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Spending a weekend in San Diego is almost always a good idea, if just because the weather is almost always fantastic. There is a surprising amount to discover in the closest major U.S. city to the Mexican border, so we think you’ll want to carve out enough time for at least a 3 day San Diego itinerary.
The best thing to do to plan your trip to San Diego is to ensure you’ve brought a car or hired a car. Like most of the U.S., there isn’t a great deal of public transport (and certainly below the standard Europeans and East Asians are used to), so you should expect to drive to the different areas during your trip.
Having said that, San Diego isn’t like LA in the sense that the distance and time between the places you’ll want to visit aren’t so great – especially if you follow our itinerary.
Where to stay in San Diego
There are a number of different sides to San Diego. Where you choose to stay in San Diego is certainly an important choice, but most of the places of interest in the metropolitan area are within a short drive of each other. Having said that, where you choose to base yourself will dictate the type of experience that you have.
(Village of) La Jolla
If you’re looking for more of an upmarket beach feel, there’s no better place than Village of Jolla (not to be confused with La Jolla Village which is due west of Village of La Jolla). It’s virtually a self-contained city with its own cove, tide pools, beaches, a huge variety of art galleries, and some of the best restaurants in San Diego more broadly.
The pick of hotels is unequivocally La Valencia Hotel with its elegant pink and orange hues set in a pretty historic building. When you’re heading toward La Jolla Cove, you quite literally cannot miss the Spanish-tiled tower known as the “Pink Lady.” The feel is somewhere between Mediterranean riviera retreat and Hollywood glamour.
Otherwise, Scripps Inn is a great choice if you’re willing to walk a little bit into the center of town, or Pantai Inn if you want to be literally steps away from La Jolla Cove. You can also find excellent little homes on Vrbo in the style of Spanish casitas dotted around the area. Village of La Jolla is also a great place for families.
Coronado
Coronado feels like something separate entirely from San Diego. There is only one bridge to get on and off the island which makes it slightly more difficult to be a base for exploring San Diego, but in return for a little bit of distance you’ll get charming cafes, boutique shopping and a real village feel. Hotels are pricier on Coronado, but it’s the top choice for families and beaches.
If money allows, we would choose Shore House at The Del for the ultimate luxury experience. Otherwise, check out 1906 Lodge for a Tuscan-style resort right in San Diego or Glorietta Bay Inn for top quality but without the price tag.
Hillcrest
Hillcrest is a little known area that has become both chic and hip in the past few years. If you want more of a city break feel than a beach feel (and you’re a foodie), Hillcrest is the right option. A particularly special option is Legacy Resort which delivers a five-star experience at a much lower rate per night.
Hillcrest is also the heart of San Diego’s LGBTQ+ community, and diversity often fosters entrepreneurship which means some of the best dining, shopping and nightlife is in Hillcrest. The area is also amazingly pedestrian-friendly which, if you’ve traveled in California, you will know is not so easy to find. The joy of Hillcrest is that there really is something for everyone.
Reconsider: Gaslamp Quarter
Many people will tell you that the Gaslamp Quarter is one of the best areas to stay in San Diego. The truth is that Gaslamp isn’t quite what it used to be. It feels grungier and dirtier than would otherwise be considered cool, and generally Gaslamp has been quiet in recent years. It feels a bit been and done, and most places in Gaslamp are in desperate need of rejuvenation.
There are still a number of great hotels in Gaslamp Quarter including The Horton Grand and Pendry which are both very pleasant experiences, but we think your time is best spent in other areas closer to the water.
Weekend in San Diego: 3 Day Itinerary
Day 1
Morning: Settle in
You’re going to need a moment to settle into San Diego. Carve out some time to get your bearings and make sure you’ve made all the reservations you need for your weekend in San Diego. Things get booked up, so you want to book everything in advance, whether restaurants or your kayaking tour.
