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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(1,991 Reviews)

Page 16 of 16377 listings

7 Day Cruise aboard Lagoon 470 Cruising Catamaran in Sainte-Anne
Sailing in Grande-Terre · 8 guests

7 Day Cruise aboard Lagoon 470 Cruising Catamaran in Sainte-Anne

New
$1,179/day
Charter a Cruising Monohull in Foster Hall, Barbados
Sailing in Less Beholden · 15 guests

Charter a Cruising Monohull in Foster Hall, Barbados

New
$10,667/day
Beneteau First 40.7 Cruising Monohull - up to 6 people in Antigua and Barbuda
Sailing in English Harbour · 6 guests

Beneteau First 40.7 Cruising Monohull - up to 6 people in Antigua and Barbuda

5.0
$920/day
51' Neel Cruising Catamaran Rental in Le Marin, Martinique
Sailing in Rivière-Salée · 9 guests

51' Neel Cruising Catamaran Rental in Le Marin, Martinique

New
$1,601/day
' Center Console in Frigate Bay
Basseterre · 6 guests

' Center Console in Frigate Bay

New
$113/hour
TORTOLA BVI - PRIVATE DAY SAILS ON 48' Privilege Catamaran Charter
Sailing in Wickhams Cay 1 · 20 guests

TORTOLA BVI - PRIVATE DAY SAILS ON 48' Privilege Catamaran Charter

New
$3,000/day
Private Catamaran Charter In Punta Cana, Dominican Republic
Sailing in El Cortecito · 50 guests

Private Catamaran Charter In Punta Cana, Dominican Republic

New
$350/hour
Beach Monohulls Rental in Saboga, Panama
Sailing in Contadora · 5 guests

Beach Monohulls Rental in Saboga, Panama

New
$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
Snoozed - Active 08 Oct 2025
Limited Availability
Luxury Catamaran Lagoon 52' Capacity up to 40
Powerboats in Cartagena · 40 guests

Luxury Catamaran Lagoon 52' Capacity up to 40

5.0
Snoozed - Active 20 Oct 2025
Ultimate Day Sailing Charter Onboard 40' Baba Sailboat in St. Thomas
Sailing in St. Thomas · 6 guests

Ultimate Day Sailing Charter Onboard 40' Baba Sailboat in St. Thomas

5.0
Snoozed - Active 23 Jan 2026
Sailing catamaran in USVI
Sailing in Charlotte Amalie · 6 guests

Sailing catamaran in USVI

5.0
Snoozed - Active 02 Apr 2026
Axe 1 Center Console Boat Rental in Montego Bay, Jamaica
Events in Montego Bay · 8 guests

Axe 1 Center Console Boat Rental in Montego Bay, Jamaica

New
Snoozed - Active 02 Oct 2025
Hanse 418 Cruising Monohull Rental in Hollywood, Florida
Sailing in Hollywood · 12 guests

Hanse 418 Cruising Monohull Rental in Hollywood, Florida

New
Snoozed - Active 02 Nov 2025
Private 65ft Catamaran for Charter Trips in Montego Bay
Sailing in Montego Bay · 40 guests

Private 65ft Catamaran for Charter Trips in Montego Bay

New
Snoozed - Active 02 Nov 2025
Leopard 46 Catamaran Sailing in Antigua & Barbuda
Sailing in English Harbour · 6 guests

Leopard 46 Catamaran Sailing in Antigua & Barbuda

New
Snoozed - Active 02 Mar 2026
Lagoon 420 Hybrid Eco Friendly Electric Catamaran
Sailing in Guna Yala Comarca · 4 guests

Lagoon 420 Hybrid Eco Friendly Electric Catamaran

New
Snoozed - Active 31 Mar 2026

Sailing Reviews in Caribbean

  1. MC

    Mev

    Luxury Catamaran Lagoon 52' Capacity up to 40

    Thank you! Captain, crew and chef were all phenomenal! Attentive, helpful and polite - all around great experience! Highly recommend this boat and crew. We had a group of 10 adults and 10 teens. Everyone raved about our day with the Sea Warriors. Just book them for a fun, luxury experience that is customizable for your group. 5 stars all the way.

  2. TW

    Terry

    41ft Metta Sailing Catamaran in Turks and Caicos Islands

    A perfect day on the Metta. After messaging about our grandkids interests, the captain took us to the boat wreck to snorkel and then to a great coral reef! Snacks, drinks and gear were provided and they were very helpful. Last, we swam and played on the most beautiful beach and the kids saw iguanas! Great hosts! We will book the Metta again!

  3. KB

    Kia

    Luxury Catamaran Lagoon 52' Capacity up to 40

    Jose’s boat was awesome! The boat itself was beautiful and spacious. The crew was helpful and knowledgeable and was able to make our full itinerary work! We had a wonderful time celebrating our friend’s bachelorette!

  4. KH

    Kanisha

    41ft Metta Sailing Catamaran in Turks and Caicos Islands

    We had an amazing time with our group of 8 adults and 3 kids under 5. We had a totally customized itinerary and the crew is so incredibly helpful and welcoming. We had an amazing time on a half day charter and would definitely do a full day with this crew any time. The highlight of our trip was JoJo the dolphin following us during the whole charter! We got to snorkel with him and the kids were so happy to see him following alongside the boat the whole way!

  5. AS

    Adriana

    Luxury Catamaran Lagoon 52' Capacity up to 40

    I can’t say enough good things about my experience after spending a day in the beautiful Cartagena waters. Since we were a big group, we had lots of questions which Mayerling answered. The entire crew truly made this day so special, from the attentiveness to the set up before we got on the boat. The boat itself is gorgeous and in very good conditions. We were a group of 15 and never felt on top of each other as there was so much space. Highly recommend to book them if you’re traveling to Cartagena!

  6. HW

    Hayley

    Luxury Catamaran Lagoon 52' Capacity up to 40

    Jose was amazing! He communicated continuously throughout the booking process and answered all of my questions promptly and accurately! We had the most amazing day on the boat and the staff was all so kind and helpful during our trip. Everything was as expected and the staff was sure to make the day exactly what we wanted in terms of experience and itinerary. I would definitely recommend this boat for large groups! 5 stars!