The 15 Best Sailing Trips in Puerto Rico

1.Culebra Snorkeling Tour by Catamaran from Fajardo

★★★★★★★★★★4.5 · 2,534 reviews · from $180Our pick

You’ll cruise from Fajardo to Culebra with East Island Excursions, snorkeling at Carlos Rosario or Luis Peña reserve before lunch and beach time. Captains Jose, Danny, and Jose Fernando are among the crew named by past passengers. Expect shared seating, a possible rough ride, and a choice of Flamenco Beach or Culebrita based on weather.

“This was an excellent, once in a lifetime experience. We were fortunate to be taken to Culebrita on the day we went. Literal paradise! The seas sickness is real! Definitely prepare yourself as you might experience motion sickness. But once you pass that, 10/10 experience!!!!”

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2.Icacos Deserted Island Catamaran, Snorkel, and Picnic Cruise

★★★★★★★★★★5.0 · 2,202 reviews · from $138Top rated

From Fajardo, you sail about 45 minutes aboard the Barefoot IV Catamaran to Icacos or a nearby Fajardo Key. Swim, snorkel with supplied gear, stroll the beach, and enjoy a cold lunch with water, sodas, piña coladas, and rum punch. Captain Robert, Luis, Matthew, Edgar, and the crew are known for attentive service and a lively onboard atmosphere.

“The staff was good (2 people). Switched our boat to a smaller one. Hard to get around. Very small up front and tight to go around to the back. No covered area. No rum punch, just pina coladas (not blended). Snorkeling was nice and the beach. Just wish they had more options for drinks.”

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3.Icacos Island Catamaran Day Sail from Fajardo

★★★★★★★★★★5.0 · 1,483 reviews · from $140

Set sail from Puerto del Rey Marina on a six-hour catamaran trip to Cayo Icacos, or Palominitos when sea conditions require it. Swim, snorkel with provided gear, relax on the sand, and enjoy a deli buffet with rum drinks, juice, and soda. Captains Jose and Carlos and crew members such as Neff, Adrian, and Andres have been praised for warm, careful service.

“Crew was amazing I loved the beach/island I loved everything about this day and the hospitality was greats”

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4.Historical San Juan Bay Sunset Sailing Tour

★★★★★★★★★★4.5 · 710 reviews · from $115

Sail San Juan Bay for about two hours aboard a 30-foot J30 racer-cruiser, passing El Morro and the harbor as the sun drops over the Caribbean. Captains such as Ivan and Joe share local history, take photos, and serve beer, sangria, rum and Coke, water, and soft drinks. The boat is small, sporty, and limited to six people.

“What an incredible experience! The sunset sail was intimate, relaxing, and absolutely beautiful. Our captain was interesting, knowledgeable, and genuinely funny—he brought so much personality to the trip and made the whole experiRead more”

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5.San Juan Catamaran Sunset Sail with Drinks Included

★★★★★★★★★★5.0 · 622 reviews · from $119

Settle aboard a 37-foot catamaran at San Juan Bay Marina for a two-hour sunset sail limited to six people. Your captain and mate point out El Morro, San Juan Gate, and the executive mansion while serving rum punch, sparkling wine, beer, and soft drinks. Shoes come off before boarding, and the cruise returns to the same dock.

“The friendly and courtesy staff. The small amount of guest on the sail not crowded! The drinks were great!”

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6.Culebra Full Day Beach and Fun Experience by Catamaran

★★★★★★★★★★4.5 · 563 reviews · from $195

Sail from Fajardo toward Culebra, Culebrita, Icacos, or Vieques, depending on sea conditions. You get about four hours at a beach, lunch, snacks, drinks, kayaks, paddleboards, and beach games. The crew, including Captain Jose on some departures, keeps the day lively and organized, though rough seas and shared seating are part of the deal.

“If you are visiting PR for the first time, this is a must! Nael and the rest of the crew were very friendly and accommodating since the start of the tour. Unlimited food and drinks since there were around 15 people. We were lucky enough to have the beach for ourselves for a few hours. Definitely worth it!”

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7.Icacos Double Dip Power Catamaran Snorkel & Beach Tour

★★★★★★★★★★5.0 · 236 reviews · from $135

Set out from Fajardo on a power catamaran for reef snorkeling in the Cordillera Cays Nature Reserve and beach time at Cayo Icacos. The crew supplies masks, fins, lunch, water, juices, sodas, and rum drinks. Captains and crew members may include Jay, Gabriel, Kenny, Kiwi, Luis, or Penelope, depending on the sailing.

“One of the only boat tours I found that allowed children under 3 which was perfect for our family traveling with kids ages 1-11 years old. We had an amazing time! Highly recommended for families!”

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8.San Juan Historical Bay Daytime Sailing Tour

★★★★★★★★★★4.5 · 173 reviews · from $99Best value

You’ll sail San Juan Bay aboard a small J30 racer cruiser, not a motorized sightseeing boat. Captains such as Joe or Ivan may point out Old San Juan, San Cristóbal Castle, El Morro, Isla de Cabras, and the Governor’s Mansion while you enjoy beer, sangria, rum and Coke, and water. Groups are limited to six.

