Meet your guides in Portland and transfer up the coast to the idyllic harbor of Camden. Our first order of business is a lunch highlighting some fresh Atlantic seafood, followed by a quick ferry ride 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. After a stop into the general store for a pick-me-up, we’ll catch the ferry back to the mainland. Get settled at our waterfront hotel, followed by our first dinner together at one of Camden’s charming local restaurants.
This morning we’ll explore “Vacationland” on foot, hiking a path that winds through the Maine woods to a stunning view of Megunticook Lake. Continue through pine forests and up the main ridge of Mount Megunticook to the summit, where the entirety of Penobscot Bay unfolds before you. Watch the boats sail in and out of the Camden Harbor as we trek back into town for a well-earned lunch. After, go for a swim in the nearby lake or take some time to relax at our hotel. In the early evening, we’ll board a historic windjammer sailboat and take a sunset cruise—complete with a lobster dinner onboard.
Meals: Breakfast / Lunch / Dinner
Destinations: Maiden Cliff, Mount Megunticook, Mount Battie
Accomplished: 5 miles / 8 km hiking, elevation gain: 1,256 feet / 383 meters
Accommodations: Inn at Ocean’s Edge or Camden Harbour Inn
Today we depart mainland Maine on a ferry out of Rockland. Our destination is Vinalhaven, a New England island unlike anywhere else: formerly one of the country’s most important quarries, it’s now a quaint and peaceful enclave of lobster fishing in the waters of Penobscot Bay. Beginning from the pier, we’ll bike the entire length of Vinalhaven, then catch a ferry to its sister island, North Haven. A visit with a local oysterman piques our appetite for lunch at a picturesque organic farm. After lunch, opt for some extra cycling, swim in the crystal-clear waters of an abandoned quarry, or settle into an adirondack chair on the hotel’s deck while sipping a glass of wine.
Meals: Breakfast / Lunch / Dinner
Destinations: Vinalhaven, North Haven
Accomplished: 18 miles / 29 km, elevation gain: 1,030 feet / 314 meters
Longer Option: 28 miles / 45 km, elevation gain: 1,581 feet / 482 meters
Accommodations: The Tidewater or Nebo Lodge
It may measure only nine miles across, but Vinalhaven has nearly 270 miles of coastline—which makes kayaking an ideal way to explore the island. Paddle through the quiet inlets and rugged bays to a deserted beach. If you’re bold, finish your day of water sports with a brisk plunge. Back in town, we’ll line up with the locals to try some of the state’s best lobster rolls at an iconic island food truck. The afternoon is yours to relax, take an optional hike, or opt for a two-hour cruise to Seal Island for some puffin sighting. Tonight, we invite you to explore the local restaurant scene for dinner on your own.
For our last day of adventure, we’ll take a private boat to one of Maine’s most remote islands: Isle Au Haut, population 71. Pedal the full circuit of the island through deep pine forests, past remote lighthouses, and along rugged coastline. The southern half of the island is within the borders of Acadia National Park—we’ll set our bikes aside to discover the tide pools of Boom Beach, take a dip in Long Pond, and soak up the wild beauty of the coastal trails. Ride back to Vinalhaven at day’s end and enjoy a final dinner together to celebrate our last night on Maine’s islands.
Take one final early morning spin of Vinalhaven before catching the ferry back to the mainland. Your guides will transfer you back down the coast to Portland before sending you off to your next destination.
Destinations: Rockland, Portland
DuVine itineraries may be subject to slight route changes, hotel substitutions, and other modifications.
Airport City: Portland, Maine Pick-Up Location: Downtown Portland or Camden, Maine Pick-Up Time: 9:30 am
Airport City: Portland, Maine Drop-Off Location: Portland Airport or Downtown Portland Drop-Off Time: 12:30 pm
Travelers Take Note
Ferry and boat rides rely on daily sailing conditions, so weather may dictate itinerary changes or activity cancellations.
The variety of accommodations on Maine’s islands is limited. Some hotels on this tour are therefore simpler than typical DuVine accommodations, but were chosen for their unique location and island proximity.
- Thoughtfully selected accommodations that reveal the true character of the region
- Luggage transfers
- Daily breakfasts, all lunches, nutritious snacks, and après velo cocktails
- 4 gourmet dinners at our favorite local restaurants and renowned culinary establishments
- Carefully selected local wine, beer, or spirits with every meal
- Wine tastings and activities as outlined in the tour itinerary
- Entrance fees to historic sites, museums, parks, and all other exclusive events
- Gratuities for baggage, porters, and hotel service
- Top-of-the-line bicycle selection
- Bike helmet
- Complimentary DuVine gear, including a custom cycling jersey, DuVine t-shirt, water bottle, and drawstring bag
- GPS in most destinations
- Expert bilingual guides with extensive local knowledge
- Support vehicle that follows the day’s route, distributes refreshments, and offers lifts
- Pick-up and drop-off before and after your tour from predetermined meeting points
- Daily bike maintenance to ensure optimal performance