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 and further South near Crescent Beach State Park. 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. 

Looking for a more affordable alternative to our guided multi-day trips? If you are an experienced camper consider setting up a Guided Rental


Jewell Island Overnight

2018 Trips: June 9-10, June 23-24, July 8-9, July 20-21, August 5-6, August 18-19, September 1-2, September 8-9, and 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.

This two-day trip is great for anyone with some kayaking and camping experience. The paddle to Jewell Island is roughly 8 to 10 miles, which is typically a comfortable amount of paddling in one day for a generally fit person who is comfortable spending a few hours at a time in a kayak. The group will island-hop along the way, providing at least two chances to stop for breaks. Most routes to Jewell involve significant crossings over waters exposed to the open ocean. The exposed nature of the route make the paddling experience unique for every trip. If the sea conditions are too challenging due to strong winds or dense fog the guide may make the decision to take the group to a more protected island, such as Little Chebeague Island, Cow Island or Crow Island. (Our cancellation policy allows for a full refund if the trip is canceled altogether due to weather conditions). 

We provide three meals for this trip: dinner, breakfast and lunch for day two. We also provide plentiful snacks. However, you should bring along your own lunch for the first day of the trip. We 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.  $220 per person.

Click here for a detailed trip itinerary and packing list for the Jewell Island Overnight trip. 

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Richmond Island OVernight 

2018 Trips: We are still working on scheduling this trip. Let us know if you'd like to request certain dates! 

As a sea kayaking destination, Richmond Island strikes a rare balance between rugged beauty, remote solitude and relatively easy access. The island is only about a mile from Portland Paddle's shop at Crescent Beach State Park, so it's usually a fairly quick paddle to reach the campsites along its shores. However, that mile is fully exposed to the open ocean and is scattered with breakers, ledges and unobstructed swells originating from the distant reaches of the Gulf of Maine. And even though the island is close to the mainland it feels like another world, with miles of wild coastline, expansive meadows, meandering trails and barely-touched beaches.

This trip allows people of all skill levels -- beginners included -- to get a taste of expedition sea kayaking on the coast of Maine without needing to paddle for many miles. Your guide will start off your trip with paddling instruction that prepares you for the journey to the island. They'll choose a route that's comfortable for everyone in the group while also offering plenty of adventure. Once you arrive at the island and set up camp your guide will offer a tour of the island that includes some stories from its rich history, including its use by the Abenaki people, English settlement in the 1620s and the first recorded worker strike (by fishermen) in American history. 

The trip starts at noon at Portland Paddle's shop at Crescent Beach State Park in Cape Elizabeth. The group will return by 1:00 PM the next day. Two delicious meals are provided: Dinner on the first day and breakfast on the second day. Plentiful snacks are also provided. $195 per person


Casco Bay Traverse

2018 Trips: June 16-18, July 3-5, July 13-15, August 17-19, August 20-23, August 31- September 2 and 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. $395 per person.

Click here to view a detailed trip itinerary and packing list for our 3-day kayak trips. 

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Muscongus Bay Three-Day Expedition

2018 Trips: July 15-17, July 26-28, August 14-16 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. $420 per person.

Click here to view a detailed trip itinerary and packing list for our 3-day kayak trips. 

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We support experienced paddlers as they plan expeditions on the Maine Island Trail. Our Guided Rentals offer the chance to bring a guide on your trip at a more affordable cost than our fully-outfitted trips. 

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 or arranging a guided rental

SELF-GUIDED TRIPS: This is the option for experienced sea kayakers who are comfortable with skills such as navigating in fog, rescuing capisized kayaks in rough seas and crossing busy shipping channels. If you (or someone in your group) fits that description then we can help you arrange a self-guided trip. We will provide all the gear you need and help you plan your route. We can also arrange van transportation or boat transportation so that you can take a one-way route that maximizes the territory you cover. If you have some solid sea kayaking experience but are lacking skills in a certain area we can 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-$100), wetsuit rental ($5 per day), tent rental ($20 per night), 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.

GUIDED RENTALS: This is the best option if you'd like the expertise of a guide but you'd prefer going without the added cost and support of our fully-outfitted trips. You'll provide your own meals and camping gear and we'll provide a guide and paddling gear. Learn more on our Guided Rentals webpage

Explore the Maine Island Trail with a Guided Rental

We provide the Guide & Paddling Gear, You provide your own food & Camping Gear

Rates for Rentals, Guided Trips and Guided Rentals 

A guided rental is a great option for experienced campers who want the expertise of a guide for an overnight sea kayak trip on the Maine coast. Guided rentals are more affordable than our regular guided trips, but we still provide all the paddling gear you need and a licensed Maine guide to help you navigate your course along the Maine Island Trail.

Even if you have lots of kayaking experience you're likely to find that the expertise of a local guide is invaluable.  The thousands of islands along the coast of Maine and the hundreds of campsites allow for nearly infinite trip-planning possibilities. Your guide will help you choose the right campsite for your group based on the weather conditions, along with your interests and experience level. The presence of your guide also provides opportunities for you to develop and strengthen kayaking and trip-planning skills and to learn all about the local natural history and culture. Most importantly, having a guide along on your trip will ensure you have the safety gear, rescue skills and navigation abilities to safely navigate the dynamic sea conditions found along the Maine coast. 

Trips of any length are possible for guided rentals.  If you are interested in setting one up please fill out the form below or email us at portlandpaddle@gmail.com. 


  • Sea kayaks. We have a wide range of solo and tandem kayaks. Most are made by Wilderness Systems or Necky Kayaks. 
  • Basic paddling gear (paddles, PFDs, sprayskirts)
  • Drybags. We will give you at least one medium to large dry bag per person and a couple others for group gear. 
  • A licensed Maine guide with a deep knowledge of the area. Your guide will be equipped with a full range of safety and communication gear, including a VHF radio, navigation equipment, basic first aid supplies and sea kayaking rescue equipment. All of our guides have undergone a rigorous testing process to earn their Maine guide licenses. 
  • Nautical chart of the area and relevant guidebooks.
  • Water for drinking & cooking. There's no freshwater on the islands, so we'll provide water bladders that you and your guide will pack in your boats. 
  • Waste management. We practice the principles of "Leave No Trace" on all our trips. On some islands this involves carrying off solid human waste. We will provide "Wag Bags," which are portable toilet systems. (You can also opt to stick to the island that have outhouses). 

potential Add-ons

  • Camping gear: We rent tents ($20 per night), sleeping pads ($10 per night), sleeping bags ($20 per night) and cooking stoves ($20 per night). 
  • Van transportation: We can drive you to or from any launch site in southern or mid-coast Maine. This opens up an enormous range of options for routes and destinations. One terrific route involves starting at our main site in Portland and paddling across Casco Bay to be picked up in Phippsburg or Harpswell. 
  • Boat transportation to anywhere within a few miles of Portland. We can use our small powerboat to transport gear and kayaks to the islands surrounding Portland harbor. This allows us to transport supplies for longer trips or transport kayaks so you can start or end your trip at a spot of your choosing. 

What's not included with a guided rental

  • Meals: You will provide your own food, cooking stove and cooking supplies. 
  • Camping gear: If you aren't able to provide your own tent, sleeping bag and sleeping pad we rent these items (see above). 

Guided Rental Inquiry Form

If you would like to inquire about setting up a guided rental please submit the below form or contact us by email (portlandpaddle@gmail.com) or phone (207-370-9730). 

Approximate as best you can. If the timing is flexible or uncertain, please explain.
Do you have a destination in mind? Is there anything in particular you'd like to see or do on your trip? Is there any camping gear or other supplies you'd need from us?