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Osbourn, Saint George Boat Rentals

40ft Thriller Private Luxury Power Boat with Captain
Powerboats in Saint John's · 20 guests

40ft Thriller Private Luxury Power Boat with Captain

New
$750/hour
Luxury Day Catamaran Charters ANTIGUA
Sailing in Saint John's · 65 guests

Luxury Day Catamaran Charters ANTIGUA

5.0
$1,000/hour
44' Wellington Sailing Yacht In Antigua
Sailing in Jolly Harbour · 6 guests

44' Wellington Sailing Yacht In Antigua

5.0
$100/hour
Sail In Caribbean Paradise with Jeanneau Sun Odyssey 44
Sailing in Jolly Harbour · 6 guests

Sail In Caribbean Paradise with Jeanneau Sun Odyssey 44

4.8
$280/day
Rent the 19' Boston Whaler in Jolly Harbour
Powerboats in Jolly Harbour · 6 guests

Rent the 19' Boston Whaler in Jolly Harbour

4.9
$310+/day
Luxury Afloat In Antigua Onboard Jeanneau Sun Odyssey 519 Sailboat
Sailing in Jolly Harbour · 8 guests

Luxury Afloat In Antigua Onboard Jeanneau Sun Odyssey 519 Sailboat

New
$80/hour
37' Mainship in Jolly Harbour Marina
Events in Jolly Harbour · 12 guests

37' Mainship in Jolly Harbour Marina

5.0
$135/hour
Antigua Barbuda Sailing lessons and expedition!
Sailing in Jolly Harbour · 10 guests

Antigua Barbuda Sailing lessons and expedition!

New
$1,401/night
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
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
Hobie Cat Rental on Cockleshell Bay
Sailing in Saint George Basseterre Parish · 1 guest

Hobie Cat Rental on Cockleshell Bay

New
$100/hour
Surf Lessons with Experienced Coach at Sandy Bank Bay
Adventures in Saint George Basseterre Parish · 1 guest

Surf Lessons with Experienced Coach at Sandy Bank Bay

New
$180/hour
Kiteboarding Lesson with IKO Certified Instructor in Saint Kitts and Nevis
Adventures in Saint George Basseterre Parish · 1 guest

Kiteboarding Lesson with IKO Certified Instructor in Saint Kitts and Nevis

New
$125/hour
Wakeboarding Lessons in Saint Kitts and Nevis
Water Sports in Saint George Basseterre Parish · 1 guest

Wakeboarding Lessons in Saint Kitts and Nevis

New
$60/hour
"Taonaba" Eco Tours on Houseboat in Deshaies, Guadeloupe
Tours in Deshaies · 20 guests

"Taonaba" Eco Tours on Houseboat in Deshaies, Guadeloupe

New
$233/hour
33' Sport Fishing Charter In Deshaies
Fishing in Deshaies · 6 guests

33' Sport Fishing Charter In Deshaies

New
$175/day
Boat Snorkel Adventure
Tours in Basseterre · 14 guests

Boat Snorkel Adventure

New
$60/hour
St. Kitts Coastline Cruise & Beach
Tours in Basseterre · 45 guests

St. Kitts Coastline Cruise & Beach

5.0
$147/hour
Saint Kitts Private Boat Charter
Tours in Basseterre · 55 guests

Saint Kitts Private Boat Charter

5.0
$300/hour
Twin Island Paradise Snorkel Tour
Tours in Basseterre · 45 guests

Twin Island Paradise Snorkel Tour

New
$29/hour
Shared Sunset Cruise
Powerboats in Basseterre · 25 guests

Shared Sunset Cruise

New
$24/hour
' Center Console in Frigate Bay
Basseterre · 6 guests

' Center Console in Frigate Bay

New
$113/hour
Cruising Catamaran Rental in St Kitts-Nevis
Sailing in Basseterre · 40 guests

Cruising Catamaran Rental in St Kitts-Nevis

New
$1,045/day
Sailing Catamaran Cruises in St Kitts-Nevis
Sailing in Basseterre · 55 guests

Sailing Catamaran Cruises in St Kitts-Nevis

5.0
$95/day

Osbourn Reviews

  1. JC

    Jake Patrick

    44' Wellington Sailing Yacht In Antigua

    Went to Antigua for a birthday trip with partner. Wanted to get on the water but have a more intimate experience than a 25-30 person tour from Wadadli or one of the other major group boat tours. Christian's option while a little more expensive was worth every penny. He and his stewardess Tia were absolutely fantastic from the pickup at Christian's house dock to the sailing. Christian had seats at the front of the sail boat and beverages waiting for us - making the sail along the southern coast a more romantic and intimate experience than we were anticipating. We never had an empty glass! We timed the sail so we would end at sunset (1:30-5:30) and was the perfect amount of time. We asked Christian to anchor at one of the secluded beaches so we could swim and jump off the sail boat. Christian was incredibly knowledgeable about the island and has been sailing a long time. Both he and Tia gave us space to be together and also staying attentive to make sure we didn't need anything else. The sail was the highlight of our trip and if we have family back on island will definitely be reaching back out to Christian!

  2. AD

    Amanda

    Saint Kitts Private Boat Charter

    Ricky and his crew were fabulous! We had a mixup on where to meet which led to us being late. Ricky handled things so professionally and they made the day so fun and perfect! The boat and equipment were pristine, snorkeling was so fun and Ricky’s chocolate cake was the best! Highly recommend this private charter where your group has the boat to themselves with the best captain and crew!

  3. Ilemi

    Ilemi

    37' Mainship in Jolly Harbour Marina

    Couldn’t recommend booking with Will enough. Super professional and friendly. Very accommodating and adaptable to your needs and preferences. Refreshments provided on the boat.

  4. HS

    Hilliard

    37' Mainship in Jolly Harbour Marina

    I feel like no matter what I write here it will not do our trip with captain wil justice…bucket list boat trip 1000%. Incredible private beaches, fully stocked cooler and so much great knowledge about the island. We had a party of 8 including small children. He even stayed out a bit later so we could watch the sunset. Bless you wil and EZ

  5. KM

    Kavan

    Luxury Day Catamaran Charters ANTIGUA

    So it’s my brother in law’s 50th birthday and we went to Antigua. Never been, but we needed to rent a boat that holds at least 20 people for about 5 hours of drinking partying and snorkeling around the coast of Antigua. I was nervous because I didn’t want to get scammed however, I took a chance and Craig was very responsive, gave a lot of insights on what to do and even checked in from time to time prior to our arrival on the island. We got picked up right at our hotel beach, one time and was greeted with some rum punch. The crew was friendly, fun, funny, and answered all our questions about the island. They were very flexible with what we wanted to do and the time that we needed to spend. All and all it was a great trip and I would recommend them to anyone. So if you are reading this don’t miss out on a great adventure.

  6. AC

    Anne

    44' Wellington Sailing Yacht In Antigua

    Amazing experience; writing my review 3 years later, because I came back to Antigua and want to book with Captain Christian again (didn’t realize I forgot to leave a review at the time)! Don’t hesitate to book, Christian and Jess were wonderful!!!