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All listings in Puerto Rico

Awesome sailboat rentals in Puerto Rico.

5.0
(330 Reviews)

Page 1 of 228 listings

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

Private San Juan Bay Cruise 37' Sailboat

5.0
Superowner
Best of 2026
$195/hour
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 2026
$650/day
Sailing & Snorkeling Day Charter - Fajardo, Puerto Rico
Sailing in Fajardo · 6 guests

Sailing & Snorkeling Day Charter - Fajardo, Puerto Rico

5.0
$1,395/day
Private Luxury Yatch Catamaran Sailing
Sailing in Humacao · 10 guests

Private Luxury Yatch Catamaran Sailing

5.0
$170/hour
Private Luxury Catamaran - Old San Juan
Sailing in San Juan · 12 guests

Private Luxury Catamaran - Old San Juan

5.0
$575/hour
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
Janise Sailing Afternoon Charter - Fajardo, Puerto Rico 🇵🇷
Sailing in Fajardo · 6 guests

Janise Sailing Afternoon Charter - Fajardo, Puerto Rico 🇵🇷

4.9
$995/day
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 2026
$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
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
All Inclusive 40' Catamaran Sailing Experience - Old San Juan
Sailing in San Juan · 6 guests

All Inclusive 40' Catamaran Sailing Experience - Old San Juan

New
$725/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 Tours- Snorkeling at Palomino & Beach Time at Icacos Island- Mako 29'
Tours in Fajardo · 6 guests

Private Tours- Snorkeling at Palomino & Beach Time at Icacos Island- Mako 29'

New
Superowner
Best of 2026
$650/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 Sailing Full Day Charter - Fajardo, Puerto Rico
Sailing in Fajardo · 6 guests

Private Sailing Full Day Charter - Fajardo, Puerto Rico

New
$1,995/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
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
Private Sunset Sail - South Coast of Puerto Rico
Sailing in Salinas · 6 guests

Private Sunset Sail - South Coast of Puerto Rico

New
$230/hour
Your Private Yacht for the Day – Lagoon 42 Full-Day Charter
Sailing in Fajardo · 6 guests

Your Private Yacht for the Day – Lagoon 42 Full-Day Charter

New
$2,500/day
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
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
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

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Sailing Reviews in Puerto Rico

  1. Jenny

    Jenny

    Sailing & Snorkeling Day Charter - Fajardo, Puerto Rico

    From beginning to end we had an awesome experience. Communication was great. The boat was as pictured. The captain and boat staff were very accommodating and personable. I would definitely recommend them!

  2. ML

    Michael

    Private Tours & Snorkeling at Flamenco Beach Culebra or Culebrita Island

    Perfect day on the water. Jose did a wonderful job finding the calm beaches. Can’t say enough good things.

  3. 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!

  4. SA

    Samuel

    Private San Juan Bay Cruise 37' Sailboat

    Captain Luis and Andrea are the real deal! We spent so much time figuring out the best sailing experience and we couldn’t have been more lucky to have found the of them and this sailing experience from San Juan bay watching the sunset and seeing the beauty of the fort and gorgeous old San Juan!!! They are so seasoned and know the waters so well that our ride was just a peaceful incredible magical ride and was the highlight of our trip!!! Trust me, stop looking and hurry and book. They are worth it and the experience will be for a lifetime!!! Thank you again guys for the beautiful evening for my fiance and I

  5. SD

    Sarah

    Private San Juan Bay Cruise 37' Sailboat

    My husband, 2 small kids, and I went on a morning 4 hour sail with Luis and Andrea. Luis and Andrea were kind and always looking out for us enjoying our experience. Our kids had lots of fun and my husband and I were able to relax and enjoy the scenery. I 100% recommend booking a cruise with Captain Luis!

  6. KB

    Katherin

    Private San Juan Bay Cruise 37' Sailboat

    Don’t second guess it. Just book it. Luis and Andrea were great! They were helpful before and during the trip. We had gone for a relaxing trip for my cousin’s bachelorette. They offered a charcuterie tray and some Sangria. I would definitely book again, on another trip to PR (: