Sail Training

in 3 locations

Swain Sailing School

Accredited training, and trainers

Swain Sailing School is an accredited training facility of the foremost sailing associations in the US, offering sailing certification courses and customized courses in performance sailing and racing. RSSS also offers the International Bareboat Skipper’s Certification.

3 Campuses

New England, Tortola, Antigua

From the Caribbean to New England you can enjoy a great sailing destination along with the instruction you deserve

Learn to sail!

With hands on, fun instruction

  • Basic Keelboat (Learn to Sail)
  • Live Aboard Cruising
  • Cruising Catamaran
  • Fast Track to Bareboating
  • Coastal Passage Making
  • Advanced Coastal Cruising
  • Coastal Navigation
  • .

    The Big Leagues

    Offshore Passagemaking

    Passagemaking with Swain Sailing aboard a beautiful, offshore capable vessel will put salt in your veins that you just can’t get in any other way.

    Recent ProgramsView All

    British Virgin Island Sailing School

    View courses offered from our Tortola, BVI campus TORTOLA, British Virgin Islands (BVI) The BVI offers the most consistently ideal sailing conditions for learning to sail. Trade winds blow on the norm from ten to twenty knots throughout most of the...

    Coastal Passage Making Training-Jamestown to Salem

    Itinerary: Jamestown, Rhode Island to Salem, Massachusetts Certifications: ASA 106 Certification Course; ASA 105 supplement available Training Boat: Bavaria 46 Dates: Friday, September 4 – Tuesday, September 8, 2020 Tuition: $2095pp Jamestown, RI...

    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...


    Learn to sail on J22 or J24 sailboat with tiller.

    Beneteau 39

    Locations:  Jamestown, RI June- October Tortola, BVI November - April 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...

    Astrea 42 4c/4h/ac; 2020 & 2022

    The Astrea 42 is ideal for instructional and crewed charters as well as performance ocean sailing. Boasting a high degree of comfort, and low center of gravity to afford maximum safety, with a generous sail area. Both 42s are available for...

    Beneteau 43

    Oceanis 43 3 cabins/3 heads

    Bavaria 46

    Bavaria 46 (3 cabins/2 heads)

    Hanse 548

    Available:  BVI: November - April RI: May- October Contact us to inquire about skippered and instructional charters.  The new Hanse 548 is the crème de la crème of the luxury yachts, providing an excellent sailing experience with...

    Isla 40 3c/2h/ac; 2020

    Isla 40 3 cabins/2 heads/ac; 2020 The new Fontaine Pajot Isla 40 has been exclusively designed to deliver a simply superb experience at sea and while moored. Paire de Jacques offers comfortable, light-filled living spaces and is nicely appointed...

    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...

    Lagoon 450

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

    Press Release - Post Irma

    Press Release- Post Irma October 4, 2017 We can't even begin to express our gratitude to all who have called and emailed with heartwarming messages of concern and support for our staff and for all of the BVI community in the wake of hurricane Irma. ...

    Intro to Sailing in the BVI

    VIDEO 3 hour Intro to Sailing sessions Get a hands on experience aboard our Beneteau 23 with one of our professional, certified instructors.  Spend the day with us - 6 Hour Day Sail  Enjoy a day aboard our 36' Benneteau exploring the...

    Basic Keelboat Course

    Learn to sail in the BVI.

    Live Aboard Cruising BVI

    Live Aboard Cruising- BVI Learn to sail and Intermediate to advanced sail training in the British Virgin Islands (BVI) Prerequisite: Basic Keelboat Contact Us to register for sailing courses, Tortola, British Virgin Islands. Live Aboard Cruising ...

    Bareboat Prep

    Learn to Sail in the BVI; Bareboat Cruising certification (non- live aboard option; day sail format.

    Fast Track to Bareboating- BVI

    Accelerated sailing course that takes trainees from beginner to bareboat certified.

    Cruising Catamaran - Multihull Sailing

    Multihull Sailing - BVI Cruising Catamaran Course Catamaran Sailing Instruction and Certification Contact Us to register for sailing courses on Tortola, British Virgin Islands. Prerequisites: Basic Keelboat, Basic Cruising, and Bareboat...

    Coastal Navigation Course- BVI

    Coastal Navigation Course - BVI Contact Us to register for sailing courses on Tortola, British Virgin Islands. Coastal Navigation certification Prerequisites: None Completion time: 8 hours Tuition: $295 View all tuition rates for the BVI campus ...

    Passagemaking Course

    2020 Schedule for advanced training in Passage Making and Deliveries.

    Spinnaker Training

    Spinnaker Training - Performance Sailing Boat: Beneteau 23 Tuition: $195 Completion Time: 3 hours Cruising Spinnaker Course Pre-requisites: Basic Keelboat, Basic Cruising Completion time: 3 hours Tuition: $195 as supplement to Live Aboard...

    Offshore Passage Making-Grenada

    Advanced Passage Making and Delivery training- ASA 108

    Day Sails- Newport Harbor

    Day Sails- Newport Harbor Cruise Three hour sails on a Beneteau 39 or Bavaria 46 12:30 - 3:30 and 4:00-7:00 Individual rate (in group sail with maximum 6 passengers on board) $125pp Private rate for Beneteau 39 (maximum 6 in party) $550 Private...

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