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All listings in Puerto Rico

Awesome sailboat rentals in Puerto Rico.

4.9
(344 Reviews)

Page 1 of 229 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 Yatch Catamaran Sailing
Sailing in Humacao · 12 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 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 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
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
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
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
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 · 12 guests

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

New
$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
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
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

Top Destinations Nearby

Sailing Reviews in Puerto Rico

  1. 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.

  2. Dana

    Dana

    Luxury Sailing Catamaran Charter in Fajardo, Puerto Rico

    Gabriela and her team are incredible! I’m happy to share that our experience was absolutely phenomenal from start to finish. East Island Excursions was incredibly professional and accommodating throughout the entire planning process. Communication was seamless, check-in was a breeze, and everything ran so smoothly on the day of our excursion. The boat itself was stunning and made the perfect backdrop for my sister’s bachelorette party—truly unforgettable. Most of all, the crew was exceptional. They were warm, welcoming, and attentive to every detail, making us feel so well taken care of. They genuinely went above and beyond to make the day feel special, and it showed in every interaction. We couldn’t have asked for a better experience and would absolutely recommend both Getmyboat and East Island Excursions to anyone looking for a memorable, stress-free adventure on the water. Thank you again for such a wonderful experience! Warmly, Dana

  3. DL

    David

    Sailing & Snorkeling Day Charter - Fajardo, Puerto Rico

    Had a great time on Captain Ivan's boat. Got lucky and seen a dolphin and turtles. A great boat for your day on the water.

  4. KM

    Karrah

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

    Our trip was amazing, Jose and Suri were great. Beautiful locations, snacks, drinks, equipment. They even took photos and sent them to us. They were a great team and made it an amazing day for us. Would definitely book with them again!

  5. mk

    mark

    Private Luxury Catamaran - Old San Juan

    Boat was excellent! Todd was available and very easy to work with. Captain met us in-time and had great experience. Easy process. Highly recommend Todd!

  6. BM

    Brittany

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

    100% recommend! Excellent service from booking to completion! Had a wonderful day on the water & loved everything!