Located along the coastline of sunny Southern California, you’ll find San Deigo 190km south of Los Angeles and immediately adjacent to the border with Mexico. With an estimated population of over 1.4 million, it may surprise you to learn it is the eighth-largest city in the US and the second-largest in California. With over 70 miles of beaches perfectly placed along the Pacific Ocean, fantastic weather and over 100 unique neighbourhoods, it’s the ideal spot for travellers. We spent a few days exploring colourful San Diego, sampling delicious food and getting a sense of its fascinating past, present and future. To help you plan an amazing adventure of your own, here are 19 of the very BEST things to do in San Diego!

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1. Drive your own speedboat

Climb behind the wheel of your very own speedboat and explore San Diego from the water in this awesome DIY adventure! Don’t worry, you’ll be under the watchful eye of an experienced skipper who leads the tour via radio, with all the guests following behind him in a convoy. We loved the sense of freedom and adventure the tour gave us and it was an awesome way to see San Diego from a different angle. Tours run for around 1.5 hours with up to three people per speed boat, visiting spots like the USS Midway, Coronado Bridge and Star of India. You’ll also get a chance to spot some pretty cute seals too!

We booked our Drive Yourself Speedboat Adventure Tour here

2. Visit the USS Midway Museum

Located in Downtown San Diego, the historic USS Midway Museum isn’t your average museum! We only had an hour to spend here but could have very easily spent much longer. The naval aircraft carrier museum is home to an extensive collection of over 30 restored aircraft, many of which were actually built in Southern California. You get up close and personal with helicopters and jets and can explore all the corners of the carrier, getting a sense of what life is like onboard for Navy personnel. Be sure to brush up on your Top Gun references, just in case!

We booked Skip the Line tickets for the USS Midway Museum here

3. Check out the Gaslamp Quarter

As the sun begins to set and the need for dinner and drinks begins to rise, be sure to check out the Gaslamp Quarter in Downtown San Diego. The 16 1/2 block historical neighbourhood is the historic heart of San Deigo and the hub of entertainment for travellers. You’ll find no shortage of nightlife including plenty of great pubs, bars and live music venues to choose from. If thrills are your thing, The Escape Game in Gaslamp is a must-visit. With its multiple themed rooms and exciting challenges, it’s the perfect destination for adrenaline junkies. Whether you make it out or not, you’ll have an absolute blast!

Book tickets for The Escape Game here

Gaslamp Quarter, San Diego ©Little Grey Box
The vibrant Gaslamp Quarter

4. Listen to live music at Prohibition

If you love good music and great drinks, be sure to visit Prohibition in the Gaslamp Quarter. This secret bar is an absolute must-visit and one of the highlights of our trip! You could easily walk past the hidden entrance, nestled on Fifth Avenue,  disguised by a door marked ‘Law Offices of Eddie O’Hare.’ Push through the door and wander downstairs where you’ll find a world of incredible live music! We visited on a Friday night and were treated to an evening of the blues, performed by talented local artists, paired perfectly with delicious cocktails crafted by knowledgeable bartenders. As I said, it was a highlight and definitely one of our top recommendations!

Prohibition Hidden Bar, Gaslamp Quarter, San Diego ©Little Grey Box
Prohibition was a trip highlight!

5. Visit Starry Lane Bakery

I know how hard it can be travelling with specific food allergies or preferences. On our trip to San Diego, I wanted to make sure I found at least one great food spot that everyone could enjoy. You’ll find Starry Lane Bakery on 4th Avenue, in the heart of Hillcrest, San Diego. Everything, EVERYTHING, at Starry Lane is free of gluten, soy, dairy, eggs, tree nuts, peanuts, fish, and shellfish, as well as being free of all artificial food dyes! Of course, this begs the question, “Does it taste good?” Well, you guys, given I inhaled my mocha cupcake in approximately 5 seconds then went back and ordered more, I can confirm that yes, the food here tastes amazing! The bakery is very understated given the deliciousness it serves up, including goodies like cookies, muffins, scones, tarts, amazing cupcakes, brownies, incredible fresh bread and so much more! Best of all, the bakery doesn’t allow any outside food onto the premises and prepares everything in-house so there’s no risk of cross-contamination for those with life-threatening allergies. It’s a must-visit for anyone travelling to San Diego with severe food allergies or vegans with a sweet tooth! 

 Starry Lane Bakery, San Diego ©Little Grey Box
Starry Lane Bakery is perfect for those with food allergies.

