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Top 10 Best Puerto Rico Sailing Trips

Found 28 Sailing Trips activities in Puerto Rico. Sort by Popularity.
 

Icacos Island Catamaran Day Sail from Fajardo

(4.8 of 1,101 reviews)

Live out your fantasy of island escape and hop aboard a catamaran to Cayo Icacos, a deserted island surrounded by the bright blue Caribbean. On this day cruise from Fajardo, enjoy views of El Yunque mountains and then dig your toe... More

Free Cancellation
Start From $135.00
 
Icacos Island Catamaran Day Sail from Fajardo Likely to Sell Out

Icacos Island Catamaran Day Sail from Fajardo

  • Puerto Rico
  • Superb1,101 reviews4.8

Live out your fantasy of island escape and hop aboard a catamaran to Cayo Icacos, a deserted island ....

    Free Cancellation
    Start From $135.00
 
 

Icacos Deserted Island Catamaran, Snorkel and Picnic Cruise

(4.8 of 1,644 reviews)

Our catamaran takes you to the island of Icacos. Disembark and find yourself at a beautiful beach with crystal clear blue water. The catamaran will stay at the beach until lunch. Beach comb, swim or just relax on the beach in this... More

Free Cancellation
Start From $131.21
 
Icacos Deserted Island Catamaran, Snorkel and Picnic Cruise Likely to Sell Out

Icacos Deserted Island Catamaran, Snorkel and Picnic Cruise

  • Puerto Rico
  • Superb1,644 reviews4.8

Our catamaran takes you to the island of Icacos. Disembark and find yourself at a beautiful beach wi....

    Free Cancellation
    Start From $131.21
 
 

San Juan Historical Bay Sunset Sailing Tour

(4.5 of 546 reviews)

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 straight cats, no crowds, no need to scream. We sail sideways, aboard a real racer cruis... More

Free Cancellation
Start From $109.00
 
San Juan Historical Bay Sunset Sailing Tour Likely to Sell Out

San Juan Historical Bay Sunset Sailing Tour

  • Puerto Rico
  • Exellent546 reviews4.5

Authentic sailing is culture, having a conversation with a local, with the power of the wind, no eng....

    Free Cancellation
    Start From $109.00
 
 

San Juan Catamaran Sunset Sail with Drinks Included

(5 of 479 reviews)

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

Free Cancellation
Start From $119.00
 
San Juan Catamaran Sunset Sail with Drinks Included Likely to Sell Out

San Juan Catamaran Sunset Sail with Drinks Included

  • Puerto Rico
  • Superb479 reviews5

Sit back, relax and take in the amazing sights of historic San Juan Bay with picturesque sunset ligh....

    Free Cancellation
    Start From $119.00
 
 

San Juan Bay Day Sail with Drinks Included

(4.9 of 363 reviews)

Discover San Juan, Puerto Rico aboard a 37-foot catamaran sailboat while enjoying bottomless mimosas, house rum punch, and more complimentary drinks. Take in the panoramic views on this pleasure sightseeing tour of San Juan Bay an... More

Free Cancellation
Start From $99.00
 
San Juan Bay Day Sail with Drinks Included Likely to Sell Out

San Juan Bay Day Sail with Drinks Included

  • Puerto Rico
  • Superb363 reviews4.9

Discover San Juan, Puerto Rico aboard a 37-foot catamaran sailboat while enjoying bottomless mimosas....

    Free Cancellation
    Start From $99.00
 
 

San Juan Bay Private Tour with Drinks and Tapas: 4+ people

(5 of 22 reviews)

See more do more! 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 USCG certified Captain will... More

Free Cancellation
Private Tour
Start From $133.34
 
San Juan Bay Private Tour with Drinks and Tapas: 4+ people Likely to Sell Out

San Juan Bay Private Tour with Drinks and Tapas: 4+ people

  • Puerto Rico
  • Superb22 reviews5

See more do more! Welcome aboard your private water tour aboard a choice between a 37 foot sailboat....

    Free Cancellation
    Private Tour
    Start From $133.34
 
 

Sail Away: Private Scenic Excursion from San Juan

(4.7 of 92 reviews)

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

Free Cancellation
Private Tour
Start From $595.00
 
Sail Away: Private Scenic Excursion from San Juan Likely to Sell Out

Sail Away: Private Scenic Excursion from San Juan

  • Puerto Rico
  • Superb92 reviews4.7

Private, AM. PM. or Sunset, sailing around the San Juan Bay and Harbor of Old San Juan, Puerto Rico....

