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About Swain Sailing

Sailing School and Yacht Charters British Virgin Islands -  Learn to Sail - Basic Keelboat, Bareboat Cruising, Catamaran Cruising Sailing in the British Virgin Islands is ideal, and learning to sail in the Caribbean in the steady trade winds and warm...

BVI Sail and Dive

The BVI is a sailing and diving paradise; our sail and dive cruises Integrate the best of both. Your platform for exploring the varied anchorages and dive sites of these unique islands will be a 40-45 foot catamaran. The pace is catered to each...

BVI Spring Regatta

BVI Spring Regatta 2019 March 25-31, 2019 Racing Yacht: Beneteau 43 Tuition: $2,695 Tuition includes: Accommodations on board, including night of arrival,  instructor, entry fees, provisioning for breakfasts and  lunches, snacks; crew shirts, text,...

Alumni Benefits

Go Sailing Program Benefit Program for Swain Sailing Graduates Benefits on the water: $40 per session to join group Basic Keelboat on the the water session $90 for 3 hours rental rate of the Beneteau 23 (10-1; 1:30- 4:30) + $35 damage...

Hotel Partners

Accommodations If time allows, spending a few days ashore following your charter is a terrific way to wind down your holiday and an excellent opportunity to see more of Tortola. Although Tortola is the island of embarkation for charter guests, with...

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...

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...

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...

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 The Lagoon 42 won ‘best boat of the year’ awards from both Cruising World and Sail magazine in 2017.  The 42 has an open plan saloon and cockpit with a bulkhead helm position on the port side. A beam of...

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...

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