The Ultimate Three-Day Weekend Guide To San Diego, CA
The Ultimate Three-Day Weekend Guide To San Diego, CA
Published February 28, 2023
San Diego is the perfect destination for a long weekend getaway! First and foremost, this laid-back city offers lovely warm weather all year round. San Diego is also the perfect size. It’s not a gigantic, sprawling metropolis, but it’s not so small that you’ll get bored after one or two days.
This blog post is a three-day itinerary for “America’s Finest City.” It features a ton of outdoor activities, food ideas, and visits to the city’s most iconic neighborhoods! To skip down to any day or particular attraction, click or tap on the corresponding link below.
Basic Information About San Diego
The city of San Diego is located on California’s southernmost stretch of Pacific coast, just north of the border with Mexico. It has a sunny and dry climate with relatively moderate temperatures in both summer and winter. While it may not be centrally located within the Continental US, a direct flight from Chicago only took about four hours.
A quick look at a map of San Diego reveals its main features: a rugged coastline, a massive park in the middle of the city (more on that below), and a waterfront downtown. All of these geographical aspects give the city a wonderfully unique vibe. It’s easy to explore all of this and more during a three-day visit!
Day 1
Balboa Park
Address: click for Google Maps link
Website: https://balboapark.org/
Facebook: https://www.facebook.com/BalboaPark/
Instagram: https://www.instagram.com/balboapark/
This huge park right next to the city center is a great place to get oriented after settling in to your hotel or Airbnb. It’s emblematic of everything San Diego has to offer: lots of nature, sun, and cultural attractions. El Prado, the main drive running through the park, is lined with about a dozen ornate museums and galleries.
Visiting all of the museums in Balboa Park would probably take at least half a week, but I decided to check out one: the Museum of Us (address | website), an anthropology museum housed in the exquisite California Quadrangle building. This museum showcased an interesting Mayan exhibit as well as Egyptian coffins, a history of beer, and more.
The Museum of Us and Japanese Friendship Garden both have entrance fees, but some of the museums on El Prado are free to visit! Check those out instead if you’re on a tighter budget.
Lunch in Hillcrest
After a morning of exploring Balboa Park, you’ll probably be pretty hungry! I recommend heading over to Hillcrest, a neighborhood directly to the northwest. Hillcrest is San Diego’s center of LGBTQ culture. Lots of great restaurants can be found along Fifth Avenue and University Avenue, the area’s two major cross streets. Below are some interesting places I tried.
Baja Betty’s
Address: 1421 University Ave, San Diego, CA 92103
Website: https://bajabettyssd.com/
Facebook: https://www.facebook.com/BajaBettys
Instagram: https://www.instagram.com/mosuniverse/
I loved the fun vibe of this cute Mexican restaurant! Given the name of the establishment, I figured this would be the perfect place to try a fish taco, and it did not disappoint! The entire combo plate I ordered was tasty, and their margaritas and bloody marys pack a punch.
La Vecindad Neighborhood Tacos
Address: 3827 Fifth Ave, San Diego, CA 92103
Website: https://www.clover.com/online-ordering/la-vecindad-san-diego
Facebook: https://www.facebook.com/lavecindadneighborhoodtacos
Instagram: https://www.instagram.com/lavecindadtacoshillcrest/
I’ve been learning Spanish off and on for a number of years, but I had to look up what this restaurant’s name means: vicinity or neighborhood. That really is a fitting name for this colorful Mexican restaurant! They have a large menu of tacos to choose from, so I got one fish, one shrimp, and one steak with nopales (cactus). All three were delicious and memorable!
Chiefy Cafe Hillcrest
Address: 1080 University Ave H105, San Diego, CA 92103
Website: https://www.chiefycafehillcrestca.com/
Facebook: https://www.facebook.com/Chiefycafe
Instagram: https://www.instagram.com/chiefycafe/
This was a nice place to get a quick breakfast sandwich before heading out for a full day of exploring.
Explore Embarcadero
After lunch on Day 1, I went over to Downtown San Diego and spent a few hours on the waterfront. There’s an abundance of parks, museums, and public squares along Harbor Drive. I meandered through Waterfront Park, Ruocco Park, Seaport Village, and Embarcadero Marina Park. If I had extra time, I would’ve probably come back this way to visit the USS Midway Museum, which is housed in an old aircraft carrier.
Dinner Downtown
After leisurely exploring San Diego’s downtown waterfront, I was starting to get hungry. I decided to have an early dinner at The Lion’s Share, an eccentric, low-lit bar and grill with unique meat offerings and craft cocktails.
