Giving Back – We donate a percentage of profit to the Island Heritage Trust, a nonprofit organization dedicated to conserving Deer Isle's trails, shorelines, islands, and natural resources for future generations.
There are places that feel discovered… and places that feel quietly hidden away from the rest of the world. Stonington, Maine is one of those places. Perched on the southern end of Deer Isle, Stonington is a weathered fishing village, artist community, and the largest lobster port in New England. Out beyond the harbor lies the Stonington Archipelago — one of the finest sea kayaking destinations on the East Coast, where hundreds of islands, pocket beaches, quiet coves, lighthouses, and wildlife-rich ledges create a paddler's paradise that feels both remote and remarkably accessible.
Who is this trip for?
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This trip is ideal for travelers who:
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Looking for the next island
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Itinerary
Day 1 – Sunday, June 13 – Arrival in Stonington Welcome to Downeast Maine! Arrive at your leisure and settle into Boyce's Motel, located in the heart of Stonington within easy walking distance of the harbor, restaurants, and galleries. This evening we gather for a welcome dinner, trip orientation, and a look at the week ahead. Overnight: Boyce's Motel
Day 2 – Mark Island Lighthouse After breakfast, we meet at the harbor for kayak fitting and an introduction to paddling in East Penobscot Bay. Our first day takes us to the edge of the bay where, conditions permitting, we land near the iconic Mark Island Lighthouse. Expect seals on the ledges and eagles overhead as we island-hop back through the archipelago with a picnic lunch ashore. Overnight: Boyce's Motel Paddling Distance: ~6–8 miles
Day 3 – Gooseberry Island & the Inner Archipelago Today we explore one of the archipelago's hidden gems — Gooseberry Island, complete with pocket beaches and glacial boulder gardens. We weave through quiet, protected passages, stopping for an island lunch and an optional shoreline hike. Overnight: Boyce's Motel Paddling Distance: ~6–10 miles
Day 4 – Free Day A full day to explore Maine at your own pace. Popular options include Acadia National Park, puffin and wildlife cruises, the mailboat trip to Isle au Haut, exploring Deer Isle and Stonington's galleries and waterfront cafés — or simply relaxing by the harbor. Dinner is on your own tonight. Overnight: Boyce's Motel
Day 5 – Enchanted & Saddleback Islands Back on the water, we venture farther east into the outer archipelago for open-water scenery and rugged island beauty. This is our most adventurous day, with granite shorelines, wildlife-rich ledges, and sweeping views of East Penobscot Bay. Overnight: Boyce's Motel Paddling Distance: ~8–10 miles
Day 6 – Sheep Island & Whitmore Neck We finish the week with a scenic circumnavigation and one final island adventure, followed by a farewell dinner celebrating the week. Overnight: Boyce's Motel Paddling Distance: ~6–8 miles
Day 7 – Saturday, June 19 – Departure Enjoy one last harbor-side breakfast before departing for home — or extend your stay and keep exploring the Maine coast.
Important Notes
Day 2 – Mark Island Lighthouse After breakfast, we meet at the harbor for kayak fitting and an introduction to paddling in East Penobscot Bay. Our first day takes us to the edge of the bay where, conditions permitting, we land near the iconic Mark Island Lighthouse. Expect seals on the ledges and eagles overhead as we island-hop back through the archipelago with a picnic lunch ashore. Overnight: Boyce's Motel Paddling Distance: ~6–8 miles
Day 3 – Gooseberry Island & the Inner Archipelago Today we explore one of the archipelago's hidden gems — Gooseberry Island, complete with pocket beaches and glacial boulder gardens. We weave through quiet, protected passages, stopping for an island lunch and an optional shoreline hike. Overnight: Boyce's Motel Paddling Distance: ~6–10 miles
Day 4 – Free Day A full day to explore Maine at your own pace. Popular options include Acadia National Park, puffin and wildlife cruises, the mailboat trip to Isle au Haut, exploring Deer Isle and Stonington's galleries and waterfront cafés — or simply relaxing by the harbor. Dinner is on your own tonight. Overnight: Boyce's Motel
Day 5 – Enchanted & Saddleback Islands Back on the water, we venture farther east into the outer archipelago for open-water scenery and rugged island beauty. This is our most adventurous day, with granite shorelines, wildlife-rich ledges, and sweeping views of East Penobscot Bay. Overnight: Boyce's Motel Paddling Distance: ~8–10 miles
Day 6 – Sheep Island & Whitmore Neck We finish the week with a scenic circumnavigation and one final island adventure, followed by a farewell dinner celebrating the week. Overnight: Boyce's Motel Paddling Distance: ~6–8 miles
Day 7 – Saturday, June 19 – Departure Enjoy one last harbor-side breakfast before departing for home — or extend your stay and keep exploring the Maine coast.
Important Notes
- Daily paddles are designed to balance exploration, scenery, and relaxed adventure while remaining highly adaptable to weather and tides. The order of destinations may change.
- June on the Maine coast keeps things interesting: sunny 70° afternoons, fog drifting through the harbor, cool mornings in the 40s, and changing ocean breezes. Layering is essential, and synthetic paddling clothing is strongly recommended.
What's Included and Trip Price
What's Included and Trip Price
Not included: transportation to/from Maine, alcoholic beverages, travel insurance, guide gratuities, and dinner on the free day.
Travel Notes: Portland, ME offers the best flight options (~3+ hour drive to Stonington). Bangor, ME is closer (~1.5 hours) with fewer flights. Rental cars are strongly recommended — there are no airport shuttle services to Stonington.
- Scott Locorini as your guide and host, plus a local Registered Maine Guide
- Lodging at Boyce's Motel, 44 Main St, Stonington — centrally located steps from the harbor
- All kayak equipment, instruction, and guiding
- All lunches and group dinners (except dinner on the free day)
- Standard Room: $3,695 per person — share a room and save $500 per person Apartment Upgrade: $4,195 per person — includes a small apartment with kitchen and two twin beds; share the apartment and save $500 per person
Not included: transportation to/from Maine, alcoholic beverages, travel insurance, guide gratuities, and dinner on the free day.
Travel Notes: Portland, ME offers the best flight options (~3+ hour drive to Stonington). Bangor, ME is closer (~1.5 hours) with fewer flights. Rental cars are strongly recommended — there are no airport shuttle services to Stonington.
There are a minimum number of participants required to confirm the trips. Therefore please do not make any travel arrangements (airline flights, train) until you have received confirmation from us that the trip has fully booked. A 50% deposit is due at time of reservation, with payment in full due 90 days prior to the trip’s start date. Email us, call or text (315) 316-1125 with questions.