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All listings in Puerto Rico

Awesome sailboat rentals in Puerto Rico.

5.0
(261 Reviews)

Page 1 of 225 listings

Amazing Day at Icacos & Palomino Islands
Tours in Fajardo · 6 guests

Amazing Day at Icacos & Palomino Islands

5.0
$725day
Private San Juan Bay Cruise 37' Sailboat
Sailing in San Juan · 6 guests

Private San Juan Bay Cruise 37' Sailboat

5.0
Superowner
$200hour
Island Hopping at Icacos & Palomino
Events in Fajardo · 6 guests

Island Hopping at Icacos & Palomino

5.0
$725day
Sailing & Snorkeling Day Charter - Fajardo, Puerto Rico
Sailing in Fajardo · 6 guests

Sailing & Snorkeling Day Charter - Fajardo, Puerto Rico

4.9
Best of 2023
$1,395day
Quick Sail a 35' Classic 1969 Sloop in San Juan, Puerto Rico
Sailing in San Juan · 6 guests

Quick Sail a 35' Classic 1969 Sloop in San Juan, Puerto Rico

4.9
Superowner
$99person
Private Luxury Sailing Experience out of Old San Juan
Sailing in San Juan · 12 guests

Private Luxury Sailing Experience out of Old San Juan

5.0
$725hour
Janise Sailing Afternoon Charter - Fajardo, Puerto Rico 🇵🇷
Sailing in Fajardo · 6 guests

Janise Sailing Afternoon Charter - Fajardo, Puerto Rico 🇵🇷

4.9
Best of 2023
$995day
Lagoon 42 Luxury Catamaran Sail to Icacos or Palominos
Sailing in Fajardo · 12 guests

Lagoon 42 Luxury Catamaran Sail to Icacos or Palominos

New
$575hour
⛵️ Relaxing ECO Day Sailing 🏝🤿🐠🧜‍♀️🍹🥂
Sailing in Fajardo · 6 guests

⛵️ Relaxing ECO Day Sailing 🏝🤿🐠🧜‍♀️🍹🥂

4.9
$400hour
Sunset Cruise in San Juan Puerto Rico
Sailing in San Juan · 6 guests

Sunset Cruise in San Juan Puerto Rico

5.0
Superowner
$353hour
Charter 52' Cruising sailboat in Fajardo, Puerto Rico
Sailing in Fajardo · 6 guests

Charter 52' Cruising sailboat in Fajardo, Puerto Rico

5.0
$850day
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
Superowner
$800hour
Charter Captain Services
Sailing in Fajardo · 6 guests

Charter Captain Services

4.7
Superowner
$250hour
Janise Sailing Overnight Charter - Fajardo, Puerto Rico 🇵🇷
Sailing in Fajardo · 6 guests

Janise Sailing Overnight Charter - Fajardo, Puerto Rico 🇵🇷

New
Best of 2023
$130hour
Luxury Sailing Catamaran Charter in Fajardo, Puerto Rico
Sailing in Ceiba · 19 guests

Luxury Sailing Catamaran Charter in Fajardo, Puerto Rico

5.0
$2,700day
Snorkeling & Kayak Mini Eco-Experience
Tours in Fajardo · 16 guests

Snorkeling & Kayak Mini Eco-Experience

5.0
Snoozed - Active 02 Jan 2025
🧘🏼‍♀️ HOLISTIC SAILING RETREAT 🙌
Sailing in Fajardo · 6 guests

🧘🏼‍♀️ HOLISTIC SAILING RETREAT 🙌

New
$2,659night
Private Luxury Sailing Charter around the East Coast of Puerto Rico
Sailing in Fajardo · 6 guests

Private Luxury Sailing Charter around the East Coast of Puerto Rico

New
$1,198day
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
$2,695day
Eco Sailing in Vieques, PR 🇵🇷
Sailing in Vieques · 4 guests

Eco Sailing in Vieques, PR 🇵🇷

New
$250hour
Charter 32' Cruising Catamaran In Fajardo, Puerto Rico
Sailing in Fajardo · 12 guests

Charter 32' Cruising Catamaran In Fajardo, Puerto Rico

New
$500-$700hour
Private Sunset Sail - South Coast of Puerto Rico
Sailing in Salinas · 6 guests

Private Sunset Sail - South Coast of Puerto Rico

New
$230hour
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
$1,050day
Hunter 45ft Sailboat Private Charter
Sailing in Fajardo · 6 guests

Hunter 45ft Sailboat Private Charter

New
$1,200day

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Sailing Reviews in Puerto Rico

  1. CF

    Connie

    Private San Juan Bay Cruise 37' Sailboat

    I had my bachelorette party with 6 women in Capt Luis' boat. I wanted a relaxing sailing experience in San Juan, as well as have the option to jump into the water, if we wanted. This was perfect for us. The water was very calm when we went. Capt Luis was good at listening to what the customer wants, and he adjusted to my preferred timeline, and I really liked that. He was very responsive via text, and email. And I would say, after doing my research and messaging a lot of boat companies, his pricing was the most reasonable and he was also the most responsive. My girls and I had a great time! The only thing I would give others a heads up is that the complimentary tapas and drinks that come with a 3-hour booking, is minimal. So if you and your guests are hungry and thirsty bunch, it is best to bring more of your own tapas/drinks. Regardless, I would still book him again as he was very professional and had great communication skills. It was an easy transaction despite my fickle mind.

  2. JW

    Julie

    Private San Juan Bay Cruise 37' Sailboat

    Captain Luis and First Mate Gabi were great! It was rather windy the day we went, so we appreciated their sailing experience. Luis gave us a great tour of San Juan Harbor with lots of historical facts. Gabi was very helpful, taking care of our every need. Luis contacted us the day before with all of the details which were spot on, and we were able to order additional food and drinks so all we had to do was show up. I would highly recommend Captain Luis.

  3. SM

    Samuel

    Private Luxury Sailing Experience out of Old San Juan

    I booked a trip for 12 people, which was the perfect size. The captain was amazing and took us around different areas of San Juan as well as let us dock so we could all go swimming. If you are in San Juan I highly recommend this!!

  4. MH

    Mindi

    Amazing Day at Icacos & Palomino Islands

    We had a beautiful day on the water. Victor was our captain, and he was very knowledgeable about the area and friendly and laid back. He even jumped in and snorkeled a bit, which we loved! The equipment was clean and in very good shape. They even provided a beach umbrella when we stopped at Icacos. No complaints at all - we would definitely book with them again!

  5. DA

    Dennis

    Amazing Day at Icacos & Palomino Islands

    I would highly recommend Jose and his crew, we had a very nice boat trip and they delivered exactly what was expected (light food and plenty of drinks, a good experience on the water, good equipment for snorkeling, etc.). Thank you to Jose and our captain, Victor!

  6. Madison

    Madison

    Private Luxury Sailing Experience out of Old San Juan

    10/10 experience!! Rented for myself and 6 bridesmaids for my bachelorette and had the best time ever! Service was exceptional and booking process was so easy. This is the boat to book while you’re in Puerto Rico!