Afternoon: Art and Airplanes at Liberty Station
Liberty Station is not what anyone expects it to be. It started life as a naval training center but has now been repurposed into a cultural hub filled with shops and stalls selling incredibly creative homewares, innovative food, and a number of interesting art galleries.
You absolutely must visit Liberty Public Market, a food hall housed in a converted naval building. It’s filled with some of the best of San Diego’s creative food scene, including some amazing Filipino food and fantastic empanadas. There are also great shops around the side of the market selling different wares for all occasions. It’s unequivocally the best place to buy a souvenir to take home.
Liberty Station is located immediately under a flight path. Yes, that means it can be quite loud, but it’s also one of the best places (in the world, possibly) to take a photo of a plane when it has just taken off. If you can handle the noise, it’s a pretty fantastic photo to take and will be a nice memento for your 3 day San Diego itinerary.
Evening: Mexican for dinner
For your first night, it feels right that you should have Mexican food. San Diego takes its Mexican food seriously, and the taco game is almost unparalleled this side of the border with Mexico. Your Mexican meals in San Diego will be remembered long after you’ve forgotten that hot sauce in San Diego is actually hot and you might have put a little too much.
San Diego boasts all levels of Mexican food. If you’re looking for something akin to fine dining (or at least more refined cuisine), Puesto creates artisanal tacos, bowls and salads. It’s more of an afternoon / early evening vibe, but no matter when you go, you’re guaranteed an excellent meal.
If you’d rather just throw yourself into Mexican food without the pomp, you absolutely must go to The Taco Stand which serves some of the best tacos in San Diego (and that’s saying something because there are many, many taquerias in San Diego).
Expect a queue at virtually at any time of day, but it moves quickly – and this will be one of the most memorable parts of your 3 day San Diego itinerary so you won’t be too upset.
If you need to keep your hunger at bay while queuing, pick up an empanada or two from Empanada Kitchen right next door. But really, just keep it at one or two, because the tacos are the main event, and you’ll be thankful you kept stomach real estate for them.
Day 2
Morning: Pancakes in La Jolla
I’m not really sure how pancakes became such a feature of the San Diego food landscape, but they have and I’m quite happy about that. San Diegans, as it turns out, take their pancakes very seriously; when in Rome, do as the Romans do, and that means eating pancakes by the water in San Diego.
One of the best restaurants for pancakes in San Diego is Richard Walker’s Pancake House who has been making pancakes for decades. The key standout item on the menu (and they’re not shy about it) is the baked apple pancake which is truly unlike any other pancake you’ll have tried. They really know what they’re doing here, so you can trust them with your calorie spend.
If you’d rather have pancakes outside of La Jolla, we recommend Breakfast Republic which consistently gets it right. You’ll almost always see a queue for Breakfast Republic, but one of the best ways to enjoy your pancakes is to get them packed up and to go sit by the water instead.
Afternoon: Get on the water
San Diego is nothing if not endless coastline, and the best way to enjoy that coastline is on the water. One of the best ways to spend a weekend in San Diego is to charter a boat or rent a kayak. There is so much amazing marine life to see in and around San Diego including sea lions, leopard sharks and shovelnose guitarfish (they’re as strange as they sound).
There is no shortage of companies offering boat charters and kayak tours around San Diego. What you really want to do is go on a guided kayak tour of La Jolla Sea Caves. You’ll get to paddle through the ecological reserve and explore the unique cave systems while getting an amazing lesson in marine biology from a local expert. Try to go to Clams’ Cave for some stunning views of the sandstone formations.
If kayaking doesn’t quite pique your interest, you can visit the San Diego Zoo in Balboa Park where the pandas have now returned to. The zoo leads in conservation efforts, and you can see some pretty spectacular wildlife in action – and seeing wildlife is essential on any 3 day San Diego itinerary.
