Artemis Sailing Charters 

5.0/5 (1 review)
 Harbor Loop, Gloucester, MA 01930, United States

Artemis Sailing Charters 

Gloucester, MA, United States
64 feet
6
5.0/5 (1 review)

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!

Rick Miles
Captain
Rick Miles
57 years of experience
ID & credentials verified

Trip availability and prices

Trip Date:
Group Size:
Select date to see availability
September 2026
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
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Almost there...
1 Hour Lunch at the mooring.
FREE Cancellation 3 days notice
1 hour trip starts at 11:30 AM
US $450
Private tour: up to 6 people
3 Hour Daysailing & Meal
FREE Cancellation 3 days notice
3 hour trip starts at 11:00 AM
Seasonal trip
Jun 1 - Oct 15
+2
US $750
Private tour: up to 6 people
3 Hour Sunset Sail with a meal.
In high demand Last booked: 6 days ago
FREE Cancellation 3 days notice
3 hour trip starts at 5:00 PM
US $750
Private tour: up to 6 people
4 Hour Daysailing & Meal
FREE Cancellation 3 days notice
4 hour trip starts at 11:00 AM
US $1,000
Private tour: up to 6 people
Sail and Stay Package for 2 guests
FREE Cancellation 3 days notice
18 hour trip starts at 4:00 PM
US $1,958
Private tour: up to 6 people
There are 4 people looking at this charter.

Customer reviews

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Rating

5.0
(1 review)
5.0
Boat & equipment
5.0
Captain & crew
5.0
Experience

All reviews (1)

Showing 12 of 2 reviews
Patrixk Beaudoin
Patrixk Beaudoin
us
Florida, US
Member since 2025
5.0
Verified
Amazing Experience!!!
4 hour sailing trip for Pat B on September 1, 20253 adults

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!

Yonnie Collins
Yonnie Collins
us
Massachusetts, US
Member since 2026
The captain canceled
May 29, 2026
Trip was supposed to happen on May 29, 2026

The charter operator canceled 44 days prior to the trip date. This is an automated posting.

FAQs about Artemis Sailing Charters

Artemis Sailing Charters offers the following trips to customers:
  • US $450 per group - 1 Hour Lunch at the mooring. (1 hour)
  • US $750 per group - 3 Hour Daysailing & Meal (3 hours)
  • US $750 per group - 3 Hour Sunset Sail with a meal. (3 hours)
  • US $1,000 per group - 4 Hour Daysailing & Meal (4 hours)
  • US $1,958 per group - Sail and Stay Package for 2 guests (18 hours)
When you book a trip with Artemis Sailing Charters, you can expect the following amenities onboard:
  • GPS
  • VHF Radio
  • Radar
  • Chart Plotter
  • Depth Finder
  • Sonar
  • Autopilot
  • Anchor
  • Dinghy
  • Wheel Steering
  • Life Jackets
  • Bimini
  • Kitchen
  • Shower
  • Bow Sundeck
  • Aft Sundeck
  • Bathing Platform
  • Air Conditioning
  • WiFi
  • Audio System
  • TV
  • Inside Speakers
  • Outside Speakers
  • Refrigerator
  • Ice Box
  • Grill
  • Galley Stove and Oven
  • Fishfinder
Trips booked with Artemis Sailing Charters include:
  • Snacks
  • Drinks
  • Lunch
Artemis Sailing Charters offers the following activities:
  • Boat & Yacht Tours
  • Sailing, Catamaran & Gulet Tours
  • Sunset Dinner Cruises
  • Island Hopping
  • Whale & Dolphin Watching
  • Eco-Tours

Your operator

Rick Miles
Rick Miles
Rick Miles

Gloucester, Massachusetts, United States

ID & license verified
2 Customer reviews
Response time 5 hours
Member since December 2024

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.

ID & license verified
2 Customer reviews
Response time 5 hours
Member since December 2024

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.

What the boat is like

Boat category
Other
Boat type
Sailing
Boat manufacturer
Sundeer
Boat Model
Pilothouse 64
Year built
1994
Restored in
2024
Boat length
64 ft
Capacity
6 persons
Number of cabins
3 cabins
Number of berths
6 berths
Number of heads
2 heads
Number of full baths
2 full baths
Number of toilets
2 toilets
Boat category
Other
Boat type
Sailing
Boat manufacturer
Sundeer
Boat Model
Pilothouse 64
Year built
1994
Restored in
2024
Boat length
64 ft
Capacity
6 persons

Which kind of activities are offered

Boat & Yacht Tours
Sailing, Catamaran & Gulet Tours
Sunset & Dinner Cruise
Island Hopping
Whale & Dolphin Watching
Eco-Tours

Which amenities are available onboard

GPS
VHF Radio
Radar
Chart Plotter
Depth Finder
Sonar
Autopilot
Anchor
Dinghy
Wheel Steering
Life Jackets
Bimini
Kitchen
Shower
Bow Sundeck
Aft Sundeck
Bathing Platform
Air Conditioning
WiFi
Audio System
TV
Inside Speakers
Outside Speakers
Refrigerator
Ice Box
Grill
Galley Stove and Oven
Fishfinder

What's included in the trip price

Snacks
Drinks
Carbonated and still water provided
Lunch
Yummy!!!

What’s allowed on the boat

Child Friendly
Alcohol
Drunkeness is not permitted.
Shoes

What additional terms you should be aware of

Security deposit is not required

A refundable deposit is not required by the charter operator.


How cancellations work

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.

More details

How you can pay

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.

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