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$100-$300
All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(587 Reviews)

Page 1 of 6136 listings

Private San Juan Bay Cruise 37' Sailboat
Sailing in San Juan · 6 guests

Private San Juan Bay Cruise 37' Sailboat

5.0
$200hour
Luxury 48' Leopard Catamaran in Cartagena
Sailing in Cartagena · 25 guests

Luxury 48' Leopard Catamaran in Cartagena

4.8
Superowner
Best of 2023
$210-$325hour
Tour in Las Terrenas on 45ft Fountaine Pajot Sailing Catamaran
Sailing in Las Terrenas · 15 guests

Tour in Las Terrenas on 45ft Fountaine Pajot Sailing Catamaran

New
Best of 2023
$279hour
🥰 Set sail to "Bacardi Island" Samaná ~ Private Catamaran Sailing
Sailing in Samaná Province · 12 guests

🥰 Set sail to "Bacardi Island" Samaná ~ Private Catamaran Sailing

5.0
$197hour
The 30ft in Cruises at Barbados
Sailing in Welches · 15 guests

The 30ft in Cruises at Barbados

5.0
Best of 2023
$180-$200hour
Curacao Experience, Spanish Waters, snorkel and fuik cruise ship pickup possible
Sailing in Jan Thiel · 30 guests

Curacao Experience, Spanish Waters, snorkel and fuik cruise ship pickup possible

5.0
$100person
38’ Lagoon Catamaran Charter In Miami, Florida
Sailing in Miami · 13 guests

38’ Lagoon Catamaran Charter In Miami, Florida

5.0
Superowner
$299hour
SCHAEFER V33 Luxury speedboat 34ft charter from Marigot
Powerboats in Marigot · 8 guests

SCHAEFER V33 Luxury speedboat 34ft charter from Marigot

5.0
$173hour
44ft Sailing Catamaran Charter in Bridgetown, Saint Michael
Sailing in Henrys · 20 guests

44ft Sailing Catamaran Charter in Bridgetown, Saint Michael

5.0
$198hour
Charter 45ft Cruising Catamaran In Christchurch, Barbados
Sailing in Welches · 26 guests

Charter 45ft Cruising Catamaran In Christchurch, Barbados

5.0
Best of 2023
$250hour
51ft Trimaran-Catamaran Sailing Yacht Charter in Miami, Florida
Powerboats in Miami · 15 guests

51ft Trimaran-Catamaran Sailing Yacht Charter in Miami, Florida

5.0
Snoozed - Active 02 Jan 2025
Cruise in our Bali 45 Catamaran
Sailing in Saint George's · 10 guests

Cruise in our Bali 45 Catamaran

New
$125hour
Custom Classic 68ft Sailing Yacht for Snorkeling Adventures in Klein Curacao!
Sailing in Jan Thiel · 40 guests

Custom Classic 68ft Sailing Yacht for Snorkeling Adventures in Klein Curacao!

5.0
$195hour
44ft Millennium Cruising Catamaran Charter in Bolívar, Colombia
Sailing in Cartagena · 20 guests

44ft Millennium Cruising Catamaran Charter in Bolívar, Colombia

5.0
Snoozed - Active 02 Jan 2025
Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida
Tours in Fort Lauderdale · 6 guests

Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida

5.0
Superowner
$119-$125hour
Set sail with our luxurious Sea Ray 300 Yacht!!
Powerboats in Sunny Isles Beach · 10 guests

Set sail with our luxurious Sea Ray 300 Yacht!!

New
$200hour
Larson 23ft Private deck boat with a captain included
Powerboats in Oranjestad-East · 6 guests

Larson 23ft Private deck boat with a captain included

5.0
$200-$225hour
Private Morning Tour Curacao - Sailing Yacht with crew
Sailing in Santa Barbara Plantation · 8 guests

Private Morning Tour Curacao - Sailing Yacht with crew

5.0
$225person
Fll Sun Deck 24' Final Price No Hidden Fees 10ppl max
Powerboats in Fort Lauderdale · 6 guests

Fll Sun Deck 24' Final Price No Hidden Fees 10ppl max

4.8
Superowner
$113-$171hour
30 foot Jupiter Center Console Rental in Fort Lauderdale, Florida
Powerboats in Deerfield Beach · 10 guests

