Island Hopping 2025

A Portland, Maine Bike Tour …

Portland, Maine, is a hidden gem that offers the perfect blend of vibrant city life and scenic coastal charm. Known for its thriving food scene, Portland boasts award-winning restaurants, fresh seafood, and craft breweries that have earned it a reputation as a culinary haven. The historic Old Port district, with its cobblestone streets and unique shops, provides a glimpse into the city’s maritime heritage while offering plenty of opportunities for shopping and sightseeing. Our Island Hopping Weekend Bike Tour explores the city and islands of our home town.

Check out the tour’s itinerary below and if you have any questions, please get in touch.

Highlights

Pricing

Tour Price: $1695 per person double occupancy
Single Supplement: $600

2025 Dates

June 13-15

September 19-21

October 17-19

Pickup/Drop Off

Summer Feet guides will meet you in Portland.

Portland Bike Tour Itinerary

DAY 1 Cycling Peaks Island

Guides will meet you at the Portland Regency for a bike fitting. On the short (15-minute) ferry ride to Peaks Island, you can take in great views of downtown Portland, Fort Gorges, and Casco Bay. Watch for seals in the water! Once on-island, a few small hills will get us pedaling on the road around the island. We will stop at Battery Steele to learn how this small island played a vital role in two separate wars. The jaunt around the island’s perimeter allows for stunning views of the island’s coast including looks at Ram Island Ledge Light. A late afternoon ferry returns us to the mainland for dinner at a favorite local establishment.

Cycling: 6 miles | elevation gain 324 ft
Meals: Dinner
Lodging: The Portland Regency

DAY 2 Cycling Cousins and Chebeague Island

After breakfast at the hotel, we hop on our bikes and pedal the Eastern Promenade Trail out of town and north towards Falmouth. Our route past stately homes leads us to Cousins Island. A hop and a skip of a ferry ride takes us to Chebeague Island, the largest island in Casco Bay. We cycle the quiet roads of Chebeague and enjoy lunch before an afternoon ferry carries us back to Portland.

Cycling: 23 miles | elevation gain 883 ft
Meals: Breakfast and Lunch
Lodging: The Portland Regency

DAY 3 Lighthouses and More

After breakfast, we will pedal across the Casco Bay Bridge and along the country roads of Cape Elizabeth. We will pedal the coastal road back toward Portland, visiting multiple lighthouses along Casco Bay. The first stop is Two Lights at the tip of Cape Elizabeth. From here we will pedal to the Portland Head Light, first lit in 1791, where we stop for lunch overlooking the ocean. After lunch, we will visit Spring Point Ledge Light and The Portland Breakwater Light, known by locals as Bug Light, before pedaling back into Portland for the end of of our tour.

Cycling: 26 miles | elevation gain 933 ft
Meals: Breakfast and Lunch

What's Included

Two nights’ lodging
All lodging taxes and gratuities
One dinners, two lunches, two breakfasts
All taxes and gratuities for these meals
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)
Hybrid bike rental

Views were amazing. Guides were friendly and personable. Lobster roll was delicious. I upgraded to the ebike (first time riding one) and 10/10 recommend it. I wasn’t looking for a workout. Just wanted to see the sights and enjoy myself. Portland was my favorite stop from a New England cruise.

Five Stars to Rick (our guide) and the folks at Summer Feet Cycling. The ride was perfectly tailored to our group of nine middle aged individuals. The sights were terrific and the lobster role for lunch was the best I have ever eaten. Thanks for making our time in Maine a memorable experience.

Our Summer Feet cycle along the Maine coast was glorious. In early September, we had perfect weather. We cycled along breathtaking views. Then we caught our breath in quaint Maine towns and fishing villages. Each evening our luggage was waiting for us at a charming inn, where we were served breakfast before heading out the next morning. The Summer Feet staff were friendly and efficient. We will hope to plan another Summer Feet trip soon! Pedal The Coast

Related Tours

Weekend

Exploring Acadia National Park

Escape to Maine and let us show you the best of Acadia National Park. Experience the dramatic beauty of Maine’s rocky coastlines and enjoy car-free cycling on...