Sailing Trips in Puerto Rico
Top 10 Best Puerto Rico Sailing Trips
Found 27 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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Superb1,140 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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Superb125 reviews4.9
Experience the magic of exploring the marine world at a stunning beach in San Juan. Join this beginn....
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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Exellent642 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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Superb442 reviews4.9
Discover San Juan, Puerto Rico aboard a 37-foot catamaran sailboat while enjoying complimentary mimo....
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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Superb542 reviews4.9
Sit back, relax and take in the amazing sights of historic San Juan Bay with picturesque sunset ligh....
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

Sailing and Snorkeling Day Charter in Fajardo, Puerto Rico
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Puerto Rico
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Superb130 reviews5
Come aboard the comfortable Janise Lagoon 380 for a memorable voyage in the beautiful waters of the ....
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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Superb156 reviews4.6
Authentic sailing is culture, having a conversation with a local, with the power of the wind, no eng....
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

VIP San Juan: Snorkeling Tour with Turtles with Free Videos
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Puerto Rico
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Superb103 reviews4.9
Experience the magic of exploring the marine world at a stunning beach in San Juan. Join this beginn....
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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Superb111 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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Superb34 reviews5
Get more time, See more do more!, More Space! Welcome aboard your private water tour aboard a choic....
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
Private Sail Tour Puerto Rico (Fajardo) with Drinks & Food
Hop aboard as guests, leave as family! With over 15 years of experience, Gio & Angie will create a sailing experience that will make you feel like you are being hosted by friends. Our modern 2013 Beneteau Sailboat of 41-feet is eq... More
Private Tour

Private Sail Tour Puerto Rico (Fajardo) with Drinks & Food
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Puerto Rico
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Superb17 reviews5
Hop aboard as guests, leave as family! With over 15 years of experience, Gio & Angie will create a s....
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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Superb21 reviews4.6
Paddle board experience on a tour of the Condado lagoon, where you can appreciate the old historic "....
Private Tour
Private Sunset Sail Tour in Fajardo with Open Bar and Appetizers
Best romantic option! Pop some bubbly and catch the sunset from the best seat in the house… the water! Wind down while cruising around the east coast islands of Puerto Rico. With over 15 years of experience, we'll create a uniqu... More
Private Tour

Private Sunset Sail Tour in Fajardo with Open Bar and Appetizers
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Puerto Rico
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Superb1 review5
Best romantic option! Pop some bubbly and catch the sunset from the best seat in the house… the wa....
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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Superb1 review5
Come aboard the comfortable Janise Lagoon 380 for a memorable 8-hourfull day charter in the beautifu....
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
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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Superb13 reviews5
Come aboard the comfortable Janise Lagoon 380 for a memorable voyage in the beautiful waters of the ....
Private Tour
Private Sailing & Snorkeling Tour with Bar & Food in Fajardo, PR
Explore the offshore islands of the East Coast of Puerto Rico aboard our modern 2013 Beneteau 41 ft Sailboat equipped amenities like full snorkeling gear, paddle boards and floaties. With over 15 years of experience, we'll create ... More
Private Tour

Private Sailing & Snorkeling Tour with Bar & Food in Fajardo, PR
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Puerto Rico
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Superb23 reviews5
Explore the offshore islands of the East Coast of Puerto Rico aboard our modern 2013 Beneteau 41 ft ....
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 Sail including Food & Bar, Fajardo Puerto Rico
Don't have all day? Take a quick dip in Caribbean warm waters and get pampered by our crew in your own private yacht expedition with half-day full of adventure and fun. With over 15 years of experience, we'll create a unique perso... More
Private Tour

Private Half Day Sail including Food & Bar, Fajardo Puerto Rico
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Puerto Rico
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Superb1 review5
Don't have all day? Take a quick dip in Caribbean warm waters and get pampered by our crew in your o....
Private Tour