Coastal Cruising Experience - 125NM / 7 Days
AVAILABLE: 2 Cabins
Boat: Tiger Lily
Crew: Phoebe & Xander
DETAILS:
Join us for a week of sailing through one of the finest cruising grounds in North America: downeast Maine. Departing from Rockland, this trip explores the heart of Penobscot Bay, where granite-lined shores, pine-covered islands, and fishing harbors that define the landscape. Known for its rewarding navigation, stunning anchorages, and access to unforgettable hikes and coastal towns, DownEast Maine is a place that invites sailors to slow down and truly settle into life on the water.
Short sails link protected coves and island communities, creating a perfect balance of time under sail and time ashore. Cool mornings, crisp breezes, and long summer evenings make this a deeply satisfying place to cruise.
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This is classic coastal cruising with day sailing between anchorages, peaceful nights on the hook, and the simple pleasures of life aboard. You’re welcome to be as involved in the sailing as you’d like, from helming and sail handling to navigation and anchoring, or simply enjoy the scenery from deck as the coastline slips by.
Between sails, explore by dinghy, walk island trails, swim in clear (refreshing) waters, and share meals aboard. Maine’s rugged beauty, changing light, and quiet rhythm have a way of staying with you long after the trip ends.
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Possible stops include:
Rockland Harbor – A classic sailing town and ideal base for Penobscot Bay
Vinalhaven & North Haven – Charming island communities with scenic walking trails
Merchant Row – A maze of protected islands and narrow passages
Camden Hills Area – Dramatic scenery and welcoming harbors
Isle au Haut – Remote beauty and access to Acadia National Park trails
Fox Islands Thoroughfare – Iconic Down East sailing with ever-changing currents and views
(Exact route depends on weather and conditions.)
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While this is not a formal course, the trip offers plenty of opportunities to build confidence and sharpen skills through real-world sailing. Topics may include coastal navigation, route planning, sail trim, anchoring techniques, weather awareness, and operating safely in fog and tidal waters; hallmarks of Maine cruising.
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Expect cool, comfortable summer conditions with daytime highs typically 65–75°F (18–24°C) and cooler evenings. Winds are often moderate and variable, with calm mornings and afternoon breezes. Fog is part of the Maine experience and adds to the adventure, offering excellent real-world navigation practice.
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Dinghy pickup in Rockland’s harbor. Flights to Knox County Airport (RKD), hosted by Cape Air with connections to larger hubs. Or, alternatively flights into Portland (PWM) or Bangor (BGR) with a shuttle service to Rockland with Sterling Elite or Concord Coach Lines.
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Our programs are all-inclusive once aboard, designed to let you focus fully on sailing, learning, and enjoying life at sea.
This includes all onboard meals, snacks, refreshments, evening sundowners, and standard mooring or docking fees.Not included:
Transportation to/from the program and meals or drinks ashore.Please inquire below to learn more about availability and trip details.
Click ‘Request More Info’ and fill out the form. We will get back to you with more details about the passage and how to book. If you have any questions, don’t hesitate to Contact Us! Or, maybe your questions are answered elsewhere? Check out our FAQ’s!
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