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Island Hopping

Itinerary

What’s Included

Reviews

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2026 Dates

June - Oct

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3 Days
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Difficulty Level

Easy - Sounds Like Fun

Cyclists on rocky shore pointing at lighthouse on distant island

Island Roads. Lighthouse Views. Three Perfect Days.

Discover Casco Bay’s islands, historic lighthouses, and Portland’s coastal beauty — with guides who know every turn and story.

This guided Portland bike tour is island hopping by ferry, lighthouse chasing along rocky shores, and discovering the quiet corners of Casco Bay most visitors never see. Over three unforgettable days, you’ll ride scenic coastal roads across Peaks and Chebeague Islands, hear the stories behind Maine’s historic beacons, and experience the easy rhythm of island time. We handle the bikes, ferries, routes, and reservations so you can simply pedal, breathe in the salt air, and fall in love with Portland like a local.

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

 

Highlights

  • Discover Portland
  • Bike to 5 Lighthouses
  • Cycle on Two Islands
  • Eat Maine Lobster
Pricing

Tour Price: $1895 per person double occupancy

Single Supplement: $600

E-Bike Rental: $150

 

 

2026 Dates

June 26-28
August 7-9
October 16-18

Pickup/Drop Off
Summer Feet guides will meet you in Portland.

Portland Bike Tour Itinerary

DAY 1 Cycling Peaks Island

Welcome to Island Life

We handle the details. You just ride and enjoy.

Your guides meet you at the Portland Regency for your introduction to your guides and bikes — the first of many moments where you’ll realize everything is taken care of for you. Then it’s a short 15-minute ferry ride to Peaks Island, where the adventure truly begins. Watch for Harbor Seals popping up in the water as downtown Portland, Fort Gorges, and the full sweep of Casco Bay unfold behind you.

Once on the island, a few gentle hills get your legs warmed up as you pedal the coastal perimeter road. At Battery Steele, your guide brings history to life — stories of how this small island played a vital role in two separate wars. The ride around the island delivers stunning views of the open ocean and glimpses of Ram Island Ledge Light standing sentinel in the distance.

A late afternoon ferry returns you to the mainland, where dinner awaits at a favorite local establishment. Your guides know the best spots — and they’re happy to share them.

What You’ll Feel: Like you’ve been let in on a secret. Peaks Island is Portland’s backyard playground, and you just got the insider tour.

The Day:

Island Insider Tip: Keep your eyes on the water during the ferry ride. Seals love these waters, and spotting one is pure Maine magic.

DAY 2 Cycling Cousins and Chebeague Island

 Two Islands, Endless Charm

Safe, supported, and designed for every rider.

After breakfast at the hotel, you’re back on your bikes, pedaling the scenic Eastern Promenade Trail out of town and heading north toward Falmouth. Your route leads you to Cousins Island as it winds past stately homes that have watched over Casco Bay for generations.

Then comes the fun part — a quick hop-and-skip ferry ride to Chebeague Island, the largest island in Casco Bay. Here, the quiet roads are yours to explore. Your guides lead you through the island’s best routes, stopping for a delicious lunch before the afternoon ferry carries you back to Portland.

What You’ll Feel: The rhythm of island time. No rush, no crowds — just the gentle pace of coastal Maine and the company of people who are quickly becoming friends.

The Day:

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

Local Flavor: Chebeague Island moves at its own speed. Embrace it. This is where Portlanders come to truly unwind.

DAY 3 Lighthouses and More

The Grand Lighthouse Tour

Stories you’ll tell for years.

After breakfast, you pedal across the Casco Bay Bridge and into the country roads of Cape Elizabeth. Today is all about lighthouses — and your guides know stories behind every beacon.

First stop: Two Lights at the tip of Cape Elizabeth, where twin towers once guided ships through treacherous waters. Then it’s on to Portland Head Light, first lit in 1791 and still one of the most photographed lighthouses in America. Here you’ll stop for lunch overlooking the ocean, with nothing but the sound of waves and the occasional cry of a gull.

After lunch, you’ll visit Spring Point Ledge Light and the Portland Breakwater Light — known by locals as “Bug Light” — before pedaling back into Portland. Three days ago, you arrived curious. Today, you leave knowing Portland’s islands and coastline like a local.

What You’ll Feel: Accomplished. Proud. Connected. And already telling yourself you’ll be back next summer.

The Day:

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

Lighthouse Legacy: Portland Head Light has been guiding sailors since George Washington commissioned it. You just rode to a piece of living history.

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
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  • 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 & helmet
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Karin & Chris F
★★★★★

Just the right amount of cycling with plenty of options. Leaders took great care of us.

Lauren M from Massachusetts
★★★★★

I went on your weekend trip this past weekend and wanted to say Thank You so much!!!! It was my first cycling trip ever and we had So Much Fun!!!

Frequently asked questions

What makes the island riding special?

Casco Bay is home to more than 200 islands, though most visitors experience them only from the shoreline. On this tour, you cross the harbor by ferry to Peaks Island and Chebeague Island, where quiet roads, light traffic, and open coastal views create a noticeably calmer riding environment. The short, smooth ferry crossings add variety and a natural rhythm to each day. Compared to mainland routes, island cycling feels more relaxed, more scenic, and less congested — a distinct and refreshing way to experience southern Maine.

The mileage on this tour is intentionally balanced to ease you in and build naturally over three days. Day 1 begins with a relaxed 6-mile introduction on Peaks Island, while Days 2 and 3 expand to 23–26 miles of rolling coastal terrain. The goal is to leave you feeling accomplished at the end of each ride — not depleted — so you can still enjoy dinner and the atmosphere of Portland in the evening. E-bikes are available for additional support, offering extra confidence on the hills while preserving the full experience.

Portland is one of the more bike-friendly small cities in New England. On this tour, we prioritize quieter roads, island routes with minimal traffic, and scenic coastal stretches rather than busy urban streets. Your guides provide daily route briefings and manage pacing through town sections so transitions feel organized and comfortable. Many guests are pleasantly surprised by how manageable and enjoyable cycling in Portland feels — especially compared to larger metropolitan areas.

Portland combines coastal beauty with one of the most respected food scenes in New England. Despite its small size, the city is nationally recognized for its restaurants — from refined seafood and oyster bars to intimate farm-to-table dining and thoughtful craft cocktails — and many guests find the evenings here as memorable as the riding. Beyond the dining, Portland offers walkable historic streets, a working waterfront, galleries, and harbor views, all compact enough to enjoy without feeling rushed. It’s a place where you can spend the day cycling along Casco Bay and the evening lingering over a great meal just steps from your hotel — relaxed, cultivated, and distinctly Maine.

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