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Guided Sea Kayaking Expeditions

Multi-day Guided Camping Trips on the Maine Island Trail

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

Our guided multi-day trips offer a chance to journey by sea kayak along the Maine Island Trail, a water trail tracing 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, adjacent to Portland, and we also offer trips further north in Muscongus Bay, the midcoast region, the Acadia region and along the “Downeast” coast.

If none of the trips below fit what you are looking for, let us know. We’re always willing to create customized trips or help experienced sea kayakers plan their own trips. 

From $1,185

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.

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

 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