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All listings in Puerto Rico

Awesome sailboat rentals in Puerto Rico.

4.9
(350 Reviews)

Page 1 of 226 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
$675/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 Bali 40ft Catamaran – Sail to Vieques’ Secluded Beaches
Sailing in Humacao · 12 guests

Private Luxury Bali 40ft Catamaran – Sail to Vieques’ Secluded Beaches

5.0
$170/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'

5.0
Superowner
Best of 2026
$675/day
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 Sailing Full Day Charter - Fajardo, Puerto Rico
Sailing in Fajardo · 6 guests

Private Sailing Full Day Charter - Fajardo, Puerto Rico

5.0
$1,995/day
Visit Culebra Island or Vieques Island / Private Tour
Tours in Fajardo · 6 guests

Visit Culebra Island or Vieques Island / Private Tour

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
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
Luxury Sailing Catamaran Charter in Fajardo, Puerto Rico
Sailing in Fajardo · 19 guests

Luxury Sailing Catamaran Charter in Fajardo, Puerto Rico

5.0
$450/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

3.0
$725/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 · 12 guests

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

New
$450/hour
Catamaran Lagoon 450 from Marina Puerto del Rey in Fajardo
Sailing in Fajardo · 12 guests

Catamaran Lagoon 450 from Marina Puerto del Rey in Fajardo

New
$699/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
Come and enjoy the Spanish Virgin Island onboard 38ft Hunter Marine
Sailing in Fajardo · 6 guests

Come and enjoy the Spanish Virgin Island onboard 38ft Hunter Marine

New
$200/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
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
Island Dreams on a Luxury Contender 40' Center Console
Powerboats in Fajardo · 8 guests

Island Dreams on a Luxury Contender 40' Center Console

New
$225+/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

Top Destinations Nearby

Sailing Reviews in Puerto Rico

  1. HG

    Hernan

    Private Luxury Bali 40ft Catamaran – Sail to Vieques’ Secluded Beaches

    We had an absolutely amazing experience with Captain Hugo and Marian! From start to finish, they were incredibly personable, welcoming, and made us feel right at home. Leading up to the charter, their communication was outstanding…they were proactive, responsive, and made everything seamless and stress-free. On the day of the charter, they truly went above and beyond, especially with our children. They were attentive, engaging, and made sure the kids were not only having fun but also safe and well cared for. That meant the world to us as parents. Their energy, professionalism, and genuine care made this experience unforgettable. We’ll absolutely be booking with them again and bringing more friends along next time we visit. Highly recommend!

  2. JC

    Jose

    Private San Juan Bay Cruise 37' Sailboat

    Captain Luis & Andrea were incredible. My group enjoyed their energy and appreciation and even though we dealt with some rain and gray sky’s, our experience was phenomenal. I would not only recommend Luis, but I would take another trip out with him when I return to PR. We had an exceptional time at sea. Gracias por todo y hasta la próxima.

  3. JL

    Jessica

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

    Jose was the best Captain! He took us to Icacos, Palomino, a ride by Palominito, and a ride by Islets Marina! Great food and drinks… Had a blast! Couldn’t have asked for a better experience!!!

  4. Jacob

    Jacob

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

    José and first mate were phenomenal! Seas were a little choppy on the ride over but the ride was very smoother as they had the bow trimmed up. Lunch, snorkeling, swimming, fishing - couldn’t ask for more for us and our four year old. They watched him and fished while my wife and I snorkeled.

  5. OZ

    Osmar

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

    Great trip. Our party of 6 really enjoyed it. We asked for a food option and they made an incredible BBQ. The snorkel equipment was great and they were very attentive through the trip.

  6. AM

    Andie

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

    Captain Jose was an absolute blast and made my mom’s 60th birthday so special and memorable. From the moment we stepped on board, he brought great energy, made everyone feel comfortable, and truly made the day fun. When we arrived, the original boat we had booked was unfortunately having mechanical issues, which was a bit disappointing at first. However, the team handled it well and upgraded the experience by letting us use the Seabob for free—which ended up being a huge highlight of the day. We loved visiting Icacos Island—it was beautiful, relaxing, and the perfect spot to celebrate. Captain Jose knew exactly how to make the experience enjoyable and stress-free. We would absolutely recommend Captain Jose to anyone looking for an unforgettable day on the water. He truly went above and beyond to make the celebration special.