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York Harbor to Portland self-guided Cycling Tour

Details

What’s Included

Itinerary

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

A Self-Guided Cycling Adventure in Southern Maine

Set off on a delightful biking adventure where sandy beaches, bustling lobster boats, and vibrant communities create the perfect backdrop for your journey. Our five-day self-guided cycling tour offers an unparalleled opportunity to explore Maine’s iconic summer communities and its most lively city, each teeming with unique allure and charm.

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.

As you pedal along the scenic routes, you’ll encounter picturesque lighthouses and inviting beaches. Take the iconic Casco Bay Ferry to a beautiful island, offering a refreshing change of pace. This self-guided cycling journey promises not only physical activity, but also a rich visual feast of Maine’s most captivating sights, encapsulating the very best this stunning state has to offer.

(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

One of our staff will meet you at 9am in Portland to introduce you to your bikes and answer any questions you may have. After the bike fitting, we’ll take a little road trip to the start of your grand adventure.  Trace southern Maine’s winding shoreline through York Harbor, Cape Neddick, Ogunquit, and Wells Beach to your evening’s destination of Kennebunkport.  Along the way you’ll witness the ocean waves gently being absorbed by sand beaches and the dramatic appeal of the rocky shoreline with crashing waves.  Get as close as you can to Cape Neddick’s Nubble Light (we’d get you closer but this lighthouse is on an island)! Kennebunkport is a lovely and lively town to spend the next two nights – it’s a great place to call home.

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

DAY 2 Cruising the Kennebunks

History buffs, maritime enthusiasts, and scenic cyclists – today is for you.  Explore the Kennebunks – Kennebunkport, Kennebunk, Arundel, and Cape Porpoise – towns with deep maritime history.  Take time to read the historical placards along the way to learn about the area’s prolific shipbuilding era, the many sea captains, or the early days of life along the Mousam and Kennebunk Rivers.  These towns blend the old with the new.  The sea captains’ grand homes are now cozy bed and breakfasts, and the tradition of boat building lives on with a wooden boat building school right in town.  Locals continue the multi-generational tradition of lobstering and fishing, earning their livings from the sea.  Today’s ride is coastal, rural, and just plain gorgeous!

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

DAY 3 To the Beach

Leaving Kennebunkport, you will pedal past charming houses and rural fields on your way to the East Coast Greenway, a multi-use trail stretching from Maine to Florida. Your ride will take you along the coast to the towns of Biddeford and Saco. After cycling through these historic mill towns, you will continue to Old Orchard Beach. “OOB”, as the locals call it, is an unpretentious beach town with an amusement park and pier. From here you’ll jump onto the East Coast Greenway and pedal vehicle-free through the Scarborough Marsh before getting back onto the roads that will bring you to your inn.  Situated just steps from the beach, tonight’s lodging is like a sweet beach house all set up and ready for your arrival.

  • 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

Just a 20-minute ferry ride from the bustling heart of Portland, Peaks Island is an enchanting place awaiting discovery.  It offers picturesque scenery and captures the essence of traditional island life.  Take your time this morning – watch for seals from the deck of the ferry – sift through the sand for beach glass – stop for as many photos as you’d like – and enjoy an easy pedal around the island’s perimeter.  Soak in the sights on your ferry ride back to the mainland … laugh out loud at the crazy memories you’ve created … bask in the carefree feeling of being on the water.  What a way to end a wonderful week – we’re glad you chose to treat yourself to this vacation!

  • 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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Lynne Voncanon
★★★★★

Views were amazing. Guides were friendly and personable. Lobster roll was delicious. I upgraded to the ebike (first time riding one) and 10/10 recommend it. I wasn’t looking for a workout. Just wanted to see the sights and enjoy myself. Portland was my favorite stop from a New England cruise.

Michael Brown
★★★★★

Five Stars to Rick (our guide) and the folks at Summer Feet Cycling. The ride was perfectly tailored to our group of nine middle aged individuals. The sights were terrific and the lobster role for lunch was the best I have ever eaten. Thanks for making our time in Maine a memorable experience.

Marsha Walton
★★★★★

Our Summer Feet cycle along the Maine coast was glorious. In early September, we had perfect weather. We cycled along breathtaking views. Then we caught our breath in quaint Maine towns and fishing villages. Each evening our luggage was waiting for us at a charming inn, where we were served breakfast before heading out the next morning. The Summer Feet staff were friendly and efficient. We will hope to plan another Summer Feet trip soon! Pedal The Coast

Lynne Voncanon
★★★★★

Views were amazing. Guides were friendly and personable. Lobster roll was delicious. I upgraded to the ebike (first time riding one) and 10/10 recommend it. I wasn’t looking for a workout. Just wanted to see the sights and enjoy myself. Portland was my favorite stop from a New England cruise.

Michael Brown
★★★★★

Five Stars to Rick (our guide) and the folks at Summer Feet Cycling. The ride was perfectly tailored to our group of nine middle aged individuals. The sights were terrific and the lobster role for lunch was the best I have ever eaten. Thanks for making our time in Maine a memorable experience.

Marsha Walton
★★★★★

Our Summer Feet cycle along the Maine coast was glorious. In early September, we had perfect weather. We cycled along breathtaking views. Then we caught our breath in quaint Maine towns and fishing villages. Each evening our luggage was waiting for us at a charming inn, where we were served breakfast before heading out the next morning. The Summer Feet staff were friendly and efficient. We will hope to plan another Summer Feet trip soon! Pedal The Coast

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