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York Harbor to Portland self-guided Cycling Tour

Itinerary

What’s Included

Reviews

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2026 Dates

May - Oct

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5 Days
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Difficulty Level

Easy - Sounds Like Fun

Ride the Southern Maine Coast

A self-guided journey from beach towns to working harbors, lighthouse headlands, and island shores — designed for travelers who want to slow down and take it all in.

Over the course of five days, this self-guided tour lets you experience Maine’s southern coast with a relaxed timeline. The route carries you from winding shoreline roads and classic beach towns to working harbors, lighthouse-lined headlands, and ultimately out to Peaks Island aboard the iconic Casco Bay Lines ferry. With a balance of steady riding, coastal scenery, and welcoming inns each night, the journey unfolds naturally — giving you time to notice the details that make this stretch of Maine feel authentic and home to many Mainers.

Let us make this vacation easy for you!  We’ll do the arranging, you do the adventuring. Deal?  All the logistics are on us – lodging reservations, luggage transfers, ferry tickets, route plotting, pre-tour bike futzing.  You show up and have all the fun!  Let go of the restrictions of a work week and take in all the joy found in an active vacation. The beauty of this self-guided tour lies in its freedom – cycle at your own pace, pause as often as you desire, linger at meals, and take that extra time to explore around the next corner.

(Still making up your mind about how to organize your Maine trip? Browse our entire range of Multi-Day Bike Trips in Maine.)

Highlights

  • Discover Portland and the Kennebunks
  • Enjoy a scenic ferry ride
  • Cycle past beaches and lighthouses
Pricing

Tour Pricing: $1995 per person double occupancy

E-Bike: $250

2026 Dates

York Harbor to Portland self-guided tours can start on any Sunday or Monday from mid-May through mid-October

Pickup/Drop Off
Portland, Maine

Itinerary

DAY 1 The Wiggly Bridge Awaits

Your week begins in Portland, where one of our staff will meet you in the morning to get you comfortably fitted to your bike and answer any lingering questions. Then, with everything set, you’ll take a short drive south to where the riding truly begins.

From there, you trace southern Maine’s winding shoreline — through York Harbor, Cape Neddick, Ogunquit, and Wells Beach — following a coast that constantly changes its mood. Sandy stretches soften the ocean’s edge before giving way to rockier headlands where waves crash and pull back again.

You’ll ride as close as possible to Nubble Light at Cape Neddick — just offshore, steady and unmistakable — before continuing north toward Kennebunkport. By late afternoon, you arrive in a town that is both energizing and laid back, with plenty of time to settle in and wander.

Kennebunkport makes an easy place to call home for the next two nights.

  • Cycling: 30.8 miles | elevation gain 632 ft
  • Meals: none
  • Lodging: The Colony Hotel

DAY 2 Cruising the Kennebunks

Today is about layers — history, water, and the quiet roads that connect them.

You’ll explore the towns of Kennebunkport, Kennebunk, Arundel, and Cape Porpoise, each shaped by the sea in its own way. Along the route, small details invite you to slow down: historic markers that tell stories of shipbuilders and sea captains, river views that hint at how people once lived and worked here.

Grand homes built by mariners now serve as welcoming inns. Wooden boatbuilding traditions continue quietly in the background. Lobster boats still leave the harbor in the early morning hours, following daily rhythms passed down through generations.

The riding is relaxed, coastal, and rural — the kind of day that feels full without feeling long.

  • Cycling: 20.1 miles | elevation gain 640 ft
  • Meals: Breakfast
  • Lodging: The Colony Hotel

DAY 3 To the Beach

Leaving Kennebunkport, you pedal past shingled homes and open fields before joining the East Coast Greenway, a multi-use trail stretching all the way from Maine to Florida.

The route carries you through Biddeford and Saco — historic mill towns where brick buildings and riverside paths hint at another era — before continuing on to Old Orchard Beach. Locals call it “OOB,” and it wears that nickname comfortably: unpretentious, lively, and rooted in simple seaside fun.

From here, you return to the Greenway and ride vehicle-free through the wide-open expanse of the Scarborough Marsh, where grasses ripple in the breeze and birds skim the water. It’s a quiet contrast to the beach towns behind you.

Tonight’s inn sits just steps from the shore — like a beach house waiting for you, already opened up and ready.

