San Diego

Itinerary + Recommendations (Updated: Sept. 2024)

Nicole M.
5 min readSep 4, 2024
Windansea Beach, Sunset Cliffs, La Jolla

Beaches and Outdoor Adventures

  • Windansea Beach — Stunning locals beach in La Jolla with huge waves that attract more advanced surfers. While there is a sandy beach, many opt to sunbathe on the flat cliffs next to the ocean. Visit the nearby Valley Farm Market for to-go snacks and drinks to bring to beach.
  • Coronado Beach — Family friendly, wide open beach that extends in front of the Hotel Del, where you can rent beach chairs and umbrellas (or reserve sunset s’mores bonfire). Coronado is an island within San Diego and also a popular training area for the Navy Seals.
  • Pacific Beach — The ocean-facing section has a boardwalk, bars, lively/party environment, tends to skew more towards college age; grab tacos and margaritas and sit out on beach and people watch. Alternatively, you can sit along the quieter bay (e.g., access beach at Dawes Street near ZLAC Rowing Club).
  • Sunset Cliffs Nature Reserve — Popular spot for watching sunset, but also beautiful during the day. Drive along the coast, park in reserve parking lot, walk trails or put a blanket down on cliffs for a picnic. You can also go down to the beach below.
  • Torrey Pines State Reserve — The Beach Trail is a scenic, mostly flat, takes you down to beach; really stunning and peaceful hike. Pay $20 to park near trail entrance to avoid the climb to the trailhead.
  • Torrey Pines Gliderport — Highly recommend paragliding — costs $175, no advance reservations needed. If you’re too scared to fly, still worth a stop to watch from the ground. There’s a food truck, bar, and usually, live music.
  • La Jolla Cove — Rent kayaks or surfboards from Everyday California (instructors, guided tours). Walk along the ocean to sea tons of sea lions basking on the rocks all the way down towards the “Children’s Pool”.
  • Surfing Lessons — Highly recommend “San Diego Surf School” for individual or group lessons. Lessons are in calm waters, mostly in the “whitewash” of Pacific Beach or Ocean Beach.
Lafayette Hotel, Marine Room, Madison

Restaurants

Little Italy — Very walkable and safe, blocks and blocks of restaurants and bars, including the following recommended spots:

  • Born & Raised — Steakhouse, also known for tableside martinis and carrot cake.
  • Kettner Exchange — Sit upstairs, great for pre-dinner cocktails and small plates during sunset hours.
  • Herb & Wood — Great cocktails and ambience; food is good, but not great (wood-fired with a Mediterranean influence).
  • Waterbar — Fun and lively dive bar, oldest bar in San Diego.
  • Pali Wine Co: wine bar

La Jolla— A few blocks of restaurants along the ocean, including the following recommended spots:

  • Duke’s — Hawaiian, go during day and sit outside for view of ocean
  • Marine Room — Go for drinks only, big glass windows facing ocean; perfect for sunset.
  • Puesto — Creative tacos, guacamoles, margaritas, etc. There are a few locations in San Diego.

Other

  • Lafayette Hotel — The decor is Beverly Hills meets New Orleans; roam around the different themed bars and restaurants, including a full bowling alley and old school game room, Mexican restaurant, and Great Gasby-esque jazz club.
  • Cesarina — Homemade Italian food (kitchen is surrounded in glass so you can watch them make your ravioli, etc. by hand).
  • Better Buzz — Local coffee chain with amazing iced coffees.
  • North Park and University Heights — Both are popular with locals. University Heights has Madison, Kairoa, and Stella Jean’s ice cream; North Park has Polite Provisions, Fortunate Son, Buona Forchetta, and An’s Dry Cleaning (ice cream).
  • Convoy Street — Very popular area for Asian food (go for food, not aesthetic since it’s mostly strip malls).
  • Avoid Gaslamp area unless you’re looking for a bar before or after a Padres baseball game.
  • San Diego is famous for the “California burrito” (has French fries inside), carne asada fries, and over a hundred breweries!
Bottaia Winery, Joshua Tree, Ocotillo Desert

Beyond San Diego

  • Temecula Wineries — There are a ton of wineries about an hour from San Diego. Highly recommend Bottaia (sit outside, stunning view, also has pool) and Miramonte (good for lunch). There are also olive farms with olive oil tastings in this area.
  • Ocotillo — Book a guided ATV tour through the desert. Fun at all hours, but particularly beautiful during sunset.
  • Joshua Tree National Park — Since this is almost three hours from San Diego, recommend making this an overnight trip (check out the Pluto House Airbnb with an outdoor tub). Top spots within the park include the Cholla Cactus Garden and Hidden Valley Nature Trail. Other popular spots include the Integratron for a relaxing sound bath (books up quickly, so book in advance) and Pioneertown (visit Pappy and Harriet’s for live music).
  • Palm Springs — Famous for mid-century modern houses and resort pools; tons of hiking options if you’re visiting in non-summer months.
  • Catalina Island — Ferry ride from San Diego to Avalon (resort town); very popular for scuba diving.

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Nicole M.

Emergency Manager | Humanitarian | Rebel with a Cause | NOLA Proud