An overnight expedition to a gem of the Maine Island Trail

2020 TRIPS

June 6-7, June 21-22, June 29-30, July 7-8, July 21-22, August 4-5, August 17-18, August 24-25, August 31- September 1, September 4-5. And by request.


$235 per person (or $185 if you use your own sea kayak)


  • Paddling along the open ocean on the crossing to Jewell.

  • Exploring Jewell Island’s network of gorgeous trails

  • Watching the sun set over Casco Bay from an oceanside campsite

  • Climbing the WWII submarine tower on Jewell Island to enjoy a spectacular view of Casco Bay


  • Three well-rounded, delicious meals (dinner, breakfast and lunch)

  • Kayaks and other paddling gear

  • Dry bags for packing your belongings

  • Licensed Maine guide

  • Tent(s)


  • Prior sea kayaking experience

  • Ability to paddle for several hours in one day (with many breaks)

  • Comfort with tent camping

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.

Where you’ll paddle

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. Along the way you can expect to visit at least a couple other islands of the Maine island Trail.

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). 

Logistical Details

We provide three meals for this trip: dinner, breakfast and lunch for day two, along with plentiful snacks. However, we ask that you bring along your own lunch for the first day of the trip.

Portland Paddle provides an expert guide, all the kayaking gear and dry bags you'll need, drinking water, tents and basic camping and cooking gear. We can provide sleeping bags and sleeping pads for an additional fee. The group meets at 8:00 AM on the first day and aims to return by 3:45 PM the second day.

CLICK HERE for a detailed trip itinerary and packing list for the Jewell Island Overnight trip. 

If you have signed up for a multi-day trip with us every member of your party must fill out our our multi-day trip questionnaire by clicking on the button below.