  • Cycling: 30 miles | elevation gain 770 ft
  • Meals: Breakfast
  • Lodging: Higgins Beach Inn

DAY 4 The Lighthouse Ride

Lighthouses stand as a steadfast connection to our nation’s coastlines and maritime history. Today is all about these lighthouses. Leaving the inn, you pedal first to Two Lights State Park, and then onto the famous Portland Head Light, the most photographed lighthouse in America. Hungry?  We highly recommend taking time to grab a lobster roll from Bite into Maine or maybe a gelato from Gelato Fiasco.  When you leave Fort Williams Park, you’ll continue on to Spring Point Ledge Light before rounding out your lighthouse tour at Bug Light.  Isn’t it as cute as a bug?   Wind your way through the Knightville neighborhood of South Portland before finally pedaling “across the bridge” into Portland.

DAY 5 Pedal Peaks Island

Your final day begins on the water.

A short ferry ride carries you away from Portland toward Peaks Island, where island life moves at its own pace. Watch for seals from the deck. Feel the breeze shift as the city fades behind you.

On the island, take your time. Ride the perimeter road, stop for photos, wander the shoreline, or sift through sand for beach glass. There’s no rush — just an easy pedal and the simple pleasure of being somewhere slightly removed from everything else.

The ferry ride back offers one last chance to reflect, laugh at the moments that stand out, and enjoy the rare feeling of having truly slowed down for a few days.

It’s a gentle, fitting finish to the week — and a reminder of why you chose this kind of travel in the first place.

  • Ferry Times: to Peaks at 9:15am | return to Portland at 12:45pm
  • Cycling: 6.3 miles | elevation gain 324 ft
  • Meals: Breakfast
  • End of Tour: 1:15pm with transfer to the airport, train or bus station, or your post-tour hotel

Please Ask a Question or give us a call at 1.866-857-9544 if you have any questions.

What's Included

  • 4 nights’ lodging
  • All lodging taxes and gratuities
  • 4 breakfasts
  • Hybrid bike rental and helmet
  • Scenic ferry ride
  • Detailed route notes and maps and turn by turn navigation using the Ride with GPS app (no cellular data needed)
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  • Emergency support
  • Summer Feet Souvenirs – a cycling water bottle and t-shirt (available in men’s and women’s fit)
  • Transportation from Portland, ME, to the ride start and to post-ride destination in Portland, ME
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Patti & Tom F - 2025 guests
★★★★★

Loved the opportunity to ride in this part of Maine at our own pace; super convenient to have Summer Feet moving our stuff each day.

Barbara - 2025 guest
★★★★★

A few highlights – Kennebunkport stay, ride to Scarborough, lighthouses, water views, ferry rides.

Alan & Toni P from California
★★★★★

We had a great first biking adventure and are inspired to do another.

Frequently asked questions

Is this tour suitable for riders without prior multi-day cycling experience?

Yes.  The York Harbor to Portland tour is designed as an approachable introduction to inn-to-inn cycling.  Daily routes are manageable and scenic, and there is plenty of time to rest and explore along the way.

You ride independently, at your own pace, using provided routes and turn-by-turn instructions.  We handle lodging, luggage transfers, and support so you can focusing on enjoying the ride.

Your luggage is transferred each moving day and will be at your next inn by 4pm.  You ride with only what you need for the day.

Yes.  E-bikes are available and make the tour accessible for a wider range of riders.  They provide pedal assistance on hills and longer stretches, while still allowing you to ride at your own pace and enjoy the scenery.

Maybe! Some of the lighthouses you will see along your rides offer tours. Check out Friends of Wood Island Lighthouse – they offer tours of Wood Island Lighthouse in Biddeford on select days in July & August. You can also look into Spring Point Ledge Lighthouse – they offer guided tours on select days of the week starting in July.

It’s your vacation and if beach walking is your thing, then we certainly encourage you to do so! From south to north, some great beach options include: Long Sands Beach in York, Wells Beach in Wells, Laudholm Beach in Wells, Mother’s | Middle | and Gooch’s Beach in Kennebunk, Goose Rocks Beach in Kennebunkport, any of the seven miles of sand beaches on the Saco Bay, Higgins Beach in Scarborough.

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