BOOTHBAY HARBOR, SAILING FIELD GUIDE
Hoist the Sails on Schooner Apple Jack: Two Hours across Boothbay Harbor’s Outer Islands
A 2-hour day sail from Boothbay Harbor aboard the historic Schooner Apple Jack—an opportunity to help raise sails, take the wheel, and scan for porpoise and bald eagles.
Hoist the Sails on Schooner Apple Jack: Two Hours across Boothbay Harbor’s Outer Islands.
Embark on an unforgettable 2-hour sailing adventure aboard the historic Schooner Apple Jack in Boothbay Harbor. Join the crew to hoist sails or stand at the wheel as the schooner works its way past Burnt Island Light, Squirrel Island, Ram Island Light and the outer islands of Boothbay, with chances to spot porpoise, osprey, bald eagles and harbor seals along the way.
Highlights
Outing Highlights
Past Harbor Lights and Outer Islands
The cruise sets a course out of Boothbay Harbor and past notable markers including Burnt Island Light, Squirrel Island and Ram Island Light, giving clear coastal views of the outer Boothbay islands.
Hands-On Sail Handling
Passengers are invited to take part: help hoist sails or take a turn at the wheel aboard Boothbay Harbor’s oldest windjammer, guided by the schooner’s crew during the two-hour outing.
Coastal Wildlife & Working Water
Keep watch for porpoise, osprey, bald eagles and harbor seals as the schooner slips by local boats hauling in the day’s lobster catch—an authentic glimpse of Maine’s coastal life.
What the day feels like
What the two‑hour day sail feels like
The two-hour day sail is brisk and participatory: a short, focused outing aboard a traditional windjammer where the rhythm of raising canvas and trimming sheets punctuates sightings of lighthouses, islands and coastal wildlife.
Suitability
Who it's for
Who this sail suits—and who should look elsewhere.
Practical planner
Details to review before reserving
The Schooner Apple Jack day sail runs two hours.
Guests meet at 20 Commercial St, Boothbay Harbor, ME 04538.
No specific gear list is provided in the supplied data.
An early-bird discount is noted for 9:00 AM sailings (save $5 on 9AM sailings).
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
How long is the Schooner Apple Jack day sail?
The outing is two hours in duration.
Where do we meet before departure?
Guests meet at 20 Commercial St, Boothbay Harbor, ME 04538.
What will we do on board?
Passengers can help hoist sails and take a turn at the wheel while the schooner sails past Burnt Island Light, Squirrel Island, Ram Island Light and the outer Boothbay islands.
Will we see wildlife?
Yes—watchers may spot porpoise, osprey, bald eagles and harbor seals while transiting the islands and coastal waters.
Are there any age or mobility restrictions?
This activity is not for children under the age of 5 or adults with mobility issues.