30 foot Jupiter Center Console Rental in Fort Lauderdale, Florida

5.0
$200hour
 LAGOON 440 CATAMARAN
Sailing in Cartagena · 20 guests

LAGOON 440 CATAMARAN

New
$235-$249hour
Luxury Sailing Catamaran in Key West
Sailing in Key West · 10 guests

Luxury Sailing Catamaran in Key West

5.0
$250hour
Luxury Catamaran Lagoon 52' Capacity up to 40
Powerboats in Cartagena · 40 guests

Luxury Catamaran Lagoon 52' Capacity up to 40

5.0
$250hour
Charter Cruising Monohull In Nassau & Paradise Island, The Bahamas!
Sailing in Nassau · 12 guests

Charter Cruising Monohull In Nassau & Paradise Island, The Bahamas!

4.7
$140person

Sailing Reviews in Caribbean

  1. SB

    Shirley

    44ft Sailing Catamaran Charter in Bridgetown, Saint Michael

    Kirk and Caroline are absolutely wonderful people to go sailing with. Our party was us (grandparents), our daughter and son-in-law and their two boys aged 4 and 2. I hired a private catamaran to repeat an experience I had had some years ago when I was in Barbados for my job. I wanted my family to swim with the turtles and over ship wrecks. I didn’t want to be getting in the water as part of a huge group as this detracts from the experience. Communication was fast and extremely friendly throughout. Everything was made easy for us. Kirk and Caroline are super warm and friendly people. They made a huge effort to ensure we saw everything and had a fun experience. They were great with the children. Both the boys, to our surprise, went in the sea. Caroline was always there to assist with getting them in and out of the water, she offered to look after them when they got out and ensured they had lovely cold drinks! The boat is immaculate. There are fun places to sit in the sun or shade. All of the equipment was provided and again was immaculate. We had a wonderful time with them. Everyone was on a real high when we got back. I cannot recommend Kirk and Caroline highly enough. It was a truly memorable time.

  2. Michelle

    Michelle

    44ft Sailing Catamaran Charter in Bridgetown, Saint Michael

    Kirk and his wife made the adventure wonderful. Loved seeing the sea turtles and shipwrecks. I was not feeling well with rare rougher waters in the bay and their kindness meant the world to me. I loved learning about the area and them. I would HIGHLY recommend booking them over getting on a boat that’s crammed with other people, so much more enjoyable.

  3. Laura

    Laura

    Curacao Experience, Spanish Waters, snorkel and fuik cruise ship pickup possible

    Captain Daniel was a wonderful host! The boat is large and spacious with lots of places to sit and relax. There is a grill on the boat and the lunch was fabulous. Nice ride out to the sea and then relaxing in a bay by a small beach. Lots of swimming and snorkeling opportunities. Highly recommend!

  4. AK

    Aja

    Private San Juan Bay Cruise 37' Sailboat

    I had a great time sailing on Captain Luis’ boat! It was a nice and easy sail. We felt safe and comfortable the entire time and were well provided for. Plus, it was a great way to see the sites of Old San Juan!

  5. Kathy

    Kathy

    Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida

    A glorious day at sea! Do yourself a favor and book this experience! You won’t regret it! Feeling at ease on the water and really enjoying the element was what were were striving for! As a local realtor, I make sure to enjoy what this beautiful place has to offer and this is one of them!

  6. CF

    Connie

    Private San Juan Bay Cruise 37' Sailboat

    I had my bachelorette party with 6 women in Capt Luis' boat. I wanted a relaxing sailing experience in San Juan, as well as have the option to jump into the water, if we wanted. This was perfect for us. The water was very calm when we went. Capt Luis was good at listening to what the customer wants, and he adjusted to my preferred timeline, and I really liked that. He was very responsive via text, and email. And I would say, after doing my research and messaging a lot of boat companies, his pricing was the most reasonable and he was also the most responsive. My girls and I had a great time! The only thing I would give others a heads up is that the complimentary tapas and drinks that come with a 3-hour booking, is minimal. So if you and your guests are hungry and thirsty bunch, it is best to bring more of your own tapas/drinks. Regardless, I would still book him again as he was very professional and had great communication skills. It was an easy transaction despite my fickle mind.