The 15 Best Sailing Trips in Puerto Rico

1.Culebra Snorkeling Tour by Catamaran from Fajardo

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

Ride a high-speed catamaran from Puerto del Rey Marina to Culebra with East Island Excursions. Snorkel at Carlos Rosario or Luis Peña reserve, enjoy lunch and drinks, then swim at Flamenco Beach or Culebrita. Captains including Jose and Danny adjust the plan to sea conditions.

“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

Sail 45 minutes from Fajardo to Icacos aboard a catamaran for beach time, swimming, shell hunting, snorkeling, lunch, and drinks. The crew may include Captain Robert, Luis, Matthew, Edgar, Zoe, or Adrian. Expect a social boat day, not a quiet private charter.

“The staff was fantastic. Very friendly and very nice. The boat is just smaller, extremely limited in moving around, using the restroom you have to bend completely over etc. The staff took great care of us and it was a beautiful ride, but it is just a small catamaran which makes it less comfortable.”

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3.Icacos Island Catamaran Day Sail from Fajardo

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

Sail from Fajardo to Cayo Icacos aboard East Island Excursions’ catamaran for about six hours. Captain Jose, Carlos, Robert, and the crew may guide you to Icacos or Palominitos, with snorkeling gear, floating belts, lunch, music, and rum drinks included.

“Our catamaran excursion was the highlight of our vacation! We had the most gorgeous weather, the best crew and most incredible Captain, Jose! The food and drinks were delicious and it was 6 hours of non stop fun!”

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4.Historical San Juan Bay Sunset Sailing Tour

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

You’ll spend about two hours sailing San Juan Bay aboard a 30-foot J30 racer-cruiser with a captain such as Ivan or Joe. Expect close views of El Morro, Puerto Rican history, sunset photos, and complimentary beer, sangria, rum and Coke, water, and soft drinks. The boat carries no more than 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

Spend two hours on a 37-foot catamaran with a captain and first mate, sailing San Juan Bay at sunset. The group is limited to six, with rum punch, sparkling wine, beer, rum and Coke, soft drinks, juice, and water included. Expect views of El Morro Fort, San Juan Gate, and the old city from the water.

“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

From Safe Harbor Puerto Del Rey, you sail with East Island Excursions toward Culebra, Culebrita, Icacos, or Vieques. Expect about four beach hours, lunch, snacks, drinks, kayaks, paddleboards, and a crew led by captains such as Jose Perez. The exact beach depends on sea conditions.

“The ambiance in this boat is 🔥. The whole trip was a good time and Flamenco beach is beautiful. The best part is getting unlimited drinks 🍹”

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7.Icacos Double Dip Power Catamaran Snorkel & Beach Tour

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

Sail from Fajardo to Cayo Icacos aboard a capped-group power catamaran. You’ll snorkel a Puerto Rico reef, relax on a sandy beach, and enjoy lunch, soft drinks, juices, and rum cocktails. Crew members such as Kenny, Kiwi, Jay, and Gabriel are known for attentive service, but the reef stop depends on weather.

“Well organized fun trip. The crew took extra care to ensure we had a good time. Lunch and drinks provided were good. Met some fun people.”

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8.San Juan Historical Bay Daytime Sailing Tour

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

Sail San Juan Bay aboard a small authentic sailboat for about two hours with a captain such as Joe or Ivan. You’ll view Old San Juan, Castillo San Cristóbal, El Morro, La Fortaleza, and Isla de Cabras while enjoying beer, sangria, rum and Coke, and water. Expect real sailing, limited deck space, and a small group of up 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

From Puerto del Rey Marina, you’ll sail about an hour toward Piñeros or Palomino with a captain and first mate. Expect reef snorkeling, white-sand beaches, a floating lily pad, onboard barbecue lunch, fruit, snacks, beer, wine, sangria, and a group capped at six.

“Lovely day, very relaxing. Perfect food service and drinks. Very accommodating crew. Would do again.”

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

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

Sail from Fajardo aboard Getaway Too, a 54-foot catamaran limited to 49 people. You’ll snorkel with a guided clinic, relax on a beach in the Cordillera Cays, enjoy water slides and swings, and eat a Puerto Rican lunch. Captain Gabriel and Stephanie have been praised for warm, professional 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 Fajardo to Vieques in about 45 to 55 minutes, taking in El Yunque views before spending roughly four hours at a beach such as Sun Bay, Blue Beach, Green Beach, or Isla Yayí. Expect a deli lunch, rum, local beer, soft drinks, water, swimming, and snorkeling, with a friendly crew that may include Nathan, Alex, Luis, and Captain Christopher.

“Nathan, Alex, Luis and captain Christopher were very friendly. They made my friend’s birthday very special. We had a great time. Will definitely be back!”

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12.Puerto Rico Private Catamaran Sail from Fajardo

★★★★★★★★★★5.0 · 45 reviews

You’ll sail from Marina Puerto del Rey aboard a private catamaran for up to six people, with a captain and crew handling the boat while you snorkel, swim, sunbathe, and visit Cayo Icacos or nearby islands. Captains including Carlos González and Leo have received praise for thoughtful service.

“The views are exceptional. It’s private since Fajardo isn’t full of tourists. The yatch is comfy and the staff is excellent.”

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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 Fajardo with a licensed captain and crew. Visit Icacos, Palomino, or Piñero, swim, snorkel, enjoy a light lunch, and bring your own alcohol. The boat has shade, a bathroom, coolers, and room for up to six.

“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

Meet Captain Iván, Captain Charlie, and the crew at Puerto del Rey Marina for a three-hour afternoon sail aboard the Janise Lagoon 380. Swim from the anchored catamaran, enjoy snacks, beer, wine, sangria, and a sunset near Ramos Island. Groups of up to six can arrange a private charter.

“Ivan and Carlos were amazing hosts. Had such a great memorable experience. I will definitely be booking again the next time I’m in Puerto Rico.”

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15.Island Hopping and Snorkeling Sailing and Boat Tours Fajardo

★★★★★★★★★★4.5 · 13 reviews

Set sail from Fajardo with a private crew of sailors, instructors, and seamen for snorkeling, beach time, food, drinks, and music. Half-day trips can visit Cayo Icacos and Isla Lobos, while full-day outings may reach Vieques by request. Nomar, Laura, Lara, or Tyrone may lead your group.

“We were looking for a peaceful, picturesque trip and that is exactly what Tyrone delivered!! From laid back music, to light snacks and “not the normal” locations-It was great!”

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