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Boston - Kennebunkport - Bar Harbor - Bangor (Self Drive)

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6 to 9+ Nights from $1,562*
* Sample price: priced within the past 7 days for a 7/17/2025 arrival, departing Miami MIA (FL), US. Choose departure city, cabin and dates.

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This 6 night sample itinerary includes:

  • Flight into Boston and out of Bangor
  • Hotel for 2 nights in Boston
  • Rental Car for 5 days
  • Hotel for 1 night in Kennebunkport
  • Hotel for 2 nights in Bar Harbor
  • Hotel for 1 night in Bangor
  • Driving Time
    Boston - Kennebunkport: 1 hrs. 35 min. approx.
    Kennebunkport - Bar Harbor: 3 hrs. 30 mins approx.
    Bar Harbor - Bangor: 1 hr. 10 mins approx.

Rolling green hills, beautiful panoramic views of the sea, and thrilling's cities you will discover with this Self-Drive package across Massachusetts and Maine States. Start in Boston (one of the oldest and populous cities of Massachusetts, famous for its baked beans and the Boston Marathon). After that, drive up to Maine Coast and spend pleasant days under the sun in Kennebunkport (known for its beaches, including long, sandy Goose Rocks Beach and smaller Arundel Beach) and Bar Harbor (the getaway to the mountains and cliffs of neighboring Acadia National Park). Finally, visit; Bangor (the city has much to offer to visitors with its small town charm, like a visit to its best-known resident, author Stephen King house).

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
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Flexible Itinerary

  • Boston, MA

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  • Kennebunkport, ME

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  • Bar Harbor, ME

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  • Bangor, ME

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Customer Reviews

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Trip Summary

  • Boston, MA
    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, 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!

  • Bar Harbor, ME
    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, 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!

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