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Rob Swain

Swain Sailing School is an owner operated school with Rob Swain leading our team of instructors. Rob has taught sailing in the BVI for over 25 years. He directed the Tortola branch of Offshore Sailing School for 8 years before starting Swain Sailing...

Beneteau 235 First

Location: Tortola, BVI The 235, 23 feet, with a tiller,  is a terrific learn to sail boat.  It's swift responsive and safe.  "Simply put, this is one of the finest boats in this size range and exciting to sail. I actually don’t know many other boats...

Paul Todd

Toddy Paul Todd An Englishman, Paul Todd (Toddy) began sailing at the age of 12. He completed his schooling aboard HMS Conway, on the Menai Straits of North Wales, before joining the UK Merchant Fleet as an apprentice Deck Officer, later joining the...

Burton Robson

As a resident of the British Virgin Islands, Burton has enjoyed thousands of nights in beautiful BVI anchorages and logged thousands of dives on the islands' outstanding reefs and wrecks. Burton is an ASA Sailing Instructor and PADI SCUBA Instructor as...

Evan Swain

Evan was raised in the BVI. He spent his formative years sailing, surfing and wind surfing - and wearing shoes as little as possible. He relocated to Rhode Island to complete his high school years and attend college. After completing his...

Beneteau 39

Location: Conanicus Marina, Jamestown, Rhode Island This large 39 footer sails like a 44' monohull,  Pretty Girl offers great space above and below deck for her size, with three spacious cabins, equally sized and 2 heads. This yacht moves very well...

Beneteau 43

Oceanis 43 3 cabins/3 heads (2011)

Jeanneau SO 439

PR Princess, 3 cabins/ 2 heads Location: Conanicus Marina, Jamestown, Rhode Island At first glance, she is clearly a Sun Odyssey; dynamic lines, a hard chine on the hull, lots of hatches and windows along with bevelled edges on the deck combine to...

Hanse 505

Hanse 505 (4 cabins/2 heads)

Lipari 41 4c/4h/ac

Lipari 41  4 cabins + crew cabin/4 heads/ac (2015) The Lipari 41 has wide open decks, boasting a beam of over 22 feet.  The cockpit has seating for eight at the table, and the cockpit and saloon are on one level, giving a stable platform underway...

Lagoon 420

Lagoon 420 4 cabins/4 heads/ac Location: BVI

Lagoon 450

Lagoon 450 4 cabins/4 heads/ac Location: BVI

Fleet Charter Rates- BVI

Fleet Charter Rates- BVI

Testimonials

"My first offshore sailing trip and Hurricane Sandy is bearing down on the Northeast. I showed up at Newport anyway and helped John, the owner of 47-ft 2 If By Sea, and instructor Tom Farbanish, prep for Sandy’s arrival. No problem for these two...

Antigua Coastal Passage-Making

Antigua Sailing School- Cruising and Passage-Making Courses Coastal Passage Making- Sailing from Antigua Certification: ASA 106 Passage Making/ Advanced Coastal Cruising Prerequisites: ASA 104 Bareboat Cruising, ASA 105 Coastal Navigation (can be...

Antigua Live Aboard Cruising

Please contact us for dates and availability. Live Aboard Cruising Dates: February 27- March 4, 2017 Basic Cruising; Bareboat Cruising certifications Prerequisite: Basic Keelboat The Live Aboard Cruising program offers the discerning and active...

Long Bay Beach Resort BVI Sail & Stay

Long Bay Beach Resort Sail and Stay Deluxe double Hidden away on a 52-acre estate, Long Bay Beach Resort rises from a mile of talcum-powder sand caressed by the gentle Caribbean Sea. Dive or sail around the island’s hidden treasures, or just relax...

Fort Recovery BVI Sail & Stay

Sail and Stay Sailing Vacation Packages - combine your sailing course with relaxation. Fort Recovery Together with Ft. Recovery Beachfront Villas, Rob Swain Sailing School is pleased to offer the ultimate sail and stay holiday. Learn to sail in...

5 Day Charter Itinerary

Live Aboard Cruising - 5 Day Itinerary See our 7-day itinerary Course Itinerary Virgin IslandsDay 1 Following an afternoon of big boat tacking, crew over boards, maneuvering under power, sail trim, and eyeball navigation, we find our...

7 Day Charter Itinerary

Family Sail Itinerary - 7 day (5 day charter is also available) Cooper IslandDay 1 - Cooper Island Setting sail from Nanny Cay Marina we will make our way to Cooper Island with a series of tacks up the Sir Francis Drake Channel. We'll pick up...

Family Charters

Private Family Charters- instructional and non instructional.

About Family Charters

Sailing is a fantastic family activity and an ideal choice for active families looking for an adventure filled holiday where the sport of sailing is enjoyed together and teamwork is emphasized. Parents with children of all ages are encouraged to...

The Crazy Ivan

This maneuver was developed to increase both downwind and upwind performance especially at night. We all know the difference between sailing close hauled and close reaching. Your most efficient way of getting to an upwind destination is close hauled...

The Short Spring

Any technique that relieves the stress when coming to a dock is a good thing. This is especially true when the boat is large, or handled by a small crew. Try the short spring trick early on and save yourself a lot of hassle. It works best when coming...

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