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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8

(2,354 Reviews)

Page 5 of 19 • 440 listings

Sailing in Miami Beach · 42 guests

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

3.0

Superowner

$700+/hour

Events in Sosúa · 150 guests

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

4.4

$300/hour

Sailing in Fort Lauderdale · 12 guests

57' Fountaine Pajot Sailing Catamaran - A Luxury Experience

5.0

$450/hour

Powerboats in Puerto Plata · 100 guests

Puerto Plata-private And Luxury VIP Party Yachts

New

Superowner

Best of 2026

$50/hour

Events in Bávaro · 150 guests

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

4.0

Superowner

Best of 2026

$45/hour

Powerboats in Long Bay Hills · 8 guests

Private Boat Rental Turks & Caicos

5.0

$200/hour

Sailing in Nassau · 26 guests

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

4.4

$607+/hour

Sailing in Fajardo · 6 guests

Charter 52' Cruising sailboat in Fajardo, Puerto Rico

5.0

$850/day

Events in Uvero Alto · 150 guests

Amazing-Private Island Punta Cana: Affordable Charter with Crew

New

Superowner

Best of 2026

$45/hour

Powerboats in Montego Bay · 10 guests

Montego Bay Private Champagne Sunset Catamaran Cruise

New

$1,896/hour

Sailing in Jolly Harbour · 6 guests

44' Wellington Sailing Yacht In Antigua

5.0

$100/hour

Sailing in St. Thomas · 12 guests

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

5.0

$1,550/day

Sailing in Oranjestad-West · 24 guests

Sailing Catamaran Yacht for up to 20 Guests in Aruba

4.6

Superowner

$675/hour

Sailing in Jan Thiel · 6 guests

Curacao Private Morning Tour All Inclusive

5.0

$250/hour

Sailing in Key West · 12 guests

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

4.6

$199+/hour

Events in Bávaro · 120 guests

YOUR DREAM ALL-INCLUSIVE CATAMARAN CHARTER PARTY 🎉

5.0

Superowner

Best of 2026

$117/hour

Caribbean · 22 guests

Luxury Catamaran Trips in St Maarten and Surrounding Islands

5.0

$475/hour

Sailing in San Juan · 6 guests

Sunset Cruise in San Juan Puerto Rico

5.0

Superowner

$353/hour

Events in Cabarete · 100 guests

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

New

Superowner

Best of 2026

$45/hour

Limited Availability

Sailing in Leeward Settlement · 12 guests

41ft Metta Sailing Catamaran in Turks and Caicos Islands

5.0

$450/hour

Tours in Basseterre · 55 guests

Saint Kitts Private Boat Charter

5.0

$300/hour

Sailing in St. Thomas · 12 guests

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

4.9

$390/hour

Sailing in Fort Lauderdale · 6 guests

Fort Lauderdale - Bahamas Sailing Charters

5.0

$130+/hour

Events in Bávaro · 200 guests

Amazing Punta Cana Sand Bar Party with Chaparral Motor Yacht!

5.0

Superowner

Best of 2026

$17/hour

Top Destinations Nearby

Sailing Reviews in Caribbean

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!
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!
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!
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!!
Cristina

Charter 52' Cruising sailboat in Fajardo, Puerto Rico
I need more stars to rate this trip and Domingo a 10!!! Everything about this day was beyond amazing!!! The sailing, the amazing beach and swimming….THE LUNCH!!!! But most of all his kindness and hospitality are top notch!!!! Worth every penny and every second of the day!
Diane

Charter 52' Cruising sailboat in Fajardo, Puerto Rico
If you are looking for a beautiful day on the waters of Puerto Rico we can highly recommend booking your day with Domingo. He and Laura were the perfect hosts and the sailing was gorgeous. We went snorkeling and swimming in the crystal waters. The lunch they cooked and served was delicious.