“It was a super fun time. We sailed while our tour guide explained a lot about Old San Juan and other parts of Puerto Rico that we passed.”

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9.Sailing and Snorkeling Day Charter in Fajardo, Puerto Rico

★★★★★★★★★★5.0 · 144 reviews · from $285

Spend about five hours aboard a small catamaran from Fajardo with Captain Ricardo, Captain Bill, Monica, Ashley, or another professional crew member. You may sail to Piñeros or Palomino, snorkel quiet reefs, swim near sea turtles, relax on a beach, and enjoy a cooked Puerto Rican lunch with beer, wine, sangria, and soft drinks.

“We had such an amazing experience, from start to finish the day was exceptional! The food and drink was a great addition to a wonderful day. We felt so relaxed having so many options of what to do, where to sun and sit while sailing. The intimacy of the day made it even more memorable. Our Captain, Ricardo, and First Mate Scott were attentive, welcoming and knowledgeable. We felt very safe; would highly recommend this excursion!”

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10.Icacos: Luxury Sailing Catamaran All Inclusive Beach and Snorkel

★★★★★★★★★★5.0 · 96 reviews · from $195

Sail from Fajardo aboard the 54-foot Getaway Too, limited to 49 people. Swim and snorkel near Icacos and the Cordillera Cays, use the slide and water swings, then enjoy a Puerto Rican lunch, tropical rum drinks, and sorbet. Captain Gabriel is among the captains praised for attentive service.

“Meet up in the morning was easy. The staff was wonderful and made sure we had everything we needed the entire trip. The drinks were yummy and the food was delicious. It was great that it was authentic food and not just cold cuts like others offered. They had plenty of floating devices, two swings, a slide, and Frisbee and balls. Seating was cozy for the trip in and out. It rained and we all had enough room for cover and party continued anyway!”

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11.Beach and Snorkeling Tour by Catamaran from Fajardo

★★★★★★★★★★5.0 · 58 reviews · from $180

Sail from Marina Puerto Del Rey to Vieques in about 45 to 55 minutes, with El Yunque views along the way. Your crew chooses a beach such as Sun Bay, Blue Beach, Green Beach, or Isla Yayí for swimming, beachcombing, and snorkeling. Lunch, water, soda, rum, and local beer are included. The boat returns to Fajardo.

“Our trip to Vieques with East Island Tours was absolutely unforgettable! The tour guides were fantastic—always attentive, super friendly, and full of energy, which made the whole day even more enjoyable. The beach itself is breathtakRead more”

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12.Puerto Rico Private Catamaran Sail from Fajardo

★★★★★★★★★★5.0 · 45 reviews

Sail from Fajardo’s Puerto del Rey Marina on a private six-hour catamaran charter for up to six people. Your captain and crew handle the day while you swim, snorkel, paddle board, or relax near Icacos, Pineros, Lobos, or Palominos. Snorkeling gear is included, and lunch is optional.

“Captain Leo & Hiram go above and beyond to make this trip a once in a lifetime tour. They meet you at the reservation desk you take a golf cart over to the boat they cater to every need every moment of the trip. The food is amazing and caRead more”

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13.Private Luxury 36′ Yacht from Fajardo to Icacos or Palomino

★★★★★★★★★★5.0 · 25 reviews

Spend six private hours aboard a 36-foot yacht from Puerto Del Rey in Fajardo. Your captain and crew take your group of up to six to Icacos, Palomino, or Piñero. Expect shaded seating, a bow for sunbathing, a cabin bathroom, snorkeling gear, snacks, lunch, water, soda, and a dog-friendly setup. Karina helps coordinate the details.

“Honestly, amazing family run company, well organized and super friendly and accommodating. Would absolutely recommend to anyone who is in the area. Karina was super helpful and attentive and reached out to coordinate everythiRead more”

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14.Janise Sailing Afternoon Charter in Fajardo, Puerto Rico

★★★★★★★★★★5.0 · 14 reviews · from $229

Sail from Puerto del Rey Marina aboard the Janise Lagoon 380 with Captains Ivan and Charlie. You’ll cruise near Fajardo, anchor for swimming and snacks, and watch the sunset with Ramos Island behind you. The three-hour charter serves water, soda, beer, wine, and sangria. It is shared unless six people or a private upgrade are booked.

“Amazing experience! Such a friendly crew. Very relaxing. The private island and sunset were beautiful”

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15.Island Hopping and Snorkeling Sailing and Boat Tours Fajardo

★★★★★★★★★★4.5 · 13 reviews

Book a private Fajardo sailing trip for up to six people with Ouuttahere Tours. Your crew may visit Cayo Icacos, Isla Lobos, or Vieques, with snorkeling gear, food, drinks, music, and time on the beach. Guides including Nomar, Laura, Lara, and Tyrone have been praised for friendly service and flexible help on the water.

“Great time in a great location. Nomar and Lara were great. Current was a bit too strong for me, but the girls said the snorkeling was cool. Lunch was great! Glad we just went out in a small group.”

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