Tour Highlights
- Bike three of Maine’s coastal islands, offering quiet roads and a relaxed lifestyle away from the mainland
- Experience the simple thrills of a New England summer, swimming in lakes, ponds, quarries, and even the Atlantic Ocean
- Share a lobster bake with the locals and sample sun-warmed blueberries at a farm in the St. George River Valley
- Cruise the pristine waters surrounding North Haven with our friends, Conner and Oakley, two local fishermen
Eat
Wild blueberries, vegetables and cheese from local organic farms, Maine seafood including lobster and oysters
Drink
Craft micro-brews, ciders, and local wines
As featured in:
Itinerary
Print Itinerary- Day 1
Island Life in Isleboro
Meet your guides in Portland and transfer up the coast to Lincolnville where we’ll catch the ferry to the island of Isleboro. With just 560 permanent residents, Islesboro has long been a summer retreat for artists, actors, and writers. After a bike fitting and safety briefing, we’ll set out on our first ride, pedaling past rocky coves and secluded beaches to the island’s northernmost point. No visit to the islands is complete without a lobster roll—perhaps Maine’s most emblematic meal. Back on the mainland, we’ll make a quick coffee stop on our way to the top of Mount Battie, the best place for pristine views of Camden Harbor. End the day at our postcard-perfect hotel overlooking Penobscot Bay. This evening we’ll regather and head to dinner at our favorite local restaurant.
Meals: Lunch / Dinner
Destinations: Camden, Isleboro
Accomplished: 24 miles / 38 km, elevation gain: 1,148 feet / 350 meters
Accommodations: 16 Bay View - Day 2
Lavender and Blueberries
This morning we’ll 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 farm where we’ll have a lunch featuring hand-picked ingredients and fresh lobster. 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.
Meals: Breakfast / Lunch
Destinations: Hope, Appleton, Union
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
Accommodations: 16 Bay View - Day 3
Spruce Head
Today begins with a short transfer to the quaint town of Rockland where our ride begins. Heading south, we’ll cruise along the craggy Maine coastline, breathing in the salty sea air and enjoying sweeping views of Penobscot Bay. Pause at Birch Point Beach State Park, where a short path through the forest reveals rocky headlands with panoramic vistas of the bay and surrounding islands. From there, continue cycling to Spruce Head Island for lunch at one of Maine’s most beloved lobster shacks—a laid-back spot that feels like it’s at the end of the Earth. Afterward, opt to bike back or linger a while for a dip in the sea before hopping into the van. Back in Rockland, we’ll board the ferry to North Haven. Picturesque and pastoral with a deep sense of place, this charming island may be mid-coast Maine’s best-kept secret. Check into our next hotel, a rambling Victorian in the heart of town. Settle in and enjoy a glass of wine on the porch before gathering for a hyper-local meal at the Lodge’s inviting restaurant.
Meals: Breakfast / Lunch / Dinner
Destinations: Rockland, Owl’s Head, Spruce Head Island
Accomplished: 37 miles / 59 km, elevation gain: 1,814 feet / 552 meters
Shorter Option: 20 miles / 32 km, elevation gain: 952 feet / 290 meters
Accommodations: Nebo Lodge - Day 4
North Haven
After a hearty New England breakfast, we’ll set off on a ride spanning the entire length of the island, with stunning views across Penobscot Bay unfolding along the way. A visit to the local historical society offers a window into the island’s agricultural heritage and maritime traditions. From there, continue cycling. working up an appetite for lunch on a picturesque organic farm. Afterward, we’ll join our friends Conner and Oakley aboard their boat for a jaunt around the surrounding islands. Both local fishermen, the two will share their commitment to regenerative practices and explain how the movement could help shape a more sustainable future for the island’s farms and fisheries. This evening, we’ll raise a glass to our adventures together before a festive final dinner with the locals.
Meals: Breakfast / Lunch / Dinner
Destinations: North Haven
Accomplished: 23 miles / 37 km, elevation gain: 1,246 feet / 380 meters
Shorter Option: 13 miles / 21 km, elevation gain: 702 feet / 214 meters
Accommodations: Nebo Lodge - Day 5
Back to Portland
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.
Meals: Breakfast
Destinations: Rockland, Portland
DuVine itineraries may be subject to slight route changes, hotel substitutions, and other modifications.
Arrival Details
Airport City: Portland, Maine Pick-Up Location: The Press Hotel, Portland or 16 Bay View Pick-Up Time: 9:00 am at the Press Hotel or 11:00 am at 16 Bay View
Departure Details
Airport City: Portland, Maine Drop-Off Location: The Press Hotel or Portland Airport Drop-Off Time: 11:30 am
Arrival and departure details for alternate itineraries and future year departures may be subject to change.
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. Please note that there are very few rooms available with two beds. Additionally, we are unable to offer triple occupancy on this tour.
Dates + Availability
Inclusions + Details
Accommodations
- Thoughtfully selected accommodations that reveal the true character of the region
- Luggage transfers
Meals
- 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
Activities
- 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
Gear
- 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 with pre-programmed route maps
Support
- 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
