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...

    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 beautiful...

    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

    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 supplement to Live Aboard Cruising $695 for private day sail on Beneteau 43 Enhance your downwind performance with spinnaker...

    Offshore Passage Making-Grenada

    Advanced Passage Making and Delivery training- ASA 108


    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 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...

    Peter Island Resort

    Peter Island Resort Enjoy the lush beauty and luxury of your onshore stay at Peter Island Resort in combination with an exciting three days of sail training with Swain Sailing School. Accommodations For your accommodations, choose either an Ocean...

    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- Dominica- Iles des Saintes

    Jamestown, RI Sailing School

    47 Conanicus Ave. Jamestown, Rhode Island Swain-Rhode Island is located in beautiful Jamestown Village on Conanicut Island.  A short drive from downtown Newport, our location in the New England Sailing Center offers a friendly, welcoming community in...

    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...

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