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.
The first half of our season will be based in Maine and Nova Scotia:
Our 2026 sailing school schedule will start the summer based out of our homeport, Rockland, doing what we do best, cruising somewhere between Portland and Nova Scotia! We are offering two Rockland based coastal expeditions (261, 262) plus another Rockland-Yarmouth (263) roundtrip expedition this season.
The second half of our season will take us across the Atlantic and into the Mediterranean Sea in four passage making legs:
264 • Maine-Newfoundland
265 • Newfoundland-Azores
266 • Azores-Gibraltar
267 • Gibraltar-Barcelona
2026 Expedition Schedule
| MoA 261 | May 25-30 | 6 Days 200nm | Cruising: Coastal w/ Overnight Sail Rockland, ME | $3000 | 4 available |
| MoA 262 | June 1-6 | 6 Days 200nm | Cruising: Coastal w/ Overnight Sail Rockland, ME | $3000 | 2 available |
| MoA 263 | June 7-13 | 7 Days 350nm | Coastal Passage: Yarmouth Rockland, ME | $4000 | 4 available |
| MoA 264 | June 21-July 3 | 13 Days 950 nm | Passagemaking: Canadian Maritimes Rockland, ME – St. Pierre, FR – St. John’s, NL | $7800 | 3 available |
| MoA 265 | July 8-22 | 15 Days 1300nm | Ocean Crossing St. John’s, NL – Horta – Ponta Delgada, Azores | $8950 | Waitlist |
| MoA 266 | July 27-August 8 | 13 Days 1000nm | Ocean Crossing Ponta Delgada, Azores – Gibraltar | $7800 | Waitlist |
| MoA 267 | August 12-21 | 10 Days 600nm | Passagemaking: Western Mediterranean Gibraltar – Balearic Islands – Barcelona | $6000 | 3 available |
Availability updated: Sept 2
261 & 262 • Rockland, Maine • Coastal w/ Offshore Overnight Sail
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.
261: May 25-30 • 200nm • $3000
262: June 1-6 • 200nm • $3000
263 • Rockland – Yarmouth (Roundtrip)
This multi-day expedition include a round trip passage from Rockland to Yarmouth, Nova Scotia. This will be a challenging expedition of approximately 300nm that will require 2 separate overnight passages. You’ll experience big tides and currents, commercial fishing traffic, ocean waves, rapidly shifting weather, fog, and a foreign country check-in. We plan to make 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.
7 Days • June 7-13 • 350nm • $4000
264 • Maine – Newfoundland
Join us for Leg 1 of the Atlantic Crossing. We will sail in Penobscot Bay, cross The Bay Of Fundy, round the infamous Cape Sable, where the current can get up to 4 knots, and make way for St. Pierre, a French Territory. After a stopover in St. Pierre for un petit taste de France, we will head East towards St. John’s. This will be our 3rd expedition to Newfoundland, a most magical destination.
13 Days • June 21-July 3 • 950nm • $7800
265 • Newfoundland – Azores
Leg 2 of the Atlantic Crossing, is the bulk of the crossing. We will depart Newfoundland, head south to find whales and an anchorage, before heading east for the Azores. We plan to make landfall in Horta, then explore some of the other Azorian Islands, before finishing the crossing in Ponta Delgada. Celestial navigation will be a part of the offshore curriculum.
15 Days • July 8-22 • 1300nm • $8950
266 • Azores – Gibraltar
Leg 3 of the Atlantic Crossing. The Azores are beautiful, but we will leave their volcanoes behind as we continue East towards the gateway to the Mediterranean Sea – Gibraltar. Hone your offshore sailing skills, and gain experience standing watches, using a sextant and navigating our way to the Med.
13 Days • July 27-August 8 • 1000nm • $7800
267 • Gibraltar – Barcelona
This exciting passage from the mouth of the Med to the Spanish coastline and the Balearics is an iconic sail through history and culture. Explore the best of the Western Med, while honing your navigation and seamanship skills. These are training passages.
10 Days • August 12-21 • 650nm • $6000
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.