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Maine Multi-Sport Tour

Itinerary

What’s Included

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2026 Dates

June-September

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5 Days
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Difficulty Level

Easy/Moderate - I Own Bike Shorts

Explore Coastal Maine. On Land and Sea.

A five-day fully guided multi-sport adventure built around hiking, cycling, kayaking, and coastal exploration of the Camden Hills, Penobscot Bay, and Acadia National Park.

This isn’t just a hiking trip. Or a cycling tour. Or a kayak adventure. It’s all of it — thoughtfully woven together into five active, unforgettable days along the Maine coast. You’ll climb forested trails in the Camden Hills, pedal island roads and Acadia’s famous carriage paths, paddle quiet coves timed with the tide, and watch the sunrise from the highest peak on the Atlantic coast. With expert guides handling the logistics and setting the pace, you’re free to immerse yourself in the landscape — mountains meeting the sea, granite cliffs rising from crashing surf, salt air filling your lungs. By the end, you won’t just have seen Maine. You’ll have experienced it from every angle.

(Visiting Portland during your stay in Maine? Browse our Portland, Maine, Day Tours before you go.)

Highlights

  • Hike and bike Acadia National Park
  • Kayak on the ocean
  • Bike a pristine Maine island
  • Sail on a classic wooden schooner
Pricing

Tour Price: $3595.00 per person double occupancy

Single Supplement: $800.00

2026 Dates

June 21-25
July 12-16
July 19-23
August 9-13

Pickup/Drop Off
Portland, Maine (PWM)

Camden, Maine, and Islesboro Island Tour Itinerary

DAY 1 Hiking the Camden Hills

Where Mountains Meet the Sea

We handle the details. You just explore and enjoy.

Your leaders collect you from your hotel at 8:00 am for a scenic one hour and forty-five-minute transfer to the picturesque town of Camden, where mountains tumble right into the sea.

Your adventure begins with an easy hike in the Camden Hills State Park. Follow an old dirt road to the trailhead and climb through fragrant pine forests to Bald Rock, where some of the best views of Penobscot Bay await. The view alone is worth the trip — but you’re just getting started.

After hiking and lunch, you are free to explore Camden’s beautiful harbor, shops, and galleries. Be sure to visit the reading room of the public library — its design is stunning. In the afternoon, you’ll sail on the Schooner Olad, a 90-year-old classic wooden schooner. Wind in the sails, salt air on your face, and the Camden Hills fading behind you.

What You’ll Feel: Like you’ve stepped into a postcard. Camden is where mountains, forests, and ocean converge — and you just experienced all three in one perfect day.

  • Transfer: 1 hour 45 minutes
  • Today’s Activity: hike 1.3 miles
  • Meals: Lunch and Dinner
  •  First of 2 nights: The Blue Harbor House Inn

Local Secret: The Camden Public Library’s reading room overlooks the harbor. It’s the kind of place that makes you want to move to Maine.

DAY 2 Cycling Islesboro Island

 Island Life at Its Finest

Not a tourist — an explorer.

An early morning ferry carries you from Lincolnville to Islesboro Island in the heart of Penobscot Bay. The twenty-minute crossing offers beautiful views of the Camden Hills you hiked just yesterday — a perfect reminder of how far you’ve come.

Stately pines and grand 40-room “cottages” (as some folksmodestly call their summer estates) serve as your backdrop as you cycle around one of Maine’s prettiest islands. Your guides set the perfect pace, sharing stories of island life and pointing out hidden coves along the way.

After cycling, you have options: visit a coastal winery for a tasting, or take a refreshing swim in Lake Megunticook. Your guides know the best spots — and they’re happy to lead the way or give you space to explore on your own.

What You’ll Feel: The rhythm of island living. Where 15 miles feels like pure freedom, and afternoon swims in freshwater lakes are just what summer afternoons are made for.

  • Today’s Activity: cycle 15 or 26 miles (your choice)
  • Meals: Breakfast, Lunch and Dinner
  •  Second of 2 nights: The Blue Harbor House Inn

Island Insider Tip: Islesboro has been a summer retreat for over a century. Today, you’re riding the same roads that generations have pedaled before you.

DAY 3 To Bar Harbor and Kayaking

The Quiet Side of Acadia

Safe, supported, and designed for every adventure.

The morning begins with a scenic transfer to Bar Harbor, gateway to Acadia National Park. The anticipation builds with every mile.

In the afternoon, you kayak the quiet side of Mt. Desert Island with expert guides who time your paddle with the tide — letting the ocean do some of the work while you soak in the views. Keep your eyes open for seals lounging on rocks, Harbor Porpoise cutting through the water, and Bald Eagles soaring overhead. Your guides know where to look, and they’ll make sure you don’t miss a thing.

What You’ll Feel: Connected to the water in a way you’ve never experienced. Kayaking isn’t just about the paddling — it’s about the silence, the wildlife, and the way the coastline reveals itself when you’re moving with the currents and the tides.

