Maine Coastal & Overnight Expeditions

Coastal Overnight Description

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, hands on navigation, drills, scenarios and fun.

We sail among the islands, ledges, and schooners of Maine’s bold coast, most likely encountering some fog and other challenges along the way. Our Coastal & Overnight expeditions leave Rockland, and anchor in a different harbor each night. We will analyze the forecast together and decide on the best weather window to sail one overnight of approximately 100nm so that you can learn and experience watch standing routines and protocols for coastal passages. We only return to Rockland on the final day of the expedition, all other days will be spent exploring, cruising and most importantly learning.

While every day offers opportunity to work on perfecting sail trim, tacking and gybing, or setting the spinnaker if conditions are favorable, you will quickly learn that “sailing” is just one small part of the bigger “cruising” picture. Our days are shaped by weather, logistics, and the needs of the boat and crew rather than a rigid schedule or pre-planned curriculum.

All hands are actively involved in taking care of Rocinante and her crew. You will be engaged in the management of resources: electric, water and fuel. You’ll learn to observe and check all onboard systems.

Learn Essential Cruising Skills

We anchor 90% of the time. Anchoring is a core skill that needs to be mastered just like cleating a halyard. You learn how to evaluate and choose good anchorages, set and retrieve the anchor efficiently, and manage swing room.

Weather dictates every move we make, or don’t make. Knowing how to obtain and interpret weather forecasts to use the data they provide to make smart, informed decisions and plans is a fundamental skill, and safety consideration.

​Throughout the expedition, you will gain a better understanding of the resources—time, energy and expenses—required to cruise efficiently and happily.

Logistics

Rockland expeditions begin at 3:30 pm. If you plan to take the bus from Portland or Boston you will arrive on time.

Fly into Boston Logan Airport (BOS) or Portland International Jetport, Portland Maine (PWM). Take the Concord Coach Lines bus from Boston or Portland to Rockland. The bus arrives at 3:30pm and Teresa will pick you up and take you to the boat (notify her).

If you’re driving to Rockland and you plan to park your car at our house, please let us know at least a few days before the expedition. Arrive at our house at 3:20. It is not necessary to arrive early. The address is 37 Lake View Terrace, Rockland, ME.

The boat will arrive at Schooner Warf at 3:30. If the dock is full and we need to change plans, we will call you on the cell number you provided on your application. Please ensure that it is correct. Schooner Warf is located at 314 Capt Spear Drive, Rockland, ME. This is a shared/private dock. There is a parking lot, but we do not have any parking spaces, and therefore our guests cannot park there. If you need parking, contact Teresa. We do not have an office at the dock and there are no public restrooms. You can use the restroom (head) aboard Rocinante. The boat will on time, but not early. At 3:30pm look for Rocinante’s white hull and thick black stripe and come on down!

Expect to depart around 1-2pm on the final day. While we do anticipate the last day ending early afternoon, your course may be delayed due to weather, or unforeseen circumstances, so please keep your travel plans somewhat flexible on the last day. Often, students staying in Rockland that night, will get together for a final celebratory dinner!

Our 2026 Coastal & Overnight Expeditions

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