Maine

Come live-aboard the sailing vessel Boundless for a hands-on adventure exploring rugged islands, quiet coves, quaint towns, and iconic lighthouses. 

5-Day Summer Sailing Adventure — Portland, Maine 

​

Day 1 — Portland Harbor ➜ Cliff Island (Ice Cream) ➜ Jewel Island

Morning — Portland, ME

• Meet Capt. Jeff at the public boat ramp and "dinghy" out to Boundless waiting at anchor. Safety briefing, bunk assignments, boat tour, gear check.

• Intro seamanship lesson: points of sail, basic knots, life aboard.

Late Morning — Sail to Cliff Island

• Student-led sail trim practice.

• Short shore visit: Small general store for ice cream, beach walk, rock skipping village views.

Afternoon — Continue to Jewel Island

• Set anchor in Cocktail Cove, one of the most scenic anchorages in Casco Bay.

• Hike to the WWII naval lookout towers and explore the island’s thick forest trails and rocky coast.

Evening

• Dinner onboard.

• Play "The Envelope Game" to get to know everyone on board!

• Star-gazing from the deck of Boundless — early introduction to constellations used in navigation.

• Board games in main cabin.

Learning Focus: seamanship basics • island ecology • navigation towers history

Day 2 — Jewel Island ➜ Eagle Island (Admiral Peary’s Home) ➜ Snow Island

Morning — Sail to Eagle Island

• Students rotate through helm, lookout, and navigation stations.

• Onshore visit to Admiral Robert Peary’s historic home and museum, learning about Arctic exploration, survival, and mapping.

• Short wooded hike and shoreline exploration.

Afternoon — Sail to Snow Island
A quiet, sheltered destination perfect for education and exploration.

Late Afternoon — Treasure Hunt!

• Hand-compass navigation challenge across trails and shoreline.

• Teams follow clue envelopes, bearings, and pacing instructions to locate “hidden treasure” (small waterproof box with treats or challenge cards).

Evening

• Kayak in protected coves (good area for seal sightings).

• Dinner and campfire-style "life goal" talk circle on deck.

Learning Focus: magnetic bearing navigation • maritime history • compass skills • team leadership

Day 3 — Snow Island ➜ Cundy’s Harbor (Lobster Night)

Morning — Marine Science & Navigation

• Plankton tow lesson, water temperature/salinity reading, basic chart plotting.

• Short sail deeper into the New Meadows region.

• Watch for seals hauled out on ledges.

Midday — Arrive at Cundy’s Harbor
One of Maine’s oldest and most picturesque fishing villages.

Afternoon

• Shore exploration of the harbor, working waterfront, lobster boats, and wharf culture.

• Optional short hike along nearby coastal trails.

• Purchase lobsters for evening's dinner.

Evening — Lobster dinner!​

• Students learn about lobster biology, trap engineering, and fisheries sustainability.

Night

• Sunset kayak paddle (conditions permitting).

• Onboard board games and journaling.

Learning Focus: fisheries science • coastal culture • plankton ecology • seamanship

Day 4 — Cundy’s Harbor ➜ Bath, Maine (Museum, Pizza, Souvenirs)

Morning — Sail up the Kennebec River toward Bath, anchor across from U.S. Navy battleships being built at the Bath Iron Works.

• Students practice reading river currents, buoys, and aids to navigation.

• Weather lesson: interpreting clouds, wind, pressure, and local forecasting.

• Visit the Maine Maritime Museum: shipbuilding, lighthouse lens exhibits, 19th-century boatyards, and hands-on learning.

• Students complete a quick “museum challenge” sheet identifying three things that surprised them.

Afternoon — Town Time!

• Pizza lunch downtown.

• Walk through Bath’s historic streets for souvenirs, bookstores, and ice cream.

• Return to Boundless.

• Anchor in a quiet cove (e.g., near the mouth of the New Meadows).

• Free swim (conditions permitting).

• Star-gazing lesson: circumpolar constellations, latitude from Polaris.

• Movie night aboard and/or board games.

Learning Focus: maritime history • river navigation • meteorology • leadership reflection

Day 5 — Return Across Casco Bay to Portland

Morning — Student-Led Sail
Students run the passage with instructor oversight:

• Assign skipper of the day

• Navigator plots course to Portland

• Helm, sail trim, lookout team rotations

Midday — Arrival in Portland

• Lunch onboard; vessel clean-up; gear pack-out.

Afternoon — Final Debrief

• Journaling: write a “Letter to Future Self”.

• Group reflection: what they learned about teamwork, self-confidence, problem-solving, and seamanship.

• Students receive a “Seamanship Skills Log” summary.

Learning Focus: mastery demonstration • teamwork • confidence building

Optional Add-Ons​

• Knot-tying competition

• Guest wildlife biologist session

• Marine debris microplastics sampling

​​

Cost: $1,275 per student (based on 6) and includes 5 days/4 nights lodging on Boundless, a Captain and First Mate, all educational materials, instruction, museum entrance fees, dockage, fuel, and all meals on board. Meals ashore (group's choice), extra museums/events not on our itinerary, and/or airport pickup, additional. Airfare/transportation to/from Portland, ME not included. A teacher attends for free including airfare with six students.

​

Adult, family/friends getaway Maine sailing adventures available too!

​

​​Boundless sails Maine mid-June thru September.