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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(2,356 Reviews)

Page 5 of 19440 listings

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
Sailing Hobie Cat Rental in Noord, Aruba
Sailing in Oranjestad-West · 4 guests

Sailing Hobie Cat Rental in Noord, Aruba

4.4
$89/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
Puerto Plata-private And Luxury VIP Party Yachts
Powerboats in Puerto Plata · 100 guests

Puerto Plata-private And Luxury VIP Party Yachts

New
Superowner
Best of 2026
$50/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

4.0
Superowner
Best of 2026
$45/hour
Private Boat Rental Turks & Caicos
Powerboats in Long Bay Hills · 8 guests

Private Boat Rental Turks & Caicos

5.0
$200/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
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
Amazing-Private Island Punta Cana: Affordable Charter with Crew
Events in Uvero Alto · 150 guests

Amazing-Private Island Punta Cana: Affordable Charter with Crew

New
Superowner
Best of 2026
$45/hour
Montego Bay Private Champagne Sunset Catamaran Cruise
Powerboats in Montego Bay · 10 guests

Montego Bay Private Champagne Sunset Catamaran Cruise

New
$1,896/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
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
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

4.6
Superowner
$675/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
Curacao Private Morning Tour All Inclusive
Sailing in Jan Thiel · 6 guests

Curacao Private Morning Tour All Inclusive

5.0
$250/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
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
Sunset Cruise in San Juan Puerto Rico
Sailing in San Juan · 6 guests

Sunset Cruise in San Juan Puerto Rico

5.0
Superowner
$353/hour
Exclusive Private Yacht Snorkeling, Natural Sea Pool, Wild Beach, Book Now!
Events in Cabarete · 100 guests

Exclusive Private Yacht Snorkeling, Natural Sea Pool, Wild Beach, Book Now!

New
Superowner
Best of 2026
$45/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
Saint Kitts Private Boat Charter
Tours in Basseterre · 55 guests

Saint Kitts Private Boat Charter

5.0
$300/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

4.9
$390/hour

Sailing Reviews in Caribbean

  1. M

    M

    Luxury Catamaran Trips in St Maarten and Surrounding Islands

    Capt Neil was an amazing host and allowed a personalized day on the water to satisfy a group of ten. Great professionalism, communication and overall customer satisfaction. Would highly reccommend!

  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. PC

    Peter

    Sailing Hobie Cat Rental in Noord, Aruba

    Lisa was a great host as she welcomed us and got us squared away with the 16 ft Hobie Cat w/jib! The whole experience was incredible and we got some great speed on the Hobie Cat. It was a high wind day (25-30 mph) and we couldn’t have asked for a better time on the water. Lisa was gracious, helpful, and fun!

  5. 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!

  6. 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!