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.

4.7
(2,411 Reviews)

Page 9 of 20 • 460 listings

Private 42-Foot Sailing Catamaran Charter in Bocas del Toro
Sailing in Bocas del Toro Province · 22 guests

Private 42-Foot Sailing Catamaran Charter in Bocas del Toro

New
$199/hour
Private Deep-Sea Fishing Cabo Rojo, Dominican Republic
Fishing in Dominican Republic · 4 guests

Private Deep-Sea Fishing Cabo Rojo, Dominican Republic

New
$300/hour
Private 3-Hour Sunset Catamaran Cruise to Media Luna Pool
Sailing in Dominican Republic · 45 guests

Private 3-Hour Sunset Catamaran Cruise to Media Luna Pool

New
$1,100/hour
Private 40ft Catamaran Charter in Miches, El Seibo: Snorkeling & Lunch
Sailing in Dominican Republic · 35 guests

Private 40ft Catamaran Charter in Miches, El Seibo: Snorkeling & Lunch

New
$1,050/hour
51ft Beneteau Cyclades Crewed Sailing Charter in St. John, U.S. Virgin Islands
Sailing in St. John · 8 guests

51ft Beneteau Cyclades Crewed Sailing Charter in St. John, U.S. Virgin Islands

New
$1,990/day
Private Bravo VIP Double Deck Catamaran with Waterslide for 80 Guests in Sosúa
Sailing in Sosúa · 80 guests

Private Bravo VIP Double Deck Catamaran with Waterslide for 80 Guests in Sosúa

New
$250+/hour
Captained 80' Sailing Schooner Charter In Key West, Florida
Sailing in Key West · 32 guests

Captained 80' Sailing Schooner Charter In Key West, Florida

5.0
$475+/hour
Private Sunset Catamaran Tour in Barbados – Turtles & Open Bar
Sailing in Bridgetown · 12 guests

Private Sunset Catamaran Tour in Barbados – Turtles & Open Bar

New
$933/hour
Puerto Plata Party Catamaran Jacuzzi Slide Barbecue and Bar
Sailing in Sosúa · 20 guests

Puerto Plata Party Catamaran Jacuzzi Slide Barbecue and Bar

New
$425/hour
Puerto Plata Private Sunset Catamaran Cruise with Open Bar and BBQ
Sailing in Sosúa · 10 guests

Puerto Plata Private Sunset Catamaran Cruise with Open Bar and BBQ

New
$260/hour
Private Double-Deck Party Catamaran with Waterslide in Sosúa
Sailing in Sosúa · 80 guests

Private Double-Deck Party Catamaran with Waterslide in Sosúa

New
$220+/hour
Puerto Plata Boat Budget-Friendly B-day Party Charter with Deals!
Powerboats in Sosúa · 80 guests

Puerto Plata Boat Budget-Friendly B-day Party Charter with Deals!

New
Superowner
Best of 2026
$50/hour
Limited Availability
53' Leopard Power Catamaran – Private Bahamas Day Charter
Sailing in Nassau · 15 guests

53' Leopard Power Catamaran – Private Bahamas Day Charter

5.0
$1,160+/hour
50ft Luxury Catamaran – Rose Island, Gilligan’s Island & Green Cay
Sailing in Nassau · 12 guests

50ft Luxury Catamaran – Rose Island, Gilligan’s Island & Green Cay

5.0
$1,375/hour
St. Martin Private Boat Tour with Lagoon 450 Cruising Catamaran
Sailing in Saint Martin · 20 guests

St. Martin Private Boat Tour with Lagoon 450 Cruising Catamaran

New
$1,782/day
Luxury Sailing Catamaran 45' Lagoon in Cayman Islands
Sailing in George Town · 30 guests

Luxury Sailing Catamaran 45' Lagoon in Cayman Islands

New
$500/hour
Snorkeling And Party Boat For Private Groups
Powerboats in Uvero Alto · 80 guests

Snorkeling And Party Boat For Private Groups

5.0
$167/hour
Private Barbados Catamaran – Turtles, Wrecks & Lunch
Sailing in Bridgetown · 12 guests

Private Barbados Catamaran – Turtles, Wrecks & Lunch

New
$640/hour
Private Sail tour to Les Saintes with Skipper Sailing teacher
Sailing in Saint Charles · 9 guests

Private Sail tour to Les Saintes with Skipper Sailing teacher

5.0
$1,337/day
Private 45ft Catamaran — Rosario Islands & Cartagena
Sailing in Cartagena · 40 guests

Private 45ft Catamaran — Rosario Islands & Cartagena

New
$4,999/day
Private 44ft Catamaran in La Romana – Saona or Catalina – Up to 20 Guests
Sailing in La Romana · 20 guests

Private 44ft Catamaran in La Romana – Saona or Catalina – Up to 20 Guests

New
$225/hour
Instant Book
Sail St Maarten on 42ft Gibsea SunDowner Crusing Monohull
Caribbean · 10 guests

Sail St Maarten on 42ft Gibsea SunDowner Crusing Monohull

5.0
$1,200/day
🛥️🏝️ Snorkeling Cruise Charter in Puerto Plata🛥️🏝️
Sailing in Barrio Las Yaguitas · 18 guests

🛥️🏝️ Snorkeling Cruise Charter in Puerto Plata🛥️🏝️

New
Superowner
Best of 2026
$75/hour
Sunset Cruise on Cartagena Bay Aboard 48' Leopard Catamaran with DJ and Open Bar
Sailing in Cartagena · 30 guests

Sunset Cruise on Cartagena Bay Aboard 48' Leopard Catamaran with DJ and Open Bar

New
$120/hour

Sailing Reviews in Caribbean

  1. MW

    MAESHEN

    Private Sail tour to Les Saintes with Skipper Sailing teacher

    Une journée de Rêve à ne pas manquer! Le voilier porte bien son nom!!! La croisière était super! On a vraiment aimé voir la Guadeloupe depuis la mer. Avec possibilité de prendre la barre et d'aider avec les voiles. Nous avons déjà fait du voilier, mais jamais participer, donc c'était une bonne expérience. Skipper m très sympa et intéressant et nous avons appris beaucoup sur la Guadeloupe et le voilier. Apéro et repas aussi très bon😊. Vous ne regretterez pas! Je recommande! Vraiment belle journée!

  2. CT

    Cassie

    Sail St Maarten on 42ft Gibsea SunDowner Crusing Monohull

    We had a great experience with Garth and Byron! They shared lots of fun information about the island and we had a great day of snorkeling and sailing. Would definitely recommend for a group of 6-8 versus jumping on a big boat with lots of people.

  3. Kurt

    Kurt

    Private Sail tour to Les Saintes with Skipper Sailing teacher

    Oliver is a great captain and knows how to create a wonderful and safe experience. I highly recommend you consider a sailing trip with Oliver.

  4. PG

    Paul

    50ft Luxury Catamaran – Rose Island, Gilligan’s Island & Green Cay

    If you have the chance to book this charter. DO IT! 5* service all around! What a special day. Cannot recommend this charter more!

  5. JH

    Jill

    Snorkeling And Party Boat For Private Groups

    Thank you my family had so much we didn't want to leave the staff was Excellent, fun and friendly my birthday was amazing!!!!

  6. JR

    Janell

    Sail St Maarten on 42ft Gibsea SunDowner Crusing Monohull

    Garth and Byron really made sure that we had a good time! I would definitely use them again when I come back to St Martin!