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Massachusetts and Maine Coastal (Self-Drive)

10 to 15+ Nights from $2,860*
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* This sample price: priced within the past 7 days for arrival on 8/17/2024, departure from Houston HOU (Hobby) (TX), US. Choose your own departure city and dates.

This 10 night sample itinerary includes:

  • Flight into Boston and out of Bangor
  • Hotel for 3 nights in Boston
  • Rental Car for 8 days
  • Hotel for 2 nights in Kennebunkport
  • Hotel for 1 night in Boothbay Harbor
  • Hotel for 3 nights in Bar Harbor
  • Hotel for 1 night in Bangor
  • Driving Time
    Boston - Kennebunkport: 1 hr. 35 mins. approx.
    Kennebunkport - Boothbay Harbor: 1 hr. 45 mins. approx.
    Boothbay Harbor - Bar Harbor: 2 hrs. 50 mins. approx.
    Bar Harbor - Bangor: 1 hr. 15 mins. approx.

Enjoy this Road Trip to The Bay and The Pine Tree States; with their charming coastal towns. Make sure you are hungry, as you will be find many delicious lobster dishes throughout the trip. Start in Massachusetts, visiting Boston (historic city and capital of Massachusetts famous for the Boston Tea Party); then, drive to Maine State and explore; Kennebunkport, them, Boothbay Harbor (a popular yachting and tourist destination during summer time), Bar Harbor, and finally, Bangor (best-known resident, author Stephen King, the city has much to offer to visitors with its small town charm). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.

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Arrival date

Please contact us for any special arrangements such as more than three rooms and partial stays.

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Flexible Itinerary

  • Boston, MA

  • Kennebunkport, ME

  • Boothbay Harbor, ME

  • Bar Harbor, ME

  • Bangor, ME

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Price Guidance

The package rates displayed are your total price per person based on Double Occupancy and your Arrival Date and Number of Nights selected. You can change details after selecting your travel date.

Price history for this itinerary (past 7 days):

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*Sample prices on display include ALL taxes & fuel surcharges... read more

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Going To:
Staying For:
Boston, MA
Kennebunkport, ME
Boothbay Harbor, ME
Bar Harbor, ME
Bangor, ME

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Trip Summary

  • Boston, MA

    Whether you are looking to take in the skyline or enjoy art, visit a museum or spend the day getting pampered, you will find what you want in Boston. Laced with parks, and pathways you can easily take in the skyline, while enjoying walking the Greenway, Harborwalk, Esplanade or Freedom Trail.

    Explore The Freedom Trail, the Museum of Fine Arts, the Faneuil Hall Marketplace, the Boston Tea Party Ships & Museums, the Boston Public Garden and so much more!

  • Kennebunkport, ME

    Kennebunkport is a coastal town in southern Maine. It cycles through four seasons annually, making it a versatile and desirable year- round destination. Kennebunkport is known for its beaches, including long, sandy Goose Rocks Beach and smaller Arundel Beach. The Dock Square area has a district of souvenir shops, art galleries, schooner attractions, seafood restaurants, and bed and breakfasts.

    Explore The Seashore Trolley Museum, the Ocean Avenue, the Goat Island Lighthouse, the Dock Square, the Cape Porpoise Harbor, the Gooch`s Beach, the Walkers Point and so much more!

  • Boothbay Harbor, ME

    Boothbay Harbor is a town in Lincoln County, Maine, United States. It welcomes you with its bright summer colors and beautiful snowy winters. During summer months, the entire Boothbay Harbor region is a popular yachting and tourist destination.

    Explore the The Coastal Maine Botanical Gardens, the Pemaquid Point Lighthouse, the Maine Maritime Museum, the Popham Beach, the Reid State Park, the Popham Beach State Park and so much more!

  • Bar Harbor, ME

    Bar Harbor is a town on Mount Desert Island along Maine`s Frenchman Bay. Bar Harbor is known for its stunning coastal beauty, its many yachts and lobster boats, and its view of islands and ocean in settings that can range from glistening sunlight to thick fog and mist.

    Visit The Acadia National Park, the Cadillac Mountain, the Sand Beach, the Jordan Pond, the Park Loop Road, the Carriage Road, the Schoodic Peninsula, the Thunder Hole and so much more!

  • Bangor, ME

    Bangor is a city along the Penobscot River in the U.S. state of Maine. Bangor is known as the `Queen City` of Maine. Modern Bangor was established by European Americans in the mid-1800s, based on the lumber and shipbuilding industries. The city proper has a population of 33,039, making it the state`s 3rd-largest settlement, behind Portland (66,882) and Lewiston (36,221).

    Visit The Acadia National Park, the Stephen King House, the Hollywood Casino Hotel and Raceway Bangor, the Maine Discovery Museum, the Cole Land Transportation Museum, the Paul Bunyan Statue and so much more!