Quick Details
A Three-Day, Island-Hopping Journey Across Casco Bay
There are more than 300 islands in Casco Bay, creating endless possibilities for exploration by sea kayak. This three-day trip crosses the breadth of the bay, visiting dozens of islands along the way. Nestled within these islands are some of our favorite campsites on the Maine Island Trail. Every trip is different, with a route tailored to fit the conditions and the group, but it’s common to visit Jewell Island, with miles of trails and wild beaches, or Whaleboat Island, a rarely-visited, forested preserve beside the open ocean.
Where You’ll Paddle
You’ll start out kayaking along the working waterfront of Portland harbor, past the scenic hamlets of the inner islands and past the exposed shorelines of the bay’s wildest islands. Along the way, you’ll pass hidden beaches and rugged, rocky headlands. It’s likely you’ll spend your first night on Jewell Island, a large, forested island with stunning cliffs and gorgeous trails to explore. Or you may head to Bangs Island, a less visited gem with panoramic views of the bay. From there you’ll island-hop towards Harpswell, either returning to Jewell or Bangs for a second night or camping on Whaleboat Island, Rasperry Island, Little Chebeague Island or another nearby site on the Maine Island Trail.
As you paddle across the bay you’ll encounter abundant wildlife like seals and seabirds, and you’ll experience a diverse range of marine environments, from exposed ocean shorelines to the calm waters of coastal estuaries. You’ll also witness fascinating remnants of the past, like abandoned forts and centuries-old lighthouses, and glimpses of the working waterfront that is the heart of Maine’s island communities.
The itinerary will depend on the conditions and the group. You can expect to paddle for several hours each day, with many breaks along the way. There will also be plenty of time for exploring and relaxing on the islands. Your guide will choose a route that takes maximum advantage of the wind direction and tidal currents, while ensuring that the group moves at a pace that is comfortable for all participants.
More Info
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You’ll meet your guide and the other participants at our retail location at 233 Warren Avenue in Portland at 8:30am on the first day of the trip. After checking in and unloading anything you plan to bring on the trip, our staff will direct you to where you can store any extra bags for the duration of the trip. Overnight parking is available behind the building, accessed via Hicks Street. Next your guide will offer a brief overview of the itinerary, select a kayak for you, help you pack your boat and deliver a brief paddling lesson. Your group will then load into our van for a short drive to a put in site on Casco Bay in Portland or a neighboring town. Next, it’s time to hit the water!
We ask participants to pack a lunch for the first day of the trip, but after that all meals are provided, along with snacks and drinking water, tea and coffee. Portland Paddle also provides all the necessary kayaking gear and dry bags for packing your belongings. Tents are provided at no extra cost, though some people prefer to use their own. There is a small rental fee to use a sleeping bag and sleeping pad if you are not able to bring your own. Cold water paddling gear such as wetsuits and neoprene booties are also available for rent, and are recommended early in the season (May & June) when the water is still especially cold.
Your trip may end at a different location on the northern side of Casco Bay. In that case, you will be driven back to Portland. Depending on the conditions and the route your guide chooses, you may also paddle a loop and end your trip back in Portland. Either way, you can expect to arrive back at the starting point in Portland between 3pm and 4:30pm.
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- Island-hopping across one of Maine’s largest bays and visiting several islands on the Maine Island Trail
- Watching the sun set from oceanside campsites
- Experiencing the many sides of Casco Bay — from open ocean to protected estuaries
- Viewing abundant wildlife, as well as working lobster boats, lighthouses and centuries-old forts
- Exploring trails that lead to hidden beaches facing the open Atlantic and to lookout towers with panoramic views
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- Well-rounded, delicious meals and snacks – two of each breakfast, lunch and dinner (pack a lunch for the first day)
- Kayaks and other paddling gear
- Dry bags for packing your belongings
- Licensed Maine sea kayaking guide with a deep knowledge of the region
- Tent(s)
Please Note: Tents are included in the cost of this trip, but we ask participants to either bring their own sleeping bags and sleeping pads or rent them from us for a small additional fee.
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You don’t need to have experience with kayak camping or long sea kayaking trips to join this trip. This trip can be a great fit for first-time kayak campers. However, since the group will paddle for several hours each day we ask that each participant meet the following requirements:
- Prior experience paddling a sea kayak (sea kayaks are somewhat different than the “recreational” kayaks common on lakes and rivers)
- Ability to paddle at a moderate pace for several hours in one day (with plenty of island breaks)
- Ability to walk comfortably on uneven surfaces (such as following a short, rocky trail from a beach to a campsite)
- Comfort with tent camping
If you are lacking any of the requirements, we suggest signing up for one of our lessons or guided day tours before booking this trip. That said, your guide will provide basic instruction, and there will be plenty of opportunities to improve your paddling skills along the way.
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If you would prefer to book a private trip that is just for your group we would be happy to make that happen. A private trip allows your guide to customize the itinerary to fit the interests and experience levels of those in your group. It’s also a good option if the dates of our public trips listed on the calendar above don’t work for your group.
To get more information and request a private trip please submit the form on this page.
CLICK HERE for a detailed packing list and tips on packing a sea kayak!
For an depth sample trip itinerary, CLICK HERE!