Take some time away this winter and enjoy time with loved ones surrounded by plenty of sand, sun, water, and fun. The beach towns of San Diego County have something for everyone during a winter trip to San Diego. Relax and unwind indoors or out, on-shore or off-shore. Air temperatures hold steady in the mid-60s range, while water temperatures plunge down into the 60s, so unless you can brave the colder temperature, you may want to hold off on the swim until spring.

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Skating by the Sea

When you think of ice skating, you may think of blistering cold, wrapping yourself in warm winter clothing, and skating in circles until you take a break from some hot cocoa and a snack inside the warming house. With a trip to San Diego this winter, you can get the skating experience in the warm beach weather. The historic Hotel Del on Coronado has been offering the experience on their beachfront skating rink for nearly 20 years. Skating by the Sea is available November 17-January 7.

Coronado Island

Come for the skating, stay for the atmosphere. While your ultimate destination may have been the skating rink, the whole of Coronado Island is a day trip that’s not to be missed. Take a guided tour and learn about the island’s history, including the first military flying school, where sailors first learned to take off into the wild blue yonder.

San Diego Bay Parade of Lights

The theme for the 53rd annual event is Christmas Traditions Around the World. Participating boats will decorate their vessels according to the theme, then cruise the parade route, which starts at Shelter Island and ends at the Coronado Ferry Landing. The parade takes place December 10 and December 17, with the first vessel leading the way each night at 5:30 p.m.


The San Diego area is known for its many theme parks. Kids and kids-at-heart on a winter vacation to the area will want to make sure to include a stop at LEGOLAND in Carlsbad. Based on the building blocks of the same name, the park offers rides, shows, and other attractions. The water park is closed during the winter and winter months, but the main park offers a fun, family-friendly holiday experience. Starting November 18 and taking place on various dates through January 7, is their “The Jolliest Time of the Year” event. Experience the resort in all its holiday trimmings, meet holiday characters like Santa, the Toy Soldier, and the Gingerbread Man, then check out the 30-foot, fully decorated LEGO Christmas tree with over 400 LEGO ornaments or a seasonal show.

Stop by Legoland California in Carlsbad

Whale Watching

While people flock to warmer climates in the winter months, so do animals. Starting in mid-December, the gray whales that called Alaskan waters home during the summer begin their migration toward Baja in Mexico. The trip is one of the longest taken by any mammal anywhere. From their arrival until about April, you can spot the majestic animals about 20 miles off the coast.


If you’re not planning on braving the cooler water, lay out and sunbathe or build sandcastles with the kids. Change up your exercise routine with a run or walk on the beach, or plant your beach umbrella, spread your towel, and kick back with a good book. Paddle your way through the water on a stand up paddleboard, kayak, or canoe. Up the adrenaline and the speed and take off on a jet ski or fly up to 500 feet above the water on a parasailing adventure!

San Diego beach surfers

San Diego Hop On Hop Off Trolley Tour

When most people think of California trolleys, their mind may jump straight to San Francisco and their iconic system, but there’s one in San Diego, too! The trolley isn’t just a fun mode of transportation for tourists and locals alike, it’s an affordable way to get around the city without having the headache of busy parking areas with expensive rates at popular attractions. If you want to take a tour of the whole route, there are at total of 11 stops around the city. Your conductor is a knowledgeable guide who can fill you in on everything there is to see and do along the route. “Hop off” and explore further, then hop back on at a later stop or when the trolley loops around to your location once more.

Witch Creek Winery

The Carlsbad winery might not grow its own grapes, but it’s still a maker of delicious and award-winning wines. The winery also offers live music, open mic comedy nights, and other entertainment. There’s also a wine tasting room where adults of the group can taste by the one- or two-ounce taste. Choose from an array of white, rose, red, or a variety of other specialty wines to pair with your next home-cooked meal.

Winter Fun in San Diego County

When you start planning all the fun activities and adventures for your winter San Diego County retreat, make booking comfortable and fun accommodations a priority. Kick off the winter planning when you book a vacation rental with Vacation Rentals by Kimberly. We have accommodations as small as one-bedroom, all the way up to a seven-bedroom home so you and all your loved ones can enjoy a beach retreat full of winter fun.

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