Lighthouses & Landscapes

Itinerary 

Pick Up / Drop Off

Portland, ME (PWM)

Day 1 – Biddeford Pool and South

Guides will collect you in the morning from your Portland hotel for a short transfer south to Biddeford Pool and the start of your cycling tour. Take your time taking in the scenery as you hug the shore from Biddeford Pool to a sweet little pocket beach where we encourage you to take your shoes off and stay a while. Sunday afternoon we’ll take a boat out into the Cape Porpoise Harbor to explore the Goat Island Lighthouse. Tonight we’ll enjoy seasonal creations at a great restaurant right in Kennebunkport’s Dock Square.

• Cycling Options: 9 or 15 miles
• Meals: Lunch & Dinner
• Lodging: First of 3 Nights at The Captain Jefferds Inn

Day 2 – Cape Porpoise & Walker’s Point

A visit to Kennebunkport is not complete without exploring the town’s inland farms and coastal village of Cape Porpoise. Today’s loop will check those two items off your “to do” list and end with the best views possible of Walker’s Point and the crashing waves of Cape Arundel’s rocky coast. Tonight you’ll get your hands dirty at Kennebunkport’s most classic lobster shack.

• Cycling Options: 14 or 21 miles
• Meals: Breakfast & Lunch & Dinner
• Lodging: Second of 3 Nights at The Captain Jefferds Inn

Day 3 – Kennebunk’s Bridal Path & Beaches

This morning we head inland again to downtown Kennebunk. Take your time in town and when you’re ready, cycle the historic Bridal Path as it follows the Mousam River to the sea. We end today’s riding by following Kennebunk’s beaches to Lower Village and then across the bridge into Dock Square. This afternoon we set sail aboard the Schooner Eleanor – seeing Kennebunkport’s shorelines and homes from a delightfully different perspective.

• Cycling Options: 15 miles
• Meals: Breakfast & Dinner
• Lodging: Final Night at The Captain Jefferds Inn

Day 4 – North Towards Portland

We’ll ride northward today through the towns of Biddeford, Saco, Camp Ellis, and finally stopping in the quaint oceanside community of Ocean Park. Play a game of shuffleboard, eat an ice cream cone, and get some sand between your toes from Maine’s largest sand beach (the 7-mile sand beach of Saco Bay). Once all our riders are here, we’ll load up the van and finish our journey to Portland. Tonight you are on your own for dinner, so if you’re inspired to just keep riding, let your guides know and they’ll point you in the right direction to log a few more miles!

• Cycling Options: 20 or 27 or 47 miles
• Meals: Breakfast
• Lodging: First of 2 Nights at The Danforth

Day 5 – Cape Elizabeth & Lighthouses

Today we head south of Portland and visit 4 lighthouses. We begin by cycling to Bug Light Park where we walk the causeway to Bug Light and explore the Liberty Ship Park. Then we pedal to the Spring Point Light and its quaint little museum. Our ride then carries us along Shore Road, one of Portland’s most exclusive addresses and onto the famous Portland Head Light. From Portland Head Light we cycle to 2 Lights State Park, famously painted by Winslow Homer. Enjoy a lobster roll over looking the ocean and choose either a shuttle, or to cycle back to town and a scrumptious dinner in-town Portland (America’s foodiest small city).

• Cycling Options: 12 or 24 miles
• Meals: Breakfast & Lunch & Dinner
• Lodging: Final Night at The Danforth

Day 6 – Island Hopping

After a wonderful breakfast we cycle to Casco Bay Lines’ ferry terminal and grab a morning ferry to Chebeague Island, one of the larger islands in Casco Bay. Great views, farmland, and a charming island community greet us as we cycle around the island. We enjoy a lunch at the Island Inn before catching a ferry to Cousin’s Island. We cycle Cousin’s Island, take yet another ferry to the mainland, and enjoy an optional ride back to Portland through the upscale town of Falmouth. The tour will conclude in the later afternoon hours, around 4pm.

• Cycling Options: 10, 25, or 40 miles
• Meals: Breakfast & Lunch