San Diego Guide: Planning Your Trip

Downtown Skyline of San Diego Over Seaport Village
sandiegoa / Getty Images

California’s first tourist, Spanish conquistador Juan Rodriguez Cabrillo, stepped ashore in San Diego in 1542. Visitors haven’t stopped coming to the Plymouth Rock of the West Coast, now America’s eighth largest city, ever since. Its 70 miles of scenic coast, favorable year-round climate boasting 266 days of sunshine, endless outdoorsy offerings, singular craft beer scene, plentiful bounty of quality produce and seafood, family-friendly attractions, diverse cultural population, and general laidback vibe make it a quintessential Golden State getaway.

Planning Your Trip

Best Time to VisitSan Diego is a true year-round destination so it depends what kind of vacation you’re after. Sun and sand? Go August through mid-October. Fall, non-holiday winter weeks, and early spring bring the shortest lines at family-friendly attractions and generally cheaper hotel rates. Avoid Comic-Con week unless superheroes and sci-fi are your reasons for living. 

• Language: English, but you’ll also hear and see lots of Spanish.

• Currency: US Dollar

• Getting Around: Driving is the most common mode of transportation in this giant county although many people rely on rideshare apps to avoid having to find/pay for parking or limit alcohol intake when going out at night. Walking, if your destination is close enough, is usually safe in the best neighborhoods to visit. There is also a bus line, mass transit trolley, and app scooter rentals.

• Travel Tips: Layer, layer, layer as this beach-meets-desert location, location, location is subject to bright sun, marine layers, ocean breezes, hot Santa Ana winds, occasional rain, and post-sunset 10 degree temperature drops even in the summer, sometimes all in one day. Everyone keeps it pretty casual, especially clothing wise, but with an abundance of dogs, babies, military personnel, and fitness freaks the city tends to get an early start on the day.

Things to Do

Whatever floats your boat, even if that is literally floating in a boat, San Diego has you covered. It’s easy to fill an itinerary for a family vacation, a romantic retreat, an active or outdoorsy adventure, or a city excursion.

• Play Outside: From sunny sea-level scenery to mountaintop panoramas, from the lushest of the 93 golf courses to the desolate Anza-Borrego Desert, and from the gnarliest wave to the calmest lake, San Diego’s a gorgeous place for nature lovers and sports enthusiasts to roam. Hike the five-peak challenge at Editor's Choice Award winner Mission Trails Regional Park, selfie at Potato Chip Rock, or step back in time at Carlsbad’s Calavera Nature Preserve. Spend a sun day fun day at these 12 beaches.

Get out on the water by whatever means necessary, be it a surfboard, kayak, sailboat, paddleboard, etc. Go apple-picking, golfing, paragliding, mountain biking, rock climbing, snorkeling, or kite-surfing. Heck, you can even join a naked volleyball game at the unofficial nude beach. 

• See Animals: It’s easy to make furry friends here. There’s of course the San Diego Zoo and their sister attraction, the Safari Park. Something’s fishy at Birch Aquarium and LEGOLand’s SEA LIFE. You can also experience animals in the wild while hiking, birding, taking a whale-watching tour, or simply going to a beach seals call home. Lqa Jolla and Cabrillo National Monument also have excellent tidepools.

• Explore pocket neighborhoods: Downtown is a good place for your trip’s home base, but it by no means paints the full picture of what the city has to offer visitors. Little Italy has a great farmers market, trendy nightlife, and quality cafes. Hillcrest is the heart of the LGBTQ community. The historic Gaslamp Quarter buzzes at all times of the day thanks to museums, theaters, restaurants, bars, and club. North Park, South Park, and University Heights are hipster havens with taprooms, taquerias, boutiques, and thrift shops.

Barrio Logan, once plagued by a bad reputation, is the epicenter of the city's Mexican-American culture and has become a hotspot for art. La Jolla, Del Mar, and Coronado are upscale enclaves with luxury hotels. And the beach-side hamlets, such as Ocean Beach, Encinitas, Carlsbad, and Solano Beach, are some of California’s chill-est.

Explore more attractions with our full-length articles on the best free fun things to do with kids, Balboa Park’s coolest attractions, and where to catch an outdoor concert.

What to Eat and Drink

Like most of California, the San Diego culinary scene is culturally diverse and heavily influenced by the immigrants who work there or have moved there. Given the city’s proximity to Baja—the border is less than 15 miles away from downtown—you can gorge on Mexican cuisine all day, every day. There’s gourmet, fast casual, fusion, and even vegan options. Area eateries especially excel at fish tacos aka battered and fried goodness wrapped in a soft tortilla with cabbage, salsa, crema, and lime. Also like the rest of California, there’s an emphasis on farm-to-table and pole-to-plate sourcing, which is easy to accomplish with access to fresh produce and seafood year-round.

