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All listings in Puerto Rico

Awesome sailboat rentals in Puerto Rico.

5.0(Average of 157 reviews in this area)
Page 1 of 2 (26 listings)
Private San Juan Bay Cruise/37 Foot Sailboat/FREE Tapas and Drinks/See Old San Juan/Sunset/Swim
Sailing in San Juan · 6 guests

Private San Juan Bay Cruise/37 Foot Sailboat/FREE Tapas and Drinks/See Old San Juan/Sunset/Swim

5.0
$195hour
Instant Book
Sunset Cruise in San Juan Puerto Rico
San Juan · 6 guests

Sunset Cruise in San Juan Puerto Rico

5.0
Superowner
Best of 2022
$353hour
MINI RETREAT ✌️ HOLISTIC  🙌  YOGA 🧘🏼‍♀️ SAILING ⛵️ SOBRIETY 🙋‍♀️ CRUISE 🇵🇷
Fajardo · 4 guests

MINI RETREAT ✌️ HOLISTIC 🙌 YOGA 🧘🏼‍♀️ SAILING ⛵️ SOBRIETY 🙋‍♀️ CRUISE 🇵🇷

New
$1,999day
Janise Sailing & Snorkeling Day Charter - Fajardo, Puerto Rico 🇵🇷
Sailing in Fajardo · 6 guests

Janise Sailing & Snorkeling Day Charter - Fajardo, Puerto Rico 🇵🇷

4.9
$1,399day
Puerto Rico Catamaran Sailing Charter Family Friendly, Groups, 5 Stars
Sailing in Fajardo · 6 guests

Puerto Rico Catamaran Sailing Charter Family Friendly, Groups, 5 Stars

5.0
$209hour
Janise Sailing Afternoon Charter - Fajardo, Puerto Rico
Sailing in Fajardo · 6 guests

Janise Sailing Afternoon Charter - Fajardo, Puerto Rico

5.0
$995day
⛵️ Exclusive ECO & Healthy Sailing 🙌🏝🤿🐠🧜‍♀️🧘🏼‍♀️🥗🥙🌯🥪🫐🍉🍍🍇🥭🍹
Sailing in Fajardo · 6 guests

⛵️ Exclusive ECO & Healthy Sailing 🙌🏝🤿🐠🧜‍♀️🧘🏼‍♀️🥗🥙🌯🥪🫐🍉🍍🍇🥭🍹

4.9
$300hour
Instant Book
Quick Sail a Classic 1969 Sloop in San Juan, Puerto Rico
Sailing in San Juan · 6 guests

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

4.9
Superowner
Best of 2022
$99person
Catamaran Sailing Charters 5 Stars Puerto Rico Families and Groups Welcome
Sailing in Fajardo · 6 guests

Catamaran Sailing Charters 5 Stars Puerto Rico Families and Groups Welcome

5.0
$249hour
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
Best of 2022
$800hour
Charter Captain Services
Sailing in Fajardo · 6 guests

Charter Captain Services

4.7
Superowner
Best of 2022
$250hour
🥰 SAIL AWAY - ANCHOR - RELAX - DINNER - NIGHT in CABIN - BREKKIE - SAIL BACK ⛵️
Sailing in Fajardo · 4 guests

🥰 SAIL AWAY - ANCHOR - RELAX - DINNER - NIGHT in CABIN - BREKKIE - SAIL BACK ⛵️

5.0
$1,399day
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
Leopard 43 Sailing Catamaran with USCG Certified Captain and Crew in Ceiba, Puerto Rico
Sailing in Fajardo · 6 guests

Leopard 43 Sailing Catamaran with USCG Certified Captain and Crew in Ceiba, Puerto Rico

5.0
$440hour
12 passengers Luxury Sailing Catamaran Charter in Fajardo, Puerto Rico
Sailing in Ceiba · 19 guests

12 passengers Luxury Sailing Catamaran Charter in Fajardo, Puerto Rico

New
$2,600day
Catamaran Sail to VIEQUES for your BIO BAY kayak tour
Fajardo · 6 guests

