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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(2,116 Reviews)

Page 4 of 17393 listings

DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY
Events in Uvero Alto · 80 guests

DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY

5.0
$50/hour
Captained Charter on Lagoon 440 Cruising Catamaran in Cartagena
Sailing in Cartagena · 23 guests

Captained Charter on Lagoon 440 Cruising Catamaran in Cartagena

4.9
$1,650/day
Marlowe Hunter 33’ Sailing in Fort Lauderdale
Sailing in Fort Lauderdale · 6 guests

Marlowe Hunter 33’ Sailing in Fort Lauderdale

5.0
$90+/hour
50' Party Boat Catamaran in Miami ($1,200  PER HOUR)
Sailing in Miami Beach · 42 guests

50' Party Boat Catamaran in Miami ($1,200 PER HOUR)

4.8
$1,100/hour
🥂AMAZING PRIVATE YACHT🥂
Powerboats in La Romana · 50 guests

🥂AMAZING PRIVATE YACHT🥂

5.0
Superowner
Best of 2025
$50/hour
Impressive 56' Sailing Yacht in Nassau! Private charters & small group cruises.
Sailing in Nassau · 26 guests

Impressive 56' Sailing Yacht in Nassau! Private charters & small group cruises.

4.4
$607+/hour
Luxury Beneteau Sense 55 Sailing Yacht Rental in George Town, Cayman Islands
Sailing in George Town · 20 guests

Luxury Beneteau Sense 55 Sailing Yacht Rental in George Town, Cayman Islands

5.0
$425/hour
Beautiful 41' Sailing Yacht in Nassau! Small group cruises & private charters.
Sailing in Nassau · 12 guests

Beautiful 41' Sailing Yacht in Nassau! Small group cruises & private charters.

4.7
$252+/hour
Catamaran Party Boat 42-people Includes: 1-Captain, 1-Mate and 1-Bartender
Sailing in Miami · 42 guests

Catamaran Party Boat 42-people Includes: 1-Captain, 1-Mate and 1-Bartender

3.0
Superowner
Best of 2025
$800/hour
Instant Book
Captained Charter On 33ft The Key West's Most Versatile Sailboat! (With Captain Only)
Sailing in Key West · 12 guests

Captained Charter On 33ft The Key West's Most Versatile Sailboat! (With Captain Only)

4.6
$199+/hour
Private Full Day, Aboard SY Mazu - Luxury Gemini Catamaran w/Holiday Pricing
Sailing in St. Thomas · 12 guests

Private Full Day, Aboard SY Mazu - Luxury Gemini Catamaran w/Holiday Pricing

5.0
$1,550/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
Punta Cana Booze Shared Cruise, Snorkeling and Sand-Bar (Only adults)
Events in Bávaro · 100 guests

Punta Cana Booze Shared Cruise, Snorkeling and Sand-Bar (Only adults)

New
$240/hour
44ft Helia Fountinae Pajot Catamaran for sailing in Turks and Caicos
Sailing in Leeward Settlement · 18 guests

44ft Helia Fountinae Pajot Catamaran for sailing in Turks and Caicos

5.0
$999+/hour
Luxury Catamaran Trips in St Maarten and Surrounding Islands
Sailing in Simpson Bay · 22 guests

Luxury Catamaran Trips in St Maarten and Surrounding Islands

5.0
$475/hour
Curacao Private Morning Tour All Inclusive
Sailing in Santa Barbara Plantation · 6 guests

Curacao Private Morning Tour All Inclusive

5.0
$250/hour
Private Yacht Luxury Turquoise Adventure Ocho Rios, Jamaica
Sailing in Ocho Rios · 40 guests

Private Yacht Luxury Turquoise Adventure Ocho Rios, Jamaica

5.0
$1,560/hour
PRIVATE BOAT TOUR with snorkeling, blue lagoon and wild beach.
Events in Macao · 6 guests

PRIVATE BOAT TOUR with snorkeling, blue lagoon and wild beach.

