Casco Bay Traverse Three-Day Trip

A Sea Kayaking Expedition Across Casco Bay

2020 TRIPS: May 30- June 1, June 19-21, July 3-5, July 17-19, July 31-August 2, August 14-16, September 5-7. And by request.

COST: $420 per person


  • Island-hopping all the way across Casco Bay in a one-way route

  • Visiting several islands on the Maine Island Trail

  • Watching the sun set over Casco Bay from oceanside campsites

  • Experiencing the many sides of Casco Bay -- from open ocean to protected estuaries


  • Well-rounded, delicious meals

  • 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

This three-day guided expedition begins in Portland and ends all the way on the other side of Casco Bay in Phippsburg or Harpswell. 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.

Where You’ll Paddle

You’ll start out kayaking alongside the busy working waterfront of Portland harbor and quickly pass into calmer waters and past tiny island hamlets, hidden beaches and rugged, rocky headlands. We often spend the first night on Jewell Island, a large, wild island with gorgeous trails to explore. From there we island-hop west towards Harpswell to camp on Whaleboat Island, Rasperry Island or one of the other sites on the Maine Island Trail.

Our route will depend on the conditions and the group, but you can plan on several hours of paddling each day (with many breaks) as we traverse the bay. There will also be plenty of time for exploring and relaxing on the islands.

Logistical Details

This trip is great for first-time kayak campers as well as those who have experience with paddling expeditions. Some prior sea kayaking experience is required, however. Your guide will provide basic instruction, and there will be plenty of opportunities to improve your paddling skills along the way.

Portland Paddle will provide all meals, an expert guide, kayaking gear, dry bags, drinking water, tents and basic camping and cooking gear. You should bring your own sleeping bag and sleeping pad, or you can rent from us for an additional fee.

The group will gather at 9am on the first day. After meeting your guide you will be given dry bags for packing and everyone will briefed on the plan for the day. Your guide will select a kayak for you, help you pack your belongings.

At the end of your trip the group will be picked up on the northern side of Casco Bay and driven back to Portland, returning by 3:30pm.

Click here to view a detailed trip itinerary and packing list for this trip. 

If you have already 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.