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Gloucester - Kennebunkport - Concord NH - Boston (Self Drive)

7 to 10+ Nights from $1,769*
* This sample price: priced within the past 7 days for arrival on 5/6/2024, departure from Sacramento SMF (CA), US. Choose your own departure city and dates.

This 7 night sample itinerary includes:

  • Flight into and out of Boston
  • Rental Car for 6 days
  • Hotel for 2 nights in Gloucester
  • Hotel for 2 nights in Kennebunkport
  • Hotel for 1 night in Concord NH
  • Hotel for 2 nights in Boston
  • Driving Time
    Boston Airport - Gloucester: 55 min. approx.
    Gloucester - Kennebunkport: 1 hr. 40 mins approx.
    Kennebunkport - Concord NH: 1 hr. 30 mins approx.
    Concord NH - Boston: 1 hr. 10 mins. approx.

These New England' States; Massachusetts, Maine New Hampshire are combined in this Self-Drive Package for an unforgettable holiday. Start in Gloucester (worth visiting for its history, seafood restaurants, whale watch cruises, artists' colony, historic houses, and its fine beaches). Then drive up to the southern Maine coastal area, to Kennebunkport (summer destination with diverse shops, restaurants and venues specially at the Dock Square area). After that, continue to Concord-NH in New Hampshire, with its well known carriage making, and the `Concord coaches`. Finally , spend a nice stay in Boston (one of the oldest and populous cities of Massachusetts, famous for its baked beans and the Boston Marathon). 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

  • Gloucester, MA

  • Kennebunkport, ME

  • Concord, NH

  • Boston, MA

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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:
Gloucester, MA
Kennebunkport, ME
Concord, NH
Boston, MA

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Trip Summary

  • Gloucester, MA

    Gloucester lies between Ipswich Bay to the north and Massachusetts Bay to the south. The city is bordered on the east by Rockport, and on the west by Ipswich, Essex and Manchester-by-the-Sea to the west. Gloucester is worth visiting for its history, for fishing, seafood restaurants, whale watch cruises, artists` colony, historic houses, and the fine beaches.

    Explore The Hammond Castle Museum, the Halibut Point State Park, the Wingaersheek Beach, the Annisquam Lighthouse, the Good Harbor Beach, the Singing Beach, the Cape Ann Museum, the Stage Fort Park, the Cape Ann Whale Watch 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!

  • Concord, NH

    Concord is the capital city of New Hampshire. In the 19th century, Concord became a hub for the railroad industry, with Penacook a textile manufacturing center using water power from the Contoocook River. The city is home to the State House, a gold-domed building dating from 1819, with a visitor center and the Hall of Flags.

    Explore The McAuliffe-Shepard, the Canterbury Shaker Village, the Bear Brook, the New Hampshire State House, the Chuckster`s, the NH Audubon, the New Hampshire Historical Society and so much more!

  • 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!