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Lobsters, Sailing & Music Adventure in Rockland, Maine - Portland, Maine

Lobsters, Sailing & Music Adventure in Rockland, Maine

Rocklandmoderate

Difficulty

moderate

Duration

3–4 days

Fitness Level

Participants should be in moderate physical shape to manage light sailing tasks, board the schooner comfortably, and walk on uneven beaches.

Overview

Enjoy a sailing getaway near Rockland, Maine with fresh lobster feasts, music-filled evenings, and scenic coastal exploration. Discover the magic of a handcrafted journey on the water designed by nature.

Rockland, Maine

Lobsters, Sailing, and Music - September 14, 2025

3-night trip • Starting at $970 per person based on double occupancy • Ages 12+

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About This Adventure

Embark on a unique sailing adventure from September 14 to 17, 2025, where the journey is shaped by nature. Experience tranquil evenings filled with music and conversation, explore secluded coves, and indulge in an unforgettable lobster picnic on a pristine beach. Relax in cozy cabins designed for your comfort.

Duration

  • Board Sunday, September 14, 2025 between 6 pm and 8 pm
  • Disembark Wednesday, September 17, 2025 before noon.

Trip Description

Enjoy days of sailing, and evenings of relaxing conversation, music provided by the captains, or quiet reflection on your day and surroundings.

No set itinerary. We'll let the winds, weather, and tides determine where we sail and where we anchor. Our favorite anchorages are in the harbors of fishing villages or small coastal communities, or quiet coves of secluded islands.

If you’d like to go for a walk while the schooner’s anchored, we’ll organize a rowing party using one of our shore boats. There are also a couple of small boats for individual use or small groups.

Sometime during the trip, enjoy an all-you-can-eat lobster picnic on an uninhabited island's pristine beach. For those with restricted diets, an alternate choice is available with advance notice.

This trip is perfect for letting go of everyday stress or when combining activities during your vacation.

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
  • A deck light allowing for natural light
  • Large skylights in forward and midships compartments provide fresh air circulation as well as natural light

Accommodations & Pricing

  • Double Cabin $1,940 Double-occupancy cabin with one double bed.

  • Upper/Lower Bunk Cabin $970 per person, $1,940 for the cabin. Double occupancy cabin with one upper single bed and one lower single bed.

  • Single Cabin $1,090 Single occupancy cabin with single bed.

  • Private Head Cabin $2,180 Double occupancy cabin with one double bed and your own private head.

Adventure Tips

Book Early for Cabin Availability

Cabins are limited, so reserving your spot well ahead ensures you’ll have the cozy accommodations included in this experience.

Pack Layers for Changing Weather

Maine’s coastal weather can shift quickly, so bring layers including windbreakers and fleece to stay comfortable on deck.

Bring Seasickness Medication

If you’re prone to motion sickness, carry remedies as the ocean can be choppy at times, especially in open waters.

Don’t Forget a Camera

Capture stunning coastal views and music gatherings, especially around sunset when lighting is perfect.

Local Insights

Wildlife

  • Harbor seals resting on nearby rocks
  • Bald eagles soaring above the coastline

History

Rockland’s maritime history dates back to the 19th century and played a key role in lobster fishing and shipbuilding industries.

Conservation

Efforts to protect Maine's coastal waters focus on sustainable lobster harvesting and preserving fragile estuarine habitats.

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Adventure Hotspots in Portland, Maine

Frequently Asked Questions

Recommended Gear

Windproof Jacket

Essential

Protects against coastal winds and sudden weather changes during the day.

summer specific

Comfortable Boat Shoes

Essential

Provides grip and comfort on deck while protecting your feet.

Reusable Water Bottle

Essential

Stay hydrated throughout your sailing adventure while reducing plastic use.

Compact Camera or Smartphone

Capture scenic views, wildlife, and memorable moments on board.