2025 Sailing Expedition Schedule

6 day Maine Expeditions: 250, 251, 2510
4 day Maine Expedition: 257 (no overnight sailing, we will anchor each night)

The coast is where all the action and challenge is: commercial traffic, rocks, tides and currents. Maine is one of the most difficult areas to sail in the US, notorious for large tides and thick fog—but the beauty is unbeatable! These expeditions feature long days of lessons, planning, navigation, drills, scenarios and fun. We’ll sail among the islands, ledges, and schooners of Maine’s bold coast, most likely encountering some fog and other challenges along the way. These Coastal & Offshore expeditions include an overnight sail of approximately 100nm so you can learn and experience watch standing routines and protocols for passages.

Travel Recommendations: Fly round trip into Portland (PWM) or Boston (BOS). From there, take the Concord Coach Lines bus to Rockland, rent a car (Budget, Avis and Enterprise have offices nearby), or fly to Knox County Airport via Cape Air. Many students coordinate shared car rentals when their flight schedules align.

7 day Round Trip Yarmouth Expeditions: 252

This multi-day expedition include a round trip passage from Rockland to Yarmouth, Nova Scotia. This will be a very challenging expedition of approximately 300nm that will require 2 seperate overnight passages. You’ll experience the downeast coastal challenges, big tides and currents, commercial fishing traffic, ocean waves, rapidly shifting weather, fog, and a foreign country check-in. We will sail Penobscot Bay, the mouth of The Bay Of Fundy, and cross The Gulf Of Maine. We plan to make only a quick overnight stop in Yarmouth, for some leg stretching ashore. This roundtrip expedition packs in ALOT of coastal and offshore sailing miles, plus the added convenience of both departure and arrival in Rockland.

Travel Recommendations: Fly round trip into Portland (PWM) or Boston (BOS). From there, take the Concord Coach Lines bus to Rockland, rent a car (Budget, Avis and Enterprise have offices nearby), or fly to Knox County Airport via Cape Air. Many students coordinate shared car rentals when their flight schedules align.

7 day Halifax Expeditions: 253, 254

These multi-day passage expeditions will take us across the Canadian Border! We’ll be route planning and sharing weather reports with you even before the expedition begins, so you can learn the process in detail. The passage to/from Halifax is approximately 300nm and challenging in many ways. Cape Sable in particular has been described as The Hatteras of The North. Strong currents, high potential for fog, and lots of commercial fishing vessels make this one of the tougher passages you can do in the Northeast. The rugged coast of Nova Scotia provides a few gorgeous anchorages to explore along the way, historical Lunenberg could be one, if conditions permit. We will sail Penobscot Bay, The Gulf Of Maine, and the South Coast of Nova Scotia. This expedition will give you a real taste of making a tough coastal hop and insight into what multi-day offshore sailing is like. This is an ideal learning passage with the perfect real-world combo of coastal and offshore time.

Travel Recommendations:
If starting in Rockland: See above.

If starting in Halifax: Book your flight into Halifax (YHZ). To return take the Concord Coach Lines bus from Rockland to Portland (PWM) or Boston (BOS).

7 day Boston Expeditions: 256, 257

These multi-day passages transit the busy waters of New England. We’ll encounter fishing fleets, whales on Stellwagen Bank, shipping traffic into Boston and spend a night in Provincetown on the tip of Cape Cod. We’ll share weather reports and discuss route planning with you before the expedition begins, so you can see the full process. The roughly 220nm passage transits between Constitution Marina in Boston, and our homeport of Rockland, Maine. We will sail Penobscot Bay, The Gulf Of Maine, Cape Cod Bay, Massachusetts Bay, and Boston Harbor. There will be options for potential anchorages – Islands in Maine, Gloucester, Provincetown, etc. This is an ideal learning passage with the perfect real-world combination of coastal and offshore time.

Travel recommendations:
You can purchase round trip flights to Logan International Airport (BOS). From there, take the Concord Coach Lines bus to Rockland, rent a car (Budget, Avis and Enterprise have offices nearby), or fly to Knox County Airport via Cape Air. Many students coordinate shared car rentals when their flight schedules align.

You can take the same bus from Rockland back to Logan/Boston!

7 day Newport Expeditions: 258, 259

These multi-day passages transit the busy waters of New England. Staying focused while on watch is imperative. We’ll share weather reports and discuss route planning with you before the expedition begins, so you can see the full process. The roughly 250nm passage will offer offshore routines, commercial traffic, ocean waves, strong currents, rapidly shifting weather, and of course, “Land-Ho!” We will sail Penobscot Bay, The Gulf Of Maine, Massachusetts Bay, The Cape Cod Canal, Buzzards Bay, and Narragansett Bay. There will be options for potential stops – Islands in Maine, Gloucester, Provincetown, Martha’s Vineyard, New Bedford, etc. There may even be whale sightings near Stellwagen Bank. This is an ideal learning passage with the perfect real-world combo of coastal and offshore time, and of course Newport is the “capitol of sailing!”

Travel recommendations:
For expeditions starting in Rockland: See above.

In Rhode Island, use T.F. Green International Airport (PVD). There is a $12 ferry from Newport to Fox Point Providence. From there, you can take a 10min cab ride to the airport. Uber/Lyft are also options.