Explore Bar Harbor and Portland


Meander down rocky coastline as you discover the stunning landscape and quaint towns that Maine has to offer. Build up your appetite to find out why Portland truly is the lobster capital of the world.

American Experiences: Explore Bar Harbor and Portland

from $779

per person

Details

Each American Experiences trip is designed for you to craft and customize your own adventure. Pick your own date, add or remove nights, upgrade your car, reverse cities, add on activities, and more. Our team of adventure experts has curated suggestions to make your trip incredible, and our team is standing by to assist you in creating your incredible adventure.

While crafting your road trip, be assured that your package includes centrally-located hotels, a Hertz car rental, breakfast daily, free hotel WiFi, and an adventure all your own.

*Above pricing quoted is per person, land, and air from Chicago.

Suggested Itinerary

Show Full Itinerary

Day 1: Arrive in Bar Harbor

Explore the most Northeastern state in the United States, known for its rocky coastline, maritime history and natural beauty. Start your adventure in Bar Harbor with its picturesque downtown, local culture and outdoor activities. The sights and activities are endless - quaint shops, restaurants, art galleries and entertainment await in Bar Harbor Center.

Day 2: Bar Harbor

Acadia National Park is one of the nation's most visited National Parks. Here you will find many hiking trails, rocky beaches and glacier-scored granite peaks such as Cadillac Mountain. Take a climb to the top for a photo op and incredible views. If hiking isn't for you, there is a Summit Road that twists around the north and eastern side of the mountain that will take you to the top. Watching the sun set (or sunrise if you're an early bird!) atop the mountain is a must.

Day 3: Bar Harbor to Portland

Set south for Portland today, this vibrant city known as America's Foodies Small City. From its tiny pastry shops to the Maine Lobster roll, every appetite is sure to be satisfied. Overwhelmed by options? Partake in a foodie walking tour for an inside look and taste of the area! Want to work up an appetite beforehand? Hop on a bicycle for a guided tour around the Portland Peninsula. Or, if you want something a little more unique, check out remote locations aboard a hovercraft! This evening, take a walk along the West End, which is known for its quiet waterfront park promenade, as well as its beautiful sunset views.

Day 4: Portland

Another day in foodie heaven! Today, choose to take your time exploring the many coffee shops and lobster shacks! Or, hop on New England's first and only human powered boat tour with Maine BayCycle! Want to embrace the lumberjack lifestyle of Portland? Try your hand at axe throwing at the Axe Pit bar! Whatever you choose to do, the adventure is up to you!

Day 5: Farewell

Stop at Dock Square for some shopping at one of the local boutiques and galleries that are filled with handcrafted Maine gifts before heading home. If driving south, stop in Kennebunkport known for its beaches and many surrounding Lighthouses.

Add-On Adventures

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Around The Peninsula Bike Tour

Explore the Portland Peninsula by bike with this guided tour. Start at the Eastern Promenade, making your way along the waterfront bike path until you reach the Back Cove Trail. Your guide will take you to the Old Port to see some of Portland's prettiest old brick buildings, where you learn the significance of local food, history and culture of this area.
$61 per person

5 Lighthouse Bike Tour with XL Lobster Roll

Discover Portland Maine and the shores of Casco Bay by bicycle! The 5 lighthouse bicycle tour of Portland, Maine features the Maine coast, lighthouses, and Portland’s history. Cycle along gorgeous routes then dig into authentic local cuisine!
$133 per person

Local Portland Brews Evening Tour

Spend the evening in the company of a guide learning about Portland's beer scene. You'll taste several samples, munch on vegetarian snacks and hear commentary about the history of brewing in the city.
$83 per person

Paint Outdoors in Portland, Maine

Immerse yourself and interpret the natural beauty of Maine by capturing the moment in a painting. Hike to the location then paint right in that spot! No experience necessary. This is an all level class that can be enjoyed by beginner painters as well as more experienced artists.
$95 per person

Hovercraft Tours of Portland Maine

The only hovercraft tour on the East Coast! Travel into areas to see natural beauty and wildlife that no other tour can access. Because the craft travels at a higher speed than other modes of transportation, you'll get to your destination quicker and will be able to spend more time exploring. Get a closer look at historical sights due to the shallow draft capability of the craft. If you would like a customized tour there is no limit to the possibilities. Find a remote beach for a picnic or go to that secluded Island restaurant you've been eyeing. Observe Osprey and Eagles in their environment and watch seals and fish swim off the ledges of the Bay.
$65 per person

Portland: Land, Sea, to Fork Food Tour

Uncover Portland's culinary scene as you eat your way through the historic Old Port area with this small-group walking tour. You and your fellow food tasters will get a chance to try cuisine from several restaurants —be prepared for everything from Italian fare to locally sourced seafood. You'll also get an insider’s look at the local food scene, with the opportunity to meet local chefs at some of your stops.
$90 per person

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American Experiences: Explore Bar Harbor and Portland

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Unscripted experiences, insider access and authentic local flavors


Our team of travel specialists and local contacts have curated some of the best, most exclusive and authentic experiences, restaurants and accommodations to truly immerse yourself in a way that wouldn't be possible in larger groups or just on your own.

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