The best way to experience Windjammer Days and beautiful Boothbay Harbor is to get out on the water. Below are the many ways to do just that….

Pilot Cutter Hesper was built in 2004 in Cornwall England, and is currently owned by Boothbay sailor Eben Wilson. During the summers, she operates private Windjammer Expeditions out of Camden Maine, taking people up and down the coast for a hands-on adventure of a lifetime. 

Hesper is a 60' Gaff Rigged Pilot Cutter, with plenty of deck space to walk around and relax. 

We are excited to be able to offer public daysails during windjammer week. During the mornings she has individual tickets available, and afternoons are available for private charters. You can find us at the Bristol Marine dock at the Shipyard at Boothbay Harbor, and you can book online by visiting https://canvasandpinesailing.com/boothbay-harbor-windjammer-days, or give us a call at 207-701-7928. 

Schooner Alert hosts public and private sails on June 28: 10-11:30 dockside viewing; 12:00-3:00 sail; 3:30-5:30 sail; 6:30-8:30 pm sail with dockside fireworks.

Contact information: (207) 841-9125; TevakeSailingCharters@hotmail.com

Offering several trips to see the Windjammers as they sail into Boothbay Harbor including a Photography Cruise aboard the Balmy Days II, sailing cruise on the Bay Lady, and a cruise among the windjammers on the Novelty. Private charters are available on the Miss Boothbay anytime and also for the fireworks Wednesday night.

For more information: 207-633-2284; ticket booth is Pier 8, 42 Commercial Street. info@balmydayscruises.com

Take in a harbor tour aboard the Bennie Alice and then on to Cabbage Island for a quintessential Maine clambake experience.

For more information: call our ticket booth at 207-633-7200. Our ticket booth is at Pier 6, 22 Commercial Street in Boothbay Harbor, Maine

Enjoy several kinds of trips during Windjammer Days including a reggae music cruise, windjammer and whale watch combo, and sail with the windjammers. For more information: 207-613-7339 or sales@capnfish.com.

Boothbay Harbor’s very own Schooner Eastwind and Schooner Apple Jack offering special sails during Windjammer Days.

Schooner Eastwind, built in 1999 and measuring at 65-feet, is the largest schooner whose home port is Boothbay Harbor. Eastwind was built by Herb and Doris Smith on their farm in Albion and has a 14-foot beam, a frame of local white oak, planking out of Oregon cedar two inches thick.

Schooner Apple Jack is a scaled-down topsail schooner, constructed from long-leaf yellow pine planking over white oak frames and measures 48ft. in overall length, with a 12 ft. beam and a full keel that draws 6 ft. Under a full press, Schooner Applejack carries a mainsail, foresail, staysail, jib, jib topsail, and a fisherman. Call for all the details.

MAINE LIGHTHOUSE TOURS - Come join us to view some of Maine's most beautiful Lighthouses.

MAINE ISLAND TOURS  - Guided Maine Island tours including Boothbay Harbor, Southport Island, Boothbay, Monhegan Island, Wiscasset, and Bath, aboard the Hay Val. 

MAINE WILDLIFE TOURS - Wild life cruises Maine aboard the Hay Val

CUSTOM ON THE WATER TOURS-MAINE - Come aboard the Hay Val for a exciting private sightseeing tour of the Maine Coastline. Let me create a tour that fits you perfectly, adjusting for physical limitations or time restraints.

207-319-8123, www.hayvalcharters.com.

Boothbay Harbor Oceanside Golf Resort is now offering private coastal tours on our luxurious boats. See historic lighthouses, seals, puffins or simply explore our quaint harbors and beautiful coastline.

Island Mode - a 37’ Hinckley Picnic Boat and Oceanside - a 21’ Crosby Launch

Contact us for more information: https://boothbayharboroceansideresort.com/boating-excursions or 207-633-4455

Redhook Charters - See the beauty of the Maine coast up close and personal.  Enjoy a personalized, narrated boat trip without the crowds of the big tour boats.  Captain Mark Stover, a lifelong resident of Boothbay Harbor, will guide you through the history of the area as you take in the breathtaking scenery.  See seals, lighthouses and miles of rocky coastline as you cruise the Maine waters.  Bring your sunscreen, binoculars, a camera and a picnic! Redhook is a 32' luhres with twin diesel engines.  You'll find a totally relaxed atmosphere, plenty of deck space and comfortable seating for up to 6 people. For more information: redhook59@gmail.com or 207-720-0547

Matador Network has published a new cruise roundup, Matador's Guide to Cruising the World.  The information is based on input from Matador’s contributing writers, a group of savvy, well-traveled individuals that definitely know what makes a great cruise so appealing to our readership. Check it out!