Life Aboard

Every morning begins with a plan- That plan starts with setting sail and using Hesper’s grace to find a new remote island to explore. Coffee and breakfast are used to go over the charts and find our next destination. Do we want to go to a sandy beach and have a island lobsterbake? Or perhaps visit Vinalhaven and hike the quarry? Maybe you are looking forward to kayaking a quaint small cove? It all starts with hoisting the mainsail on Hesper. Guests are welcome to be as involved as they’d like. Voyage plan and take the helm to steer us to our next cove, or just sit back and relax and let our professional crew do it.

Each afternoon after Hesper drops anchor is a new adventure. Row, swim or dinghy ashore and explore beautiful Maine Islands. Let us know your preferences for activity level. We love exploring our MITA (Maine Island Trail Association) lands and islands and providing great hikes for our guests, but are equally as adept in providing a peaceful spot for a hammock read, or just a lazy kayak around a cove.

WIndjammer Vacation- to us, this means relaxation. You tell us how to achieve that. Evenings are low key- dinners by the oil lantern, lobster bakes on a island, scrabble and wine on the foredeck while watching the sunset. Browse our ships library, or just stare out at the endless beauty in front of you. This is a total disconnection.

-Boarding begins at 10am on Thursday. Meet and greet, introductions and review ships safety information and quarters.

-Set sail for across Penobscot Bay. Learn the ropes and feel Hesper harness the wind towards our first island destination.

-Lunch served aboard. See our Food + Sustanance page. You won’t leave hungry.

-Mid Afternoon arrive at our first island destination. Perhaps we’ve arrived at Hog Island, home of a sandy beach and eagle nests. Anchor is dropped, and kayaks are brought out. Kayak to shore and explore the various island trails. Keep aware for that smell tho- the crew will be busy preparing your first night island lobster bake! When you hear the bell ring, come back to the beach for Lobster.

-Enjoy a traditional lobster bake ashore. Music, drinks and story telling.

-Return to Hesper after sunset. Rocked to sleep by the gentle waves.