Guided Sea Kayaking Expeditions

Island-Hopping Trips on the Maine Island Trail

Journey by sea kayak to stunning wild islands with ocean-side campsites, wander hidden trails and beaches, and watch seals and osprey feeding on the ocean’s abundance. Our multi-day sea kayaking trips, led by expert Maine guides, are unforgettable adventures along one of the world’s most beautiful coastlines.

Our guided multi-day trips are kayak camp expeditions along the Maine Island Trail, which traces the length of the Maine coast. All trips are led by licensed Maine guides with abundant knowledge about the history and ecology of the region. Many of our trips venture into the islands of Casco Bay (near Portland) and we also offer trips further north in Muscongus Bay, the Midcoast region, Acadia region and even Down East.

If none of the trips below fit what you are looking for, let us know. We love customizing expeditions and helping experienced sea kayakers plan their own trips.

UPCOMING TRIPS

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Our Multi-Day Expeditions

From $525

Ages 13+
3 Days

Casco Bay Traverse Three-Day

Experience the breadth of Casco Bay and its hundreds of islands by joining this three-day journey on the Maine Island Trail. This is our most popular trip, and it includes visits to some of the most fascinating islands on the Maine coast.

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From $645

Ages 13+
3 Days

Muscongus Bay Three-Day

This three-day trip explores the sea kayaking wonderland that is Muscongus Bay. This bay, speckled with tiny islands, sparsely populated and home to abundant wildlife, makes it one of our favorite destinations for multi-day sea kayaking trips on the Maine coast.

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From $975

Ages 13+
4 Days

Penobscot to Acadia Expedition

This 4-day expedition explores the island-dense stretch of waters between Penobscot Bay and Acadia National Park. The pink granite of the islands and the views of Acadia’s mountains create a magical sea kayaking experience like no other.

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From $1,225

Ages 13+
5 Days

Downeast Ramble

August 18, 2025 - August 22, 2025

This expedition for intermediate to advanced paddlers explores the most rugged, wild and gorgeous stretch of the Maine coast — the Downeast region that extends to Canada. The tides are more powerful here, the wildlife more abundant and the cliffs more dramatic. It has all the makings for an epic sea kayaking trip.

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From $545

Ages 13+
3 Days

Midcoast Expedition Three-Day

Maine’s southern Midcoast is a dense network of river estuaries, long peninsulas and small islands. This three-day trip travels along the tidal rivers, rocky islands and pristine beaches of the region, camping on the Maine Island Trail along the way.

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1-14 Days
Maine

Private Multi-Day Trips

We love creating custom sea kayaking expeditions on the Maine coast for groups of all kinds. Our expert licensed Maine guides will customize an itinerary that fits your group’s interests and experience level. Please submit the form below and we will get back to you as soon as possible.

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Maine

Guided Rental

A guided rental is a great option for experienced campers able to provide their own camping gear and food, but who want to rent paddling gear and benefit from the expertise of a local registered sea kayaking guide.

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Want to learn what it's like to paddle the Maine Island Trail? Watch this video.

What Our Customers Say About Our Trips

A new passion for ocean kayaking Casco Bay Traverse kayak camping

We came back with a new passion for ocean kayaking and exploring more of the Maine waters. Our expert guide made us feel safe, he educated us along the way with facts and lore about the islands, prepared amazing food, and gave us space to explore on our own when we were on each island either for the night or for a lunch break. We feel empowered and knowledgeable enough after this guided trip to head out on our own for short ventures and will use Portland Paddle again to learn more- they have so many wonderful options!

– KDC, 2023, TripAdvisor

A wonderful experience in beautiful place Three days on Muscongus Bay

We just completed a guided three day, two night kayaking and camping trip in Muscongus Bay, Maine through Portland Paddle. Our experience was wonderful. Our guide was friendly, knowledgeable and very organized, and we had everything we needed to make a wonderful experience. The paddling was great in a most beautiful place. I would recommend this company to others.

– Carol Hatch, 2023, Google Review

Fantastic! A 4-day kayaking camping tour of Maine coastal islands

I was on a 4 day/3 night kayak-camping tour of the islands off the coast of Maine. I/we could not have had a better guide: competent, personable, calm, and fantastic at meal prep! Being from Minnesota, I am used to beauty in the great outdoors. This trip did not disappoint. I can’t think of a better way to see the ‘real Maine.’ “

– Kathryn K, 2023, TripAdvisor