Catamaran Sail to VIEQUES for your BIO BAY kayak tour

New
$1,827day
Culebra Catamaran Charter Culebrita Beach The Baths Lighthouse Hike
Sailing in Fajardo · 6 guests

Culebra Catamaran Charter Culebrita Beach The Baths Lighthouse Hike

New
$2,499day
Leopard L40 Catamaran Charter Culebra The Baths & Lighthouse Hike
Sailing in Culebra Pueblo · 6 guests

Leopard L40 Catamaran Charter Culebra The Baths & Lighthouse Hike

New
$2,499day
Snorkel, Swim, Beach, Private Island, Private Catamaran Tour
Sailing in Fajardo · 6 guests

Snorkel, Swim, Beach, Private Island, Private Catamaran Tour

New
$209hour
Charter 32' Cruising Catamaran In Fajardo, Puerto Rico
Sailing in Fajardo · 12 guests

Charter 32' Cruising Catamaran In Fajardo, Puerto Rico

New
$700hour
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

New
$635day
Private Sunset Sail - South Coast of Puerto Rico
Sailing in Salinas · 6 guests

Private Sunset Sail - South Coast of Puerto Rico

New
$460day
Wellcraft Coastal Motor Yacht Rental in Fajardo, Puerto Rico
Events in Fajardo · 6 guests

Wellcraft Coastal Motor Yacht Rental in Fajardo, Puerto Rico

New
$1,000day

Top Destinations Nearby

Sailing Reviews in Puerto Rico

  1. NM
    Natanael
    Private San Juan Bay Cruise/37 Foot Sailboat/FREE Tapas and Drinks/See Old San Juan/Sunset/Swim

    We have an amazing time Captain Luis and his team are very knowledgeable and professional. He will take you to the amazing view of el morro from the water side.They have the local beer and local rum for us and the tapas were delicious. If you want to have a great time book it now sail away to the fun you will have an amazing experience Great Family experience.

  2. PB
    Philip
    Janise Sailing & Snorkeling Day Charter - Fajardo, Puerto Rico 🇵🇷

    We actually had Capt Bill and Ashley..not knocking the other captains but Bill and Ashley were awesome! We would highly recommend and shouid we come back to PR soon, we will certainly request them. If you’re considering taking a charter, these folks are a class act!

  3. EL
    Erin
    ⛵️ Exclusive ECO & Healthy Sailing 🙌🏝🤿🐠🧜‍♀️🧘🏼‍♀️🥗🥙🌯🥪🫐🍉🍍🍇🥭🍹

    Me and my five girlfriends had the most amazing time! Osva and Osva were kind and made us feel right at home. They took us to the most beautiful island and were trustworthy and great. Couldn't recommend more!

  4. AF
    Afton
    Puerto Rico Catamaran Sailing Charter Family Friendly, Groups, 5 Stars

    We had such an amazing time with Bryan and Marie. They kept us laughing and really strived to make the experience a good one. We have done charters before and they really provide a special touch. We were able to bring our children and not only were they great with them, they were in the water playing and helping them have a good time as well. The only problem is we had to leave. We hope to see them again soon. Thank you guys for a wonderful trip!

  5. RS
    Rajvir
    Private San Juan Bay Cruise/37 Foot Sailboat/FREE Tapas and Drinks/See Old San Juan/Sunset/Swim

    We went on Captain Luis’ boat for a bachelorette party and had a wonderful experience. Captain Luis was very accommodating and make our experience very memorable.

  6. Tonya
    Tonya
    Private San Juan Bay Cruise/37 Foot Sailboat/FREE Tapas and Drinks/See Old San Juan/Sunset/Swim

    This is the trip you want to book! Capt Luis is the best! He is very communicative, knowledgeable, and safe on the water! He made sure we were comfortable the whole time. He went above and beyond and surprised me with a birthday cake and song! His wife made the cutest (and delicious!) charcuterie tray and he provided us with soda, water, and beer. He shared some Puerto Rican history with us as we went along our sunset cruise. He took pictures of my family together behind the wheel, and even let me drive!!! This was the most perfect birthday I have ever experienced, and Capt Luis made it even better than I had hoped for. I will most certainly book again with Capt Luis!!! Thank you! Thank you! Thank you!!!