2023 Cruise Schedule
Cultivate your next adventure
A trip for everyone. All bespoke sailing charters provide the experience you are looking for. We pride ourselves on being flexible, and we are passionate about giving a traditional sailing experience. A journey aboard Hesper is a class on wooden boat history, Maine and a culinary treat.
We have no set cliental. Our trips accommodate every vacation and adventure type. From those who wish to lay back and just enjoy beachcombing and reading on deck, to those who’d like to expand on their sailing skills, learning the ins + outs of sailing a traditional English pilot cutter.
We keep our trips private. We have no minimums and welcome solo sailors. Because we are a small business, our bookings are based off of a two person occupancy, with additional guests after that charged at a per person rate. A 50% deposit reserves your date. We recommend travel insurance for complete peace of mind. Once booked, we begin our process of curating your trip. We will reach out to find a time to chat and talk about your preferences.
10/24 Final fall expedition
4 Day 3 Night Fall Foliage Windjammer Expeditions
$3,200 for two guests, $1,600 per additional guest all inclusive
The final trip of the season concludes. Explore the bay with no interruption. Great winds bring endless possibilities to our destination! Roque Island? Isle au Haut?
10/18 Orionids Meteor shower Expedition
4 Day 3 Night Fall Foliage Windjammer Expedition
$3,200 for two guests, $1,600 per additional guest all inclusive
Join Hesper for one of two Foliage Expeditions that will conclude our 2023 sailing season. This Orionids Expedition brings us to peaceful harbors to watch a beautiful meteor shower! Don’t be fooled- fall sailing is the best time of the year for a pure sailing experience. Temperatures are still pleasant, the wind is fine, and the foliage is breathtaking. Nights are spent with the wood stove, board games and good wine.
10/12 October expedition
Charter Cost: $1,800 for two guests. ($899 per additional guest).
3 Night Trip
SOLD OUT
10/5 Foliage and Wind Cruise
Foliage and Wind Cruise
Charter Cost: $2,200 for two guests. ($1,100 per additional guest).
3 Night Trip
As the leaves begin to turn it provides excellent photography opportunities..
Click the Photo for Booking and More Info
9/28 Penobscot Bay Expedition
Penobscot Bay Expedition
Charter Cost: $1,800 for two guests. ($1,000 per additional guest).
3 Night Trip
Fall winds give us excellent sailing. All of late September and October provides great sailing.
SOLD OUT
9/21 Summer Barn Series
Summer Barn Series
Charter Cost: $2,000 for two guests. ($1,000 per additional guest).
3 Night Trip
Join us for an expedition with a delicious twist. A trip to Turner Farm, where we anchor out and go ashore and enjoy a 5 course barn supper on the almost 250 year old island farm.
SOLD OUT
9/14 Eggemoggin Reach Expedition
Eggemoggin Reach Expedition
Charter Cost: $1,800 for two guests ($899 per additional guest up to 6)
3 night trip
Destination- Wooden Boat School. A chance of seeing the Schooner Fleet as they depart the reach from the Wooden Boat Sail In….
SOLD OUT
Click on the Photo for Booking and More Info
9/7 Penobscot Bay Expedition
Penobscot Bay Expedition
Charter Cost: $1,800 for two guests ($899 per additional guest up to 6)
3 night trip
Fall still brings great weather, and lovely winds for exploration…
SOLD OUT
8/31 Camden Windjammer Festival
Camden Windjammer Festival
Charter Cost: $2,000 for two guests ($1000 per additional guest up to 6)
3 night trip
Sticking close to home, we get to experience and view the Camden Windjammer Festival. Watch as some of the oldest working schooners in the world take over Camden….
SOLD OUT
8/17 solo sailor and sail training expedition
Penobscot Bay Expedition
Charter Cost: $2,200 for two guests (additional guests charged at $1,100 per person up to 6)
3 night trip
Summer weather takes over as we island hop to our favorite swimming spots. Beaches, hiking and cool sailing prevail.
Click on the Photo to Book and for More Info
8/10 Perseid Meteor Shower Expedition
Penobscot Bay Expedition w/ Perseid Meteor Shower
Charter Cost: $1,800 for two guests ($899 per additional guest up to 6)
3 night trip
Join us for a classic Maine expedition with the added bonus of the 2023 Perseid Meteor shower.
SOLD OUT
8/3 Eggemoggin Reach Regatta
2023 Eggemoggin Reach Regatta
Charter Cost: $2,200 for two guests ($1,100 per additional guest up to 6)
3 night trip
Our favorite- The pinnacle of racing and wooden boats in Maine. Join us for two races and a amazing afterparty at the Wooden Boat School.
SOLD OUT
7/29 Camden Classics
2023 Camden Classics Cup
Charter Cost: $1,200 per day. Available for full event charter
3 night trip
2023 Camden Classics, one of the most famous regattas in the Country. Racing, storytelling and more…..
Click the Photo for Booking and More Info
7/20 Cabbage Island Expedition
Cabbage Island Expedition
Charter Cost: $1,800 for two guests ($899 per additional guest up to 6)
3 night trip
A Cabbage Island Clambake…a Race…and our first venture West…
SOLD OUT
7/13 Wooden Boat Traditional Sailing Class
Wooden Boat School Traditional Sailing Expedition
Charter Cost: $1,300 per person
3 night trip
Join us for a Wooden Boat exclusive- A traditional sailing course departing from the Wooden Boat School in Brooklin Maine.
SOLD OUT
7/6 Schooner Race
46th Great Schooner Race
Charter Cost: $1,800 for two guests. ($899 per additional guest).
3 Night Trip
Maine is about traditional wooden sailing vessels, and the Maine Windjammer Fleet is the pinnacle of that. Join us for a viewing of the 46th annual Great Schooner Race
SOLD OUT
6/29 Summer Barn Series
Summer Barn Series
Charter Cost: $2,000 for two guests. ($1,000 per additional guest).
3 Night Trip
Join us for an expedition with a delicious twist. A trip to Turner Farm, where we anchor out and go ashore and enjoy a 5 course barn supper on the almost 250 year old island farm.
SOLD OUT
6/22 Penobscot Bay Expedition
Penobscot Bay Expedition
Charter Cost: $1,800 (for two guests). $899 Per Additional Guest.
SOLD OUT
Click Photo for Booking and More Info
6/15 Sommes Sound Expedition
Charter Cost: $1,800 (for two guests). $899 Per Additional Guest.
Join us as we attempt to make passage to the magical Sommes Sound.
SOLD OUT
6/8 Penobscot Bay Expedition
Penobscot Bay Expedition
$1,500 for two guests ($750 per additional guest up to 6 passengers)
SOLD OUT
Click Photo for Booking and More Info
6/1 Shakedown Cruise
Charter Cost: $1,500 (for two guests)——— $750 Per Additional Guest.
Our first trip of the year. Come shakedown Hesper with us! Destinations unknown.
SOLD OUT
Click Photo for Booking and More Trip Info