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.

4.8
(2,276 Reviews)

Page 18 of 19438 listings

Beneteau 50 Sailing Yacht Charter in San Blas Islands
Colón · 10 guests

Beneteau 50 Sailing Yacht Charter in San Blas Islands

New
$1,400/day
Romantic Sunset Sailing in La Boquilla, Bolívar
Sailing in La Boquilla · 4 guests

Romantic Sunset Sailing in La Boquilla, Bolívar

New
$260/hour
Bali Catspace 40' Catamaran in Ft Lauderdale for charter to Florida Keys
Sailing in Fort Lauderdale · 12 guests

Bali Catspace 40' Catamaran in Ft Lauderdale for charter to Florida Keys

New
$1,400/day
Sailing Yacht Charter with amazing crew all inclusive
Sailing in Panama City · 6 guests

Sailing Yacht Charter with amazing crew all inclusive

New
$876/night
Jamaican Party Boat In Punta Cana Noahs Ark
Sailing in Bávaro · 50 guests

Jamaican Party Boat In Punta Cana Noahs Ark

New
$265/hour
Explore the British Virgin Islands on  a Boston Whaler
Powerboats in Wickhams Cay 1 · 10 guests

Explore the British Virgin Islands on a Boston Whaler

New
$2,400/day
28 GUESTS - OCEAN VOYAGER 53 CRUISING CATAMARAN
Events in The Valley · 28 guests

28 GUESTS - OCEAN VOYAGER 53 CRUISING CATAMARAN

New
$691/hour
Luxury Sailing Experience  – The Ultimate Caribbean Adventure
Sailing in Cruz Bay · 6 guests

Luxury Sailing Experience – The Ultimate Caribbean Adventure

New
$250/hour
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
$1,152/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
Bavaria 50 CR / 2013 Yacht in Saint Lucia Rodney Bay Marina
Sailing in Gros Islet · 8 guests

Bavaria 50 CR / 2013 Yacht in Saint Lucia Rodney Bay Marina

New
$729/night
Boston Whaler Center Console Rental in Road Town, Tortola
Powerboats in Wickhams Cay 1 · 10 guests

Boston Whaler Center Console Rental in Road Town, Tortola

New
$2,400/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
"Monocoque" Sailboat's - 8 Days / 7 Nights Cruise in Guadeloupe And Its Islands
Sailing in Pointe-a-Pitre · 6 guests

"Monocoque" Sailboat's - 8 Days / 7 Nights Cruise in Guadeloupe And Its Islands

New
$10,093/day
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
28 GUESTS - OCEAN VOYAGER 53 CRUISING CATAMARAN
Sailing in Gustavia · 28 guests

28 GUESTS - OCEAN VOYAGER 53 CRUISING CATAMARAN

New
$576/hour
Beneteau Oceanis Yacht 62 - Miami Charter with Captain for up to 10 Guests
Sailing in North Bay Village · 10 guests

Beneteau Oceanis Yacht 62 - Miami Charter with Captain for up to 10 Guests

New
$800+/hour
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
$1,565/day
The SeaPro Sun: Private 50-Person Charter w/ Open Bar & Snorkel
Sailing in El Cortecito · 50 guests

The SeaPro Sun: Private 50-Person Charter w/ Open Bar & Snorkel

New
$699/hour
Yacht Charter in Split Lagoon 46 Catamaran
Sailing in Florida · 13 guests

Yacht Charter in Split Lagoon 46 Catamaran

New
$802+/hour
Beach Monohulls Rental in Saboga, Panama
Sailing in Contadora · 5 guests

Beach Monohulls Rental in Saboga, Panama

New
$50/hour
15 Days14 Nights Cruise To The Islands Of The Wind  - Antilles
Sailing in Pointe-a-Pitre · 6 guests

15 Days14 Nights Cruise To The Islands Of The Wind - Antilles

New
$37,174/day
🌴 St. Lucia Yacht Escape – Sail, Snorkel & Soak in Paradise
Sailing in Gros Islet · 12 guests

🌴 St. Lucia Yacht Escape – Sail, Snorkel & Soak in Paradise

5.0
Snoozed - Active 02 Dec 2026
Cartagena Sunset & Bay Tour on a Large 38 feet Luxury Boat (Private Tour)
Powerboats in Cartagena · 16 guests

Cartagena Sunset & Bay Tour on a Large 38 feet Luxury Boat (Private Tour)

5.0
Snoozed - Active 02 Aug 2026

Sailing Reviews in Caribbean

  1. Kathy

    Kathy

    🌴 St. Lucia Yacht Escape – Sail, Snorkel & Soak in Paradise

    What a wonderful time we had on the Karen P sailboat! Captain Nico went over our intinerary and was flexible and accomodating with our requests of sailing, docking, fishing, eating! The first mates Marlin and Grayson were always willing to please! We had 11 adults on board, sailed down to Soufriere to see the Pitons and back, with snacks and drinks, and were able to see the sun setting on our way home. It was a wonderful experience and we will be looking to hire the same crew in the future. Thank you Captian Nico!

  2. JO

    James

    🌴 St. Lucia Yacht Escape – Sail, Snorkel & Soak in Paradise

    We had the best time with Capt. Nico and his crew! I would highly recommend booking this boat and crew. Everyone in our group thoroughly enjoyed the day. Snorkeling was amazing. Capt. Nico picked us up on time and got us back to the ship in plenty of time, we even had time to go to the open air market across the street from the port. Beverly provided great communication before our trip and everything went as arranged. When I come back to St. Lucia I will definitely book this trip again.

  3. ek

    elizabeth

    🌴 St. Lucia Yacht Escape – Sail, Snorkel & Soak in Paradise

    Captain Nico and his crew did a great job providing our family of 5 a very fun day! The scenery was beautiful! The boat was comfortable and accommodating. We had fun snorkeling and they prepared a delicious lunch for us! We booked them during our port day on our cruise. Highly recommend!

  4. BR

    Brandi

    🌴 St. Lucia Yacht Escape – Sail, Snorkel & Soak in Paradise

    What a great trip! They met us at the port entrance and walked us to the sailboat. The crew was amazing, interactive and helped us have a great day! We rode to see the Pitons, stopped for swim and snorkeling, and enjoyed a yummy fresh cooked lunch on the way back to port. We listened to music and the Pitons beer and rum punch was flowing!

  5. Ricky

    Ricky

    🌴 St. Lucia Yacht Escape – Sail, Snorkel & Soak in Paradise

    This was an amazing experience. Communication from beginning to end was excellent. The captain and his crew went above and beyond for everyone involved. I cant recommend this highly enough. Ill be doing a YouTube video review of the whole experience soon. Highly satisfied customers.

  6. OS

    Olga

    🌴 St. Lucia Yacht Escape – Sail, Snorkel & Soak in Paradise

    Captain Nico and his crew made my 30th birthday unforgettable! Great hospitality, relaxed atmosphere and great vibes all around. Highly recommend!