Late Afternoon: Sea lion and seal spotting
Even if you feel you’ve had your fill of sea creatures, no weekend in San Diego would be complete without getting an ice cream (ideally from Bobboi which makes the best gelato in San Diego) and going to watch the sea lions and seals at Seal Rock. They sea lions and seals can be found all around the cove so you will catch them wherever you walk.
You can get so close you can touch them but I wouldn’t recommend that you do. It’s fun to just watch marine life laze around, sunbathing and enjoying the good weather. It might inspire you to move somewhere sunnier (they certainly did it). It’s great to see them in their natural habitat making sounds and interacting with each other.
Evening: A night out in Little Italy
We’ve said it before and we’ll say it again: the best place for a night out in San Diego isn’t, in fact, the Gaslamp Quarter, but rather Little Italy. This vibrant neighborhood has all the culinary delights your heart desires, a lively atmosphere and fantastic views over San Diego Bay if the food isn’t enough to keep you.
For dinner, if you’re looking for a real treat, we highly recommend Herb & Wood which consistently serves some of the best food in San Diego and will make your weekend in San Diego memorable. If you’d rather get into the spirit of Little Italy and eat Italian food, head to Mona Lisa or some of the best.
After dinner, we’ve got a couple of options for you: stay in Little Italy and get some craft cocktails at False Idol, or, if you like murals, Chicano Park in Barrio Logan is home to one of the largest collections of outdoor murals in the U.S. It’s an unexpectedly fantastic addition to a weekend in San Diego when you go at night because the park and the murals within it are light up beautifully.
Day 3
Morning: Breakfast and Surf
Do as San Diego locals do and start the day with a freshly squeezed juice (or pancakes, as we’ve suggested below). Head to Juice Wave right in the middle of Mission Beach for a particularly great start to your weekend in San Diego.
With your juice or smoothie in hand, go directly to the Ocean Front Walk. You can return to the shops on Mission Boulevard in the late morning (I promise), but for now, you really want to be soaking up the glory of a morning walk around Mission Beach, especially if the marine layer has cleared from the sky.
If you’re a true early riser and want to make the best of San Diego’s gorgeous waterfront, Mission Beach is one of the best places in California to surf. There are plenty of beginner surf lessons available if you want to try your hand (or balance, really) at surfing.
Afternoon: Lazy lunch at Seaport Village
The best way to finish your weekend in San Diego is to enjoy a lazy lunch at Seaport Village, a waterfront shopping and dining complex which boasts amazing views over San Diego Bay and Coronado. There’s a lot to choose from at Seaport Village, but the some of the best food and views can be had at Edgewater Grill.
You’re about to spend the rest of the afternoon shopping the streets of San Diego, so start with the unique shops in Seaport Village. There are some interesting stores in the complex including one that sells far too many hot sauce options.
Late Afternoon: Shopping in Hillcrest & North Park
There’s a reason why San Diegans leave their beachside suburbs for the inner areas of Hillcrest and North Park: they’re just cool. There’s super cool vintage shops, stores selling locally made crafts, and unique clothing boutiques that you can’t find elsewhere in the city.
The area immediately around 5th Avenue and University Avenue is the heart of Hillcrest. For North Park, you’ll find everything around 30th Street and University Avenue. There’s lots to keep you occupied in both areas, and a huge concentration of coffee shops to keep you going and plenty of bars catering to queer clientele to pass the time.
Evening: La Jolla Playhouse
Something you didn’t know you want to do during your weekend in San Diego is to watch a show at La Jolla Playhouse. In our view, it’s the best way to cap off your three days in San Diego. This is the launchpad of many a Broadway hit including two of my personal favorites, Come from Away and Bonnie and Clyde.
The thing about La Jolla Playhouse is that it’s easy to look past if you’re from LA or will visit LA and California as part of your trip. There’s just so much on offer in LA in terms of theatre, but some of the best theatre experiences are to be had at the smaller venues. La Jolla Playhouse also does an excellent job of showing theatre that relates to the area, with plenty of drag shows to reflect the character of the neighborhood.
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