Artemis Sailing Charters
You may qualify for a Loyalty discount with Artemis Sailing Charters. To check if the Loyalty discount is available for your selected dates, please sign in.
Set sail on an unforgettable journey with Artemis Sailing Charters aboard the beautifully restored 1994 Sundeer Pilothouse 64 Sailing vessel, based out of Gloucester. Perfect for up to 6 guests, we offer flexible trips ranging from 3-hour and 4-hour excursions and longer if you desire. Our special sail-and-stay package includes a 3 hour sunset sail followed by a delicious dinner and after a cocktail or coffee on deck under the stars, enjoy a restful night in your fully equipped cabin. Wake up the next morning to coffee on deck and an incredibly delecious ships breakfast before you depart for shore. This trip is for 2-4 guests.
The boat features top-of-the-line amenities, including a grill, ice box, refrigerator, WiFi, and both inside and outside speakers for your entertainment. Relax on the aft sundeck or bow sundeck, or take a refreshing dip from the bathing platform, all while enjoying the delecious treats created in our galley ( kitchen).
Captain Rick Miles, who has been sailing since the age of 6, brings decades of experience to ensure a safe and memorable journey. With over 40 years of safe and happy guest experiences under his belt, you’re in expert hands.
Whether you're looking for a peaceful day on the water or a fun-filled adventure, alcohol( in moderation)and children are welcome to join in the excitement. Artemis goes above and beyond concerning passenger safety.l so you can relax and enjoy every moment.
Book your trip today and experience the magic of sailing with Artemis Sailing Charters!
Set sail on an unforgettable journey with Artemis Sailing Charters aboard the beautifully restored 1994 Sundeer Pilothouse 64 Sailing vessel, based out of Gloucester. Perfect for up to 6 guests, we offer flexible trips ranging from 3-hour and 4-hour excursions and longer if you desire. Our special sail-and-stay package includes a 3 hour sunset sail followed by a delicious dinner and after a cocktail or coffee on deck under the stars, enjoy a restful night in your fully equipped cabin. Wake up the next morning to coffee on deck and an incredibly delecious ships breakfast before you depart for shore. This trip is for 2-4 guests.
The boat features top-of-the-line amenities, including a grill, ice box, refrigerator, WiFi, and both inside and outside speakers for your entertainment. Relax on the aft sundeck or bow sundeck, or take a refreshing dip from the bathing platform, all while enjoying the delecious treats created in our galley ( kitchen).
Captain Rick Miles, who has been sailing since the age of 6, brings decades of experience to ensure a safe and memorable journey. With over 40 years of safe and happy guest experiences under his belt, you’re in expert hands.
Whether you're looking for a peaceful day on the water or a fun-filled adventure, alcohol( in moderation)and children are welcome to join in the excitement. Artemis goes above and beyond concerning passenger safety.l so you can relax and enjoy every moment.
Book your trip today and experience the magic of sailing with Artemis Sailing Charters!

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The family and I had an amazing time on Artemis sailing with Captain Rick and his wife Deb. What an amazing experience to sail on such a beautiful yacht and with such wonderful people. If you've never sailed or are an experienced sailor, you will truly enjoy this great experience and discover Gloucester and the surrounding area. This sailing yacht is super stable, fast and fun. Make new friends, new experiences and amazing memories to last a lifetime! Sail Artemis!

The charter operator canceled 44 days prior to the trip date. This is an automated posting.
Captain Rick has extensive experience in the maritime industry. Since 2013, he has overseen the operation of all fleet vessels at Boston Harbor Cruises LLC, managing over 50 vessels and up to 300 daily departures, serving over 2.5 million passengers annually. His responsibilities include ensuring safety compliance, coordinating vessel repairs, managing USCG inspections, and overseeing captains and crews. Prior to this, Captain Rick was the owner/operator of Wanderbird Expedition Cruises, specializing in expedition voyages between the Arctic and the Caribbean, operating a 90-ft trawler with 150,000 sea miles. He also commanded Timberwind on week-long Maine cruises as owner/operator of Rockport Schooner Cruises, and before that, he ran Ariel Cruises in New England and the Caribbean. Earlier, he worked as a commercial fisherman with Sea Star Fisheries, progressing from deckhand to captain in the offshore lobster industry. Captain Rick holds a BA in Business Administration from Norwich University and graduated from Marblehead High School in 1976. He holds a US Coast Guard Master's License (up to 200 GRT, Near Coastal) and a valid TWIC card.
Captain Rick has extensive experience in the maritime industry. Since 2013, he has overseen the operation of all fleet vessels at Boston Harbor Cruises LLC, managing over 50 vessels and up to 300 daily departures, serving over 2.5 million passengers annually. His responsibilities include ensuring safety compliance, coordinating vessel repairs, managing USCG inspections, and overseeing captains and crews. Prior to this, Captain Rick was the owner/operator of Wanderbird Expedition Cruises, specializing in expedition voyages between the Arctic and the Caribbean, operating a 90-ft trawler with 150,000 sea miles. He also commanded Timberwind on week-long Maine cruises as owner/operator of Rockport Schooner Cruises, and before that, he ran Ariel Cruises in New England and the Caribbean. Earlier, he worked as a commercial fisherman with Sea Star Fisheries, progressing from deckhand to captain in the offshore lobster industry. Captain Rick holds a BA in Business Administration from Norwich University and graduated from Marblehead High School in 1976. He holds a US Coast Guard Master's License (up to 200 GRT, Near Coastal) and a valid TWIC card.
Security deposit is not required
A refundable deposit is not required by the charter operator.
Free cancellation up to 3 days prior to trip
You can cancel or modify your booking up to 3 days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.
Pay online in full
Pay online in full through BoatBooker and save on credit card fees at the dock.
No additional fees.
Reserve with a 20% booking deposit, pay the captain the rest
When the captain confirms your trip, BoatBooker charges your credit card a 20% booking deposit to guarantee your reservation.
The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:
Cash
Visa
Mastercard
American Express
When paying the remaining balance with a credit card, an additional 2% charge will apply.
