Sailing Trips in Puerto Rico
Top 10 Best Puerto Rico Sailing Trips
Found 23 Sailing Trips activities in Puerto Rico. Sort by Popularity.San Juan Sunset Harbor Boat Ride
Hop aboard and join us for a captivating journey on a sunset pontoon boat tour, exploring the timeless allure of San Juan Bay, the historical gem of Puerto Rico. Our Sunset Tour offers a perfect fusion of cultural exploration, a... More

San Juan Sunset Harbor Boat Ride
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Puerto Rico
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Superb1,207 reviews4.6
Hop aboard and join us for a captivating journey on a sunset pontoon boat tour, exploring the timele....
San Juan: Snorkeling with Turtles Adventure and Free Videos
Experience the magic of exploring the marine world at a stunning beach in San Juan. Join this beginner-friendly adventure led by a professional guide in small groups of up to 10, ensuring a personalized and high-quality experience... More

San Juan: Snorkeling with Turtles Adventure and Free Videos
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Puerto Rico
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Superb184 reviews4.9
Experience the magic of exploring the marine world at a stunning beach in San Juan. Join this beginn....
San Juan Catamaran Sunset Sail with Drinks Included
Sit back, relax and take in the amazing sights of historic San Juan Bay with picturesque sunset lighting. This 2-hour sail aboard a 37ft catamaran sailboat completely powered by the wind is the perfect setting for a romantic momen... More

San Juan Catamaran Sunset Sail with Drinks Included
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Puerto Rico
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Superb565 reviews4.9
Sit back, relax and take in the amazing sights of historic San Juan Bay with picturesque sunset ligh....
Historical San Juan Bay Sunset Sailing Tour
Sailing is authentic to San Juan culture- having a conversation with a local, the power of the wind, the peace from no engine noise, no crowds, no fake pirates, no crowds, no need to scream. We sail aboard a real racer cruiser (J3... More

Historical San Juan Bay Sunset Sailing Tour
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Puerto Rico
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Exellent668 reviews4.5
Sailing is authentic to San Juan culture- having a conversation with a local, the power of the wind,....
San Juan Bay Day Sail with Drinks Included
Discover San Juan, Puerto Rico aboard a 37-foot catamaran sailboat while enjoying complimentary mimosas, house rum punch, and other drinks in moderation (not a booze cruise type open bar). Take in the panoramic views on this pleas... More

San Juan Bay Day Sail with Drinks Included
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Puerto Rico
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Superb462 reviews4.9
Discover San Juan, Puerto Rico aboard a 37-foot catamaran sailboat while enjoying complimentary mimo....
San Juan Historical Bay Daytime Sailing Tour
Authentic sailing is culture, having a conversation with a local, with the power of the wind, no engine noise, no crowds, no fake pirates, no stray cats, no crowds, no need to scream . . . we sail sideways, aboard a real racer-cru... More

San Juan Historical Bay Daytime Sailing Tour
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Puerto Rico
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Superb162 reviews4.7
Authentic sailing is culture, having a conversation with a local, with the power of the wind, no eng....
Sail Away: Private Scenic Excursion from San Juan
Private, AM. PM. or Sunset, sailing around the San Juan Bay and Harbor of Old San Juan, Puerto Rico. (Prices already include all taxes and fees) This sightseeing, sailing tour will pass historical, Old San Juan Forts and views o... More
Private Tour

Sail Away: Private Scenic Excursion from San Juan
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Puerto Rico
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Superb124 reviews4.8
Private, AM. PM. or Sunset, sailing around the San Juan Bay and Harbor of Old San Juan, Puerto Rico....
Private Tour
San Juan Bay Private Tour with Drinks and Tapas: 4+ people
Get more time, See more do more!, More Space! Welcome aboard your private water tour aboard a choice between a 37 foot sailboat ot a a high performance Powerboat. Enjoy complimentary local drinks. Your personal tour guide and Pro... More
Private Tour

San Juan Bay Private Tour with Drinks and Tapas: 4+ people
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Puerto Rico
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Superb38 reviews5
Get more time, See more do more!, More Space! Welcome aboard your private water tour aboard a choic....
Private Tour
Sailing and Snorkeling Day Charter in Fajardo, Puerto Rico
Come aboard the comfortable Janise Lagoon 380 for a memorable voyage in the beautiful waters of the Caribbean Sea. Great for birthdays and any special private event. Come experience first class service by our professional and frie... More
Private Tour

Sailing and Snorkeling Day Charter in Fajardo, Puerto Rico
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Puerto Rico
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Superb135 reviews5
Come aboard the comfortable Janise Lagoon 380 for a memorable voyage in the beautiful waters of the ....
Private Tour
VIP San Juan: Snorkeling Tour with Turtles with Free Videos
Experience the magic of exploring the marine world at a stunning beach in San Juan. Join this beginner-friendly adventure led by a professional guide in small groups of up to 8, ensuring a personalized and high-quality experience ... More
Private Tour

