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All listings in Puerto Rico

Awesome sailboat rentals in Puerto Rico.

4.9
(351 Reviews)

Page 1 of 227 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
Limited Availability
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 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
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
Private Luxury Bali 4.0 Catamaran with 3 Cabin from Old San Juan
Sailing in San Juan · 12 guests

Private Luxury Bali 4.0 Catamaran with 3 Cabin from Old San Juan

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

Janise Sailing Afternoon Charter - Fajardo, Puerto Rico 🇵🇷

4.9
$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
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
Limited Availability
All Inclusive, Luxury 42 Lagoon Catamaran Adventure in Fajardo, Puerto Rico
Sailing in Fajardo · 12 guests

All Inclusive, Luxury 42 Lagoon Catamaran Adventure in Fajardo, Puerto Rico

5.0
$467+/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
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
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
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
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
Private Charter Adventure to Palomino or Icacos, Fajardo PR - 26' Hydra Sports
Powerboats in Fajardo · 6 guests

Private Charter Adventure to Palomino or Icacos, Fajardo PR - 26' Hydra Sports

New
$650/day

Top Destinations Nearby

Sailing Reviews in Puerto Rico

  1. LL

    Luke

    All Inclusive, Luxury 42 Lagoon Catamaran Adventure in Fajardo, Puerto Rico

    Minell was awesome helping set up everything. We rented a catamaran and it was so much fun. Hands down highlight of our trip! She took care of the bus there and back as well which was nice.

  2. CL

    Catherine

    All Inclusive, Luxury 42 Lagoon Catamaran Adventure in Fajardo, Puerto Rico

    5/5 star experience. I’m really happy to have chosen Minell and her team for my birthday celebration. Really lovely captain and crew to work with and nothing more I could have asked for from the all-inclusive experience with food, drink, and equipment for chilling and exploring the seas. Thank you!

  3. TL

    Tyler

    Private Luxury Bali 4.0 Catamaran with 3 Cabin from Old San Juan

    Amazing experience! Was the perfect addition to a bachelorette itinerary. Boat was clean, Manuel and Rene were so attentive and friendly. Cant recommend enough!

  4. EJ

    Ed

    Private San Juan Bay Cruise 37' Sailboat

    A beautiful sunset cruise with my family. Wind was amazing on the bay and there was a bright moon and amazing breeze when we sailed back. Captain Luis and his deckhand Gabby were filled with information about Puerto Rico and the history. Highly recommended!

  5. JL

    James

    Private San Juan Bay Cruise 37' Sailboat

    We took a private boat tour with Captain Luis and Gaby, and it was hands-down one of the best parts of our vacation. From the moment we arrived, we were greeted warmly and walked right over to the boat, which was the perfect size for our group of friends to relax and spread out. Captain Luis is an incredible captain—he navigated the waters with total ease, took us to gorgeous spots all over, and shared fascinating tidbits about Puerto Rico along the way. Both he and Gaby kept the vibes immaculate, sharing delicious sangria and making sure we had everything we needed. We spent the day listening to our favorite music, swimming, enjoying some snacks, and soaking up the sun. If you are looking for a top-tier, stress-free day on the water, I cannot recommend Captain Luis and Gaby enough! We’d book them again in a heartbeat.

  6. GW

    Gigi

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

    Jose was great. We visited two islands. He gave background about the islands. He provided refreshments and drinks. I highly recommend!