Our multi-day trips offer a chance to island-hop along the Maine Island Trail, a water trail running parallel to the Maine coast that features some of the best sea kayaking in the world.  All trips are led by licensed Maine guides with lots of knowledge about the history and ecology of the region. Most of our trips venture into the islands of Casco Bay, adjacent to Portland, but we also offer trips further North in Muscongus Bay. Our guides prepare healthy, delicious meals on our trips using as many locally-sourced ingredients as possible. If none of the trips below fit what you are looking for, let us know. We're always willing to create customized trips. 

Jewell Island Overnight

2017 Trips: June 24-25, July 7-8, August 6-7, August 26-27, September 9-10 or by request

Jewell Island is less than a full-day paddle from Portland Harbor, but the island lies on the boundary between the ocean and Casco Bay and feels remarkably remote and wild. With its gorgeous rugged coastline, its extensive network of trails and its ample camping spots, the island is one of the best kayak camping destinations on the Maine Island Trail in southern Maine.

Bring your own lunch for the first day and then we'll provide the meals from there (including dinner, breakfast, lunch on day two)  This two-day trip is great for anyone with some kayaking and camping experience. We'll provide all the kayaking gear, dry bags and an expert guide. The group meets at 9:30 AM on the first day and aims to return by 3:45 PM the second day. Upon booking you will receive a packet with a more detailed itinerary and packing list. $225 per person.

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Casco Bay Traverse

2017 Trips: July 3-5, July 21-23, August 20-23, September 1-3 or by request

This three-day guided expedition begins in Portland and ends all the way on the other side of Casco Bay in Phippsburg. Along the way, we'll camp on the islands of the Maine Island Trail and experience the diverse environments found in the bay -- from the exposed ocean-like conditions along the outer islands to the calm and peaceful estuaries of the inner waters.

Our route will depend on the conditions and the group, but you can plan to do a significant amount of paddling as we traverse the bay. Sea kayaking experience is required. Portland Paddle will provide all meals and paddling gear. The group will be picked up at the end of the trip and driven back to Portland. Upon booking you will receive a packet with a more detailed itinerary and packing list. $370 per person.

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Mike with blue sky.jpg

Muscongus Bay Three-Day Expedition

July 18-20, August 16-18, or by request

This trip begins with a roughly one-hour drive north to Muscongus Bay, one of our favorite destinations for multi-day trips on the Maine coast. It offers a prime environment for viewing wildlife, and its countless small islands provide plenty of options for exploring the Maine Island Trail. Muscongus Bay doesn't attract many large boats due to its lack of big harbors and many shallow ledges, but it's absolutely perfect for sea kayaking. This trip will depart near Round Pond on the south side of the bay and island-hop north, with possible camping spots including Thief Island, Black Island, Hog Island and Crow Island. You'll see seals and other wildlife; Muscongus Bay is especially well-known as a great place to view birds of all sorts.

Delicious and healthy meals are included. We'll also provide all the kayaking gear, along with dry bags for packing your items. Your guide will be customize the route to match the interests and experience level of the group, and they will be happy to offer paddling instruction throughout the trip. The group meets at 9:00 AM on the first day and will return by 4:00 PM two days later. Upon booking you will receive a packet with a more detailed itinerary and packing list. $410 per person.

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Camping on the Maine Island Trail


We support experienced paddlers as they plan expeditions on the Maine Island Trail. If you have an idea for a trip let us know and we'll offer advice, rentals and logistical support. 

If none of our guided trips fit what you're looking for (or don't work with your schedule or budget), consider planning your own trip into the islands of the Maine Island Trail. Portland Paddle can provide all the gear you need and help you plan your trip. We can also arrange shuttle transportation so that you can take a one-way route that maximizes the territory you cover. However, you will need some sea kayaking experience and we may suggest you arrange a session with one of our instructors to ensure you have the skills and knowledge needed to safely navigate the islands. The baseline cost of a self-guided trip will reflect the cost of renting kayaks (paddles, PFDs, dry bags come included). Potential add-ons include shuttle service ($40-$90), wetsuit rental ($5 per day), tent rental ($10 per day), private lesson ($75-$150), nautical chart purchase ($20). 

If this option interests you please send us an email or call us. If possible, let us know the dates you are available for your trip and provide a brief summary of your past sea kayaking experience.