2024 Expedition Schedule
A primer to your Maine Sailing Adventure
Most of Pilot Cutter Hesper’s expeditions are private trips. When you make a reservation, you book the vessel. Our reservations are based on a 2 passenger flat rate, with your additional guests being charged at a per person rate. A private charter aboard Hesper is a curated event. From your booking process to stepping aboard, we create a bespoke Expedition Experience.
10/9 October Foliage Expedition
4 Day + 3 Nights
$2,800 for two guests, $1,400 per additional guests up to 6.
Maine in the fall! Join us for two of our Foliage Expeditions as we harness the great fall Penobscot Bay winds and sail in to Fall Foliage Heaven! Expect chillier night temperatures, but cozy down below hangouts with our stove and board games! The days bring sunshine, great wind, and picturesque Maine views.
10/3 Sommes Sound Expedition
SOLD OUT
4 Day + 3 Nights
$3,200 for two guests, $1,600 per additional guests up to 6.
A journey to the classic Fjard of Sommes sound in Acadia National Park. Boat to trail hiking, classic views and a breathtaking journey up the 5 mile long Sommes Sound. This is some great foliage viewing as well!
9/27 Penobscot Bay Expedition
SOLD OUT
4 Day + 3 Nights
$3,200 for two guests, $1,600 per additional guests up to 6.
A classic Penobscot Bay expedition, join us as we sail with the prevailing winds to places like North Haven, Vinalhaven, Cape Rosier and more. Fall winds bring great opportunities and we are excited to share our stories from our recent offshore adventure to Nova Scotia!
9/12 Solo Sailor Expedition 1.1
$1,299 Per Person
3 Guest Crew Spots Available!
Join us for one of our two Solo Sailor expeditions this year! We had great success opening up our schedule to this last year and want to continue sharing this experience with all of you. A hands-on sailing experience aboard a Pilot Cutter.
Topics covered and shown include:
-Navigation
-Steering and watchkeeping
-Communication and Leadership and how they are major parts of seamanship
-Traditional Vessel upkeep and techniques
9/5 Coastal Towns of Maine Expedition
4 Day + 3 Nights
$3,200 for two guests, $1,600 per additional guests up to 6.
September brings great weather, good sailing and a great opportunity to visit some idyllic Maine Coastal Villages. Stonington and Burnt Coat Harbor top the list of scenic views.
8/29 Wooden Boat School Expedition
4 Day + 3 Nights
$3,200 for two guests, $1,600 per additional guests up to 6.
Join Hesper for a classic sailing expedition to Cape Rosier and down the Eggemoggin Reach, bound for the WoodenBoat School in Brooklin Maine. Tour the grounds, watch traditional boats being built and enjoy classic sailing surrounded by traditional wooden vessels.
8/22 Isle Au Haut Expedition
SOLD OUT
4 Day + 3 Nights
$3,200 for two guests, $1,600 per additional guests up to 6.
Isle Au Haut brings classic Acadia National Park views and wilderness exploration. This is a great trip for hikers and nature enthusiasts alike! Different anchorages provide different challenging hiking trips and great stargazing.
8/15 Islands of Merchants Row and Kayaking Expedition
SOLD OUT
4 Day + 3 Nights
$3,400 for two guests, $1,700 per additional guests up to 6.
Mid-August brings great swimming and watersports weather. On this expedition our focus is gunkholing! We will hop from swimming hole to swimming hole to enjoy the warmer ocean temps during this time of year. In Merchant’s Row, we will anchor our by Pond Island and enjoy a guided Kayaking tour. The guides and kayaks come to us!
8/8 Perseid Meteor Shower Expedition
SOLD OUT
4 Day + 3 Nights
$3,200 for two guests, $1,600 per additional guests up to 6.
Our Perseid Meteor shower expeditions brings us to more remote destinations to allow for clearer views and low light pollutions. Expect stops in Swan’s Island, or even Isle au Haut for this trip. Guests are encouraged to sleep on deck, bring hammocks and soak in a spectacular evening event from the deck.
8/1 Eggemoggin Reach Regatta Expedition
SOLD OUT
4 Day + 3 Nights
$3,900 for two guests, $1,950 per additional guests up to 6.
One of our favorite trips of the year, this will be Hesper’s 3rd Eggemoggin Reach Regatta. In 2022, Hesper received the Mendlowitz Award as the most photogenic boat in a fleet of over 100! This expedition features two regattas, but both low-key and enjoyable for any wooden boat enthusiast. Boarding begins on Thursday and we will get everyone acclimated with a short day-sail. Friday is the Camden to Brooklin Feeder race, sponsored by the Camden Yacht Club. ERR participants race from Camden to Brooklin via the southern route (25.5 Nautical Miles) and get into Brooklin and the Wooden Boat School by 5PM generally.
