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
(2,413 Reviews)

Page 5 of 20 • 461 listings

sunbathe and relax on our island in the middle of the ocean
Events in Punta Cana · 100 guests

sunbathe and relax on our island in the middle of the ocean

3.7
Superowner
Best of 2026
$50/hour
🤩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
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
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
Curacao Private Morning Tour All Inclusive
Sailing in Jan Thiel · 6 guests

Curacao Private Morning Tour All Inclusive

5.0
$250/hour

Sailing Reviews in Caribbean

  1. BB

    Brandy

    BEST IN CLASS All Inclusive Catamaran Charters

    We had Captain Fox and Jaclyn. They were both fantastic. Attentive to every detail. Food was great, we had the beef and fish burger bar, along with the fruit, meat and cheese plate, salad, pasta salad, and dessert. There was always something to eat if you wanted. The water toys were perfect to lounge and enjoy the water, along with jumping from top deck, its higher than you think so quite a little thrill. We also included a jet ski which I highly recommend, a lot of fun to add to the experience along with the famous swimming with the pigs. Even if you don’t think you’re interested, try it, we had several people with us who were on the fence whether or not they wanted to and after they did they were shocked how much they enjoyed the experience. The trick is to lure the pigs into the water and make them swim before giving them their treat. Also, we did not bring shoes because we left them on the boat but the worst thing about swimming with the pigs was the sharp rocky reef to get the pigs out far enough to swim, had I known we would have took some sort of sandal or water shoe to help from slicing your feet. Over all day was amazing. Most importantly Jaclyn was very sweet, she was little shy, but warmed up, but she was never lacking in anything we needed. Captain Fox was awesome, and fun. They both had warm personalities that made our group feel at ease and we were able to laugh and have fun with them too. Thank you both for creating a day we’ll never forget!

  2. DS

    Dahlia

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

    Thank you for a fantastic day!! The crew were super courteous, relaxed, welcoming and highly competent. The sail itself was lovely. They pointed out the best snorkeling spots and changed up the itinerary for us with no notice when we decided ON THE BOAT on swimming with the turtles and adding an extra hour! The entire experience was perfect from the ease of booking, the prompt responses to my multiple email questions, the extra adventure add-ons … to the boat itself which is is impeccably kept. The cabin is the cleanest we have ever been in, and we have sailed a lot! The drinks and food were fresh and delicious. All in all a Father’s Day to remember!!

  3. vc

    vince

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

    Great trip, real sailing, amazing captain and crew. Best experience we've had ever on a charter sail. Fun at the beach, snorkeling from the boat, and really, really good BBQ. If you're looking for something special to do while in the Bahamas - this is it.

  4. LJ

    Lauren

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

    We had a large group and several specific requests. Eryn was wonderful to work with ahead of time on all the details and made the planning process very easy. Captain Randy and his crew were amazing. Their service and attentiveness to our group were exceptional. We had a wonderful experience on our outing will definitely be doing this again the next time we are in the Bahamas!

  5. Sean

    Sean

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

    What an amazing day. They crew was incredible. Attentive, engaging, thorough, just awesome. Not only did we snorkel on a great reef, have our own private beach to relax on, have a shark circle us...but we saw a solar eclipse on a boat, in the middle of the Bahamas. That's truly a once in a lifetime experience. We will be back!

  6. JW

    Jacki

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

    This was the highlight of our cruise!! It was the perfect way to spend the day at Nassau. We had a large group (16 adults, 3 children) and everyone had a great time! From booking to the end of the trip, it was all handled in such a friendly and professional manner! Next time we are in Nassau, we will use them again!!