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A Traveling Insider’s Guide To San Diego

Plan your San Diego vacation using this expert’s guide to America’s Finest City. By Paul Oswell | August 13, 2021

Welcome to San Diego, the second largest city in the largest state, a destination that has been experiencing a travelers' renaissance in recent years. The city is teeming with family-friendly activities and a newly revived nightlife scene.

Come for the surf culture, border town flavor, laid-back Southern California charm and fresh contemporary attitude. San Diego is also a year round beach town with more than 70 miles of coastline, perfect for young families, partiers and nature lovers.

In our guide, we'll ride the waves of San Diego's many attractions so that you can navigate the city seamlessly, get the most out of your stay and come away with unforgettable experiences. Here are some ideas for making memories in America's Finest City:

  • Surf's up: Jump on a surfboard at La Jolla Shores, build sandcastles with the kids at Coranado Beach or party with the in-crowd at Mission Beach and Pacific Beach Boardwalk.

  • Food's up: The region grows some of the best produce in the country, and the fresh seafood, fruits and vegetables make their way onto local restaurants' menus. It's a top choice for surf-and-turf, tacos or ceviche in the U.S.

  • Stay up: Catch a production at The Old Globe Theatre or La Jolla Playhouse before cocktails and dancing as you bounce among the many venues of the Gaslamp Quarter.

Why should you visit San Diego?

San Diego boasts a riviera atmosphere and laid-back SoCal charm, including a diversity of neighborhoods and natural surroundings. Take in the seaside beauty at San Diego Bay, enjoy the pristine beaches of La Jolla and the vintage allure of the Gaslamp Quarter.

Green spaces abound and joining the locals to bask in the lush surrounds of Balboa Park is never a bad idea.

Roaring good time

You can sunbathe near the resident sea lions at La Jolla’s Ellen Browning Scripps Park.

For more wildlife encounters, the San Diego Zoo and San Diego Zoo Safari Park are internationally known attractions and add to the city’s family-friendly reputation.

A stroll along the Embarcadero includes everything from tall ships to Navy aircraft carriers that now house museums. The San Diego Natural History Museum, San Diego Air & Space Museum and The San Diego Museum of Art are fascinating and memorable and filled with exhibits that will appeal to a wide range of ages. The San Diego History Center and the African Museum Casa del Rey Moro celebrate cultural histories, too.

When is the best time for your trip to San Diego?

Temperatures hover around 60-70 degrees Fahrenheit (15-21 degrees Celsius) year round, so there’s no bad time to visit the city. There are some overcast weeks, but March through May and September through November are ideal times to visit.

Summer is hot and sunny, of course, but crowds rise at the same time. The winter months see some rainfall, but there’s still a charm to the place and freezing temperature are extremely rare. The spectacular San Diego Bay Parade of Lights is in December, where you can see dazzlingly adorned boats, and July’s San Diego Comic-Con International is a world-famous comic book convention.

Getting to and around San Diego

San Diego International Airport is the country’s busiest single-runway airport. It’s efficient, but most global travelers arrive at Los Angeles International Airport. The airport is 3 miles from downtown, and there are great skyline views as you descend, so try to book a window seat.

Amtrak’s Pacific Surfliner route also stops at the Santa Fe Depot, and the city is well served by Greyhound buses and cruise ships.

Take the San Diego Metropolitan Transit System bus to downtown, within a couple of blocks of the Santa Fe Depot train station. Taxis and ride-hailing apps are both in good supply and cab rides downtown are between $15 and $30, depending on the neighborhood.

Ding, ding, ding

Downtown San Diego is served by a trolley system. The three lines (blue, green and orange) span more than 50 miles and stop at most of the major attractions and tourist spots, including the Gaslamp Quarter. The bus network is equally extensive.

A car rental could be worth considering if you’re planning on covering a lot of ground (San Diego County is huge), but not if you’re sticking to the main downtown areas. The city has both bicycles and scooters for rent, available at various hubs around downtown. You may have to take a cab or public transport between neighborhoods, but then it’s relatively easy to explore on foot once you’re there. Remember to pack comfortable shoes and a refillable water bottle for strolling, especially during the summer months.

Things to do in San Diego

There are 266 reasons why families, couples, foodies and sun-seekers all love San Diego. With that many days of sunshine per year plus 70 miles of golden beaches and an urban versatility, it’s easy to understand San Diego’s continued popularity.

