The Ultimate Getaway Guide to San Diego

02/05/2020

San Diego is a popular US destination for history, culture, and tourism. With its alluring proximity to Mexico, generous amount of yearly sunshine, and array of activities to suit all travelers, it’s an ideal region for a weekend getaway.

However, such a venture can quickly get expensive and convoluted without a bit of pre-planning. Peak tourist seasons and mammoth events throughout the year can leave travelers stranded without accommodation, or simply forking out more money than they have to.

With that in mind, here’s our ultimate getaway guide. When you get to town, start by lining up luggage storage in San Diego. Stashing your extra gear will save you precious time on your whirlwind weekend of fun.

When to Go

While San Diego is blessed with around 250 days of sunshine every year, May and June are commonly referred to as “Grey May” and “June Gloom.” July through to October are the hottest months, so if your getaway intent is to soak up maximum sun on beautiful beaches, then you’ll probably be considering traveling during this time.

Bear in mind this period includes Comic-Con, a gargantuan yearly expo in July celebrating comic book fandom and popular culture. The event lures up to 150,000 attendees, making accommodation heinously expensive and nearly impossible to find on short notice. August also gets very busy, when people from nearby Arizona flock to San Diego to escape the summer heat.

Months with the lowest hotel occupancy are January, September, November, and December. Sunbathers and surf bums might want to consider traveling sometime between peak and low seasons to achieve the ideal balance of weather and busyness.

How to Get Around

San Diego is huge, and unfortunately not boasting extensive public transport. It’s possible to stay close to and explore via San Diego’s trolley network for cheaper and greener travel. Otherwise, travelers will have to opt between driving (if coming from nearby states), renting a car, taking a tour, or hitching rides with Uber or Lyft.

Neighborhood Guides

Where you choose to stay in San Diego will depend on your wants and needs. The city is far-reaching, with many neighborhoods and outer regions. As mentioned, public transport is not extensive, so pick your accommodation based on how much you can be bothered driving or hitching rides with Uber and Lyft.

Gaslamp Quarter

Named for the gas lamps of the Victorian era that lit up many parts of the city, this neighborhood retains much of its antiquated character. The industrial chic of the street lights and architecture, insightfully preserved over nearly two centuries, makes for a hip area to hang out. Gaslamp is ideally located in downtown San Diego, and nightlife and dining options are plentiful (albeit carrying a premium price tag).

Do: lean into the nightlife, starting with the rooftop bar at Rustic Root or Alice in Wonderland-themed Vin de Syrah Wine Parlour.

Eat: While Gaslamp has a range of boujee restaurants you could try, one recommendation after a big night out is The Morning After. Their creative menu features dishes that’ll appease one’s pounding headache, including Fruity Pebble pancakes, savory buttermilk waffles with sriracha maple, and the aptly named Hangover Burger.

Sleep: Go large here with presidential stays at the Pendry or US Grant.

Little Italy

Once home to generations of Italian families who made their living off the ocean, Little Italy is now swimming with sophistication. Its streets are lined with patio cafes, bustling restaurants (Kettner Boulevard is locally known as “Top Chef Alley”), craft breweries and urban wineries, shops, galleries, and more. For keen Italian cuisine connoisseurs and boutique window shoppers, Little Italy might be your neighborhood.

Do: Roam around the Kettner Art and Design district, drink Italian coffee from a patio cafe, shop the quaint Architectural Salvage, and explore the weekly mercato (market) on Saturdays.

Eat: Snag a pizza or deli sandwich from the Mona Lisa Italian Foods Deli, or indulge down Top Chef Alley. Juniper & Ivy, with its focus on molecular gastronomy and seasonal menus, is regarded among San Diego’s “best of the best”.

Sleep: AirBnB Little Italy has some attractive choices. Or, try the Wyndham Bayside for its proximity to the San Diego Zoo, Seaport Village, and the airport.

Balboa Park and Hillcrest

Hillcrest stands as San Diego’s hub of LGBTQI+ culture. You’ll know exactly where you stand when you spot the neighborhood’s towering rainbow flag, just off the main thoroughfare of University Avenue. The area is studded with diversity and bohemian eclectica — vintage stores, farmer’s markets, independent cinemas, nightclubs, and a gay brewery — and ideally located to the famous Balboa Park.

Do: Balboa Park is beloved by locals for its attractive buildings, series of gardens, and vast array of activities. Stroll or ride a bike, see a Shakespeare play, tour San Diego’s famous zoo, or try and split your time between 15 museums.

Eat: Foodies can graze their way through Food Truck Fridays in Balboa, or consider signing up for a full food tour to eat the most of what Hillcrest has to offer.

Sleep: Shoestring travelers can try ITH Hostel and Eco Lodging, Balboa Park. Mid-range and more luxurious options include Hillcrest House Bed and Breakfast.

