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 Caribbean

Awesome sailboat rentals in the Caribbean.

4.7
(2,411 Reviews)

Page 5 of 20 • 460 listings

🤩DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY in Sosua Beach.
Events in Sosúa · 150 guests

🤩DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY in Sosua Beach.

5.0
$425/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
$1,800/day
BEST IN CLASS All Inclusive Catamaran Charters
Sailing in Nassau · 20 guests

BEST IN CLASS All Inclusive Catamaran Charters

5.0
$1,080/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
5-Star Vibes: All-Inclusive Captain & Crew - 65ft Ocean Explorer Catamaran
Events in Bávaro · 150 guests

5-Star Vibes: All-Inclusive Captain & Crew - 65ft Ocean Explorer Catamaran

4.2
Superowner
Best of 2026
$10/hour
Stunning 56' Sailing Yacht in Nassau! Up to 26 guests.
Sailing in Nassau · 26 guests

Stunning 56' Sailing Yacht in Nassau! Up to 26 guests.

4.4
$607+/hour
Exclusive Private boat rental to any occasion in punta cana🥳
Events in El Cortecito · 30 guests

Exclusive Private boat rental to any occasion in punta cana🥳

New
Superowner
Best of 2026
$10/hour
Luxury Catamaran Trips in St Maarten and Surrounding Islands
Caribbean · 22 guests

Luxury Catamaran Trips in St Maarten and Surrounding Islands

5.0
$475/hour
ALL INCLUSIVE luxury day and overnight charter on the sailing catamaran Amura
Sailing in Nassau · 40 guests

ALL INCLUSIVE luxury day and overnight charter on the sailing catamaran Amura

5.0
$960/hour
Beneteau Oceanis 41 for sailing adventures in San Blas Islands
Sailing in Guna Yala Comarca · 3 guests

Beneteau Oceanis 41 for sailing adventures in San Blas Islands

New
$700/day
Sailing Catamaran Yacht for up to 20 Guests in Aruba
Sailing in Oranjestad-West · 24 guests

Sailing Catamaran Yacht for up to 20 Guests in Aruba

4.7
Superowner
$675/hour
⛵️ Catamaran Party Boat 42-people Includes: 1-Captain, 1-Mate and 1-Bartender
Sailing in Miami Beach · 42 guests

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

3.0
Superowner
$700+/hour
🛥🤩LUXURY YACHT PARTY SAILING AND Swimming in SOSUA, Puerto Plata.
Events in Sosúa · 150 guests

🛥🤩LUXURY YACHT PARTY SAILING AND Swimming in SOSUA, Puerto Plata.

4.4
$300/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
Luxury Sailing Catamaran for up to 12
Sailing in Cruz Bay · 12 guests

Luxury Sailing Catamaran for up to 12

5.0
$350/hour
Instant Book
YOUR DREAM ALL-INCLUSIVE CATAMARAN CHARTER PARTY 🎉
Events in Bávaro · 120 guests

YOUR DREAM ALL-INCLUSIVE CATAMARAN CHARTER PARTY 🎉

5.0
Superowner
Best of 2026
$117/hour
Available in Puerto Plata  Private Yacht Experience: Beautiful Views book now
Powerboats in Puerto Plata · 100 guests

Available in Puerto Plata Private Yacht Experience: Beautiful Views book now

5.0
Superowner
Best of 2026
$50/hour
41ft Metta Sailing Catamaran in Turks and Caicos Islands
Sailing in Leeward Settlement · 12 guests

41ft Metta Sailing Catamaran in Turks and Caicos Islands

5.0
$450/hour
5-Star Luxury Boat : B-DAY PARTY TOTALLY PRIVATE 🎉
Events in Bávaro · 70 guests

5-Star Luxury Boat : B-DAY PARTY TOTALLY PRIVATE 🎉

New
Superowner
Best of 2026
$17/hour
44' Wellington Sailing Yacht In Antigua
Sailing in Jolly Harbour · 6 guests

44' Wellington Sailing Yacht In Antigua

5.0
$100/hour
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
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

4.9
$390/hour
33ft The Key West's Most Versatile Sailboat! (With Captain Only)
Sailing in Key West · 12 guests

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

4.6
$199+/hour
Fort Lauderdale 43' Beneteau Sailing Charter – Day Sails & Bahamas Trips
Sailing in Fort Lauderdale · 6 guests

Fort Lauderdale 43' Beneteau Sailing Charter – Day Sails & Bahamas Trips

5.0
$130+/hour

Sailing Reviews in Caribbean

  1. 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.

  2. 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.

  3. 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!

  4. 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.

  5. AM

    Amber

    Captained Charter on Lagoon 440 Cruising Catamaran in Cartagena

    Jose is professional and his boat is just as described. Big and beautiful. Everything was amazing. Everyone had the best time. We went to a variety of islands and played in the water. The Crew was amazing Captain Wilfredo got us to and back safely. Deckhand Jenny was the best, she was a hard worker, funny and a great dancer!! Chef William prepared 3 fabulous delicious meals for us. My 40th birthday was one to remember with this crew!! THANK YOU!! :)

  6. kk

    kasper

    Captained Charter on Lagoon 440 Cruising Catamaran in Cartagena

    We had a great bachelor party onboard the catamaran Lagoon 440. Staff were nice and we had a good communication with the rental company. We stacked up on drinks/snacks/fruit and other stuff at a supermarket two blocks from the marina. Will highly recommended renting a catamaran for a bachelorparty in cartagena.