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WoodenBoat Sail-In: Rockland Maine Schooner Experience - Portland

WoodenBoat Sail-In: Rockland Maine Schooner Experience

Rocklandmoderate

Difficulty

moderate

Duration

6–8 hours

Fitness Level

Participants should be in good health with basic mobility and able to manage some movement on uneven and moving surfaces.

Overview

Join the WoodenBoat Sail-In on September 7, 2025, aboard a classic Maine schooner. Experience coastal sailing, live music nights, and breathtaking views on this unique Rockland adventure.

Rockland, Maine

WoodenBoat Sail-In - Fleet Gathering - September 7, 2025

6-night trip • Starting at $1,540 per person based on double occupancy • Ages 12+

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About This Adventure

Embark on a unique sailing adventure aboard a traditional Maine schooner, exploring picturesque fishing villages and iconic lighthouses. Experience the thrill of open-ended itineraries shaped by nature, enjoy evenings filled with live music, and immerse yourself in the rich windjamming tradition amidst stunning coastal views. Relax in cozy, well-equipped cabins.

Duration

  • Board September 7th, 2025 between 6 pm and 8 pm
  • Disembark September 13th, 2025 before noon.

Trip Description

This trip is perfect to experience what it's like sailing on a traditional Maine schooner and to see up close the fishing villages and lighthouses that dot the coastline. Come see Maine from the right side, from the water! Enjoy days of sailing and evenings of live music, great conversation, or quiet reflection.

The itinerary is open-ended with the winds, weather, and tides determining where we sail, and where we anchor. We'll celebrate the windjamming tradition one afternoon with our final fleet gathering of the season. Imagine looking around the harbor and seeing a half-dozen or more windjammers anchored around us.

For fans of WoodenBoat, this will be a real treat as we anchor in front of the home of WoodenBoat School and Publications. Take a walk around the campus, visit the school's workshops or stop by the store for all things WoodenBoat.

Your Cabin

Your bed has already been made for you before you arrive. All you’ll have to do is unpack and relax.

  • Bed and bath linens are provided
  • Sinks w/ hot and cold running fresh water
  • 110 volt power outlets just like at home
  • Reading light over your pillow
  • Shelves and space to store your personal items
  • Deck lights in all cabins allow for natural light
  • Large skylights in forward and midships compartments allow for fresh air as well as natural light

Accommodations

  • Double Cabin $3,080 Double-occupancy cabin with one double bed.

  • Upper/Lower Bunk Cabin $1,540 per person. $3,080 for the cabin. Double occupancy cabin with one upper and one lower single bed.

  • Single Cabin $1,780 Single occupancy cabin with single bed.

  • Private Head Cabin $3,560 Double occupancy cabin with one double bed and your own private head.

Adventure Tips

Dress in Layers

Maine’s coastal weather can shift quickly, so bring layers to stay comfortable both on deck and below.

Bring Seasickness Medication

The open water can cause motion sickness; taking preventative medicine can help you enjoy the trip fully.

Wear Non-Slip Footwear

Decks can be wet and slippery, so sturdy, non-slip shoes will keep you steady and safe aboard.

Charge Your Devices

Photography and communication devices will capture amazing memories but have limited charging options on board.

Local Insights

Wildlife

  • Harbor seals basking on rocky shores
  • Ospreys diving for fish near fishing villages

History

Rockland has a deep maritime history as a fishing and shipbuilding hub dating back to the 19th century, reflected in its preserved schooners and harbor architecture.

Conservation

Schooner Heritage actively supports marine conservation efforts, promoting sustainable sailing and respectful wildlife observation to preserve Maine's coastal ecosystems.

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Frequently Asked Questions

Recommended Gear

Windbreaker Jacket

Essential

Protects against brisk winds and sudden weather changes on the water.

spring specific

Waterproof Boots

Essential

Keep your feet dry while walking on wet decks and docks.

fall specific

Sunglasses

Essential

Shield your eyes from strong sunlight reflecting off the open water.

summer specific

Binoculars

Enhance views of wildlife, lighthouses, and distant coastal villages.