Meet your guides in Portland and transfer up the coast to the idyllic harbor of Camden. Enjoy a fresh lunch and get fitted on the bikes for our first ride. Pedal out of town along the coast on quiet country lanes. Our destination is Rockport, one of the “prettiest small towns in America” and home of Andre the seal. Visit the picturesque harbor before continuing our ride through the fields and forests of the New England countryside. Get settled at our postcard-perfect hotel, followed by our first dinner together at our favorite local restaurant.

Accomplished: 16 miles / 25 km, elevation gain: 1,118 feet / 341 meters

Longer Option: 23 miles / 37 km, elevation gain: 1,870 feet / 570 meters

Catch a boat this morning out to the island of Isleboro. With just 560 permanent residents, Isleboro has long been a summer retreat for artists, actors, and writers. We’ll get to know the island by bike, pedaling past rocky coves and secluded beaches to its northernmost point. Stop into the classic general store for a pick-me up and admire the architecture of the stately mansions. No visit to the islands is complete without a fresh lobster roll, as local as it gets. Tonight meet our friend Sara, a local chef, for a private dinner overlooking the Penobscot Bay.

Accomplished: 24 miles / 38 km, elevation gain: 1,148 feet / 350 meters

Today we get back on our bikes and pedal out of Camden into the scenic St. George River Valley. Our farm country route is lined with lakes, forests, and spacious meadows, and we’ll stop at a lavender farm where this fragrant herb flowers throughout the summer. Continue riding to a blueberry grower and enjoy lunch featuring hand-picked ingredients from the farm. After, choose to ride back to Camden or opt for a lift in the van. Tonight, we invite you to explore the local restaurant scene for dinner on your own; your guides are happy to make recommendations and reservations.

Accomplished: 27 miles / 43 km, elevation gain: 2,139 feet / 652 meters

Shorter Option: 18 miles / 29 km, elevation gain: 1,210 feet / 369 meters

Depart mainland Maine on a boat out of Rockland. Our destination is North Haven, a New England island unlike anywhere else: formerly dedicated to farming and fishing, it’s one of Maine’s best-kept secrets where families return to their vacation homes for generations. From the town pier, we’ll bike the entire length of the island with coastal views that stretch across the Penobscot Bay. A visit with a local oysterman piques our appetite for lunch at a picturesque organic farm. After lunch, pedal to our cozy hotel back in town to relax and explore before dinner.

Accomplished: 23 miles / 37 km, elevation gain: 1,246 feet / 380 meters

Shorter Option: 13 miles / 21 km, elevation gain: 702 feet / 214 meters

Today we’ll cross the thoroughfare to North Haven’s sister island: Vinalhaven. The former hotbed of a quarrying industry, we have Vinalhaven to thank for the paving stones that now line the streets in Boston and Philadelphia. Over time, the quarries have filled with water and become a refreshing place to stop for a mid-ride swim. Though Vinalhaven only measures nine miles across, it boasts nearly 270 miles of coastline—which makes kayaking an ideal way to explore. We’ll paddle through a tidal basin on the lookout for harbor seals, cormorants, and sea ducks. After, board our friend Bobby’s lobster boat as we learn about lobstering and lobster lore. We’ll return to North Haven for a festive final dinner on the islands.

Accomplished: 15 miles / 26 km, elevation gain: 958 feet / 292 meters; 2 hours kayaking

Catch a boat back to the mainland as we say goodbye to North Haven. Your guides will see you off for the drive home or transfer you down the coast to Portland before you head to your next destination.