Our 100% liveaboard sail training and cruising prep program offers an educational experience for people of all levels who want to prepare for anything from weekend sails to long-term cruising and ocean passage making. Our 2026 sailing school schedule will start the summer based out of our homeport, Rockland, doing what we do best, cruising somewhere between Monhegan, Petit Manan, and Mt. Desert Island in the Gulf of Maine.

The second half of our season will take us across the Atlantic in three legs:
Leg 1: Maine-Newfoundland
Leg 2: Newfoundland-Azores
Leg 3: Azores-Gibralter

2026 Expedition Schedule

MoA 261May 25-30 6 Days 200nmCruising: Coastal w/ Overnight Sail
Rockland, ME
$30005 Available
MoA 262June 1-66 Days 200nmCruising: Coastal w/ Overnight Sail
Rockland, ME
$30005 Available
MoA 263June 14-207 Days 300nmCoastal Passage: Yarmouth
Rockland, ME
$40005 Available
MoA 264June 28-July 1013 Days 950 nmPassagemaking
Rockland, ME – St. Pierre, FR – St. John’s, NL
$75004 Available
MoA 265July 15-July 2915 Days 1300nmOcean Crossing
St. John’s, NL – Horta – Ponta Delgada, Azores
$90004 Available
MoA 266Aug 3-1513 Days 1000nmOcean Crossing
Ponta Delgada, Azores – Gibralter
$78004 Available

Please note: this schedule is subject to slight changes.
We have not opened these expeditions up for booking yet, but if you are interested, get your name on the list now!

Rockland Based Expeditions: Coastal w/ Offshore Overnight Sail

How to sail to the Maine Coast. Its gorgeous.

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.


Private Expeditions:

We offer 4 and 5 day Private Maine Coast Expeditions, or a 5-day Coastal with an overnight sail. You’ll have the whole boat to yourself (minimum 2 people) and be able to choose your dates. We’ll work with you to create an itinerary to help you reach your goals. All private expeditions start and end in Rockland, ME. Please contact us to discuss your goals and our availability. Please note, we do have a busy summer schedule and there often isn’t much time to add in private charters. We often encourage students to re-consider our group expeditions, as the group learning environment offers many educational benefits.

MoA PC4 • Dates TBD  • 4 Days: Private Coastal
MoA PC5 • Dates TBD  • 5 Days: Private Coastal
MoA PO5 • Dates TBD  • 5 Days: Private Coastal + 1 Overnight Sail

Other Offerings:

We also offer trainings and deliveries on your boat in special cases. If you don’t see an expedition here that fits your schedule or needs, please contact us to inquire about our other offerings.