Overnight Windjammer Trips+Expeditions

Our bespoke, custom Windjammer Expeditions. Curated to your individual group- This is a completely private experience for up to 6 passengers. Our trips depart weekly from Camden Maine.

Boothbay Harbor + Shipyard Cup

July 22nd-23rd

Join Hesper for the 2nd annual Boothbay Harbor Yacht Club Shipyard cup. Boothbay Harbor is one of the most protected harbors in Maine, while still providing great technical sailing opportunities. A quaint town, nestled amongst a singular street running through it, this is a great opportunity to experience a classic Maine regatta. Join Hesper for 1 day of racing, or charter for the whole weekend!

Camden Classics

July 28th-29th

Join Hesper for one of the worlds most renowned weekends of racing, the Camden Classics, sponsered by Lyman Morse in Camden Maine. Camden is known as the gem of the midcoast- nestled into Mt Battie, where the mountains meet the sea. A harbor singularly dedicated to wooden boats and sailing, this is a most see oppurtunity for any classic boat enthusiast. Join us as crew, or sit back and enjoy as we participate in two days of racing, eating and tall tales. Join us for 1 day, or charter for the whole event.

Eggemoggin Reach Regatta

August 5th

Join Hesper for can be considered the most famous gathering of wooden vessels in the world. Known as “the Woodstock” of wooden boat racing, the Eggemoggin Reach Regatta is a once in a lifetime experience. Sponsered by Wooden Boat, owners of the Wooden Boat school and Wooden Boat Magazine, the 15 NM course down the reach is a great racing experience. After, a ceremony of awards, food and drink and meeting other sailors. Join Hesper for this 3 day event.

Wooden Boat Sail-In

September 12-15th

As the cruising season for the Maine Windjammers comes to a close, a final hurrah at the meccah of wooden boats- the Wooden Boat Sail-in. Join Hesper and witness some of the oldest working wooden boats in the world as the sail into Brooklin Harbor for a day of live music, refreshments and tours of the Wooden Boat School.