Search
Tour

Bar Harbor and Portland 5-day Itinerary (5 days)

Tour Operator
Overseas Network

Portland, ME, United States to Bar Harbor, ME, United States

Valid for Departures Now Through: 03 Sep 2025
Virtuoso Benefits
For availability and pricing:

Discover New England charm in two popular Maine destinations: Bar Harbor and Portland

Portland has grown from a small colonial seaport to Maine’s largest metropolitan area – and one of the hippest towns on the East Coast – over the past 400 years. In the last few decades, urban renewal projects breathed new life into the historic waterfront and downtown areas, where trendy restaurants and galleries sit side by side with handsome heritage landmarks. Despite this city’s cultural and culinary flair, it’s still a thriving fishing port offering a bit of grit alongside its graciousness.

After just one stop in Bar Harbor, it becomes evident why the Mount Desert Island city has long been a draw for vacationers. With a focus on conservation, the village exudes natural beauty in its mountain-top views, New England charm, and many outdoor adventures.

Itinerary

Day 1
Portland, ME United States

Hotel: The Westin Portland Harborview
Meals: Dinner

Arrive in Portland and Check-in to The Westin Portland Harborview

Enliven your Maine getaway at The Westin Portland Harborview, where you'll dwell in historic charm. Originally opened in 1927 as the Eastland Park Hotel, our hotel is immaculately restored while maintaining its rich beauty. In our New England town, you can explore the seafood restaurants and unique shops in Old Port, and admire river and mountain views on Western Promenade.

Private New England Cooking Class

The Maine Coast is known for its amazing seafood. Learn how to cook the staple of Maine food: Chowder! There are 3 different ways to prepare this dish. Choose your style, gather the ingredients, and put your hands to the test! While you prepare dinner, enjoy a nice bottle of wine - and while the chowder is cooking, chuck some oysters! The whole experience is set on a professional kitchen, with all the necessary gear.

Day 2
Portland, ME United States

Hotel: The Westin Portland Harborview
Meals: None

Portland, Lighthouses, and Kennebunkport Private Tour

Start your private day trip with a narrated tour of Portland’s historic landmarks. Portland was founded in 1632 and has a long and colorful history. After a short drive to Cape Elizabeth, stop and explore Portland Head Light which was first lit in 1791. Commissioned by President George Washington, it is Maine’s oldest lighthouse.

Explore Kennebunkport, which is alive with history, grand ocean views, wonderful restaurants, and interesting shops. You will see many historic ship-captain homes from the 19th century with interesting stories. Stop for the freshest lobster rolls and seafood to have a memorable lunch and explore the nearby local shops.

Day 3
Bar Harbor, ME United States

Hotel: Under Canvas Acadia
Meals: None

Roadtrip to Bar Harbor and Check-in to Under Canvas Arcadia

With breathtaking views of the Maine coastline and Acadia National Park, Under Canvas Acadia is the perfect base camp for an ideal New England getaway. Enjoy glamping in the Stargazer tent on 100 acres of waterfront land, with more than 1200 feet of coastline, just 35-minutes to the acclaimed Cadillac Mountain Trail and more broadly, Acadia National Park. Under Canvas Acadia allows you to explore the beauty of Maine by day and the comforts of home by night.

Day 4
Bar Harbor, ME United States

Hotel: Under Canvas Acadia
Meals: Lunch

Lobsters, Seals & Lighthouses w/ Island Picnic

Ride on a real lobstering boat through the coast of Bar Harbor, and spot not only the lighthouses scattered around the sea, but also the local wildlife: seals, birds, and with some luck... whales! The waters around Acadia are very calm, and the ride is super smooth. We will also stop at a secluded island, hop out of the boat, and enjoy a tasty picnic, before heading back to the water. The captain will share stories about Bar Harbor, and show some of the most amazing sights around.

Day 5
Bar Harbor, ME United States

Hotel: Under Canvas Acadia
Meals: Lunch

Bar Harbor Hike & Eat

Experience: Explore the streets and restaurants of Bar Harbor in this exciting walking tour! The city is an amazing place to eat - and is filled with history! We will stop at a few local restaurants, grab some snacks and learn about the history of the city.

Check-out of Hotel and Return to Airport

Virtuoso Benefits

Product Terms & Conditions

Terms and conditions vary by program. Details will be provided upon booking/request.



The trademarks VIRTUOSO, the Globe Swirl Logo and SPECIALISTS IN THE ART OF TRAVEL are registered trademarks of Virtuoso, Ltd. Virtuoso, Ltd. has a U.S. copyright registration for the Globe Swirl Logo, ©2000. All rights reserved. Virtuoso CST#2069091-50. California CST# 2069091; TA# 808 - Registered Iowa Travel Agency; Washington UBI # 601 554 183. Registration as a seller of travel does not constitute approval by the State of California.