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Winter Weekend Getaways

Winter Weekend Getaways

Your Next Road Trip Destination from San Diego

For those of us lucky to call San Diego home, we are not short of beautiful weather all-year-round. However, it’s still nice to take a quick getaway in these long winter months. With an endless array of options surrounding the region, you can have amazing experiences beyond surf and sand in just a short drive.

That’s why I’ve rounded up some of my favorite “Winter Weekend Getaway” destinations that are just a road trip away from America’s Finest City. From mountains and camping to exploring wine country (in literally, another country!), here are my top five destinations for your next weekend adventure.


Photo via San Diego Tourism

1 Hour Away to the country

Ready to escape the city for that small town feel? Julian has you covered. Nestled among the beautiful Cuyamaca Mountains, Julian truly makes you feel like you stepped out of the big city and into the 1870’s Gold Rush. Here you can explore the many shops on Main Street dating back to the 19th century with a self-guided tour, sample some famous Julian Apple Pie, and enjoy cider and wine tasting rooms. I definitely recommend this destination if you are looking to wind-down and unplug.

Joshua Tree

Photo via National Park Service

2-3 Hours Away to the desert

For the adventurer looking for their next hike, Joshua Tree is the perfect destination. The area is full of raw desert landscape, hiking trails, rugged mountains, gold mind ruins, and amazing campsites for sleep under the stars. Joshua Tree offers 400 granite formations and 8,000 climbing routes for adrenaline junkies to choose from. Not to mention, February is a great time to visit as it is cooler (mid 60’s) and less crowded.

Valle de Guadalupe, Baja Mexico

Photo via Discover Baja

2-3 Hours Away to the best in wine country, Mexico

If you’re up for an adventure that involves a little bit (or a lot bit) of wine and delicious eats, then the Valle de Guadalupe is your place. The Valle, known as the “Napa Valley” of Mexico, is filled with five-star tours, lush family-run vineyards, and sustainable fine dining. While you’re there tasting the bold flavors of Baja, make sure to reserve a seat at top-rated restaurants like Finca Altozano, Laja, and Deckman’s.

Palm Springs

Photo via Sparrows Lodge

3-4 Hours Away to Hollywood’s desert getaway

Looking for a luxury-filled experience without leaving the country? Although Palm Springs has the beautiful weather like San Diego, it is like driving into a bright new world complete with private resorts, golf courses, and relaxation by the pool. If you’re looking for an adults-only getaway, try the 21+ boutique hotel Sparrows Lodge, that comes with upscale outdoor dinners under the desert stars. The winter is the perfect time to visit with the desert heat subsiding in the cooler months.

Mammoth Mountain

Photo via MtnScoop

6-7 hours away to ski, snowboard & après ski fun

How can I round up winter getaways without a little snow? This one may be a little more of a drive, but it is one of the best mountains accessible by car from San Diego and a must-visit destination. Mammoth Mountain gets, on average, more than 30 feet of snow covering their mountains each season and over 300 days of sunshine each year (making the resorts perfect for après-ski time on the mid-mountain sundecks). Even if you’re not a fan of winter sports, Mammoth is a go-to for exploring village shops, breweries, nightlife, and gondola rides overlooking 11,053 feet of picturesque landscape.


Garret Milligan

A lifelong resident of Rancho Santa Fe, Garret was raised in a family deeply integrated in the historic and vibrant community. Garret developed an affinity for the real estate industry at a young age by observing his mother—one of the community’s most successful real estate agents for more than 30 years—and learning the secrets to becoming a personable, yet results-oriented Realtor. He became the youngest partner in an elite luxury real estate legacy in ‘the Ranch’ in 2012 and quickly honed his skills, developed a vast network of industry resources, and built an impressive list of satisfied clients.

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