San Juan · SAILING
10 reviewed
Out of 10 sailing trips on the site, these 10 are the ones to book. Prices, durations and the details that set them apart are laid out below, so the choice takes minutes, not hours.
Snorkel Culebra’s reefs, then relax on Flamenco or Culebrita by fast catamaran from Fajardo, with lunch and drinks included.
“Capt Jose Fernando, Naher, Jean Paul, and Cindy gave us the best experience. Extremely attentive, this is our second time booking and this experience I must say was a 10 out of 10!!!!! Some of the nicest crew!!!”
Sail from Fajardo to Cayo Icacos on a Barefoot IV catamaran. Snorkel, swim, shell hunt, and enjoy a build-your-own picnic lunch.
“Trip was fantastic, staff were true shipmates, could not have been better! Reef at island is still recovering, but there are clear signs of new growth. Saw all the regular reef fish plus a moray eel and huge lobster!”
Six-hour catamaran day sail from Fajardo to Cayo Icacos for snorkeling, swimming, deli lunch, and rum cocktails with East Island Excursions.
“A beautiful and relaxing day trip to Icacos Island. Everything is super organized and efficient with the best captain and crews. You don't need to worry about a thing once you step onto the boat, and the island is absolutely gorgeous!”
Small-group San Juan Bay sunset sail past El Morro with captain stories, photo stops, and included beer, sangria, and rum punch.
“Beautiful evening! Ivan was wonderful! Very knowledgeable and friendly! Great drinks! We enjoyed every second! Highly recommend! Thank you Ivan!”
Small-group San Juan sunset catamaran with drinks included. Sail past El Morro and San Juan Gate for a chill, scenic 2-hour cruise.
“Catamaran smaller than I imagined. Also catamaran could use some updates. Hector and Nicola were informative . I thought the engine was a bit noisy. It was a nice two hours.”
Full-day catamaran from Fajardo to Culebra with snacks, lunch, drinks, and beach time plus kayaking or paddleboarding. Weather-dependent.
“Everything about this experience was wonderful . Quality of the equipment (boat, kayak, etc), brunch, attentiveness of crew, etc. Wonderful experience from beginning to end !”
Catamaran double-dip snorkel and beach day to Cayo Icacos from Fajardo, with guided reef stops, lunch, and all-day drinks.
“This boat excursion exceeded my expectations! I booked it for my best friend’s bachelorette party. Even though it wasn’t private, all 9 of us got to sit together and it was so much fun. I messaged the tour guide to schedule pick up from San Juan. They only pick up from major hotels, but that was no big deal. On the boat, the crew was amazing. They were friendly and had good energy. I loved snorkeling for the first time and the beach we went to was so nice. I am vegan and gluten free so I wasn’t really expecting to be able to eat the provided lunch, but I…”
A small-group, wind-powered daytime sail in San Juan’s bay with Old San Juan views, fort landmarks, and included drinks—about 2 hours.
“Our captain was very engaging, pointing out landmarks and interesting sights within the bay. His crewmanwas also knowledgeable. It was a laid back trip with just our group of 4. A new experience for all of us, which we enjoyed very much”
Sail from Fajardo to Piñeros or Palomino for snorkeling, beach time, and barbecue lunch with drinks on a small-group catamaran.
“Fun and relaxing day! We saw sea turtles and weren’t even expecting that. The food was awesome. Ashley and Captain Ricardo were super friendly and professional. The food was excellent and drinks plentiful and delicious!”
Luxury 54-foot catamaran cruise from Fajardo with guided snorkeling, rum drinks, and a real Puerto Rican lunch plus beach time.
“Be prepared to have a good time, however, be sure to bring sunscreen. The crew was phenomenal, accommodating, and very professional! #TheTypeThatDoesn’tSpray”
Catamaran day trip from Fajardo to Vieques with beach time, snorkeling, and a deli-style buffet plus rum and local beer.
“Had a really fun time with friends, and the crew was really accommodating and welcoming! Honestly would love to come again”
