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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(2,288 Reviews)

Page 18 of 18428 listings

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
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
Punta Cana: Tasting the Tides - Rum, Sail and Swim | 4 hrs to full day options
Sailing in Punta Cana · 8 guests

Punta Cana: Tasting the Tides - Rum, Sail and Swim | 4 hrs to full day options

New
$85/hour
28 GUESTS - OCEAN VOYAGER 53 CRUISING CATAMARAN
Sailing in Gustavia · 28 guests

28 GUESTS - OCEAN VOYAGER 53 CRUISING CATAMARAN

New
$578/hour
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
"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
$10,127/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
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
Yacht Charter in Split Lagoon 46 Catamaran
Sailing in Florida · 13 guests

Yacht Charter in Split Lagoon 46 Catamaran

New
$802+/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
$1,570/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
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
$37,299/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 20 Apr 2026
50ft Catamaran Charter with Water Toys -Boca Raton, FL
Sailing in Deerfield Beach · 12 guests

50ft Catamaran Charter with Water Toys -Boca Raton, FL

5.0
Snoozed - Active 30 Mar 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
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 03 Sep 2026
Enjoy Sailing in Fort Lauderdale Aboard the Sailing Vessel V1
Sailing in Fort Lauderdale · 4 guests

Enjoy Sailing in Fort Lauderdale Aboard the Sailing Vessel V1

New
Snoozed - Active 02 May 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
Montecarlo 43’ private sailing boat in San Blas Islands
Sailing in Guna Yala Comarca · 2 guests

Montecarlo 43’ private sailing boat in San Blas Islands

New
Snoozed - Active 22 Apr 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. Ivan

    Ivan

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

    The crew was amazing — friendly, professional, and made sure we had a great time the whole day. They even cooked delicious wings and prepared great food and drinks for us on board. Highly recommend this experience to anyone visiting St. Lucia!

  3. 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.

  4. 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!

  5. JA

    Jonathan

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

    A great day with captain Nico and crew. They met us right at the cruise ship dock and we sailed along the coast to a beautiful snorkeling spot. We were then treated to drinks and some great snacks. Thank you for such a fun day.

  6. 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!