2024 Boothbay Harbor Windjammer days

Join us for a week of day sails and private events aboard Hesper during the 2024 Windjammer Days event in Boothbay Harbor!

About the Pilot Cutter HEsper


We are excited to participate in the 2024 Boothbay Harbor Windjammer Days Festival this year! The Pilot Cutter Hesper operates hands-on traditional Windjammer Expeditions out of Camden Maine in the summer. Hesper is a 60โ€™ Gaff Rigged Pilot Cutter build in Cornwall England in 2004 by Luke Powell. Sheโ€™s a replica of the Isles of Scilly Pilot Cutters that were integral in protecting commercial shipping of the west coast of England in the 1850โ€™s.

Hesper is owned by Eben Wilson of East Boothbay, and we are taking a short week long break from our busy expedition schedule to participate in this wonderful event in our hometown. We have several different options for the public to get onboard and experience what sailing on a Cornish Pilot Cutter is like. Our morning trips offer flexibility and individual ticket options, while our afternoon and evening trips are available for private charters. You can book directly via the online link, where a 50% deposit is required to hold your space. Full payment is due the day of sailing. We offer full refunds for inclement weather.

Sunset Sails just added below!

Sunset Sails just added below!

Wednesday June 26th

2024 Windjammer Days Gathering of the Fleet

11:30-3:30

$120 Per Person (SOLD OUT|

The Shipyard in Boothbay Harbor

Boothbay Harbor, Maine

Bring your camera and prepare for some of the most incredible sights you can witness on the water! As we depart the inner harbor we make our way undersail out to Fishermanโ€™s Island where the larger windjammers begin to gather for their approach into the Harbor. Hesper will join in line with them, sailing into Boothbay for an unforgettable parade of sail. A light lunch of sandwiches is included in this.

Windjammer Days Fireworks Sail

7:30-9:30

$499 for up to 6 guests (Private Charter)

The Shipyard in Boothbay Harbor

Boothbay Harbor, Maine

Enjoy a romantic and intimate evening aboard Hesper for the 2024 Boothbay Harbor Windjammer Dayโ€™s Fireworks! Bring your favorite bottle of champagne or wine aboard and lounge on our spacious deck. A charcuterie board with local cheeses is complimentary.


Thursday June 27th

The History of Pilot Cutters

9:00AM-12:00PM

$65 per person

5/6 Spots Available

The Shipyard in Boothbay Harbor

Boothbay Harbor, Maine

Join us for a 3-hour sail through time as we learn about the beginnings of the Pilot Cutter as we know it, and those who have taken up the task of keeping them alive. Our hands-on sailing seminar covers everything from the start of the Isles of Scilly Pilot Cutters, to Luke Powell, Hesperโ€™s builder and Pilot Cutter savant! We have 6 spots available for this trip which runs every morning from Wed-Saturday.

Afternoon Tea Private Charter

Departure Times: 1PM + 3:30PM

$399 for up to 6 guests (Private Charter)

Available

The Shipyard in Boothbay Harbor

Boothbay Harbor, Maine

How about some classic Cornish Cream Tea aboard a traditional wooden Pilot Cutter? We have Afternoon Tea sails available each day. These are private charters and are available for up to 6 of your guests. Tea, Coffee and baked goods from our galley are all included.


Friday June 28th

The History of Pilot Cutters

9:00AM-12:00PM

$65 per person

4/6 Spots Available

The Shipyard in Boothbay Harbor

Boothbay Harbor, Maine

Join us for a 3-hour sail through time as we learn about the beginnings of the Pilot Cutter as we know it, and those who have taken up the task of keeping them alive. Our hands-on sailing seminar covers everything from the start of the Isles of Scilly Pilot Cutters, to Luke Powell, Hesperโ€™s builder and Pilot Cutter savant! We have 6 spots available for this trip which runs every morning from Wed-Saturday.

Afternoon Tea Private Charter

Departure Times: 1PM

$399 for up to 6 guests (Private Charter)

Available

The Shipyard in Boothbay Harbor

Boothbay Harbor, Maine

How about some classic Cornish Cream Tea aboard a traditional wooden Pilot Cutter? We have Afternoon Tea sails available each day. These are private charters and are available for up to 6 of your guests. Tea, Coffee and baked goods from our galley are all included.


Saturday June 29th

The History of Pilot Cutters

9:00AM-12:00PM

$65 per person

4/6 Spots Available

The Shipyard in Boothbay Harbor

Boothbay Harbor, Maine

Join us for a 3-hour sail through time as we learn about the beginnings of the Pilot Cutter as we know it, and those who have taken up the task of keeping them alive. Our hands-on sailing seminar covers everything from the start of the Isles of Scilly Pilot Cutters, to Luke Powell, Hesperโ€™s builder and Pilot Cutter savant! We have 6 spots available for this trip which runs every morning from Wed-Saturday.

Afternoon Tea Private Charter

Departure Times: 1PM + 3:30PM

$399 for up to 6 guests (Private Charter)

Available

The Shipyard in Boothbay Harbor

Boothbay Harbor, Maine

How about some classic Cornish Cream Tea aboard a traditional wooden Pilot Cutter? We have Afternoon Tea sails available each day. These are private charters and are available for up to 6 of your guests. Tea, Coffee and baked goods from our galley are all included.

Just Added

BOOTHBAY HARBOR SUNSET SAILS

Sunset sail Elegance during windjammer days

Join us for a 2 hour elegant and intimate Sunset Sail during Boothbay Harbor Windjammer Days! We have availability for up to 6 passengers for our sunset sails and plenty of space to move around. Our sunset sails include a charcuterie board made straight in our galley, complimentary water and soft drinks and personalized attention from our crew.

Our two hour sunset sail is $95 per person plus tax. You can book by clicking on the link below, or give us a call at 207-701-7928