  • Transfer: 1 hour 45 minutes
  • Today’s Activity: 2 hour guided kayak tour
  • Meals: Breakfast and Lunch
  •  First of 2 nights: The Harborside Hotel

Paddler’s Promise: While wildlife sightings aren’t guaranteed, your guides know these waters intimately — and they’ll give you the best chance of spotting Maine’s coastal creatures.

DAY 4 Great Head Peninsula and Acadia’s Carriage Roads

The Best of Acadia

Earn the view. Savor the moment.

Begin your day walking along Acadia’s famous Sand Beach. Pause to dip your toes in the ocean (fair warning: it’s bracing!) before continuing to the trailhead. A moderate climb through white birch trees leads to stunning views of the islands of Frenchman Bay and Otter Cliffs.

After your hike, take time to explore Bar Harbor and find lunch on your own — your guides can point you toward the best spots. In the afternoon, you’ll cycle Acadia’s famous Carriage Roads. Late afternoon is magical here — the crowds have disappeared, the light is golden, and the forest feels like it’s yours alone.

What You’ll Feel: The perfect blend of challenge and reward. Your legs have earned these views. Your spirit has earned this peace. And tonight’s dinner? You’ve definitely earned that too.

  • Today’s Activity: hike 1.6 miles | cycle 15 miles
  • Meals: Breakfast and Dinner
  •  Second of 2 nights: The Harborside Hotel

Carriage Road Magic: Rockefeller built these roads for horses and carriages. Today, they’re some of the most beautiful car-free cycling in America. And you’re riding them at the best possible time.

DAY 5 Park Loop Road

The Grand Finale

Stories you’ll tell for years.

For early risers, your guides offer a pre-dawn van ride up Cadillac Mountain to watch the sunrise from the highest peak on the North Atlantic seaboard — with an optional hike down for those who want to earn their breakfast. Coffee awaits the brave souls who made it to the summit.

Then it’s time for the main event: cycling Acadia’s Park Loop Road as it follows the dramatic coastline. The ambitious can choose to cycle up Cadillac Mountain (you’ve already been to the top — now earn it on two wheels). Everyone will enjoy magnificent ocean views as the road winds between granite cliffs and crashing surf.

At noon, you depart for the 3.5-hour transfer to Portland, where your leaders will drop you at the airport, train station, or your post-tour hotel. But the memories? Those travel home with you. Along with the confidence that comes from knowing you hiked, cycled, sailed, and paddled your way through some of Maine’s most stunning landscapes.

What You’ll Feel: Accomplished. Proud. Alive. Transformed. And already planning your next adventure.

  • Today’s Activity: hike 3.5 miles | cycle 12 to 24 miles
  • Meals: Breakfast
  • Transfer: 3.5 hours to Portland

Sunrise Reward: Watching the first light hit the Atlantic from Cadillac Mountain is something you’ll remember for the rest of your life. Set your alarm. It’s worth it.

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
  • Most meals – including three dinners, four breakfasts, and three lunches
  • All taxes and gratuities for these meals
  • Hybrid or E-Bike or All-Road bike rental and helmet
  • Expenses paid for ferry transits, kayaking, and sailing aboard the schooner
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  • Entrance fee for Acadia National Park
  • 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)
  • Alcoholic beverages are not included in the package price and are always at your discretion
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Carol & Bill W from Massachusetts
★★★★★

We had a wonderful time as usual with Summer Feet Cycling. This was our second trip with you and you did not disappoint. The trip was all that was expected and more. The weather was gorgeous, the cycling superb, the accommodations wonderful and comfortable, the sunset cruise and dinner terrific. Best of all, the group and guides were a lot of fun to be with. We certainly enjoyed ourselves immensely. We give Kim and our guide high marks for availability, friendliness, assistance, and trying to meet all the needs of a varied cycling group. You get a 10.

Joann F from New York
★★★★★

We just started biking this past March … on the land that is basically flat. It was a rude awakening when we started the bike tour. … I never worked so hard in my life. BUT I LOVED IT. It made me a better biker and it inspired me to get better. I had a wonderful time!

Bob & Tyko K from Florida
★★★★★

The trip was great in itself, but our guides … they added another level of “greatness” to the entire experience.

Frequently asked questions

How physically demanding is the Maine Multi-Sport Tour?

The tour is moderately active. Guests hike between 1.3 and 3.5 miles, cycle 12 to 26 miles on select days, and participate in a 2-hour guided sea kayak tour. Most active travelers who are comfortable exercising on consecutive days are well suited for this itinerary.

No prior kayaking experience is required. The 2-hour sea kayaking tour near Mount Desert Island is led by professional guides who provide instruction and paddle with the tide to make the experience accessible for beginners.

Cycling distances range from 12 to 26 miles depending on the day and selected routes. Terrain includes island roads, Acadia National Park’s Carriage Roads, and sections of the Park Loop Road. You can always opt for an e-bike which will help with the hills and the longer distances.

The tour’s itinerary includes hiking in the Camden Hills State Park and Acadia National Park, cycling on Islesboro Island and Acadia’s Carriage Roads, a 2-hour sea kayaking experience, and a sail aboard the historic Schooner Olad. The itinerary combines multiple outdoor experiences across Penobscot Bay and Mount Desert Island.

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