North and South Park

These hip districts will fill you with art and culture up to your eyeballs. Find street art on rooftops, walls, and down alleyways, including a two-story mural of a Burmese monk by famed street artist Shepard Fairey. Lovers of live music will also dig this area, with its abundant rock, indie, and jazz venues.

Do: Catch live music at the Observatory North Park, The Irenic (a converted church), and Seven Grand. Get inspired by the many boutiques and galleries in the area, and take part in an art class at Art on 30th.

Eat: North and South Park have so many delectable food options. Notable mentions are $3.50 tacos from City Tacos, peanut butter milk stout from Belching Beaver, creative lattes and cold brews from Holsem Coffee, and farm-to-table offerings from One Door North.

Sleep: Have some fun at the Colonial-style Lafayette Hotel and Swim Club.

Old Town and Mission Valley

Once California’s first settlement with only a mission and fort, Old Town is San Diego’s historical hub. Travelers can experience many kinds of museums and tours through the district’s heritage sites, and admire 1800s Spanish architecture. Old Town is across the street from the Trolley Transit Centre, making it an ideal neighborhood for explorers without cars.

Do: Tour Old Town State Park, take a ghost tour or brewery tour, linger in the meditation garden of the Mission, read newspapers from the 19th century, or watch blacksmiths and woodworkers hone their craft.

Eat: Try the homestyle South American fare at Berta’s Latin Cuisine, or fill your belly with tortillas on a Tequila, Tacos, and Tombstones Tour.

Sleep: The Victorian Cosmopolitan Hotel is great for a deluxe weekend getaway. Budget travelers can sleep in comfort at the Old Town Inn.

Ocean Beach

Those with a little flower power love in their hearts might want to set up shop in Ocean Beach. This area is bursting with laidback hippie vibes, crystal shops, street tacos, and tie-dye everything, and facilities for kids and pets alike so that every kind of vacationer is welcome here.

Do: explore the protected tide pools, swim in the ocean, play or picnic in the expansive Mission Bay Park, catch views of the city from Cabrillo National Monument and Park, or go gray whale watching during the migration period of December-March.

Eat: Poke your nose into It’s Raw Poke Shop, chomp on a vegan wrap or burger at Plant Power Fast Food, or feast on French fusion dishes at Bo-beau Kitchen Bar.

Sleep: Stay steps away from the sand in style at Ocean Beach Hotel. Alternatively, beach bums on a budget should try the trippy USA Hostels Ocean Beach.

La Jolla

Pronounced la hoya, the La Jolla neighborhood is consistently ranked among the best beach destinations in the world. This area is upscale and celebrity-studded, and weekend getawayers will swoon over the range of luxury accommodations and thrilling outdoor activities on offer. Those traveling on a shoestring might struggle to stay within their budget here.

Do: play golf at the famous Torrey Pines golf course, picnic in Scripps Park, surf, or take a kayaking tour of La Jolla Caves.

Eat: La Jolla is packed with fine dining options celebrating local seafood and global cuisines. Mosey into Masala Street for California-Indian fusion dishes cooked by a former Taj Mahal executive chef, or try Nine-Ten Restaurant & Bar for modern American with a Jamaican twist.

Sleep: For a weekend getaway in La Jolla, you can’t go past the Balinese-themed Pantai Inn, or the Grande Colonial Hotel with some of the best happy hours in the city from Nine-Ten Restaurant (mentioned above).

Bonus Activities

Every spring (March-May), the 50-acre flower bulb crop known as Carlsbad Flower Fields bloom into multi-colored wonder. This accidental tourist attraction is located in north San Diego county, off interstate highway 5. Tickets are $18; visitors should allow 1-2 hours for a good wide-eyed stroll.

For a weekend getaway centered around nature and outdoor recreation, consider camping at Mission Trails Regional Park. With over 7000 acres to explore, this is one of the largest urban parks in the country, with abundant options for tours, hiking, and native flora and fauna viewing. Campers can pitch up on Friday and Saturday nights at the Kumeyaay Lake campground; be sure to reserve ahead of time.

Avid surfers and sunbathers can make a day of enjoying Coronado Island and its beach (voted the best beach in the US). This resort district has some gorgeous mansions, a quaint central strip of shops and galleries, and plenty of oceanfront dining. It’s an idyllic setting for a San Diego weekend getaway…so much so you’ll be jostling with a lot of traffic to get there.

Finally, if you haven’t had your fill of sun, sand, and tasty tacos, then travelers can always hop across the border into Mexico. Tijuana is a mere half-hour drive or trolley ride from San Diego – perfect for a novelty weekend getaway. Just remember to pack your passport, allow for wait times at the border, and (if driving yourself) get auto insurance before you go.


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