Cookies!

We use cookies to improve your browsing experience. By continuing to browse or closing this banner, you agree to our use of cookies. Find out more about our cookies policy here.

All listings in Puerto Rico

Awesome sailboat rentals in Puerto Rico.

5.0
(347 Reviews)

Page 1 of 226 listings

Private Sail Aboard Classic 1969 Sloop in San Juan, Puerto Rico
Sailing in San Juan · 6 guests

Private Sail Aboard Classic 1969 Sloop in San Juan, Puerto Rico

4.9
Superowner
$198/hour
Instant Book
Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'
Tours in Fajardo · 6 guests

Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'

5.0
Superowner
Best of 2025
$650/day
Private San Juan Bay Cruise 37' Sailboat
Sailing in San Juan · 6 guests

Private San Juan Bay Cruise 37' Sailboat

5.0
Superowner
$195/hour
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
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
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
Superowner
Best of 2025
$1,500/day
Charter 52' Cruising sailboat in Fajardo, Puerto Rico
Sailing in Fajardo · 6 guests

Charter 52' Cruising sailboat in Fajardo, Puerto Rico

5.0
$850/day
Unwind at Sea on the Spacious Voyage 500 Catamaran
Sailing in Fajardo · 6 guests

Unwind at Sea on the Spacious Voyage 500 Catamaran

4.9
$400/hour
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
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
$800/hour
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
Luxury Sailing Catamaran Charter in Fajardo, Puerto Rico
Sailing in Ceiba · 19 guests

Luxury Sailing Catamaran Charter in Fajardo, Puerto Rico

5.0
$450/hour
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
Private Luxury Catamaran Experience - SAILING TO VIEQUES Full day
Sailing in Humacao · 12 guests

Private Luxury Catamaran Experience - SAILING TO VIEQUES Full day

New
$140/hour
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
$450/hour
Luxury Leopard 47' Power Catamaran for Daily Charter or Scuba in Fajardo
Sailing in Fajardo · 6 guests

Luxury Leopard 47' Power Catamaran for Daily Charter or Scuba in Fajardo

New
$583/hour
Luxury Leopard 47' Power Catamaran for Daily Charter or Scuba in Fajardo
Sailing in Fajardo · 12 guests

Luxury Leopard 47' Power Catamaran for Daily Charter or Scuba in Fajardo

New
$450/hour
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
Luxury Leopard 47' Power Catamaran for Daily Charter or Scuba in Fajardo
Sailing in Fajardo · 6 guests

Luxury Leopard 47' Power Catamaran for Daily Charter or Scuba in Fajardo

New
$350/hour
Private Charter Catamaran up to 6 passengers
Sailing in Fajardo · 6 guests

Private Charter Catamaran up to 6 passengers

New
$400/hour

Top Destinations Nearby

Sailing Reviews in Puerto Rico

  1. GS

    Genevieve

    Private San Juan Bay Cruise 37' Sailboat

    I booked with Captain Luis for my sister’s 30th birthday trip, and we all had the best experience! There were 4 of us in San Juan for a long weekend and this was the highlight of our trip. We felt safe, welcome, and taken care of the whole ride - the captain brought refreshments including Sangria that his wife had made which we all loved. He sailed us around and anchored at a beautiful spot to jump in and swim which was so fun. I highly recommend!

  2. SE

    Sofía

    Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'

    José was the best host we could ever ask for! He provided us with food and beverage and took us to the best spots on the islands. The boat is beautiful and so comfortable with so much room. Overall great experience 10/10!!

  3. KB

    Krystal

    Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'

    Jose was amazing, super nice and very professional. We enjoyed the areas he took us too, and the views were fantastic. I will definitely be booking this again when I return to Puerto Rico.

  4. KJ

    Keisha

    Private Luxury Sailing Experience out of Old San Juan

    The boat is exactly as pictured and is very clean. Captain Willie and crewmate David were great. They ensured we had a great time. I would definitely charter this boat again. If you’re thinking about it, just do it!

  5. Rw

    Rodey

    Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'

    Jose was a great captain and ensured we had a great day on the boat.

  6. MM

    Martina

    Janise Sailing Afternoon Charter - Fajardo, Puerto Rico 🇵🇷

    You don’t need to think twice, just simply book. We throughly enjoyed our experience from start to finish. I will definitely be returning. Thank you for having us !