Sailboats and Summer Folk


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  • 3 Days
  • 2024 DatesJuly-Oct
  • Difficulty LevelEasy/Moderate - I Own Bike Shorts

Tour Overview

Nestled amongst verdant hills, with stately old houses, a picturesque harbor, and a charming main street, it is no wonder Camden has been voted the prettiest town in Maine.

Your 3-day bike tour of this classic Maine town begins with a bike ride along a tree-lined ocean preserve and through lush farmland ringed with ancient rock walls. We continue by cycling one of Maine’s most beautiful islands in the heart of Penobscot Bay with ocean views around every corner.

You conclude your tour cycling to the town of Rockland and to my favorite lighthouse, the majestic Owls Head Light. Along the way take time to explore the areas’ many galleries, and relax aboard the deck of an antique wooden sailboat as we enjoy a sunset cruise on Penobscot Bay.

What's Included

  • Two nights’ lodging
  • All lodging taxes and gratuities
  • Most meals – including dinner both evenings, lunch on Saturday, and breakfasts at the inn
  • All taxes and gratuities for these meals
  • Expenses paid to sail on the Schooner and for the ferry transit
  • 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


  • Cycle Islesboro Island and Maine’s Rocky Coast
  • Enjoy a sunset sail on Penobscot Bay
  • Explore the shops and galleries of Camden and Rockland

Meeting place

Leaders will meet you at the inn in Camden


Sailboats and Summer Folk $1495.00 per person
Bike Rentals: Hybrid Bike Rental: Included
Road Bike Rental: $150.00
E-Bike Rental: $150.00
Lodging Extras: Single Supplement: $400.00


Day 1 Cycling The Prettiest Six Miles In Maine*

We meet at 1pm Friday afternoon for an afternoon of cycling through the charming coastal village of Rockport. A delightful mix of tranquil farmlands and ocean views highlight our ride. In the evening we gather for a wine and cheese reception before dinner at one of Camden’s finest restaurants.

  • 7 or 15 miles
  • Meals: Dinner

*Yankee Magazine Fall 2005

Day 2Cycling The Pristine Island Of Islesboro And A Sunset Sail

The early morning ferry carries us to Islesboro where stately pines and 40 room cottages serve as a backdrop for our ride around one of Maine’s prettiest islands. Tonight we explore Penobscot Bay from the deck of a classic wooden schooner before a casual dinner.

  • 26, 36, or 46 miles
  • Meals: Breakfast & Lunch & Dinner
  •  The Hartstone Inn

Day 3Exploring Rockland, Owl’s Head, And Birch Point

Just south of Camden, Rockland is rapidly becoming a summer destination in its own right. Today’s ride will carry us to Rockland and the Owls Head Light. Spend the afternoon wandering the Farnsworth Museum of Art or choose to cycle the rural beauty of the St George Peninsula and around Rackliff Island. Note: The  tour generally concludes between 1:00 pm and 3:00 pm.

  • 10, 32, or 41 miles
  • Meals: Breakfast


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