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...

    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...

    Intro to Sailing in the BVI

    VIDEO 3 hour intro to sailing Get a hands on experience aboard our IC24 with on of our professional, certified captains.  ...

    Basic Keelboat Course

    Learn to sail in the BVI.

    Live Aboard Cruising BVI

    Live Aboard Cruising- BVI Learn to sail and Intermediate Sail Training in the British Virgin Islands (BVI) Prerequisite:...

    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...

    Coastal Navigation Course- BVI

    Coastal Navigation Course - BVI Contact Us to register for sailing courses on Tortola, British Virgin Islands. Coastal...

    Passagemaking Course

    2018-19 Schedule for advanced training in Passage Making and Deliveries.

    Cruising Spinnaker Course BVI

    Cruising Spinnaker Course Pre-requisites: Basic Keelboat, Basic Cruising Completion time: 3 hours Tuition: $195 as...


    Learn to sail on J22 or J24 sailboat with tiller.

    Day Sails- Newport Harbor

    Day Sails- Newport Harbor Cruise Three hour sails on a Beneteau 39 12:30 - 3:30 and 4:00-7:00 Individual rate (in group...

    Peter Island Resort

    Peter Island Resort Enjoy the lush beauty and luxury of your onshore stay at Peter Island Resort in combination with an...

    Tuition Specials

    Tuition and Charter Discounts only available this month!

    Antigua Sailing School

    Antigua Sailing School Courses Offered in Antiqua Live Aboard Cruising/Antigua Sail Week Passage Making Course- Antigua-...

    Jamestown, RI Sailing School

    47 Conanicus Ave. Jamestown, Rhode Island Swain-Rhode Island is located in beautiful Jamestown Village on Conanicut Island....

    About Swain Sailing

    Sailing School and Yacht Charters British Virgin Islands -  Learn to Sail - Basic Keelboat, Bareboat Cruising, Catamaran...

    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...

    BVI Spring Regatta

    BVI Spring Regatta and Full Moon Race 2018 BVI Full Moon Race March 27-28, 2018 BVI Spring Regatta March 30- April 1, 2018...

    Alumni Benefits

    Benefit Program for Swain Sailing Graduates Benefits on the water: $45 per session to join group Basic Keelboat on...

    Hotel Partners

    Accommodations If time allows, spending a few days ashore following your charter is a terrific way to wind down your...

    Rob Swain

    Rob Swain Swain Sailing School is an owner operated school with Rob Swain leading our team of instructors. Rob has taught...

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