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Discover Penobscot Bay Multi-Sport

Itinerary

What’s Included

Reviews

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2026 Dates

June - September

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5 Days
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Difficulty Level

Moderate - I Own Bike Shorts

Ride, Paddle, Sail—And Discover a Wilder Side of Coastal Maine

Discover Penobscot Bay! A self-guided multi-sport tour featuring cycling, kayaking, hiking, and sailing—ideal for independent travelers seeking an active Maine vacation.

Explore the islands and shoreline of Penobscot Bay by bike, kayak, sailboat, and on foot, moving through quiet coastal roads, open water, wooded trails, and small harbor towns. Each day is thoughtfully planned for you, with mapped routes, detailed ride notes, and logistics arranged—so you can focus on the experience, not the coordination.

This trip is ideal for independent travelers looking for a self-guided active vacation in Maine that offers variety, immersion, and a sense of accomplishing so much while on vacation. The feeling of adventure is real —giving you confidence, flexibility, and a smile on your face. Let the constant ebb and flow of the tides, and the breaking waves set the rhythm for your journey.

If you have any questions, please get in touch. 

Highlights

  • Cycle, Hike, Sail, and Kayak along the Maine Coast
  • Explore charming towns and coastal villages
  • Discover hidden coves and stunning coastline
  • Enjoy a variety of Maine delicacies, from lobster and smoked salmon to fresh blueberries and the local favorite “whoopie pies”
Pricing

Tour Price: $2395 per person double occupancy

E-Bike: $250

2026 Dates

Discover Penobscot Bay self-guided multi-sport tour starts any Saturday during June, July, August, and September.

Pickup/Drop Off
Portland, Maine (PWM)

Itinerary

DAY 1 Quiet Roads to Pemaquid Point

Your journey begins on Portland’s waterfront, where a member of our team meets you for the transfer north to the harbor town of Damariscotta. We’ll make sure you’re oriented, comfortable with the route materials, and ready to begin before you set out on your own.

Take time to explore town and ease into the rhythm of the coast before cycling quiet back roads toward Pemaquid Point. The riding is scenic and steady—designed to build confidence early and let you settle into traveling under your own power. Along the way, visit Pemaquid Point Light and the Colonial Pemaquid State Historic Site, where Maine’s maritime history comes into focus.

By the time you arrive at the inn, you’ll feel ready for the days ahead.

  • Today’s Activity: cycle 26 miles | elevation gain 1,437 ft
  • Meals: None
  • Lodging: The Bradley Inn

DAY 2 Island Time on Monhegan

This morning begins with a short, easy ride to the ferry terminal in New Harbor. You’ll lock your bikes on the mainland before boarding the ferry for the one-hour crossing to Monhegan Island, ten miles offshore.  Don’t forget your overnight bag!  And watch for seals, porpoise, dolphins, and other marine life while crossing the open ocean to the island.

Monhegan invites you to slow down completely. Known for its artists, cliffside trails, and open ocean views, the island rewards time on foot. Hike along the perimeter, explore the village, or simply sit and watch the light change across the water.

As the last day boat departs your discover the true peacefulness of Monhegan.

  • Today’s Activity: cycle 3 miles | hike 1.5 miles
  • Meals: Breakfast
  • Lodging: Monhegan Island Inn

DAY 3 From Working Harbors to Rockland

After breakfast and a relaxed morning, you’ll ferry back to the mainland and disembark the boat in the fishing village of Port Clyde. Take time to browse the small studios and galleries near the harbor before beginning today’s ride.

Your route follows the coast south, with a stop at Marshall Point Lighthouse, a familiar landmark for many. From there, continue north to Rockland, where art, working waterfronts, and walkable streets give the town its character.

This is a satisfying cycling day—long enough to to award a feeling of accomplishment, yet balanced with plenty of reasons to stop along the way.

  • Today’s Activity: cycle 32 miles | elevation gain 1,537 ft
  • Meals: Breakfast
  • Lodging: The Berry Manor Inn

DAY 4 Cycling to Camden and Sailing the Bay

Today is designed around choice.

The ride from Rockland to Camden is a short, scenic spin, perfect if you’re ready for a lighter day. If you’re feeling strong, additional route options let you extend the ride into rolling countryside before arriving in town.

Camden’s harbor and forested hills make it one of the most appealing stops on the coast. After time to explore, the day shifts again as you board a classic wooden schooner for a sail on Penobscot Bay—a relaxed, wind-powered way to experience the bay from the water.

Flexibility is the feature today, not the exception.

  • Today’s Activity: cycle options from 10-32 miles | elevation gain 692-2,319 ft
  • Today’s Activity: 2-hr sailing trip
  • Meals: Breakfast
  • Lodging: The Blue Harbor House

DAY 5 Kayaking Camden Harbor and the Journey Home

Your final morning begins with a guided kayaking tour of Camden Harbor. Paddling along the shoreline offers a close-in view of the Curtis Island Lighthouse and the Camden Hills rising behind town.

After kayaking, enjoy lunch at your leisure before an early-afternoon transfer back to Portland. The trip concludes with a quiet sense of completion—not because you rushed to the finish, but because you experienced the coast fully and confidently.

  • Today’s Activity: guided kayaking tour (approximately 2 hours)
  • Meals: Breakfast

Please Ask a Question or give us a call at 1.866-857-9544 if you have any questions.

What's Included

  • Four nights’ lodging
  • All lodging taxes and gratuities
  • 4 breakfasts
  • Detailed route notes and maps plus turn by turn navigation using the Ride with GPS app (no cellular data needed)
  • Daily luggage transfers
  • Emergency support
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  • Hybrid bike with panniers
  • Ferry tickets to and from Monhegan
  • Summer Feet Souvenirs – cycling water bottle and t-shirt (available in men’s & women’s fit)
  • Sailing and Kayaking
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Katherine N - 2024 guest
★★★★★

There are no accolades sufficient enough to capture how incredibly pleased we were with our Summer Feet Cycling experience! Each day offered fabulous exposure to the coast of Maine. The trip exceeded our expectations in every way. Deep appreciation for the Summer Feet team and all of the attention to detail they give to planning and offering such an extraordinary trip. We enjoyed the Discover Penobscot Bay multi-sport tour which included biking, hiking, kayaking and sailing. Highly recommend it with no hesitations.

Bob H from Texas
★★★★★

Wow! Everything I expected and more – an amazing vacation.

Kim
★★★★★

Love the rides and the gentle hills of the coastline. The “oreo cows” are a favorite and the full moon rise from the deck of the Schooner Olad is an image I’ll carry with me for quite some time. Thank you Summer Feet for wonderful riding!

Frequently asked questions

Where will we stay on the Discover Penobscot Bay tour?

You’ll stay in carefully selected coastal inns chosen for comfort, character, and proximity to the day’s activities.  The accommodations are an integral part of the overall experience.

The Discover Penobscot Bay itinerary includes cycling, hiking, kayaking, and sailing to showcase Penobscot Bay from multiple perspectives.  Each activity is thoughtfully integrated into the overall itinerary.

No.  This tour is designed for active travelers with a general comfort being outdoors.  Clear instructions and planning support are provided for each activity so you can participate confidently and at your own pace.

You travel independently using detailed turn-by-turn GPS for cycling. Lodging, activities, and logistics are organized for you, and support is available if needed.

Definitely bring a long layer or two, plus one change of clothes. Also don’t forget your more important items like any medications, your wallet and ID, phones, chargers, and motion sickness medication if you are prone to motion sickness. You don’t need much!

Most certainly! You are welcomed to bring your own food and drink onboard if that idea appeals to you.

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