Casco Bay, South Portland

Guided day trips through Casco Bay's calmest islands

No experience needed, no gear to pack. Paddle out with a USCG-certified guide who knows these islands by heart — back on shore by afternoon.

USCG-certified guidesBeginner-friendly
USCG-Certified Guides
Kids 8+ Welcome
Calm Bay Waters
All Gear Included

Three ways to spend a morning on the water

Every trip launches from our South Portland dock, includes all gear, and is led by a local guide trained for open-water rescue.

Island Hopper

A gentle 2.5-hour paddle past three islands, with a beach landing for a snack break.

2.5 hrsFrom $69

Family Bay Paddle

A relaxed 2-hour route built for kids 8+, tandem kayaks available, calm inner-bay water only.

2 hrsFrom $59

Full Bay Explorer

Our longest day trip — 4 hours covering the outer islands, for guests who want more distance.

4 hrsFrom $99

What to expect on your trip

1

Arrive & gear up

Show up 15 minutes early. We fit your paddle jacket, PFD, and kayak — no experience required.

2

Quick safety briefing

Your guide walks through paddle basics and safety on the dock — five minutes, plain language.

3

Paddle the islands

Follow your guide through calm, protected water — stopping to spot seals, ospreys, and lighthouses.

4

Back on shore

Return to the dock, towel off, and head out — no cleanup, no gear to haul home.

Guests who'd never paddled before

"We had zero kayak experience and two kids under 10. Our guide made it feel completely safe from the first minute — genuinely one of the best mornings of our Portland trip."

Dana R. — visiting from Boston

"Solo traveler, nervous about doing this alone. The guide paired me with the group right away and knew every island's story. Booked the Full Bay Explorer on the spot."

Marcus T. — solo traveler

Common questions

None at all. Every day trip is led by a USCG-certified guide and starts with a short on-dock briefing — most of our guests have never paddled before.

Just a swimsuit or quick-dry clothes, sunscreen, and water shoes if you have them. We provide the kayak, paddle, PFD, and paddle jacket.

Yes — our Family Bay Paddle is built for kids 8 and up, stays in calm inner-bay water, and offers tandem kayaks so a parent can share a boat with a younger paddler.

Your guide makes the call the morning of your trip. If conditions aren't safe, we'll reschedule you or refund your booking in full — no questions asked.

Ready to see Casco Bay from the water?

Spots fill fast on weekend mornings. Reserve your guided day trip and we'll have gear waiting at the dock.