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Top San Juan Sailing Trips

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12 San Juan Sailing Trips

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Did you know?You can reserve your spot today and pay when you're ready.
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Did you know?
You can reserve your spot today and pay when you're ready.Learn more

Old San Juan Harbor SailDay Cruises

SPECIAL OFFER

Old San Juan Harbor Sail

star-4.5
Float past more than 500 years of history and picturesque scenery during this 1.5-hour sailing excursion in Old San Juan Harbor. Climb aboard the ‘Amazing Grace,’ a topsail schooner fashioned in the style of 19th-century American sailing vessels, for an unforgettable ride past the wonders of this historic area. As you sail you’ll enjoy up-close views of Old San Juan sights such as El Morro fortress, La Fortaleza, and Paseo la Princesa. A guide and complimentary beverages and snacks are all covered.
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  • 1 hour 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
$41.30 
$59.00
$17.70 savings
From  
$41.30 
$59.00
$17.70 savings
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  • 1 hour 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

Old San Juan Sunset SailDay Cruises

LIKELY TO SELL OUT

Old San Juan Sunset Sail

star-4.5
Float past hundreds of years of history and picturesque scenery during this 2-hour sunset sailing excursion in Old San Juan Harbor. Climb aboard the "Amazing Grace," a topsail schooner fashioned in the style of 19th-century American sailing vessels, for an unforgettable ride past the wonders of this historic area. As you sail you’ll enjoy up-close views of Old San Juan sights like El Morro fortress, La Fortaleza, Paseo la Princesa and more, all set aglow by the fading late afternoon light. A guide and complimentary beverages and snacks are all covered.
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  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
$95.00 
From  
$95.00 
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  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Catamaran Snorkel and Picnic CruiseDay Cruises

LIKELY TO SELL OUT

Catamaran Snorkel and Picnic Cruise

star-5
Get a taste of island life during this full-day catamaran cruise and snorkeling trip to a nearby nature reserve, where you explore the tropical isle of Icacos. Pretend you’re Jacques Cousteau as you snorkel among the area’s fantastic marine life, then stroll the deserted beaches of a protected island for some shell hunting and sunbathing. Along the way enjoy a buffet lunch, with included rum punch or piña coladas, plus optional hotel pickup and drop-off from select properties in San Juan.
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  • 8 hours 30 minutes
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  • Free Cancellation
From  
$83.00 
From  
$83.00 
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  • 8 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

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Sunset Sail by San Juan Historical BayDay Cruises

Sunset Sail by San Juan Historical Bay

star-4.5
Go sailing and watch the sunset on a cruise from San Juan. Get great photo ops of Puerto Rico’s coastline and enjoy a comfortable sail on the Caribbean Sea. Your captain shares commentary about the region and provides complimentary drinks for your group of no more than six people.
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Small group
  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
$81.03 
From  
$81.03 
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  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

San Juan Catamaran Sunset SailSailing Trips

LIKELY TO SELL OUT

San Juan Catamaran Sunset Sail

star-5
Sail the calm, azure waters of San Juan Bay at sunset during a cocktail cruise. Enjoy a warm welcome aboard from your friendly captain and crew, then settle in for a scenic ride. Watch the island coastline glide by as the sun sinks toward the horizon. Sip a complimentary rum punch or sparkling wine with your family and friends and listen as your captain points out landmarks like El Morro Fort and San Juan Gate. Arrive back at the dock in time to continue your evening in San Juan.
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Small group
  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
$90.00 
From  
$90.00 
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  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation

San Juan Bay Day SailSailing Trips

LIKELY TO SELL OUT

San Juan Bay Day Sail

star-5
Set sail across the Caribbean on this 1.5-hour cruise from San Juan and enjoy unforgettable views of the Puerto Rican capital. Hop aboard a traditional sailboat and sip complimentary drinks as you cruise along the coast. Keep your camera to hand as you pass landmarks like San Juan Bay Marina and El Morro Fort, and spot dolphins and sea turtles swimming and playing around the boat.
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Small group
  • 1 hour 30 minutes
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  • Free Cancellation
From  
$78.00 
From  
$78.00 
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  • 1 hour 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

Sailing Excursion from San JuanSailing Trips

Sailing Excursion from San Juan

star-5
This private sailboat charter from San Juan allows you to choose your own adventure. Sail around the bay and harbor of Old San Juan with an experienced captain and crew at the helm; you can choose to help sail or just relax and enjoy the ride. Drinks are included to sip while you watch the shoreline scenery go by. Ask any questions you may have about boating or about owning a boat; your crew is there to educate you on potential future boat sailing and ownership.
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Private experience
  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
$614.36 
per group
From  
$614.36 
per group
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  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation

50ft Private Sailboat Experience!Sailing Trips

50ft Private Sailboat Experience!

star-5
We are a local company dedicated to the Transport Service, for individuals . groups . companies through the Island. In addition to transport, we offer you aquatic and land experiences with which you can give that magical touch to your stay filling it with unforgettable memories. Just tell us what you wish for your stay or experience and we will make it happen. In Transport and Experiences Puerto Rico we want you to feel like part of our family, very welcomed and lovely treated. Our team will guide and advise in the best interest so you can fulfill all your desires for your stay in Puerto Rico. Transport . Experiences . Private Service
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Private experience
  • 7 hours
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  • Free Cancellation
From  
$250.00 
Price varies by group size
From  
$250.00 
Price varies by group size
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  • 7 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Private, VIP Snorkel & Island Hopping Tour on the East Coast of PR !Sailing Trips

Private, VIP Snorkel & Island Hopping Tour on the East Coast of PR !

star-5
For maximum flexibility, choose a schedule and activity to suit you during this boutique snorkeling, swimming, and sailing excursion. Skip the large tour groups and benefit from the personalized attention of your captain, something few travelers get to enjoy, while making the most of the provided paddle boards, floats, snorkels, as you sail to either Icacos or Palomino Island.
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  • 6 hours
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  • Free Cancellation
From  
$980.77 
per group
From  
$980.77 
per group
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  • 6 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Private Sunset Sail on the East Coast of Puerto RicoSailing Trips

Private Sunset Sail on the East Coast of Puerto Rico

Bright pink sunsets set upon the gorgeous turquoise waters of the East Coast of Puerto Rico make this trip a perfect way to view the coast line of our special island! This trip holds a maximum of six passengers, giving you a private and boutique first class view of our special sunsets. Celebrate in style with appetizers and cocktails!
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Private experience
  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation
From  
$653.85 
per group
From  
$653.85 
per group
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  • 2 hours 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

Private, VIP, Island Hopping Trip on the East Coast of PR with Lunch & Bar! Sailing Trips

Private, VIP, Island Hopping Trip on the East Coast of PR with Lunch & Bar!

star-5
This price is for a private tour, for up to 6 passengers. Sandy Bottoms offers personalized & boutique snorkel tours, island hopping, & sailing lessons to the off shore islands of Puerto Rico. Our tours are designed around you and your parties desires. Our boat holds a maximum of six passengers so that we may provide you with the best service and experience. We love to sail and love the ocean. Our captains have over 20 years of experience teaching sailing and racing in regattas around the world. Our crew are all experienced sailors and swimmers. Our captain & crew are all FOODIES with food allergies! Boo. Beyond your sailing, and snorkel adventures, we focus on your food preferences for lunch and prepare everything fresh considering all your dietary needs and allergies. Our philosophy is to share our love for sailing and the ocean with you. We adapt our daily schedules around you and your sailing, snorkeling goals. We are all about you and your FUN!
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  • 6 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
$1,525.65 
per group
From  
$1,525.65 
per group
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  • 6 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Old San Juan VIP Romantic Sunset Sailing and Light Dinner Cruise ExperienceSailing Trips

SPECIAL OFFER

Old San Juan VIP Romantic Sunset Sailing and Light Dinner Cruise Experience

Live the Dream of a Lifetime Experience, while immersing your souls in a quality cruise in Old San Juan. Discover 500 years of history, as the ocean breeze and our music caresses and pampers you. Relax in the comfort of a reclining deck seat, having your favorite drink in hand. Celebrate Life and Love, embracing the beauty of the moment while learning fascinating history aboard our roomy and cozy French sailboat. ♥ Let this be one of the best days of your life, while enjoying personalized services with amazing bright daytime, glowing sunset and nighttime lights of this spectacular city. ♥ An exquisite light dinner will be served, based on your dietary restrictions. ♥ A magical reverence to enjoy the best views of the Goats Island, filled with palm trees and a fading glowing sun, setting down behind. ♥ Your souls will be filled with sunshine, brightness and happiness, while you witness El Morro Fort, La Fortaleza and many more Landmarks of unique Old San Juan. Totally relaxed...
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Small group
  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
$179.10 
$199.00
$19.90 savings
From  
$179.10 
$199.00
$19.90 savings
Learn More
  • 3 hours
  • Reserve Now & Pay Later
  • Free Cancellation

Frequently Asked Questions

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
Q:
What are the best Sailing Trips in San Juan?

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