Seas the day

Soak up the sun on the sands at Coronado Island or Mission Beach, or walk up the slopes of Mount Soledad or Mount Laguna.

San Diego is a destination that actively celebrates the outdoors, from its famous beaches to mountainside panoramas. More serious hikers can take on the five-peak challenge at Mission Trails Regional Park, or head to Calavera Nature Preserve for an easier trek.

Getting out on the water is also well worth the effort, whether it’s surfing at Mission Beach, exploring the sea caves by kayak or enjoying a sailboat tour around San Diego Bay. La Jolla has been an artsy beach town since the 1890s, and it’s free to enjoy the superb beaches. Their relatively calm waters provide an especially suitable place for beginners to learn to surf.

The city’s maritime history is centered in the Embarcadero, a bustling cruise ship hub. The Maritime Museum of San Diego has one of the largest collections of historical sea vessels in the United States. You can also board the mighty USS Midway, a former navy warship that now acts as its own museum, with an extensive collection of aircraft. A natural accompaniment is the San Diego Air & Space Museum, which houses dozens of aircraft, including a replica of Charles Lindbergh’s Spirit of St. Louis.

San Diego’s art scene flies high as well. The San Diego Museum of Art boasts renowned collections of Spanish and Italian old masters, plus South Asian and Indian paintings and sculptures. For an artistic perspective specific to region, the Centro Cultural de la Raza is a dynamic museum dedicated to preserving Chicano, Mexican, Indigenous and Latino art and culture. Most museums have a free or discounted day, and there’s also thriving street art scenes in Little Italy, University Heights and Chicano Park in Barrio Logan.

Everything from highbrow drama to country music and stand-up comedy can be found at the city’s well-respected San Diego Civic Theatre and Balboa Theatre. Watch Shakespeare at the equally evocative Old Globe and La Jolla Playhouse theaters. The San Diego Symphony Orchestra has been a go-to music spot for locals and visitors alike since 1910.

Cultural oasis

Balboa Park is home to the world-famous zoo, but it also houses a selection of magnificent Spanish structures that date back to the early 20th century, as well as popular green spaces. The preserved and restored buildings of the Old Town State Park, where some homes date back to 1821, are also worth a visit. Be sure to stop by Mission Basilica San Diego de Alcalá, the state’s first mission, which was founded in 1769.

Shopping is easy in San Diego and there is no shortage of malls to visit. The city has three major outlet centers: the Carlsbad Premium Outlets, Las Americas Premium Outlets and Viejas Outlet Center, which is about 33 miles northeast of downtown. For upscale boutiques head to La Jolla, and for gifts beyond the obvious tourist traps, visit the museum shops in Balboa Park.

San Diego culture and customs

San Diego is a laid back and welcoming city. With its near-perfect climate, world-class scenery and many ways to enjoy it, the outdoor life is really the one to pursue in San Diego. It’s also worth mentioning that Mexico is only 17 miles (27 km) south: a great option for a day trip or getaway.

Mexico’s influence is especially noticeable in the delicious cuisine, known as Cali-Baja. Check out Puesto, The Blind Burro and La Jolla’s Galaxy Cantina & Grill, but you’ll find these flavors all over the city. The less-crowded spots are in the Hillcrest, North Park and Kensington suburbs.

Eat & drink local

The locavore restaurant scene is thriving here, built on its blend of Californian and Mexican cuisines.

In addition to its world-famous zoo and an array of glitzy nightclubs and bars, the city is home to one of the best theater scenes outside of New York.

Like most tourist destinations, San Diego has a large service industry, and most people work for, and appreciate, tips. You should plan to tip at least 20% in restaurants, 10-20% for cabs and a dollar per drink minimum in bars, or more if you’re drinking fancy cocktails. Hillcrest has a thriving LGBTQ community and culture, including Hillcrest Brewing Company (1458 University Ave.), which bills itself as being the world’s first gay brewery.

San Diego’s tourist-friendly outlook and family-oriented options are backed up by world-class beaches, outdoor journeys, a thriving arts and cultural scene and the best Mexican cuisine this side of Tijuana. Make the most of the sunny climate and you’ll leave San Diego with a glowing, fresh outlook on life, along with cherished memories from a fun-filled trip.

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Paul Oswell is an award-winning travel writer, and has been reporting from all seven continents for over twenty years. He is based in New Orleans and is the author of “The Bucket List North America: 1,000 Adventures Big and Small.”

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