6. Wander around Old Town

Created in 1769 as California’s first settlement, Old Town truly is the historic heart of San Deigo and is often referred to as the ‘Birthplace of California.’ You may like to wander around the gardens, explore colour shops and boutiques, listen to live music and grab a bite to eat! We had dinner at Cafe Coyote, one of the area’s most famous restaurants and a great spot for a sunset dinner. The service was fantastic, the margaritas ice cold and the food delicious.

7. Eat at Carnita’s Snack Shack

San Diego is the birthplace of Cali-Baja cuisine, a fusion of the traditional Mexican and Mediterranean influences associated with Mexico’s Baja Peninsula. For visitors, this means an abundance of delicious, fresh food and I’m going to insist you eat as much of it as possible because each restaurant offers something different! Matt’s favourite spot was Carnita’s Snack Shack, located in Downtown San Diego. Located right near the USS Midway Museum, it’s the perfect post-visit lunch stop. The service here is fantastic and the food is absolutely delicious, offering up mouth-watering tacos, American-style sandwiches, salads, share plates and daily specials too. Matt claimed it was the best taco he’s ever had!

8. Watch the sunset at Sunset Cliffs

Dedicated in 1983, the Sunset Cliffs Natural Park is a 68-acre City of San Diego Regional Park, extending 1 1/2 miles along the Point Loma Peninsula’s western shoreline. On a sunny day, it’s the ideal spot to take in the incredible ocean views, dramatic cliff formations and explore some of the unique caves in the area. Savvy travellers might like to grab some food to go or pack a picnic before heading to Sunset Cliffs as it truly is a great spot to just sit and soak it all in. We loved it as a great photo spot, snapping off some great images of California’s iconic coastline.

Sunset Cliffs, San Diego ©Little Grey Box
Sunset Cliffs

9. Check out Ocean Beach

My advice to travellers wanted to experience San Diego’s beaches is to do a beach crawl! We started ours at Sunset Cliffs then made our way to Ocean Beach then Pacific Beach and onto La Jolla. All of these neighbourhoods line up in a nice little string, easily found by hire car, as we did. Ocean Beach, known lovingly as OB, is a vibrant, bohemian neighbourhood with a classic SoCal beach vibe. The Ocean Beach Pier is a great spot to visit, followed by a stroll along the main street, stopping in at any spots that catch your eye. Keep your eye out for the Ocean Beach Farmers Markets held each Wednesday from 4-8 pm and consider a visit to Hodad’s, purported to be home to the ‘World’s Greatest Burgers!.’

10. Take a trip to Pacific Beach

The next stop on our DIY beach tour was Pacific Beach, dubbed PB by the locals. The relaxed beachside neighbourhood is home to trendy hotel bars and casual cafes lining the boardwalk. Mission Boulevard and the surrounding streets are a must-visit for shoppers as they’re dotted with clothing boutiques, yoga studios and fabulous casual drinking spots. There are also three miles of boardwalk, making it an ideal spot to hire a vintage cruiser and cycle along the foreshore.

Sunset Cliffs, San Diego ©Little Grey Box
Sunset Cliffs

11. Wander around La Jolla

Our beach tour ended in up-market La Jolla, a coastal town renowned for its gorgeous beaches, posh boutiques and fantastic restaurants. After a quick visit to the sea lions at La Jolla Cove, we wandered up to the main street to explore the high-end stores. Nicknamed “The Jewel” of San Diego, you’ll find no shortage of upmarket spots to visit and great cafes, bars and restaurants to try. It’s also the gateway to the Torrey Pines Nature Reserve, another stunning spot to check out, should time permit.

12. Eat at Puesto

We ate a lot of great food in San Diego but our meal at Puesto in La Jolla was a real stand-out for me! This carries extra weight because Mexican food is pretty much what my entire life is all about. The restaurant’s understated exterior doesn’t quite prepare you for the delicious treats that lay within. I loved the mouth-wateringly good tacos and their unique take on guacamole and margaritas! A lot of restaurants try to mess with the classics and get it all wrong but Puesto absolutely nailed it! I got to experience some of my food favourites in new and exciting ways and, if I could, I’d be eating there at least once a week.

13. Take a trip to the San Diego Zoo

If you’re travelling with little kids or you just love animals, then you really need to visit the world-renowned San Diego Zoo! Home to more than 3,500 animals of more than 650 species and sub-species the zoo was one of the pioneers of open-air, cageless exhibits aimed at re-creating natural animal habitats. It has also been voted the #1 zoo in the world! We got to do a guided, ‘Inside Look,’ tour and, if you have the time and budget, it’s something I highly recommend. We got to go behind the scenes of the San Diego Zoo, gleaning a wealth of knowledge from our incredible guide, seeing things others don’t and gaining a deeper appreciation and respect for the animals, keepers, scientists and activists involved.

