Martha's Vineyard / Bermuda, New England, USA hosted by iYacht Club
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Corinne Steyn

Sailing from Martha’s Vineyard, Massachusetts to Bermuda aboard a luxury, blue water cruising yacht offers you the ultimate live-aboard sailing experience! Perfect for students seeking experience in between courses or sailors considering a cruising lifestyle of their own, this trip allows sailors a chance to explore the planning, preparation and techniques necessary for a longer, offshore cruise. Sailors will increase their knowledge, experience and safety skills while looking forward to an exciting and beautiful arrival in Bermuda! Add the thrill of offshore fishing for the big ones – mahi, yellowtail tuna or wahoo – the high likelihood for dolphin sightings and the chance for a green flash or two and sailors have a recipe for the perfect sailing experience!

Capt John StephensonYour Flotilla Leader

Captain John Stephenson is a 20-year USCG 100-ton Master Mariner and Certified ASA Instructor who has been sailing for 40 years. He has sailed nearly 100,000 nautical miles, which include 5,000 ocean nautical miles annually, and is an expert in Caribbean-US East Coast passages. His training in First Aid, CPR, Oxygen use, Basic Firefighting, Personal Safety & Social Responsibility, Personal Survival Techniques, and Meteorology, coupled with his love of sailing and teaching, make him uniquely qualified to put your safety & education first. He is additionally certified as an Officer in Charge of Navigational Watch for Vessels of up to 500 gross tons. His gentle and friendly personality ensure that you have fun while underway. He is extremely knowledgeable about the Gulf Stream and weather patterns along the US East Coast, Bermuda and the Caribbean Islands. Captain John has been at the helm of numerous vessels ranging from 20 to over 100 feet and is the former Senior Captain of the 139 ft Boston Tall Ship. He hails from Scituate, Massachusetts, and is a former Boston Underwater Search & Rescue Team Diver.

Location & Activities

For an extra pre-sail treat, take a quick trip from Boston to Woods Hole, Massachusetts and board the Steamship Authority Ferry to the idyllic Martha’s Vineyard Island. Your arrival by water offers the best views of the quaint, historic Vineyard Haven Harbor which is rich with wooden sailboat history and a mooring field full of beautiful sailboats. Settle into your quarters and after safety briefings and vessel preparation, we’ll set sail for the 688 mile trip on an amazing cruise south. You’ll enjoy scenic views of the East Chop lighthouse and the Jaws buoy as we round West Chop.

Sail the waters of Vineyard Haven Sound and learn techniques for aids to navigation and vessel identification. Within 24 hours of departure, we’ll watch water temperatures rise from the low 60’s to the 80’s as we depart the cooler climate and enter the Gulf Stream. Marvel at the unique weather patterns, currents, eddies and reverse eddies as we sail through the Gulf Stream. As we exit the Gulf Stream, we’ll put lines in the water and expect to enjoy a fresh, delicious dinner straight from the ocean!

Sailors will gain valuable instruction and experience in operating and maintaining a modern, ocean cruising sailing vessel; standing watches; hoisting, dousing and reefing sails; fine-tuning sail trim; identifying vessel traffic and aids to navigation and in-depth training in safety techniques associated with ocean cruising. In just 5-7 days, the Bermuda shoals appear on our charts and we begin navigating the only entrance to Bermuda, St. Georges. Enjoy a few extra days aboard and see the sights and beautiful beaches of Bermuda or reserve a hotel and stay for a longer island-based vacation before your flight home.

Some blue water experience is recommended (but not required) for sailors joining this trip. Passports are required. Contact us for full details about the safety features and equipment included on this passage. Ask us about family member discounts or discounts for multiple flotilla trips.


  • Exceptional captain, safe & well-maintained vessel, fantastic sailing destinations. New York City, Block Island and Martha’s Vineyard are perfect East Coast Sailing destinations. Love the motto, “Safety First!”

    Nathan C

  • I loved learning underway and appreciated Captain John’s patient, kind approach to teaching. There is no better way to see the US East Coast and Caribbean than sailing with Captain John! Sailing the gorgeous waters into the harbor in Bermuda was stunning. On our way further southward, we stopped in Saba before our final destination in Antigua. These gorgeous Caribbean islands felt like paradise and increased my love of sailing.

    Caroline L

  • Captain John has been an exceptional teacher and mentor. Learning weather, navigation and tide/currents on various offshore trips was fantastic real-life experience to complement my ASA training. Extremely experienced captain, and well-maintained, classic sailing vessel.

    Olivia L

  • Perfect combination of sailing education, vacation and fishing! I’ve sailed to 10 different Caribbean islands and many East Coast harbors with Captain John. I’ve been sailing for many years and appreciate Captain John’s attention to detail when determining course, sail trim and sail plan. He is capable of handling any type of weather conditions and remains calm throughout. The offshore fishing is great too – yellow tail, mahi, etc.

    Dennis K