmosphere of the candlelit performances and recommends looking for one of the holiday-themed concerts in December. Afterward, take a stroll through Balboa Park to enjoy the festive decorations and make a full evening out of it.
Where’s your favorite place to find unique holiday gifts in San Diego?
If you’ve still got a few names to check off your holiday shopping list, Annie recommends visiting the Mission Bay Beach Club. Located along Mission Bay, this waterfront favorite is one of Annie’s favorite places to spend a festive morning or afternoon.
She especially enjoys its seasonal activities, from holiday drinks and local gift shopping to special events and visits with Santa. Grab a warm or chilled beverage, browse for a few unique Christmas gifts, and enjoy the waterfront atmosphere while you’re there. Be sure to check the Beach Club’s upcoming events for holiday market dates and activities!
Make Holiday Memories on Shelter Island
From festive boat parades and neighborhood light displays to holiday cocktails and mountain getaways, there’s no shortage of ways to celebrate the season in San Diego. The only problem with so many holiday traditions? Finding enough time to enjoy them all!
And when the holiday adventures wind down, our tropical Shelter Island retreat is the perfect place to come back, relax, and enjoy a little island time. We also have plenty of festive activities and seasonal happenings right here at Humphreys! Explore everything we have planned on our holiday landing page.
Make your holiday getaway last a little longer with our Linger Longer Offer! Stay longer and save up to 20%, with complimentary parking on qualifying stays. That means more time to explore our team’s favorite San Diego holiday traditions and enjoy a little island time before heading home. We can’t wait to celebrate with you!
