Pilots Point Charters

Specialties

Corporate Retreats and Teambuilding Activities

Our corporate match racing is designed for client entertainment and executive team building. A little competition and a lot of fun on our Stars & Stripes boats will leave you and your colleagues with plenty of sea stories to take back to the office.

Weddings

If you are looking for an extraordinary way to celebrate your nuptials, let Pilots Point Charters be part of your wedding plans. We believe that we can make your special occasion even more exceptional.

Family Fun

You don’t need a special occasion to simply enjoy the water. Whether you’re a seasoned boater or just looking to get into the sport, our charter options are a wonderful way to «get your feet wet.»

Not for Yachtsmen Only

Take the helm of a high-​performance racing yacht! We know that our Stars & Stripes boats are a thrilling experience for long-​time sailors. Bring your yacht club or sailing organization to see what it’s like to sail on America’s Cup training boats.

History

Established in 2012.

Pilots Point Charters began with our two Stars & Stripes match racing boats. Built in Australia in the early nineties by four-​time America’s Cup winner Dennis Connor, these high performance racing yachts were initially used as America’s Cup training boats. Now the crown jewel of our charter fleet, these boats are perfect for teambuilding activities and anyone with a sense of adventure.

What we have to offer at Pilots Point Charters goes a lot deeper than just entertaining guests. Our highly skilled team is comprised of five U.S. Coast Guard license captains who have decades of experience at the highest level of sailing, as well a wealth of experience in the hospitality industry in New England.

To accommodate our clients’ needs, we expanded our fleet in 2013 to include fishing charters on a 31′ Ocean Master, Blues Chaser, Sound cruises on a refitted lobster boat, Sammy, and sunset sails on the classic wooden Gerda Emilie. We also have catering options available!