It’s home to 6,000 small farms and the county is the leading avocado producer in the nation. Don’t forget to eat uni plucked straight from the sea, creative donuts, and the region’s other eight must-try dishes and ingredients.

It’s also the Craft Beer Capital of the US. There are so many breweries in town whipping up batches of West Coast IPAs, fruited sours, and just about every other suds style you can think of, that if you tried one a week it would currently take you more than three years to check every one off the list. If you prefer a chardonnay to a coffee stout, there are a handful of wineries in the county like Bernardo and both Temecula wine country and Baja’s Valle De Guadalupe are short road trips. Also if you are looking for something harder, the cocktail scene has vastly improved in the last five years.

Places like False Idol, Madison, and Noble Experiment are worth their weight in gold swizzle sticks.

Still hungry for ideas? Read about the best places to get fish tacos, five restaurants for romance, and the bars with the best views.

Where to Stay

It’s a big, busy city. Besides folks who come to enjoy everything we mentioned above, the city is also a military hub, home to several college campuses, and a popular convention city. Hotels are about 75 percent full on average, and more than 85 percent during the busiest months like July when 150,000 nerds descend on downtown, which drives up rates.  

Downtown has a lot of variety and is conveniently located near the airport and attractions. The enormous Hilton San Diego Bayfront recently updated its rooms and public spaces and is a great choice for people going to a convention or a baseball game (Petco Park is across the street). The Pendry is a luxury boutique in the center of late-night fun. The Intercontinental and The Guild Hotel offer chic stays within walking distance of Little Italy and the USS Midway. 

Other hotel clusters occur near the airport, in Mission Bay, and in Hotel Circle (just off the 5 and 8 freeways). Beach resorts and posh properties can be found in Coronado, Pacific Beach, and La Jolla. 

Renting an AirBnB can be a cheaper option. Many of the available rentals in Ocean Beach, Bird Rock, and other seaside cities are a short stroll from a beach or have private pools. There’s also many great campgrounds.    

Getting There

San Diego International (SAN), the second certified carbon neutral airport in the country, is less than three miles from the downtown core. There are nearly 500 flights a day to and from more than 60 nonstop destinations in the U.S. and abroad on 17 airlines. The city is also serviced by Grayhound and Amtrak, the latter of which has a gorgeous historic station in the heart of downtown and a track that often looks directly at the Pacific Ocean.

Public transportation is limited to a couple of Trolley lines, local commuter trains, and buses. Rideshares from companies like UBER and Lyft are readily available as are rentable bikes and electric scooters. But if you want to explore further afield ( i.e. to go surfing in Encinitas, apple picking in Julian, wine tasting in Mexico’s Valle de Guadalupe,) or are traveling with a large group, you’ll want the convenience of having a rental car.

Money Saving Tips

• Family fun can be had at a discount in October through the Kids Free San Diego program, which started 30 years ago with the zoo letting children in for free to celebrate the month it was founded. Now more than 100 companies including popular attractions like LEGOLAND and the USS Midway, restaurants, and hotels participate. Usually, kids get free admission or food, but some of the deals revolve around welcome gifts or product rentals. Age limitations vary between partners. 

• The almost year-round good weather means that visitors can opt outside and take advantage of free activities like going to the beach, hiking, running through Balboa Park or along the San Diego Bay waterfront, or bird-watching on a free Sunday walk at the Tijuana River Estuary.

• Be art smart by investigating which museums offer free-entry days or hours. Some only have free days for residents but having a local friend might be enough to get you through the door. The street art scene is also thriving thus creating an al fresco exhibition. Downtown, Little Italy, University Heights, and Barrio Logan (check out Chicano Park) are all neighborhoods with lots to look at and post to Instagram. 

• Invest in a Go San Diego pass. It promises to save holders up to 55 percent on gate and ticket prices at 48 attractions, tours, and experiences. To make the most of something like this, you and your travel companions have to be willing to pack your days fairly full.

• San Diego County is sprawling. In fact, it’s bigger than two states (Delaware and Rhode Island). If you want to see a lot of it, there’s no real option other than having a car. But if a trip is focused on a particular area or event, especially if said area is downtown or the Gaslamp Quarter, visitors should book a hotel in the area like the Hilton Sand Diego Bayfront and then walk, call a rideshare, rent a scooter or city bike, or use the MTS Trolley.

• SanDiego.org has compiled this list of 25 free things to do in town. See how it compares to ours

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