Your Guide to a Long Weekend in San Diego

san diego sunset, long weekend in san diego

San Diego offers year-round appeal with its consistent average temperatures in the 70s — making it easy to explore all of the city’s lush parks, beautiful beaches, cultural attractions and its diverse dining scene. But if you only have a few days to spare, luckily for Denverites, there are plenty of direct flights from Denver to San Diego, making it easy to find time for a long weekend in San Diego.

To fully experience the best of San Diego, you’ll want to explore its vibrant downtown, iconic parks and miles of stunning coastline. The best way to do that is with a stay at these three hotels: Town and Country Resort, Westgate Hotel and The Wayfarer San Diego.

Retro Resort Style in the Heart of San Deigo

Live the resort life at San Diego’s iconic Town and Country Resort. Located in Mission Valley, the Town and Country Resort is in the center of it all and is the ideal escape for a long weekend in San Diego. Whether you need some much-needed pool time or are ready to explore the best of San Diego, this retro resort has the makings for a relaxing vacation.

long weekend in san diego, town and country resort
Town and Country Resort. Photographer: Justin Kriel

The property itself is a whole vibe. With what feels like Palm Springs in San Diego, the 1950s retro resort showcases its nostalgic charm with mid-century modern designs, vintage neon signs, colorful pop art and that Southern California beach charm. Hotel rooms offer plenty of space and style with custom mid-century modern-style furniture and colorful murals highlighting the beach culture of San Diego. Choose from valley views or pool views, with most rooms featuring a private balcony.

town and country resort san diego
King room at Town and Country Resort. Photographer: Justin Kriel

At the hotel: Beyond the comforts of your room, it’s easy to relax poolside at Town & Country’s 10,000 square-foot pool complex complete with a zero-edge entry pool, children’s pool and a four-story, 150-foot “Twister” waterslide. Make a day of it and rent a cabana or daybed, grab drinks from the poolside bar and enjoy the pink flamingos and the neon diver sign, “Thema,” that makes you feel like you’re lounging poolside with Marylin Monroe.

Stay and play with Dive In Movie nights at the pool, listen to live music at the Monkey Bar or grab a sandwich from the MRKT for a picnic at Riverfront Park. Dine under the stars with dinner at their on-site restaurant at ARLO and complete your long weekend in San Diego with their DJ brunch and bottomless mimosas.

Explore nearby: if you’re looking to explore beyond the property, the resort’s central location in the Mission Valley puts you within a 10-minute drive to some of San Diego’s most popular attractions such as the San Diego Zoo and Balboa Park and Sea World. If you don’t want to drive, the hotel connects to the Fashion Valley stop along the trolley route. From here, you’ll be able to find the latest fashions at Fashion Valley Mall, explore the city’s lively downtown and spend an evening dining in Old Town

Living in Luxury

If you’re looking for a luxurious getaway that puts you in the heart of downtown San Diego, book your stay at the Westgate Hotel. Located on the edge of the Gaslamp Quarter, the Westgate Hotel oozes elegance with its afternoon teas and old-world European luxury design —reminiscent of France’s Palace of Versailles.

Immediately upon arrival, you’ll be swooning over the elegant Grand Lobby with beautiful crystal chandaliers and opulent European decor. In your room, no luxury was left behind with luxe marble bathrooms, elegant European finishings, plush bedding and floor-to-ceiling windows offering a beautiful view of the San Diego skyline.

At the hotel: Optimal elegance is served with their afternoon tea in the Grand Lobby (think tea at the Brown Palace with a bit of French flaire) with a selection of delicious teas and champagne, bite-size sandwiches, sweet pastries and desserts — all accompanied by live music from a harpist.

Indulge in a day at the spa with a massage from AquaVie, the hotel’s fitness and wellness club. Enjoy time in their steam room and dry saunas or sweat it out with an invigorating workout at their fitness facility. Or relax and unwind at the rooftop pool overlooking downtown San Diego with poolside treats and beverages.

Explore nearby: Enjoy a night out on the town and easy access to world-class restaurants, in the Gaslamp Quarter. This historic downtown neighborhood is known for its unique Victorian architecture, iron street lamps, its diverse array of restaurants and a nightlife that is equally dynamic. Grab an Uber or explore on your own two feet to nearby favorites such as Little Italy (where you’ll find some of the city’s best restaurants), USS Midway Museum and shopping at Seaport Village.

Stay by the Beach

For those who prefer their long weekend in San Diego beachside, then a stay at the Wayfarer in Mission Bay is a must. Designed for fun in the California sun, this retro surfer-chic motel is a true diamond in the rough. A bit unassuming from the outside, but chalked full of character and ocean views from the inside.

Situated along the shores of Pacific Beach, the Wayfarer pays homage to its surfing roots with surfer-themed art, surfboards and oceanfront access. But whether you want to hang 10 or just relax by the pool, this beachside hotel is the spot.

At the hotel: Their cozy rooms with bright and colorful decor are the perfect compliment to your beachy stay in San Diego. Watch as the sun sets on another beautiful day in San Diego either from your room’s private oceanfront balcony or the hotel’s poolside deck with heated pool and outdoor firepit.

Explore nearby: Chill like the locals with a stroll down Mission Blvd. where you’ll find plenty of restaurants, bars and shops. Or take in beachfront views with a walk along the Ocean Front walkway. Watch a lively volleyball match, cruise with the roller bladers and see the surfers catch the day’s first big wave. If you want to join in on the fun, sign up for surf lessons, or take advantage of the hotel’s complimentary bike rental to explore old Mission Bay with its local surf shops, dive bars and seafood shacks. 

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