The Lion's Share
Address: 629 Kettner Blvd, San Diego, CA 92101
Website: https://www.lionssharesd.com/
Facebook: https://www.facebook.com/LionsShareSD
Instagram: https://www.instagram.com/thelionssharesd/
Deciding what to order at The Lion’s Share was tough because so many of their plates sounded amazing! In the end, I couldn’t pass up their seared duck breast. The meat was incredibly tender, and the bed of green beans, eggplant, and mushrooms the duck was served on complimented it perfectly. To top it all off, this plate was served drizzled in a delicious tangy sauce!
The cocktails at The Lion’s Share were also masterfully mixed. I ordered two: a fruity rum-based drink and a moody pink libation with a pistachio rim. Their menu helpfully listed “Future Classics” in order from crushable to sippable. I believe this part of their drink menu is seasonal, but it’s also where the most interesting offerings are.
Day 2
Return to Downtown
One awesome thing about San Diego is that its downtown is pretty vibrant. In fact, according to one study, SD is at the top of the list of American cities when it comes to downtown post-pandemic recovery. This was pretty apparent to me as I was walking around the city center. Lots of people were out and about. It honestly felt safer than many other urban areas I’ve been to post-COVID.
One noteworthy part of Downtown is the Gaslamp Quarter. This historic entertainment district was interesting to walk through on Day 2, but it admittedly seemed quieter than the waterfront. I was told that it tends to come alive at night, but I didn’t make it back here during the evening to bar hop.
I will say the Gaslamp Quarter feels a little more grungy than other parts of downtown. However, the historic architecture here made up for that.
Lunch in Little Italy
San Diego’s Little Italy is a bustling, centrally located neighborhood that is absolutely worth exploring! It was fun to walk along India Street (Little Italy’s major north-to-south avenue) and see lots of people enjoying lunch or a coffee on one of many outdoor dining patios.
Filippi's Pizza Grotto
Address: 1747 India St, San Diego, CA 92101
Website: https://realcheesepizza.com/little-italy/
Facebook: https://www.facebook.com/filippislittleitaly
Instagram: https://www.instagram.com/filippis_pizza_grotto/
Choosing a restaurant in Little Italy is tough because there are so many enticing options. I eventually decided on Filippi’s Pizza Grotto, a California chain. Despite its name, I ended up trying the spaghetti (a lot of reviews online recommended it). The pasta was indeed good, but their garlic bread was the best part of the meal!
Dinner & Drinks in North Park
The neighborhood of North Park is named for its location directly northeast of Balboa Park. Given its distance from downtown and the waterfront, North Park feels more casual and local than other parts of the city. However, it still has a vibrant food and drink scene worth exploring! If I get a chance to go back to San Diego, I’d love to spend more time here.
Serpentine Cider
Address: 2311 El Cajon Blvd, San Diego, CA 92104
Website: http://www.serpentinecider.com/
Facebook: https://www.facebook.com/SerpentineCiderSD/
Instagram: https://www.instagram.com/serpentine_cider/
There’s no shortage of bars in North Park, and Serpentine Cider is an absolute gem! They had over a dozen enticing flavors of cider, so I had to get a flight. All five flavors were phenomenal, but the mango habanero and pumpkin pie really stood out. I really appreciated the fact that the ciders here have distinct, natural-tasting flavors without being overly sweet.
Underdog Food Truck
Address: 2404 El Cajon Blvd, San Diego, CA 92104
Website: https://www.underdogsd.com/
Instagram: https://www.instagram.com/underdog.sd/
If you’re looking for a little snack after a few drinks at Serpentine Cider, consider crossing the street and checking out Underdog Food Truck! An old friend who used to live in San Diego recommended this vegan food truck, so I ordered a hot dog. It was delicious, especially with a warm toasted bun!
Shank & Bône
Address: 2930 University Ave, San Diego, CA 92104
Website: https://www.shankandbone.com/
Facebook: https://www.facebook.com/people/Shank-Bone/100063579610736/
Instagram: https://www.instagram.com/shankandbone/
For dinner in North Park, I tried Shank & Bône. This Vietnamese restaurant serves classic dishes with unique meat-based twists. I ordered their phở, which came with oxtail and bone marrow. Oxtail is common in special (combo) phở, but bone marrow is not! I feel like it enhanced the soup more than anything.
Day 3
No San Diego itinerary is complete without some outdoor activities! Since I spent Day 1 and Day 2 exploring various parts of the city, I decided to spend almost all of Day 3 on the Pacific Coast. It was a long day, but I’m glad I did it!
Torrey Pines State Natural Reserve
Address: 12600 N Torrey Pines Rd, La Jolla, CA 92037
Website: https://www.parks.ca.gov/?page_id=657
Facebook: https://www.facebook.com/TorreyPinesStateBeach/
This large nature reserve on the north side of the city may seem like it’s out of the way, but don’t let that stop you from visiting. The views from up here are well worth the effort! I recommend getting dropped off at Torrey Pines State Beach and working your way south on foot. There are a number of different trail loops to walk along in the park. I hiked almost all of them, and it took about four hours.
