Sunsets & Swing Bridges

A Boothbay Weekend

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Boothbay Harbor has been drawing visitors for over 200 years. Our 3-day Boothbay Weekend bicycle tour takes you on a local’s tour of this famous destination. We meet Friday afternoon at our inn hidden in the quiet hamlet of East Boothbay. Our rides will take you along the rock bound coast, past pristine coves and lighthouses. Following quiet country roads we will show you all of Boothbay, peaceful islands, stunning views, and my favorite place in all of Maine for a lobster roll. Our explorations will still leave you plenty of time to relax on the porch savoring the ocean breeze and to hear the stories of true sailors who built and sailed their boat around the world as we cruise along the coast with them.

Highlights 

  • Discover Boothbay Harbor and Barters Island
  • Enjoy two nights at the charming Five Gables Inn
  • Explore the Rugged Beauty of the Maine Coast

View Itinerary

Skill Levels

  • Sounds Like Fun (easy)
  • I Own Bike Shorts (moderate)

Recent Reviews

This was our 1st bike tour – we thought it was great. It appealed to all members of our family. Read More

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What's Included

  • Two nights’ lodging
  • All lodging taxes and gratuities
  • Most meals – including dinner both evenings, and breakfasts at the inn
  • All taxes and gratuities for these meals
  • Expenses paid to sail on the Schooner Eastwind
  • Experienced Summer Feet Guides
  • Detailed route notes and maps
  • Van support including fresh water, ample snacks, and “relief rides”
  • Summer Feet Souvenirs – a cycling water bottle and t-shirt (available in men’s and women’s fit)
  • Alcoholic beverages are not included in the package price and are always at your discretion

Tour Map


Itinerary 

Pick Up / Drop Off

Leaders will meet you at the inn in Boothbay Harbor

Day 1 – Cycling Ocean Point and a Lobster Dinner

We meet at 2:00pm for a leisurely ride along one of Maine’s prettiest coastal roads. In the evening we enjoy a wine and cheese reception overlooking Linekin Bay before dinner at a local favorite.

  • 12 Miles
  • Meals: Dinner
  • The First of Two Nights at the Five Gables Inn

Day 2 – A Gourmet Breakfast and Exploring the Coast

Today we embark on the grand tour of Boothbay Harbor. Following quiet roads we explore Barters Island, Southport Island and Spruce Point. Our route allows plenty of time for exploring galleries, wandering the shore, and basking in the sun.

  • 15, 24, 36, or 49 miles
  • Meals: Breakfast & Dinner
  • Final Night at the Five Gables Inn

Day 3 – The Charming Village of Damariscotta

Today we cycle the winding and tree lined River Road to the charming village of Damariscotta. Our ride leaves ample time for shopping and a leisurely lunch before we pedal back to Boothbay. Note: The trip usually concludes between 1:00 pm and 3:00 pm.

  • 17 or 34 miles
  • Meals: Breakfast

Customer Reviews 

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