Liveaboard sail training
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. Learn more about our beloved training vessel Rocinante.
The first half of our 2026 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 Penobscot Bay, The Gulf of Maine and Nova Scotia. We are offering four Rockland based coastal expeditions (261, 262, 264, 265) plus one Rockland-Yarmouth (263) roundtrip expedition this season.
If you are following the American Sailing curriculum, we now offer certifications 103 and 104 on our Maine based expeditions. These are optional certifications. You do not have to be on the ASA track to join us on any of our trips. We have added these certifications solely as a service to students who request it. This does not affect our overall mission, quality of our courses, or expedition objectives. Please note, we do not offer ASA 101 certification, as that class should be taken on a smaller boat, appropriate to the course material.
Listen to our Morning Muster podcast episode about our Maine Expeditions.
| MoA 261 | May 25-30 | 6 Days 200nm | Cruising: Coastal w/ Overnight Sail Rockland, ME (ASA 103, 104 available) | $3,600 | Waitlist |
| MoA 262 | June 1-6 | 6 Days 200nm | Cruising: Coastal w/ Overnight Sail Rockland, ME (ASA 103, 104 available) | $3,600 | Waitlist |
| MoA 263 | June 7-13 | 7 Days 350nm | Coastal Passagemaking: Yarmouth Rockland, ME (ASA 104 available) | $4,600 | 1 available |
| MoA 264 | June 15-20 | 6 Days 200nm | Cruising: Coastal w/ Overnight Sail Rockland, ME (ASA 103, 104 available) | $3,600 | Waitlist |
| MoA 265 | June 22-27 | 6 Days 200nm | Cruising: Coastal w/ Overnight Sail Rockland, ME (ASA 103, 104 available) | $3,600 | Waitlist |
The second half of our season will take us across the Atlantic and into the Mediterranean Sea in six passage making legs.
Listen to our Morning Muster Podcast episode on Transatlantic Crossings from West to East.
| MoA 266 | July 2-July 14 | 13 Days 950 nm | Passagemaking: Canadian Maritimes Rockland, ME – St. Pierre, FR – St. John’s, NL | $8,600 | 2 available |
| MoA 267 | July 18-August 1 | 15 Days 1300nm | Ocean Crossing St. John’s, NL – Horta – Ponta Delgada, Azores | $9,800 | Waitlist |
| MoA 268 | August 6-August 18 | 13 Days 1000nm | Ocean Crossing Ponta Delgada, Azores – Gibraltar | $8,600 | 2 available |
| MoA 269 | August 23-September 1 | 10 Days 600nm | Passagemaking: Western Mediterranean Gibraltar – Balearic Islands – Barcelona | $6,600 | 1 available |
| MoA 2610 | September 27-October 11 | 15 Days 1000 nm | Passagemaking: Mediterranean Italy – Greece/Turkey | $8500 | 5 available |
| MoA 2611 | Coming Soon | 7 Days 200nm | Family Coastal Training: Greece / Turkey (ASA 103, 104 available) | inquire | 4 available |
| MoA 2612 | Coming Soon | 7 Days 200nm | Family Coastal Training: Greece / Turkey (ASA 103, 104 available) | inquire | 4 available |
261, 262, 264, 265 • 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 will anchor in a different harbor each night with one overnight sail of approximately 100nm so you can learn and experience watch standing routines and protocols for passages.
6 Days • 261 • May 25-30 • 200nm • $3600
6 Days • 262 • June 1-6 • 200nm • $3600
6 Days • 264 • June 15-20 • 200nm • $3600
6 Days • 265 • June 22-27 • 200nm • $3600
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 (weather dependent) 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 • $4600
266 • 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 • July 2-14 • 1000nm • $8600
267 • 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 18-Aug 1 • 1300nm • $9800
268 • Azores – Gibraltar
Leg 3 of the Atlantic Crossing. The Azores are beautiful, but after a night or two at anchor, 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 • August 6-18 • 1000nm • $8500
269 • Gibraltar – Barcelona
This exciting passage from the mouth of the Med to the rugged Spanish coastline and the Balearic Islands is a gorgeous sail through history and culture. We have miles to make, so this won’t be a leisurely cruise. But we’ll be sailing the best of the Western Med, while honing your navigation and seamanship skills.
10 Days • August 23- September 1 • 650nm • $6600
2610 • Rome – Greece/Turkey
This lengthy passage through the Mediterranean Sea (over 1000nm!) packs a lot into a short time frame. We will be traversing over half the Med—the entire Amalfi Coast, The Strait of Messina, crossing the Ionian Sea, and exploring both The Cyclades and The Dodecanese islands of Greece. We’ll find stops along the way to rest, explore, and soak in the history, culture and cuisine. There will be multi-day passages to plan, opportunities to anchor, and Med Moor. This will be the perfect combination of real passage making and real Med cruising.
15 Days • September 27 – October 11 • 1000nm • $8500
Who will my instructors be?
Our team is comprised of excellent sailors, who are also superior educators. Ben is the primary captain and leads 85% of the expeditions. Teresa has been staying home with Haven, our 7 year old. Our primary mates are Courtney and Tara. They have worked with us since 2021. They are both USCG licensed captains, and educators through and through. We also have an alternate captain, John Calogero, who leads a few trips each summer. John is another seasoned sailor and educator, whom we trust to lead a quality expedition and take care of Rocinante! You can read about our team here.
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.