    Free Cancellation
    Private Tour
    Start From $595.00
 
 

Sailing and Snorkeling Day Charter in Fajardo, Puerto Rico

(5 of 100 reviews)

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

Free Cancellation
Private Tour
Start From $285.00
 
Sailing and Snorkeling Day Charter in Fajardo, Puerto Rico Likely to Sell Out

Sailing and Snorkeling Day Charter in Fajardo, Puerto Rico

  • Puerto Rico
  • Superb100 reviews5

Come aboard the comfortable Janise Lagoon 380 for a memorable voyage in the beautiful waters of the ....

    Free Cancellation
    Private Tour
    Start From $285.00
 
 

Puerto Rico Private Sail: Island Hopping, Snorkeling, Open Bar

(4.9 of 51 reviews)

Sandy Bottoms offers personalized & boutique snorkel tours, island hopping, & sailing lessons to the offshore islands on the East Coast of Puerto Rico. Our tours are designed around you and your parties desires. Our boat holds a m... More

Free Cancellation
Private Tour
Start From $1,498.00
 
Puerto Rico Private Sail: Island Hopping, Snorkeling, Open Bar Likely to Sell Out

Puerto Rico Private Sail: Island Hopping, Snorkeling, Open Bar

  • Puerto Rico
  • Superb51 reviews4.9

Sandy Bottoms offers personalized & boutique snorkel tours, island hopping, & sailing lessons to the....

    Free Cancellation
    Private Tour
    Start From $1,498.00
 
 

Private Day Sail - South Coast of Puerto Rico

(4.9 of 20 reviews)

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

Free Cancellation
Private Tour
Start From $680.00
 
Private Day Sail - South Coast of Puerto Rico Likely to Sell Out

Private Day Sail - South Coast of Puerto Rico

  • Puerto Rico
  • Superb20 reviews4.9

Our experienced USCG Captain and crew will make sure you experience the most beautiful and secluded ....

    Free Cancellation
    Private Tour
    Start From $680.00
 
 

San Juan Historical Bay Day Sailing Tour

(4.7 of 129 reviews)

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

Free Cancellation
Private Tour
Start From $99.00
 
San Juan Historical Bay Day Sailing Tour Likely to Sell Out

San Juan Historical Bay Day Sailing Tour

  • Puerto Rico
  • Superb129 reviews4.7

Authentic sailing is culture, having a conversation with a local, with the power of the wind, no eng....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

1-Hour Paddle Board in Condado Lagoon

(4.7 of 12 reviews)

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

Free Cancellation
Private Tour
Start From $30.00
 
1-Hour Paddle Board in Condado Lagoon Likely to Sell Out

1-Hour Paddle Board in Condado Lagoon

  • Puerto Rico
  • Superb12 reviews4.7

Paddle board experience on a tour of the Condado lagoon, where you can appreciate the old historic "....

    Free Cancellation
    Private Tour
    Start From $30.00
 
 

Private Puerto Rico Sail Adventure with Open Bar

(5 of 33 reviews)

Sandy Bottoms Sailing offers personalized snorkeling, and island hopping tours to the offshore islands of Puerto Rico. Sail with style and comfort in our 47 ft Beneteau Sailboat, while taking in the beautiful views. Our tours are ... More

Free Cancellation
Private Tour
Start From $1,498.00
 
Private Puerto Rico Sail Adventure with Open Bar Likely to Sell Out

Private Puerto Rico Sail Adventure with Open Bar

  • Puerto Rico
  • Superb33 reviews5

Sandy Bottoms Sailing offers personalized snorkeling, and island hopping tours to the offshore islan....

    Free Cancellation
    Private Tour
    Start From $1,498.00
 
 

Janise Sailing Afternoon Charter in Fajardo, Puerto Rico

(5 of 7 reviews)

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

Free Cancellation
Private Tour
Start From $229.00
 
Janise Sailing Afternoon Charter in Fajardo, Puerto Rico Likely to Sell Out

Janise Sailing Afternoon Charter in Fajardo, Puerto Rico

  • Puerto Rico
  • Superb7 reviews5

Come aboard the comfortable Janise Lagoon 380 for a memorable voyage in the beautiful waters of the ....

