Bermuda - St. Martin, Caribbean hosted by Charter House November 14th - 22nd 2019 starting from $1,800

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Corinne Steyn

This adventurous ocean passage offers sailors an exceptional opportunity to explore four Caribbean island-nations and gain more knowledge, training and experience with liveaboard/cruising sailing! Fly into Bermuda and experience the old-world charm and beauty of this British island, then set sail on an exciting voyage thru the Caribbean. Superb weather and sailing leads to landfall at the dual-island nation of St. Martin/Sint Maarten and enjoy the gastronomic capital and stunning Orient Beach of the French side plus the shopping and infamous airport runway of the Dutch side. Stay an extra day or two and take a quick hop to Anguilla, known for some of the best beaches in the world!

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 US East Coast-Caribbean 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

Sailing the Caribbean is the dream so many sailors can’t wait to realize. This trip from Bermuda to dual-nation island of St. Martin/Sint Maarten is a fantastic experience and a great way to follow the dream. We’ll traverse nearly 900 miles of beautiful Caribbean waters and reach a new and exciting destination in just 5-7 days.

Arrive by air to the stunning island of Bermuda and take in a few sights or visit the dazzling beaches. Bermuda has a rich sailing history and was home of the 2018 America’s Cup Sailing race. Familiarize yourself with the yacht and her sailing and safety features and prepare to navigate the extensive shoal around Bermuda before setting a course for our next stop. Watch for whales or other marine life, or perhaps try your hand at reeling in the big one with our offshore fishing techniques. We commonly catch Mahi-Mahi or Yellowtail Tuna underway. You’ll find sailing and training at its best as you actively operate a modern-day cruising vessel. Practice navigation, raising/trimming/dousing sails, basic charting and plotting, safety equipment usage (including jacklines, harnesses and teathers), boat handling, heavy weather techniques skills, and watch schedules. Experience the equatorial currents and easterly trade winds all while keeping our “Safety First” motto at the forefront of everything we do.

Watch for whales or other marine life, or perhaps try your hand at reeling in the big one with our offshore fishing techniques. We commonly catch Mahi-Mahi or Yellowtail Tuna underway. You’ll find sailing and training at its best as you actively operate a modern-day cruising vessel. Practice navigation, raising/trimming/dousing sails, basic charting and plotting, safety equipment usage (including jacklines, harnesses and teathers), boat handling, heavy weather techniques skills, and watch schedules. Experience the equatorial currents and easterly trade winds all while keeping our “Safety First” motto at the forefront of everything we do.

See some of the most beautiful sunrises imaginable as the light glows on the horizon and end each day with a spectacular sunset, or maybe even a green flash (yes, they’re real!). Soon you’ll see land on the horizon as we make our final approach into St. Martin. Stay aboard the vessel an extra day or two, or reserve a hotel and make a longer land-based vacation of your trip, and enjoy the sights of St. Martin as well as the quiet island of Anguilla, known for some of the best beaches in the world. Join us – paradise is calling!

Testimonials

  • Sailing into Jolly Harbor, Antigua aboard S/V Sea Witch was the best! Not only did I learn a ton underway, the whole experience felt like the vacation of a lifetime. Loved the feeling of paradise as we approached Antigua and the opportunity to visit the island at the end of the trip. I even caught a Wahoo underway – extra bonus! 5 stars!

    Emma C

  • Captain John, my fishing buddy, has been a mentor and personal friend for over 15 years. He has helped me with numerous projects to enhance the maintenance, mechanics and performance of my own sailing vessel. I’ve worked as a mate aboard S/V Sea Witch for day sails and Captain John always has a great attitude and is extremely helpful, positive and relaxed.

    Captain Laura Schaub, USCG Captain

  • Offshore experience coupled with beautiful islands and coves is sailing perfection. Loved experiencing multiple islands on one trip! Captain John is an exceptional teacher and mentor. Learning weather, navigation and tide/currents on an offshore trips was fantastic real-life experience to complement my ASA training. Extremely experienced captain.

    Wendy S