12 Puerto Rico Sailing Tours for the Logbook

1.Icacos Island Catamaran Day Sail from Fajardo

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

Sail from Puerto del Rey Marina to Cayo Icacos, or Palominitos if weather shifts. East Island Excursions provides snorkel gear, float belts, lunch, rum drinks, and friendly crew support. Expect about six hours, a group of up to 70, and easy water time for beginners, with snorkeling quality shaped by sea conditions.

“We had such a wonderful time on the Icacos Island tour. The boat ride was smooth, the island itself was absolutely stunning, and the water was perfect for swimming and snorkeling. The crew provided great service, delicious drinks, and plenty of good vibes. It was the highlight of our trip—highly recommend!”

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2.Historical San Juan Bay Sunset Sailing Tour

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

Spend about two hours sailing San Juan Bay aboard a 30-foot J30 racer-cruiser with a captain such as Ivan, Joe, or Carlos. Expect views of El Morro, harbor traffic, sunset photos, local stories, and complimentary beer, sangria, rum and Coke, water, and light refreshments. This is an authentic sailing trip, not a yacht party or catamaran cruise.

“It was such a great sailing experience with Captain Ivan. He told us a lot of history about the island and great spots to go to after the tour was over.”

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3.San Juan Catamaran Sunset Sail with Drinks Included

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

Spend about two hours on a 37-foot catamaran in San Juan Bay, with a maximum of six people aboard. Your captain and mate point out El Morro, San Juan Gate, and other waterfront sights while serving rum punch, sparkling wine, beer, soft drinks, and water. The boat may sail or motor, depending on wind.

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

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4.San Juan Bay Day Sail with Drinks Included

★★★★★★★★★★5.0 · 502 reviews · from $99Best value

Spend 90 minutes aboard a traditional sailboat with a captain and mate, limited to six people. Sail from San Juan Bay Marina, enjoy a rum punch, mimosa, beer, soda, or rum and Coke in moderation, and see San Juan’s waterfront and last remaining city gate from the water.

“I highly recommend this boat tour. 10/10, no complaints. Variety of drinks and amazing sights seeing/explanations of the Historic District! 😍”

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5.San Juan Historical Bay Daytime Sailing Tour

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

Sail San Juan Bay for about two hours aboard an authentic sailboat with a maximum of six people. Captain Joe, Ivan, or another local captain may guide the trip, pointing out Old San Juan, Castillo San Cristóbal, El Morro, La Fortaleza, and Isla de Cabras. Beer, sangria, rum and Coke, and water are included.

“The experience was amazing with breathtaking views. The captain was very knowledgeable and informative, his love of sailing and the island made the excursion top tier.”

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

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

Set sail from Puerto del Rey Marina with a captain and first mate for a five-hour trip to Piñeros or Palomino. You can snorkel secluded reefs, swim, relax on a white-sand beach, and enjoy grilled chicken, rice, fruit, snacks, beer, wine, and sangria. The catamaran carries no more than six people, with private upgrades available.

“Capt Ricardo and First Mate Monica were excellent! Dont even bother with the cattle call snorkeling ventures. Make sure to call ahead to get the slip number. You will need it to get into the marina.”

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7.Puerto Rico Private Catamaran Sail from Fajardo

★★★★★★★★★★5.0 · 45 reviews · from $2,000 whole boat, up to 6

Sail from Fajardo’s Puerto del Rey Marina on a private catamaran for up to six people. A captain and crew handle the boat while you snorkel, paddle, swim, or relax near Icacos and nearby islands. Snorkeling gear is supplied, and lunch packages are available. Crew members may include Carlos, Ari, Leo, Hiram, or Kalani.

“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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8.Janise Sailing Afternoon Charter in Fajardo, Puerto Rico

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

Board the Janise Lagoon 380 at Puerto del Rey Marina for a three-hour afternoon sail with captains Ivan and Charlie. You’ll cruise near Fajardo, stop for an ocean swim, enjoy appetizers, beer, wine, sangria, and soft drinks, then watch the sunset with Ramos Island behind you. The charter carries up to six people.

“Awesome tour. Ivan and Charlie were great hosts. My friends and I had a good time. Would highly recommended!”

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9.Island Hopping and Snorkeling Sailing and Boat Tours Fajardo

★★★★★★★★★★4.5 · 13 reviews · from $850 whole boat, up to 6

Set out from Fajardo with Outtaheretours for a private sailing trip limited to six people. With guides such as Nomar, Laura, Lara, or Tyrone, you can snorkel at Cayo Icacos, visit Isla Lobos, or request a full-day run to Vieques with paddle boarding, beach time, food, drinks, and music.

“This was the highlight of our trip! Nomar and Laura are excellents. They offered fresh fruits, Sandwiches and drinks, all for free. We did a half day excursion and visited isla Lobos where we snorkelled and cayo Icacos which has the most beautiful beach we’ve seen Thank you for the great experience!!”

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10.Private Janise Sailing Full Day Charter in Fajardo, Puerto Rico

★★★★★★★★★★5.0 · 6 reviews · from $1,995 whole boat, up to 6

Spend eight private hours aboard the Janise Lagoon 380 from Fajardo’s Puerto del Rey Marina. A USCG-certified captain and professional first mate take your group of up to six toward Palomino or Piñeros for secluded snorkeling, beach time, a floating lily pad, barbecue lunch, and drinks. Bring sun protection, a towel, and shoes you can remove before boarding.

“An unforgettable sailing experience from start to finish! The crew was professional, welcoming, and made sure our family felt safe and relaxed. The boat was clean and comfortable, and the food… Delicious! Plenty to drink as well! They know all Read more”

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11.Private Sunset Escape: Sailing an Island Paradise

★★★★★★★★★★5.0 · 6 reviews · from $399 whole boat, up to 6

Leave Marina Puerto Chico at 5:45 pm with Encanto Boat Tours for a private two-hour sunset outing to Isla Palominos. Captain Carlos or Jamille may guide your group, with time to swim, relax on the boat or island, and watch the east coast sunset. The boat returns to Fajardo.

“Such a magical experience. Carlos was amazing and attentive. Highly recommend doing this tour. He took amazing pictures of us with the sunset, gave use allot of information in the island details, pointed out things we might have missed, and was just very kind all around .”

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12.Private Half-Day Sailing and Snorkeling Tour

★★★★★★★★★★5.0 · 2 reviews · from $695 whole boat, up to 6

Spend four hours on a private sailboat from Fajardo with a USCG captain and crew. Choose Icaco or Palomino Island, then swim, snorkel, paddleboard, and relax on a floating mat. A charcuterie board, local beer, soft drinks, snorkeling gear, music, and an open swim platform are included for groups of up to six.

“Captain and mate were so helpful and friendly. Food was yummy, and the day was gorgeous!!! Thanks for a fun day!”

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