    Free Cancellation
    Private Tour
    Start From $229.00
 
 

Puerto Rico: Private Sail and Snorkel Tour with Refreshments

(5 of 18 reviews)

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

Free Cancellation
Private Tour
Start From $1,298.00
 
Puerto Rico: Private Sail and Snorkel Tour with Refreshments Likely to Sell Out

Puerto Rico: Private Sail and Snorkel Tour with Refreshments

  • Puerto Rico
  • Superb18 reviews5

Explore the offshore islands of the East Coast of Puerto Rico aboard our modern 2013 Beneteau 41 ft ....

    Free Cancellation
    Private Tour
    Start From $1,298.00
 
 

Private SAILING CHARTER in Fajardo, PR with Drinks & Food

(5 of 16 reviews)

With over 15 years of experience, we'll create a unique personalized experience just for your party. Explore the offshore islands of the East Coast of Puerto Rico aboard our modern 2013 Beneteau 41 ft Sailboat equipped amenities l... More

Free Cancellation
Private Tour
Start From $1,328.00
 
Private SAILING CHARTER in Fajardo, PR with Drinks & Food Likely to Sell Out

Private SAILING CHARTER in Fajardo, PR with Drinks & Food

  • Puerto Rico
  • Superb16 reviews5

With over 15 years of experience, we'll create a unique personalized experience just for your party.....

    Free Cancellation
    Private Tour
    Start From $1,328.00
 
 

Private Snorkeling and Sailing on the East Coast of Puerto Rico with Open Bar

(5 of 8 reviews)

Sandy Bottoms Sailing offers personalized snorkeling, and island hopping tours to the off shore islands of Puerto Rico in our 47 ft, Beneteau Sailboat. Our tours are always private (max of 6 guests) and designed around you & your ... More

Free Cancellation
Private Tour
Start From $1,498.00
 
Private Snorkeling and Sailing on the East Coast of Puerto Rico with Open Bar Likely to Sell Out

Private Snorkeling and Sailing on the East Coast of Puerto Rico w....

  • Puerto Rico
  • Superb8 reviews5

Sandy Bottoms Sailing offers personalized snorkeling, and island hopping tours to the off shore isla....

    Free Cancellation
    Private Tour
    Start From $1,498.00
 
 

Sailing and Snorkeling Experience with Lunch from San Juan

(1 of 2 reviews)

Admire unparalleled views and feel a cool breeze as you sail to your island paradise on a spacious, 54-foot (16-m) catamaran. Hop off the boat into the inviting waters of the Atlantic ocean. After spending time in the water, a sc... More

Free Cancellation
Private Tour
Start From $184.00
 
Sailing and Snorkeling Experience with Lunch from San Juan Likely to Sell Out

Sailing and Snorkeling Experience with Lunch from San Juan

  • Puerto Rico

Admire unparalleled views and feel a cool breeze as you sail to your island paradise on a spacious, ....

    Free Cancellation
    Private Tour
    Start From $184.00
 
 

2 hrs. Private Sunset Sail - South Coast of Puerto Rico

(5 of 2 reviews)

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

Free Cancellation
Private Tour
Start From $449.00
 
2 hrs. Private Sunset Sail - South Coast of Puerto Rico Likely to Sell Out

2 hrs. Private Sunset Sail - South Coast of Puerto Rico

  • Puerto Rico
  • Superb2 reviews5

Catch the most amazing sunsets from a secluded spot on the Jobos Bay National Estuarine Research Res....

    Free Cancellation
    Private Tour
    Start From $449.00
 
 

3 Hours Private Sunset Sail and Swim

(5 of 2 reviews)

Enjoy a unique location to experience a sunset sail and swim in the South Coast Of P.R. in a protected anchorage.... More

Free Cancellation
Private Tour
Start From $580.00
 
3 Hours Private Sunset Sail and Swim Likely to Sell Out

3 Hours Private Sunset Sail and Swim

  • Puerto Rico
  • Superb2 reviews5

Enjoy a unique location to experience a sunset sail and swim in the South Coast Of P.R. in a protect....

    Free Cancellation
    Private Tour
    Start From $580.00
 
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