San Diego Itinerary

San Diego is one of my favorite cities to visit. The weather is perfect. The people are friendly. There’s a TON to do. There are succulents EVERYWHERE. The food is delicious. I could go on and on and on…

Typically when I visit new cities, I do a lot of research beforehand by checking out blogs, Yelp reviews, TripAdvisor, etc. I don’t schedule activities, but I like to have options thought out, so I don’t have to use my brain too much while on vacation. I think my “itineraries” are super helpful, and I love sharing them with friends. I hope you can find something that looks appealing on this San Diego guide if you plan on making a trip there!

Did I mention that you will seriously love this city?


I recommend renting a car if you can because there are countless little cities close by. We stayed in Gaslamp 2 nights and La Jolla 2 nights, but you could easily stay in Gaslamp the whole time and drive to different spots if you’d prefer. There are tons of awesome cities no further than 30 minutes away.

Here’s some of my favorite restaurants/activities. The ones with a * next to them are my absolute favs.



  • Café 21!** It’s SO GOOD! We had brunch there, which was amazing but their dinner looked good too. Imagine colorful mimosa’s and whimsical looking brunch foods. Lots of healthy options. Make a reservation if you can.
  • Bars: SO MANY! Just walk around. Definitely check out the Altitude Sky Lounge for a cocktail. It’s on the roof of the Marriott.
  • SHOUT is a dueling piano bar. Go there.
  • BarleyMash – we went here for Happy Hour upon arriving in San Diego. The bar/restaurant is completely open so we snagged a high top and did some people watching while enjoying their great Happy Hour specials. We really liked this place with the lively music and prime location.


Little Italy: This amazing neighborhood is an inexpensive Uber from Gaslamp. It’s a must go. I’d say do cocktails, dinner, and stay out.

  • *Kettner Exchange – go upstairs and have a drink/apps on the rooftop!
  • Ironside Fish & Oyster. Really cool environment with interesting waiters. The food is awesome and fresh. (Reminds me of Prato for those of you from Winter Park, Florida).
  • Café Gratitude – Vegetarian and amazing.


La Jolla:

  • Torrey Pines obvi – This spot has great hiking with gorgeous views. You have to pay to park, but it’s worth it. The hike is actually pretty tough. Bring water and snacks.
  • Puesto is a yummy Mexican spot. Margarita’s are a must.
  • George’s at the Cove. Super nice restaurant with amazing views. Good for dinner and dessert. Pricey though. This was our anniversary date night on our trip. P.S. Order dessert. Your stomach will thank you. 


  • **The Cottage!! BEST BRUNCH. You will have to wait in line for like an hour… But worth it. Just go by and put your name in and then walk around.
  • Get an acai bowl at Juice Kaboose or Nekter! Or both!


Pacific Beach/Bird Rock Area:

  • Cool area to walk around and shop.
  • If you want to go out here, go to Beaumont’s for dinner and there will likely be live music at night. Also good for lunch!



  • Sunset Cliffs – just park along the highway and start hiking. It’s gorgeous!! Lots of surfers to watch.


  • Torrey Pines (mentioned above).



Go out to the Coronado Hotel and hang out all day. You’ll have to pay to park, but gorgeous beach and restaurants.


Unknown GEM! – Cedros Design District!

I love design, so this was an awesome area. There are a lot of interesting shops and coffee shops. It’s just a nice place to walk around. I’d compare it to a Park Avenue with fewer clothing stores. And, there are serious succulents everywhere. I wish I could have shipped them home to Florida.

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