Race Day is Saturday, afterwhich a massive BBQ and dance party is put on at the Wooden Boat School Campus!
We return to Camden by 5PM (sometimes earlier) on Sunday.
7/25 Camden Classics Regatta Day Charter
Available for Day Charter Friday and Saturday
FRIDAY- BOOKED
SATURDAY- Available
$1,200 per day. Up to 6 guests
Join Hesper for the 2024 Camden Classics regatta in Camden Maine. While this is a “Stay at Home Expedition”, its filled with over 100 classic sailing vessels with two days of outstanding racing. Guests are encouraged to get involved with our professional crew, but can also choose to sit back, relax and take in a front row seat to an absolutely outstanding show.
Boarding begins each morning at 8AM and each day is a little different!
Friday is a pure race day with a fun cocktail hour after.
Saturday brings the Parade of Sail, a must see event followed by the second and final day of racing. Saturday night includes a massive dinner, cocktail hour and dance party!
7/18 Roque Island Expedition
6 Days + 5 Nights
$5,200 for two guests, $2,600 per additional guests up to 6.
One of our longest passages of the 2024 Expedition Season, For generations of New England sailors, the Roque Island Archipelago has enjoyed a well-deserved and well-earned mythical status. Located at the mouth of the Bay of Fundy, just around the corner from our country’s northern border with Canada, this collection of barrier islands is far beyond the cruiser’s comfort zone of marinas, mooring balls, dinghy docks, and access to support services. Not very much has changed since the first “fool yachtsman and his flapper” discovered the iconic mile-long sand beach and the gracious owner/family who maintains the working saltwater farm on the Island’s northwestern tip. The voyage to Roque is a challenging thirty-five-plus miles from Schoodic Light and Petit Manan Island. One must tame a substantial tidal current and anticipate the likelihood of fog and contrary winds. As with most hard-won prizes in a cruising life, the value of the goal accomplished is measured by the effort and care taken in doing the exploration safely and without any needless drama.
7/3 Great Schooner Race
SOLD OUT
4 Day + 3 Nights
$3,200 for two guests, $1,600 per additional guests up to 6.
One of our favorites- The Great Schooner Race brings all the Maine Windjammers to Rockland. A celebration of heritage, hard work and stewardship. Join Hesper as we race around the designated course on Friday, sailing with some of the oldest working schooners in the entire world! This trip stays a bit closer to home, but is so worth the adventure. While this is a race, we encourage clients to get involved within their comfort level. We do have professional crew aboard to provide guidance, learning and involvement.
6/25 Boothbay harbor windjammer days
Come join us in Boothbay as we celebrate Windjammer Days!
6/19 Turner Farm Barn Supper
4 Day + 3 Nights
$3,200 for two guests, $1,600 per additional guests up to 6.
Join Hesper for a sail out to Turner Farm in North Haven Island for a unique Barn Supper. Turner Farm is a over 200 year old working farm which provides locally produced food to locals and visitors alike! On our first day we will sail 16 nautical miles through the Fox Island Thorofare and drop anchor in front of the sloping sides of Turner Farm, accompanied to the sound of roosters and other farm animals. Cocktail hour begins at 5PM, followed by a 5 course dinner with new friends and old. The next several days are spent in Stonington and Merchants row for a less crowded finale.
6/13 Penobscot Bay + Remote Islands Expedition
4 Days + 3 Nights
$2,800 for two guests, $1,600 per additional guests up to 6.
A classic “Go where the wind takes us” Expedition! No itinerary, just a plan to stop at different remote islands after a good day of sailing. This trip would be a great way to get the family away from the hustle and bustle of city life.
6/6 Blue Hill Expedition
SOLD OUT
4 Days + 3 Nights
$2,800 for two guests, $1,400 per additional guests up to 6.
Join us for a trip to Blue Hill and Deer Isle. Explore Stonington and Merchant Row’s classic anchorages, walk around the Wooden Boat School in Brooklin and sail underneath the iconic Deer Isle Bridge. This 4 day trip encompasses everything that is Maine.
5/30 North Haven + Vinalhaven Expedition
AVAILABLE!
Individual Bunks Available!
4 Days + 3 Nights
$650 Per bunk. Up to 4 guest crew spots available.
Join Hesper for 4 day of Expedition and Adventure while we sail around the famous Vinalhaven and North Haven Islands. Go hiking and exploring while we anchor out behind Green Island and Hurricane Island. Explore small shops in North Haven and relax after a long day of sailing in Seal Cove. The beginning of June brings mild temperatures and great wind!
This is a great opportunity to join us for one of the few trips that we have available for individual guests.