VIP San Juan: Snorkeling Tour with Turtles with Free Videos
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Puerto Rico
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Superb123 reviews4.9
Experience the magic of exploring the marine world at a stunning beach in San Juan. Join this beginn....
Private Tour
party boat sunshine's-# 1 in Puntacana/Dominican Republic
A catamaran or boat equipped for parties, with music, an open bar, and dancing. Water Activities: Snorkeling in coral reefs, visiting natural pools, and enjoying activities like slides and swings. Drinks: Open bar with alcoholic (... More
Private Tour

party boat sunshine's-# 1 in Puntacana/Dominican Republic
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Puerto Rico
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Superb13 reviews5
A catamaran or boat equipped for parties, with music, an open bar, and dancing. Water Activities: Sn....
Private Tour
1-Hour Paddle Board in Condado Lagoon
Paddle board experience on a tour of the Condado lagoon, where you can appreciate the old historic "Los Hermanos" bridge, the maritime life of our reef in a natural reserve, we can see turtles, manatees, and fish of different spec... More
Private Tour

1-Hour Paddle Board in Condado Lagoon
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Puerto Rico
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Superb22 reviews4.6
Paddle board experience on a tour of the Condado lagoon, where you can appreciate the old historic "....
Private Tour
Private Janise Sailing Full Day Charter in Fajardo, Puerto Rico
Come aboard the comfortable Janise Lagoon 380 for a memorable 8-hourfull day charter in the beautiful Spanish Virgin Islands. Come experience first class service by our professional and friendly crew. Our great reviews have positi... More
Private Tour

Private Janise Sailing Full Day Charter in Fajardo, Puerto Rico
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Puerto Rico
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Superb3 reviews5
Come aboard the comfortable Janise Lagoon 380 for a memorable 8-hourfull day charter in the beautifu....
Private Tour

Private Sunset Sail
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Puerto Rico
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Superb5 reviews5
We are the only excursion that allows you to drive the boat during this private excursion. We are th....
Private Tour
Janise Sailing Afternoon Charter in Fajardo, Puerto Rico
Come aboard the comfortable Janise Lagoon 380 for a memorable voyage in the beautiful waters of the Caribbean Sea ending in an amazing sunset setting. Great for engagements, and any special private event. Come experience the 1st c... More
Private Tour

Janise Sailing Afternoon Charter in Fajardo, Puerto Rico
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Puerto Rico
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Superb14 reviews5
Come aboard the comfortable Janise Lagoon 380 for a memorable voyage in the beautiful waters of the ....
Private Tour
Private Day Sail - South Coast of Puerto Rico
Our experienced USCG Captain and crew will make sure you experience the most beautiful and secluded spots of the Jobos Bay National Estuarine Research Reserve (JBNERR) in the comfort and privacy of our 36-foot sailboat fit for six... More
Private Tour

Private Day Sail - South Coast of Puerto Rico
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Puerto Rico
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Superb24 reviews4.7
Our experienced USCG Captain and crew will make sure you experience the most beautiful and secluded ....
Private Tour
Snorkel to a Local's Secret Spot
**CHECK-IN TIME: 1:30 PM** TOUR START TIME: 2:00 PM We meet at Marina Puerto Chico in Fajardo, to receive a quick overview of the itinerary. Aboard our classic vessel we navigate towards one of the coral reefs of Icacos Island. N... More
Private Tour

Snorkel to a Local's Secret Spot
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Puerto Rico
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Superb82 reviews4.8
**CHECK-IN TIME: 1:30 PM** TOUR START TIME: 2:00 PM We meet at Marina Puerto Chico in Fajardo, to r....
Private Tour
2 hrs. Private Sunset Sail - South Coast of Puerto Rico
Catch the most amazing sunsets from a secluded spot on the Jobos Bay National Estuarine Research Reserve (JBNERR) with our experienced USCG Captain and crew, in the comfort and privacy of our 36-foot sailboat fit for six (6) passe... More
Private Tour

2 hrs. Private Sunset Sail - South Coast of Puerto Rico
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Puerto Rico
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Superb2 reviews5
Catch the most amazing sunsets from a secluded spot on the Jobos Bay National Estuarine Research Res....
Private Tour
Private Half-Day Sailing and Snorkeling Tour
On this trip we offer you a sailboat trip experience during 4-hours tour from the coast of Fajardo to one (1) selected Island (Icaco Island or Palomino Island). Customers can swim and enjoy themselves on each island. In some cases... More
Private Tour

Private Half-Day Sailing and Snorkeling Tour
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Puerto Rico
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Superb2 reviews5
On this trip we offer you a sailboat trip experience during 4-hours tour from the coast of Fajardo t....
Private Tour
Private Karibe Sailing and Snorkeling Tour
On this trip we offer you a sailboat trip experience during 6-hours tour from the coast of Fajardo to two (2) different destinations: Icaco Island and Palomino Island, in combination with snorkeling, swimming experience and much m... More
Private Tour

Private Karibe Sailing and Snorkeling Tour
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Puerto Rico
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Superb2 reviews5
On this trip we offer you a sailboat trip experience during 6-hours tour from the coast of Fajardo t....
Private Tour