Adventure Collective
Island Hiking & Sailing Adventure in Maine - Rockland

Island Hiking & Sailing Adventure in Maine

Portlandmoderate

Difficulty

moderate

Duration

6 hours

Fitness Level

Participants should have moderate fitness to comfortably hike rocky trails and assist with sailing tasks.

Overview

Discover Maine’s rugged coast with a 6-hour Monroe Island trip that blends hiking, sailing, and a fresh lobster picnic. Get close to lighthouses, island trails, and Atlantic winds.

Rockland, Maine

Monroe Island Adventure

Hike, beachcomb and explore a pristine and isolated island away from the crowds!

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Adventure Photos

Monroe Island Adventure photo 1

About This Adventure

Embark on a unique 6-hour island adventure in Maine, exploring the stunning Monroe Island. Enjoy a scenic boat ride past iconic lighthouses, hike through lush trails, and savor a delicious lobster picnic. Experience the thrill of sailing back while participating in raising the sails and feeling the refreshing sea breeze.

Your island adventure awaits! Maine has over 3,000 miles of coastline, and almost half of that is on islands only accessible by boat. Monroe Island is a 250-acre preserve managed by the Maine Coast Heritage Trust, an organization devoted to preserving and stewarding coastal lands for public use. Join us for a 6-hour adventure with lobster rolls, hiking and more!

We will start our voyage at 9am, while the wind is usually light and ideal for wildlife viewing. We will travel past the Rockland Breakwater Lighthouse and Owl's Head Lighthouse on our way to Monroe Island (~1 hour). Once at Monroe, we will shuttle you ashore in our tender where you will have 2-2.5 hours to hike, beachcomb or just take in the beauty of the coast. Monroe has 2+ miles of very accommodating hiking trails that meander past rocky beaches and granite bluffs as well as through verdant forest and lush fern groves.

Back on the boat, we will have a lobster picnic lunch awaiting you (alternatives available upon request). We will sail into Penobscot Bay and see some of Monroe's rocky granite bluffs while we enjoy our lunch and then have a brisk sail back into Rockland on the afternoon breeze. Guests will have the opportunity to help raise the sails and steer the boat as we harness the breeze, shut down the engine and hopefully catch a little refreshing salt spray. We will return to Middle Pier in Rockland and disembark at 3pm.

Guests should be comfortable climbing down into a smaller (12ft) tender. Lifejackets must be worn by all guests at all times while shuttling to/from the island. You do not need to hike, but this is an active trip and guests will need to be able to access the ship's toilet, which is down a 6' wooden ladder. Please contact us at captaintyler@amorninginmaine.com with any questions or concerns.

Adventure Tips

Bring layered clothing

Maine’s coastal weather changes quickly; pack layers to stay comfortable on the boat and trails.

Wear sturdy hiking shoes

Island trails are rocky and uneven—good grip is a must for safe walking.

Bring sun protection

Even on cloudy days, sunburn is possible near the water. Use sunscreen and a hat.

Stay hydrated

Carry water with you, especially during summer sailing and hikes under the sun.

Local Insights

Wildlife

  • Harbor seals basking on offshore rocks
  • Ospreys nesting high in coastal pines

History

Rockland’s lighthouses, dating back to the 19th century, guided generations of mariners through Penobscot Bay’s treacherous waters.

Conservation

Monroe Island activities follow Leave No Trace principles to protect fragile coastal ecosystems and marine habitats.

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Adventure Hotspots in Rockland

Frequently Asked Questions

Recommended Gear

Waterproof windbreaker

Essential

Protects against chilly sea breezes and rain in springtime.

spring specific

Comfortable hiking boots

Essential

Necessary for navigating rugged island trails safely.

Sun hat and sunscreen

Essential

Offers protection from sun exposure on open water and trails.

summer specific

Insulated jacket

Keeps you warm during cooler autumn sailing and hiking portions.

fall specific