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Maine Coastal Biking

5 Days & 4 Nights
  • Cycle through Portland and Freeport, two of Maine's classic coastal towns
  • Wind your way along scenic coastline and pedal past historic lighthouses
  • Enjoy a scenic ferry ride through the Calendar Islands of Casco Bay
  • Fuel up on fried clams, lobster rolls, and wild blueberry pie
  • Delight in the charm and hospitality of quaint seaside villages
This five-day cycling tour in southern Maine starts in the small town of Kennebunkport and takes you up the coast to Freeport. Given the nickname Vacationland, this charming region is full of incredible scenery and Americana vibes. Experience this tour at your own pace, biking along a portion of the verdent East Coast Greenway and hopping on a scenic ferry ride that winds through the peaceful Calendar Islands of Casco Bay. You will have plenty of time on this relaxed itinerary to visit several historic lighthouses and to shop 'til you drop at the LL Bean Flagship store. Be sure to indulge in plenty of whoopie pies, a classic Maine treat!

What To Expect

This bike tour is easy to moderate, with an average daily ride of 23 miles and many short ascents and descents. It is best suited for experienced cyclists who are accustomed to sharing the road. The route offers coastal and rural riding, with rolling hills and varied terrain. If your ideal vacation combines scenic riding with beachcombing, fresh food, island vibes, and overnights at carefully-selected country inns, this tour is for you.   

Tour Style:

Self Guided | Go at your own pace on an independent active trip.


Inn to Inn Biking | A classic point to point biking tour, staying in a different location each night

This trip is suitable for:


As a guide, we would suggest that the minimum age of traveler this tour would be suitable for is: 14 Years

Ideal if you have an interest in:

  • Foodie Adventures
  • Coastal & Island


  • New

Activity Level & Terrain

This tour is graded easy to moderate. The daily rides average 23 miles. There are many rolling hills but no substantial climbs. You should be an experienced road cyclist accustomed to sharing the road with other users. At times the route has a shoulder, but its width varies, and some of the smaller, more rural roads have no shoulder. We advise high visibility clothing to be worn while riding.

The route is almost entirely paved, with infrequent and short gravel sections connecting rural roads. Surface conditions change yearly and seasonally, so gravel, potholes, and frost heaves are a possibility. The distances and ascents/descent listed are approximations of the recommended routes. For those looking for a little extra assistance, e-bikes may be an option but are subject to availability.

We provide you with detailed turn-by-turn directions on the Macs Adventure Navigation App. Using this app, you will also be able to follow the route with your phone’s GPS. As instructed below, you’ll need to save all routes to your device for use in offline mode as cell phone reception can be unreliable in rural Vermont.


Navigating is easy using the Macs Adventure Navigation App. Your daily rides will be mapped in the app with GPX tracks, route notes, and turn-by-turn directions. All of these resources are available to download for offline use, which is recommended as cell service can be unreliable in rural Vermont. Written turn-by-turn directions are included in the app. When you have cell reception, you will also have 24/7 telephone support from us here at Macs Adventure.

Experience & Fitness

This tour is graded easy to moderate. The daily rides average 23 miles. There are many rolling hills but no substantial climbs. You should be an experienced road cyclist accustomed to sharing the road with other users. At times the route has a shoulder, but its width varies, and some of the smaller, more rural roads have no shoulder. We advise high visibility clothing to be worn while riding.


One of the highlights of this tour is the high standard of accommodation. You will stay in carefully selected 3-4* small hotels. Your room will always have an ensuite or private bathroom. A delicious breakfast is also included. 

Single Rooms

If you require single rooms within your party we will always try and accommodate you subject to availability. A single supplement is payable.


A hearty breakfast is included each morning. Lunch and dinners are not included so you are free to choose from the surrounding options. Dinner is available either at your accommodation or at nearby restaurants.

  • 4 Nights in hand-picked accommodations
  • All lodging taxes and gratuities
  • 4 Breakfasts
  • Hybrid bike and helmet
  • Scenic ferry ride
  • Detailed route notes and maps
  • Baggage transfers
  • 24/7 Emergency telephone support from our US & UK offices
  • Travel to / from Kennebunkport
  • Optional upgrade to an e-bike
  • Lunches, dinners, drinks, & snacks
  • Personal equipment
  • Travel insurance (required)
  • Additional nights along the route
  • Upgrade to an e-bike

When To Go

The trip is available from May to October. Please keep in mind this trip can only depart on a Sunday. 

Weather and Climate

New England’s seasonal changes are one of its greatest charms, and there are advantages to riding in Maine at any time of the year. May and June will bring fewer crowds, cooler temperatures (in the 50s-60s Fahrenheit), and lush green hillsides speckled with flowers. The summer months of July and August are busy with summer tourists, but the refreshing swimming holes, late summer evenings, and clear blue skies are worth it. Temperatures rise to the 70s-low 80s Fahrenheit on average with some hotter days. The crisp weather of September and October (in the 50s-60s Fahrenheit) draw not only outdoor enthusiasts to Maine, but also the leaf-peepers and photographers, making it tough to secure reservations – but if you do, the colors of peak foliage season are pure magic.

Getting to the Start

Our trip starts and ends in Kennebunkport. On the last day, you also have the option of your transfer taking you to Portland if you prefer. The easiest way to travel to and from your trip is to fly in and out of Portland International Jetport. From there you can take a bus to Kennebunkport which takes roughly an hour. 

Alternatively, you may opt to fly to Boston, and then take the Amtrak train to Kennebunkport in roughly 2 hours. 

Luggage Transfer

Baggage transfer from Kennebunkport to Freeport is included in the cost of your holiday. We ask you to limit your luggage to one bag of up to 20 kg per person.


Our pre-departure information pack includes a detailed equipment list on what to take with you. This includes warm and cold weather gear, cycling clothes, rain gear, and lots of other specifics. If you have any questions about what to take, we'd be happy to share our own top tips and advice.

Bike Rental

Bike rental is included in the cost of this trip. We include a Norco VFR1 or a similar Trek bike. For a little extra assistance, e-bikes are also available (additional fee payable, subject to availability).

Please supply us with your height for your bicycle rental.

Travel Insurance

It is a requirement of booking this tour with Macs Adventure that you have suitable travel insurance that covers you for the activity and emergency evacuation and hospital care.

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Day 1 Arrive in Kennebunkport, optional loop ride 14 miles / 22.5 km Day 2: Cycle to Old Orchard Beach 23 miles / 37 km Day 3: Cycle to Portland 28 miles / 45 km Day 4: Ferry to Chebeague, cycle to Freeport 24 miles / 39 km Day 5: Optional Loop Ride, Transfer to Kennebunkport and onward travel 21 miles / 34 km

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