Cookies & Agreements

By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.

All listings in Puerto Rico

Awesome sailboat rentals in Puerto Rico.

4.9
(335 Reviews)

Page 1 of 225 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
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
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 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
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
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
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
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
Your Private Yacht for the Day – Lagoon 46 Full-Day Charter
Sailing in Fajardo · 6 guests

Your Private Yacht for the Day – Lagoon 46 Full-Day Charter

New
$2,730/day

Top Destinations Nearby

Sailing Reviews in Puerto Rico

  1. 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.

  2. BK

    Bridget

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

    Hugo is the best captain, confident and experienced. Marion is the best hostess for a full day excursion. She anticipated every question and concern. Friendly and positive. Love you both; we will all talk about this memory for years to come!

  3. EA

    Eunice

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

    We had a great time - captain Jorge was amazing- very attentive and so friendly- got us there safely and took us to both islands Food, snacks and beverages were great as listed! Would recommend and use them in the future

  4. 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!

  5. 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.

  6. 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!!!