“It is the set of the sails, not the direction of the wind that determines where we will go”

Sailing Charters Out of Gloucester, Massachusetts – 2024 Season

Sailboat Charters Out of Gloucester, Massachusetts

About Artemis

Artemis is a Sundeer 64′ Ketch built for safe, comfortable, and stylish travel. Designed by Steve Dashew and built in 1993 she is a world-famous yacht.

Sailing Charters

All of our sailing charters are custom designed for you and your guests. We currently are sailing out of Gloucester, Massachusetts.

Your Hosts

Meet Debbie and Rick, your Hosts while aboard Artemis, offering a sailboat charter experience you will remember for the rest of your life!

Sailing School

Sail aboard Artemis from Gloucester to Provincetown, MA. Experience first-hand what it takes to sail a 64′ sailboat as a working crew member!

Overnight Adventures

Feeling more adventurous? We’ve got the perfect solution. Ask about our two-night three day overnight sailing charters aboard Artemis.


We love the kind words and reviews that people who have chartered Artemis for a sailboat charter have left us in their reviews. Thank you!

About Gloucester

Gloucester Massachusetts is known as America’s oldest seaport first settled in 1623, just 30 miles northeast of Boston. You might know Gloucester as the backdrop for the hit show “Wicked Tuna.”

Q & A

Here you’ll find the most often-asked questions about chartering Artemis for your sailing adventure; pre-sailing tips, what to expect, what is included, safety issues, rates, photos, and more.

Availability & Reservations

Drop us a line and let’s talk about your sailing adventure aboard Artemis. Fill in our online inquiry form and we’ll follow-up with you promptly. We look forward to speaking with you.