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All listings in Puerto Rico

Awesome sailboat rentals in Puerto Rico.

5.0
(222 Reviews)

Page 1 of 118 listings

Private San Juan Bay Cruise 37' Sailboat
Sailing in San Juan · 6 guests

Private San Juan Bay Cruise 37' Sailboat

5.0
$195/hour
Private Tours~ Snorkeling at Icacos & Palomino Islands- Grady White 27'
Powerboats in Fajardo · 6 guests

Private Tours~ Snorkeling at Icacos & Palomino Islands- Grady White 27'

5.0
Best of 2025
$675/day
Sailing & Snorkeling Day Charter - Fajardo, Puerto Rico
Sailing in Fajardo · 6 guests

Sailing & Snorkeling Day Charter - Fajardo, Puerto Rico

4.9
$1,395/day
Private Luxury Sailing Experience out of Old San Juan
Sailing in San Juan · 12 guests

Private Luxury Sailing Experience out of Old San Juan

5.0
$725/hour
Private Tours & Snorkeling at Flamenco Beach Culebra or Culebrita Island
Tours in Fajardo · 6 guests

Private Tours & Snorkeling at Flamenco Beach Culebra or Culebrita Island

5.0
Best of 2025
$1,325/day
Private Sail Classic 1969 Sloop in San Juan, Puerto Rico
Sailing in San Juan · 6 guests

Private Sail Classic 1969 Sloop in San Juan, Puerto Rico

4.9
Superowner
$198/hour
Instant Book
Janise Sailing Afternoon Charter - Fajardo, Puerto Rico 🇵🇷
Sailing in Fajardo · 6 guests

Janise Sailing Afternoon Charter - Fajardo, Puerto Rico 🇵🇷

4.9
$995/day
Instant Book
Sunset Cruise in San Juan Puerto Rico
Sailing in San Juan · 6 guests

Sunset Cruise in San Juan Puerto Rico

5.0
Superowner
$353/hour
Private Luxury Sailing Charter around the East Coast of Puerto Rico
Sailing in Fajardo · 6 guests

Private Luxury Sailing Charter around the East Coast of Puerto Rico

5.0
$1,198/day
Private Sailing Full Day Charter - Fajardo, Puerto Rico
Sailing in Fajardo · 6 guests

Private Sailing Full Day Charter - Fajardo, Puerto Rico

New
$2,395/day
Awesome and Spacious Sea Ray 55’ 2009 Motor Yacht Rental in Fajardo, Puerto Rico
Events in Fajardo · 12 guests

Awesome and Spacious Sea Ray 55’ 2009 Motor Yacht Rental in Fajardo, Puerto Rico

5.0
Superowner
$800/hour
Luxury Sailing Catamaran Charter in Fajardo, Puerto Rico
Sailing in Ceiba · 19 guests

Luxury Sailing Catamaran Charter in Fajardo, Puerto Rico

5.0
$2,700/day
Private Day Sailboat for Charter - South Coast of Puerto Rico
Sailing in Salinas · 6 guests

Private Day Sailboat for Charter - South Coast of Puerto Rico

5.0
$635/day
Snorkeling & Kayak Mini Eco-Experience
Tours in Fajardo · 16 guests

Snorkeling & Kayak Mini Eco-Experience

5.0
$60/day
Leopard 43 Sailing Cat with USCG Certified Captain & Crew in Ceiba, Puerto Rico
Sailing in Fajardo · 6 guests

Leopard 43 Sailing Cat with USCG Certified Captain & Crew in Ceiba, Puerto Rico

5.0
$2,695/day
Lagoon 42 Luxury Catamaran Sail to Icacos or Palominos
Sailing in Fajardo · 12 guests

Lagoon 42 Luxury Catamaran Sail to Icacos or Palominos

New
$575/hour
Private Sunset Sail - South Coast of Puerto Rico
Sailing in Salinas · 6 guests

Private Sunset Sail - South Coast of Puerto Rico

New
$230/hour
Historic / Educational Private Day Sail - South Coast of Puerto Rico
Sailing in Salinas · 6 guests

Historic / Educational Private Day Sail - South Coast of Puerto Rico

New
$1,050/day

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Sailing Reviews in Puerto Rico

  1. BK

    Brian

    Sunset Cruise in San Juan Puerto Rico

    Sailing with Jimbo was the highlight of our trip to San Juan! Can’t say enough about the whole experience. Jimbo gave great historical insights, was an engaging storyteller and most importantly was a great Captain that made the sail both exciting and safe. 10/10 would book again.

  2. KT

    Kristin

    Private Tours~ Snorkeling at Icacos & Palomino Islands- Grady White 27'

    Absolutely the best experience! We are a family of 4 with 15 year old twins and everyone had the most amazing time! My husband is picky about excursions because he typically captains our own boats and he loved it! Jose was so chill and the best captain we could have asked for! If you want a private experience then this is your route!!!

  3. KP

    Kieta

    Private San Juan Bay Cruise 37' Sailboat

    It was so much fun ! Captain Luis is very informative and made sure we were all safe ! Andrea is absolutely the best !! She made sure we had everything we needed and we took a lot of great photos! Book I promise you will not be disappointed

  4. AG

    Ashley

    Private Luxury Sailing Experience out of Old San Juan

    The boat was immaculate and in pristine condition. The captain and crew were so professional and made our trip extra special. The boat was fully stocked with everything we needed. It was the perfect size for our group of 8 adults and was the highlight of our trip!

  5. Andrea

    Andrea

    Luxury Sailing Catamaran Charter in Fajardo, Puerto Rico

    boat and crew were amazing ! We had a blast and they were very accommodating and friendly. Beautiful big boat! we had a great time and saw so many beautiful places. Food was good! Drinks were good! We will definitely be using them again! Thank you for wonderful moments !

  6. Camrenn

    Camrenn

    Private Tours~ Snorkeling at Icacos & Palomino Islands- Grady White 27'

    Great captain. Highly recommend, my family and I had a great time on the boat visiting icacos and palamino.