New
Best of 2025
$130/hour
Half Day 50' Private Sailing Catamaran. Luxury, Beach/Snorkel. Departs Red Hook
Sailing in St. Thomas · 12 guests

Half Day 50' Private Sailing Catamaran. Luxury, Beach/Snorkel. Departs Red Hook

4.8
$390/hour
Unwind at Sea on the Spacious Voyage 500 Catamaran
Sailing in Fajardo · 6 guests

Unwind at Sea on the Spacious Voyage 500 Catamaran

4.9
$400/hour
Sail Miami! Beautiful Beneteau 43 Cruising Monohull
Sailing in Miami · 10 guests

Sail Miami! Beautiful Beneteau 43 Cruising Monohull

5.0
$170/hour
Curacao Private Sunset Tour Deluxe
Sailing in Jan Thiel · 6 guests

Curacao Private Sunset Tour Deluxe

5.0
$250/hour
Fort Lauderdale Bahamas Sailing Charters
Sailing in Fort Lauderdale · 6 guests

Fort Lauderdale Bahamas Sailing Charters

5.0
$130+/hour
Private Catamaran Charter - Be Happy 40ft - Discover the beautiful St Maarten
Sailing in Upper Prince's Quarter · 12 guests

Private Catamaran Charter - Be Happy 40ft - Discover the beautiful St Maarten

5.0
$1,750/day

Sailing Reviews in Caribbean

  1. Lisa

    Lisa

    Private Full Day, Aboard SY Mazu - Luxury Gemini Catamaran w/Holiday Pricing

    We were a group of 13 and rented two catamaran’s for the afternoon. Captain JW was the captain for the boat I was on and he was terrific- took us to Scott beach on St. John for snorkeling and swimming. It was very pretty and he was very attentive in providing drinks and snorkeling equipment and good music. We sailed in tandem with the other catamaran that had the rest of our group on it and also went to a beautiful private resort called Lovango for lunch. Felt like a little taste of Europe in the US Virgin Islands. Only complaint was I wish we had even more time at sea but we had to get back on our cruise ship!

  2. CB

    Chandler

    Half Day 50' Private Sailing Catamaran. Luxury, Beach/Snorkel. Departs Red Hook

    Maddy and Liv were so much fun, very attentive and a lot of fun! Cannot wait to return.

  3. AG

    Amy

    Captained Charter on Lagoon 440 Cruising Catamaran in Cartagena

    Fabulous trip - fantastic crew! Loved everything about it. The catered breakfast and seafood paella for lunch was PERFECT for our group of nine - Delicious and the presentation was incredible. All around memory maker for the trip! Would definitely book again.

  4. Carlos

    Carlos

    Captained Charter on Lagoon 440 Cruising Catamaran in Cartagena

    Jose’s staff did an amazing job adjusting to the challenges of moving a large group together and provided amazing service to everyone. The catamarans, Chicote and Xem 3, were in immaculate condition and real head turners once we arrived at the island and parked together. If you have the opportunity to do business with Jose and his staff, don’t hesitate and go for it, it’ll be part of memorable trip to Colombia.

  5. GK

    Gregg

    Captained Charter on Lagoon 440 Cruising Catamaran in Cartagena

    The crew that ran this boat was amazing. They were very experienced, kind, and professional. The boat was clean and comfortable for a large group of people. Jose, one of the deck hands, was incredibly helpful when we stopped at the island for lunch. He came to the island with us, made sure that everyone was comfortable, and ensured we were taken care of. We will for sure book this boat any time we go down to Cartagena. Thank you!

  6. am

    adriana

    Captained Charter on Lagoon 440 Cruising Catamaran in Cartagena

    Jose was an amazing host! Communication was thorough and he made it very easy to book through him. The catamaran was in excellent shape and was spacious enough for all 15 of my friends and family. The staff on board were incredibly attentive and friendly! Over all we had a blast and would recommend this company to any person looking for a fun boat day.