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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.7
(2,254 Reviews)

Page 17 of 18416 listings

Private Charter Adventure to Palomino or Icacos, Fajardo PR - 26' Hydra Sports
Powerboats in Fajardo · 6 guests

Private Charter Adventure to Palomino or Icacos, Fajardo PR - 26' Hydra Sports

New
$650/day
Captained Charter on 47ft
Sailing in Coclé Province · 8 guests

Captained Charter on 47ft

5.0
$2,000/day
Sailing Yacht Charter with amazing crew all inclusive
Sailing in Panama City · 6 guests

Sailing Yacht Charter with amazing crew all inclusive

New
$867/night
Your Private Yacht for the Day – Lagoon 46 Full-Day Charter
Sailing in Fajardo · 6 guests

Your Private Yacht for the Day – Lagoon 46 Full-Day Charter

New
$2,730/day
2024 Valentine's Week in BVi 🍹🍸👙🤟
Sailing in Fisher Estate · 8 guests

2024 Valentine's Week in BVi 🍹🍸👙🤟

New
$92,160/day
Beneteau Oceanis 50’ Luxury  Sailing Yacht – Chef on Board - Cartagena
Sailing in Cartagena · 12 guests

Beneteau Oceanis 50’ Luxury Sailing Yacht – Chef on Board - Cartagena

New
$105/hour
57ft Asante 170 Expedition Sailing Catamaran in Coconut Grove, Miami
Sailing in Miami · 12 guests

57ft Asante 170 Expedition Sailing Catamaran in Coconut Grove, Miami

New
$150/hour
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
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
Set Sail Across the East Coast on a 36ft Bavaria Sailing Yacht
Sailing in Fajardo · 8 guests

Set Sail Across the East Coast on a 36ft Bavaria Sailing Yacht

New
$300+/hour
Luxury Sailing Experience  – The Ultimate Caribbean Adventure
Sailing in Cruz Bay · 6 guests

Luxury Sailing Experience – The Ultimate Caribbean Adventure

New
$250/hour
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
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
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
"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
$9,996/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
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
$1,550/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
$36,819/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

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. GH

    Gregory

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

    This was an amazing experience for our group of 6 from Tennessee. We've traveled a lot of great places and had a lot of great experiences, but this full day sail is definitely one of our top 3. Nico and Marlin were great captain/ crew and were great hosts! Snorkeling was fantastic, and the BBQ lunch they cooked (grilled chicken, fish, green banana salad, salad, plantains) was so enjoyable! And the drinks.... Cokes, rum punch (certainly the best we've had!), piton beer, water, were available the entire sail. We loved having so many places on the sailboat to sit.... Both covered (for those who had enough sun the day before) and uncovered (plenty of sun). We enjoyed sunset on the way back to the Marina with fresh pineapple and cantalope serviced to us by Marlin. I would highly recommend sailing with Nico and Marlin. Definitely worth the money!! Will sail with these guys again when we return to Saint Lucia!