What makes Torrey Pines so special? Well, the natural beauty of jagged cliffs right next to the Pacific Ocean is a major factor. You can see miles and miles of rock formations that line the coast to the north and to the south. The weather was excellent on the day I went, and Torrey Pines was honestly the highlight of my entire trip!
Lunch near Torrey Pines & UCSD
The one thing I didn’t love about Torrey Pines is that there are very few restaurants within reasonable walking distance of the hiking trails. On the south end, there are a few options scattered across a few business parks, so this is where I ended up eating a late lunch on Day 3.
Farmer & The Seahorse
Address: 10996 Torreyana Rd Ste 240, San Diego, CA 92121
Website: https://farmerandtheseahorse.com/
Facebook: https://www.facebook.com/FarmerandtheSeahorse/
Instagram: https://www.instagram.com/farmerandtheseahorse/
This trendy restaurant with a large outdoor patio is a little walk west of North Torrey Pines Road along Callan Road. I’m glad it ended up being good, because there weren’t many other choices nearby! I got a floral cocktail and a cold brew along with a burger and fries off their brunch menu. Everything was delicious, although it felt a little odd to be eating on the ground floor of some random biotech office building.
University of California San Diego
After lunch, I made my way down to University of California San Diego. I love visiting college campuses when I travel, but in all honesty, UCSD was a little less picturesque than I was expecting. The one thing that was impressive was the Geisel Library. This intriguing structure with a relatively narrow base is somewhat reminiscent of a flying saucer. It is open to the public if you’d like to check out the interior.
Torrey Pines Gliderport
Directly west of the UCSD campus is Torrey Pines Gliderport. This panoramic cliff offers nice views of the coast looking north, along with paragliders. I liked the Gliderport, but I would say it is not an absolute must, especially if you’re exhausted after a long day at Torrey Pines State Natural Reserve. I found the latter to be more impressive.
Sunset in Point Loma
I ended my final day in San Diego with a visit to Sunset Cliffs Natural Park in the seaside neighborhood of Point Loma. This area felt a little similar to Torrey Pines, but it was less green and more residential. It really is a phenomenal place to watch the sun go down over the Pacific Ocean!
Here are a couple of tips for Sunset Cliffs Natural Park. There are steep drop-offs here with minimal barriers, and I noticed lots of people getting precariously close to the edge. Be aware of that and keep some distance! In addition, there’s only one residential street that provides access in and out of the park. Traffic will almost surely be bad directly after sunset, and there’s probably not much you can do about it.
Lastly, this area was the only part of San Diego I visited where my cell service cut out. If you need to call an Uber or Lyft to leave, you may have to walk at least a few blocks north to Hill Street.
Tips & Final Remarks
Check out this last section for a few tips on how to get around San Diego!
Getting Around: Do you need a rental car?
The short answer is no. I knew I would end up using Uber and Lyft and spent a total of about $100 on all my rides in SD. I tried to minimize using rideshares though and walked whenever possible during my long weekend visit. With all of that said, $100 is a lot less than a rental car would be for three days.
San Diego also has a trolley (light rail) system with three lines that surprisingly covers a lot of distance, especially north to south. Unfortunately, it doesn’t travel to Hillcrest, North Park, or El Prado in Balboa Park. I was able to use the trolley on Day 3 to get from Torrey Pines down to Old Town, but then had to take a Lyft to get from there to Sunset Cliffs.
Why no mention of the San Diego Zoo or SeaWorld?
I think it’s fair to say that many visitors come to San Diego to see one or both of these famous attractions. If you’re curious why I didn’t include them on this itinerary, it’s because I honestly feel like I’ve lost interest in animal-related tourism, especially when it involves animals in captivity. I don’t have extremely strong feelings about the issue, but San Diego clearly has so much more to offer! I’m guessing most travel blog posts about SD probably focus heavily on SeaWorld and the zoo, so I have no problem highlighting other things to do in the city.
Where to Stay
I stayed in Hillcrest and found it to be pretty central. It was nice to be relatively close to Balboa Park and technically within walking distance. In retrospect, I feel like maybe I should’ve stayed somewhere near a trolley station, but the system unfortunately doesn’t go to Hillcrest or North Park. Overall, Hillcrest is a nice place to stay as long as you’re willing to Uber or Lyft at least some of the time.
Go Soak Up the Sun in Lovely San Diego!
If you’re looking for beautiful weather, lots of outdoor activities, and delicious food, San Diego can’t be beat for a long weekend! Especially if you live in the Midwest like I do, a short trip to San Diego can make the winter months a little less dreary!
What do you think of this three-day itinerary? Did I miss anything critical? Where should I go next time I’m in this beautiful SoCal city? Leave a comment below and let me know! Thanks for checking out Caffeinated Excursions!
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This post was published on Feb 28, 2023
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