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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(2,125 Reviews)

Page 7 of 17395 listings

Power in Las Galeras
Sailing in Las Galeras · 10 guests

Power in Las Galeras

New
$1,580/day
Cruising Catamaran Charter for Up to 65 People in St Maarten
Sailing in Simpson Bay · 65 guests

Cruising Catamaran Charter for Up to 65 People in St Maarten

5.0
$1,800/day
S/Y Timshel Day and Term Charters, Grenada and Grenadines
Sailing in Saint George's · 6 guests

S/Y Timshel Day and Term Charters, Grenada and Grenadines

5.0
$660/day
Sailing live aboard  Charter in Montego Bay, Jamaica
Sailing in Montego Bay · 15 guests

Sailing live aboard Charter in Montego Bay, Jamaica

5.0
$950/day
40 ft Jeanneau Sloop Charter in Fort Lauderdale
Sailing in Fort Lauderdale · 6 guests

40 ft Jeanneau Sloop Charter in Fort Lauderdale

5.0
$109+/hour
St. Kitts Coastline Cruise & Beach
Tours in Basseterre · 45 guests

St. Kitts Coastline Cruise & Beach

5.0
$147/hour
80' Sailing Schooner Charter In Key West, Florida
Sailing in Key West · 32 guests

80' Sailing Schooner Charter In Key West, Florida

5.0
$475+/hour
St. Martin Private Boat Tour with Lagoon 450 Cruising Catamaran
Sailing in Anse Marcel · 20 guests

St. Martin Private Boat Tour with Lagoon 450 Cruising Catamaran

New
$1,878/day
Charter Lagoon 44 Sailing Catamaran Yacht In Cartagena, Colombia
Sailing in Cartagena · 12 guests

Charter Lagoon 44 Sailing Catamaran Yacht In Cartagena, Colombia

5.0
$250+/hour
Luxury Catamaran Leopard 48 in Santa Marta Colombia
Sailing in Comuna 2 · 10 guests

Luxury Catamaran Leopard 48 in Santa Marta Colombia

New
$150/hour
Lagoon 42' Private Sailing Adventure in Florida with Captain Eric
Sailing in Deerfield Beach · 8 guests

Lagoon 42' Private Sailing Adventure in Florida with Captain Eric

5.0
$300/hour
Punta Cana - PRIVATE MEDIUM GROUP (FRANK)
Sailing in Bávaro · 35 guests

Punta Cana - PRIVATE MEDIUM GROUP (FRANK)

New
$375/hour
Charter the Maxicat 65 Sailing Catamaran in Cartagena, Colombia
Sailing in Cartagena · 60 guests

Charter the Maxicat 65 Sailing Catamaran in Cartagena, Colombia

5.0
$3,500/day
Snorkeling And Party Boat For Private Groups
Powerboats in Uvero Alto · 80 guests

Snorkeling And Party Boat For Private Groups

5.0
$167/hour
Luxury Yacht Sailing Tour inclusive of Lunch and Drinks on board Aquila 44’
Events in Nassau · 12 guests

Luxury Yacht Sailing Tour inclusive of Lunch and Drinks on board Aquila 44’

New
$850/hour
40ft party catamaran for 13 on sand bar!
Sailing in Sunny Isles Beach · 12 guests

40ft party catamaran for 13 on sand bar!

New
Superowner
$280+/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
Private Gourmet Sailing Charters on Elegant 50ft Catamaran
Sailing in Nassau · 10 guests

Private Gourmet Sailing Charters on Elegant 50ft Catamaran

New
$595+/hour
🛥️🏝️ Snorkeling Cruise Charter in Puerto Plata🛥️🏝️
Sailing in Barrio Las Yaguitas · 18 guests

🛥️🏝️ Snorkeling Cruise Charter in Puerto Plata🛥️🏝️

New
Superowner
Best of 2025
$75/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
52 Luxury Catamaran With Ac - Rates For 2 People
Sailing in Guna Yala Comarca · 8 guests

52 Luxury Catamaran With Ac - Rates For 2 People

5.0
$2,540/day
Clear Kayak Mangrove Cay Eco Venture 2-hour tour
Adventures in Leeward Settlement · 10 guests

Clear Kayak Mangrove Cay Eco Venture 2-hour tour

New
$200/hour
Sail St Maarten on 42ft Gibsea SunDowner Crusing Monohull
Sailing in Simpson Bay · 10 guests

Sail St Maarten on 42ft Gibsea SunDowner Crusing Monohull

5.0
$1,200/day
Punta Cana - PARTY BOAT (ADULT ONLY)
Sailing in Bávaro · 200 guests

Punta Cana - PARTY BOAT (ADULT ONLY)

New
$984/hour

Sailing Reviews in Caribbean

  1. SH

    Susan

    Cruising Catamaran Charter for Up to 65 People in St Maarten

    Thank you so much Cathy and team! We had an incredible time on the Tango and would 100% do it again! The crew was fun and professional and ensured we had a wonderful snorkel and sail. Thank you again!! Definitely would recommend them and would book again!

  2. AT

    Andrew

    S/Y Timshel Day and Term Charters, Grenada and Grenadines

    Our day aboard the Timshel was the highlight of our trip. The intimacy of the statue park and private beach experience are unmatched. The best way to see the west side of the island. Would recommend this to anyone traveling to Grenada. I plan to book again upon returning.

  3. Ebony

    Ebony

    S/Y Timshel Day and Term Charters, Grenada and Grenadines

    This is an experience you won’t regret. If you are thinking about it just do it. Margaret is the best hostess, very knowledgeable about the history of the island. We were also served fresh food from Margaret’s garden as well as some grilled chicken and mahi mahi, delicious! We also got a guided snorkel tour of the under water sculpture park. We had the best time!

  4. SS

    Shaun

    40 ft Jeanneau Sloop Charter in Fort Lauderdale

    This was our first time sailing and Captain Dan was amazing 🤩. He is very knowledgeable and accommodating. We sat up front on a couple of bean bags which was perfect and very comfortable. We will definitely do this again. Oh and we saw 👀dolphins 🐬 too. 🙌

  5. Kathy

    Kathy

    40 ft Jeanneau Sloop Charter in Fort Lauderdale

    It was a great choice! Captain Dan welcomed us and prepared us so we would have a most enjoyable and safe trip! We toured beautiful areas, sailed along the coast and a great ocean adventure! We dropped anchor for a swim and lunch and had great conversation !! Thank you and we will be back!

  6. AG

    Aamira

    Charter Lagoon 44 Sailing Catamaran Yacht In Cartagena, Colombia

    Ragho and team were really great communicators throughout the process. Planning a trip from the US and not speaking much Spanish, they truly made the process seamless. Even when there was a hiccup in our boat and scheduling they made sure to accommodate by providing us champagne and snacks to make up for it. I do wish the staff spoke a little more English so that we could have an actual tour of isla de rosario but all in all we had a great time! The staff was courteous and very attentive. I look forward to sailing with them in the future!