We booked our 1-Day Pass for the San Diego Zoo here

14. Explore Balboa Park

For those with a love of cultural experiences, a visit to Balboa Park is a must. Originally called ‘City Park,’ Balboa Park was renamed after Spanish explorer Vasco Núñez de Balboa, in honour of the 1915 Panama-Calfirona Exposition, held in the park that year. It was later declared a National Historic Landmark and is on the ‘Great Places in America,’ list. For visitors, you’ll want to kick things off with a visit to the information centre so you can grab a map and figure out a plan of adventure! We grabbed a bite to eat at Panama 66, rode around on scooters, checked out the Japanese Garden and nearby amphitheatre but there is so much more to see and do! There’s a wide range of galleries, museums, gardens and attractions suitable for all ages.

15. Check out Hillcrest and North Park

The vibrant, uptown neighbourhood of Hillcrest stands as San Diego’s LGBTQIA+ hub, home to an array of bars, restaurants, coffee houses, boutiques and unique shops. If you love thrifting, there are quite a few trendy thrift stores in the area as well. Nearby North Park is a hipsters hangout, bursting with sushi spots, great coffee shops and brunch spots, craft beer bars and indie boutiques lining University Avenue. We checked out the North Park Thursday Market, held each Thursday from 3-7:30 pm, then headed to Waypoint Public an award-winning gastro pub (which unfortunately has since closed) for a delicious dinner.

Waypoint Public ©Little Grey Box
Waypoint Public

16. Soak in the views at the Cabrillo Monument

Our visit to the Cabrillo National Monument was one of the unexpected highlights of our trip! Commemorating the landing of Juan Rodriguez Cabrillo at San Diego Bay on September 28, 1542, it marks the first time a European expedition had set foot on what would later become the West Coast of the United States. Visitors will love the stunning views of the water and San Diego, just as we did! It was a great opportunity to learn about San Diego’s history, spot different types of Naval ships and use the views to gain a better appreciation for the city and natural beauty of California. There’s a fee of US$20 per vehicle, which you pay on the way into the area.

17. Feast at Liberty Public Market

If you love food as much as we do you’ll definitely want to visit the Liberty Public Market! Set in a 1920s-era naval base commissary in San Diego’s Liberty Station neighbourhood, it brings over 30 local artisans and retailers together. We had to cut at least 4 laps around the place as we tried to figure out which food we wanted to try, there was so much good stuff to choose from! I would definitely recommend arriving hungry and choosing a whole bunch of dishes to share and try as a group.

18. Grab a bite at In-N-Out Burger

Iconic California food experiences and photo opportunities don’t come much better than a visit to In-N-Out Burger! Opened in 1948 by Harry and Esther Snyder, In-N-Out was California’s first drive-thru hamburger stand. Since then, it’s grown into a beloved fast-food joint and, weirdly, something we’re drawn to try as travellers! To me, it kind of perfectly represents the fascinating aspects of American culture and how we see something so many times online and in movies that it comes to embody a uniquely American experience.

In-N-Out Burger
In-N-Out Burger

19. Plan a trip to Joshua Tree

As part of our visit to San Diego, we added on a three-night trip to Joshua Tree. It was something that had been on our travel bucket list for a very long time and we figured if we didn’t do it while we had the opportunity, we may never get around to doing it! If you’ve ever dreamed of visiting Joshua Tree, your trip to San Diego is the perfect time to do it. You can find all the information you need to plan your very own trip or just figure out if it’s something you can do by reading this: The BEST guide to California’s Joshua Tree + National Park. 

Joshua Tree National Park ©Little Grey Box

Joshua Tree National Park

Where to stay in San Diego

During our time in San Diego, we stayed at Kona Kai Resort and Spa. Situated on Shelter Island, we loved the location as it was close enough to everything to allow easy access but far enough away that we felt like we could truly relax and unwind. We stayed in one of the recently refurbished Standard Suites and absolutely loved our room! It was incredibly spacious with a very generous-sized bathroom complete with twin basins, a huge shower and a lovely bathtub. The bed was ridiculously comfortable, so much so that you just kind of sink into it and feel all your troubles melt away. The views over the harbour were fantastic and while we didn’t have time to enjoy them with all our sightseeing, there’s also a fitness centre, on-site restaurants and an adults-only pool to check out! We thoroughly enjoyed our stay and highly recommend Kona Kai based on our fantastic experience.

Book Kona Kai Resort and Spa here

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