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The Perfect Itinerary for 3 Days in Puerto Rico

3 Days in Puerto Rico Best Itinerary

What to do in 3 Days in Puerto Rico

Southern California may be our main muse, but did you know Puerto Rico is a close second?

Sara, CGS's founder, calls the island home for half of the year and is pretty much a walking guidebook of Puerto Rico tips!

Keep reading for her perfect 3-Day Puerto Rico itinerary. And save this post for the next time you’re itching to explore the Caribbean.

Ok, let's get into it.

Ocean Beach

Where to Stay in Puerto Rico:

The Ocean Park/Condado area! Lots of Airbnb and boutique hotel options. The closer to the beach, the better!

Day 1

Cafe Regina Puerto Rico

Breakfast at Cafe Regina

  • Get the Cashew Milk Iced Latte. It’s their best-selling coffee drink! They make their own cashew milk, blend it with two shots of espresso, organic maple syrup, and cinnamon.
  • All the food is delicious: the avocado toast, the almond butter toast, breakfast sandwiches, pastries, etc. They source their sourdough from a local bakery in San Juan too!
California Grip Socks Orange Stripes Classic Sock

Take a pilates or yoga class!

These all require a quick Uber or drive. Don’t forget your CGS socks ;)

Ocean Park Beach San Juan Puerto Rico Itinerary

Post-class, head to the beach:

  • My favorite beach is Ocean Park. The best beach in town. Light sand, super blue waters, and a high UV.
  • Have lunch/light bites/drinks at Numero Uno. It’s a casual beach hotel and restaurant. They have seating right on the beach!
Old San Juan Cobblestone Streets 3-Day Puerto Rico Travel Guide

Dinner & drinks:

  • Head to Old San Juan: cobblestone streets, colorful buildings, and a direct view of all the forts!
  • Go to Cafe Caleta for dinner. Everything on their menu is so good, you can’t go wrong.
  • Post-dinner, drinks and dancing at La Factoría: the most famous bar in the area! Grab a cocktail and get ready to dance. The bar has multiple rooms throughout with different music playing in each.
La Factoria

Day 2

Culebra Island Puerto Rico Travel Guide 3 Days

Boat day (go early!):

  • Drive out to Fajardo (or hire a driver) and rent a boat for the day to visit some smaller islands like Culebra, Palominos, or even Vieques. Your captain will advise which is best in terms of weather, wind, vibes, and timing!

Head back to San Juan for dinner:

  • Lala: an upscale restaurant in the Mall of San Juan. Robust menu with lots of great options and the ambiance is also really good. Fun fact: it’s co-owned by Bad Bunny!
Plumeria Flower Puerto Rico

Day 3

  • Walk to the Condado area and grab a coffee at La Hacienda and/or an açaí bowl at Açai Express!
  • Stop at Tres Palmas Surf Shop, a really cool surf shop in the Ocean Park area (they also have anything you would need for a beach vacation if you forgot it!).
  • Grab sandwiches at Kasalta Bakery in Ocean Park and head to the beach.
  • Lots of sports offered in OP: kite surfing lessons, beach tennis, beach volleyball. It’s also a lovely walk on the beach!

Dinner:

  • Cocina Al Fondo. A quaint restaurant with a gorgeous garden! Led by James Beard Award-winning Chef Natalia Vallejo (Best Chef South, 2023). Delicious Puerto Rican food, cannot recommend enough!

Dancing & drinks:

Cocina Al Fondo Puerto Rico

Other notable mentions if you have more time:

  • Anita’s Ice Cream: two locations in Condado and Old San Juan
  • Fidela Pizza: amazing pizza!
  • Paulina Escanes: get the burger (it has an English muffin bun!)
  • Malavita Sandwich Shop: in Old San Juan!
  • El Vino Crudo: really cute wine bar in Old San Juan! They have a small menu too with really good food.
  • Celeste Pt: seafood restaurant! Menu is always changing.
  • KUMO Rooftop Restaurant
  • Levain Bakery
  • El Panoteca San Miguel bakery
  • Get a surf lesson (if visiting during surf season, aka spring/winter)
  • Go to El Yunque Rainforest
  • Get a chocolate tour in El Yunque Rainforest
  • Explore towns west of San Juan: Isabella and Rincon!
  • Extend your trip and visit Saint Barthélemy! It’s a 45 minute flight from SJU.