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Maine/Boston: A New England Road Trip

New England (Maine, Massachusetts)Sep 21 – Oct 1, 202311 days · 77 places

JShared by Jake Sorce
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Day 1 · Thu, Sep 21

  • Flight

    Flight to Boston (BOS)

    Boston Logan International Airport9:15 AM

  • Stay

    Courtyard Portland Airport

    Courtyard Portland Airport, Maine3:00 PM

  • Car

    Rental Car Pickup - Thrifty

    Thrifty, Boston Logan6:15 PM

Day 2 · Fri, Sep 22

  • Event

    Welcome Reception

    North 43 Bistro, 1 Spring Point Drive, South Portland, ME 041065:30 PM

Day 3 · Sat, Sep 23

  • Event

    Harry & Emily's Wedding

    Anastos Residence, 56 Spruce Point Road, Yarmouth, ME 040963:00 PM

Day 4 · Sun, Sep 24

  • Note

    Explore Maine

    Portland, Maine9:00 AM

Day 5 · Mon, Sep 25

  • Note

    Drive to Salem / Explore

    Salem, Massachusetts9:00 AM

  • Note

    Courtyard Portland Airport - Checkout

    Courtyard Portland Airport, Maine11:00 AM

  • Stay

    Salem Waterfront Hotel & Suites

    Salem Waterfront Hotel & Suites, Salem, MA3:00 PM

Day 6 · Tue, Sep 26

  • Note

    Explore Salem / Drive to Cape Cod

    Salem, Massachusetts9:00 AM

  • Note

    Salem Waterfront Hotel & Suites - Checkout

    Salem Waterfront Hotel & Suites, Salem, MA11:00 AM

  • Stay

    Pelham House Resort

    Pelham House Resort, Cape Cod, MA3:00 PM

Day 7 · Wed, Sep 27

  • Note

    Explore Cape Cod

    Cape Cod, Massachusetts9:00 AM

Day 8 · Thu, Sep 28

  • Ferry

    Ferry to Martha's Vineyard

    Martha's Vineyard, Massachusetts12:00 PM

Day 9 · Fri, Sep 29

  • Note

    Explore Boston

    Boston, Massachusetts9:00 AM

  • Note

    Pelham House Resort - Checkout

    Pelham House Resort, Cape Cod, MA11:00 AM

  • Stay

    Hotel Commonwealth

    Hotel Commonwealth, Boston, MA3:00 PM

Day 10 · Sat, Sep 30

  • Note

    Explore Boston

    Boston, Massachusetts9:00 AM

Day 11 · Sun, Oct 1

  • Car

    Return Rental Car - Thrifty

    Thrifty, Boston Logan12:00 PM

  • Flight

    Flight home to Salt Lake City (SLC)

    Boston Logan International Airport5:05 PM

Ideas

  • Food

    Village Tavern

    Village Tavern, Salem, MA

  • Sights

    Harding Beach

    Harding Beach, Chatham, MA

  • Sights

    Coast Guard Beach

    Coast Guard Beach, Eastham, MA

  • Sights

    Provincetown

    Provincetown, MA

  • Sights

    Wood End Lighthouse

    Wood End Light, Provincetown, MA

  • Sights

    West Dennis Lighthouse

    West Dennis Lighthouse, MA

  • Sights

    Chatham

    Chatham, MA

  • Sights

    Stage Harbor Lighthouse

    Stage Harbor Light, Chatham, MA

  • Sights

    Hyannis

    Hyannis, MA

  • Sights

    Truro Vineyards

    Truro Vineyards, North Truro, MA

  • Sights

    Highland Lighthouse

    Highland Light, Truro, MA

  • Sights

    Nauset Lighthouse

    Nauset Light, Eastham, MA

  • Food

    The Seafood Shanty

    The Seafood Shanty, Edgartown, MA

  • Sights

    Jaws Bridge

    Jaws Bridge, Oak Bluffs, MA

  • Sights

    Edgartown

    Edgartown, MA

  • Food

    Nomans

    Nomans, Martha's Vineyard, MA

  • Sights

    Katama Beach

    Katama Beach, Edgartown, MA

  • Sights

    Edgartown Lighthouse

    Edgartown Harbor Light, Edgartown, MA

  • Sights

    Gay Head Light

    Gay Head Light, Aquinnah, MA

  • Sights

    Quincy Market

    Quincy Market, Boston, MA

  • Tour

    Boston Duck Tour

    Boston Duck Tours, Boston, MA

  • Sights

    Freedom Trail

    Freedom Trail, Boston, MA

  • Sights

    Harvard Square

    Harvard Square, Cambridge, MA

  • Sights

    Beacon Hill

    Beacon Hill, Boston, MA

  • Sights

    North End (Little Italy)

    North End, Boston, MA

  • Food

    Regina Pizzeria

    Regina Pizzeria, Boston, MA

  • Food

    Tree House Brewing

    Tree House Brewing Company, MA

  • Food

    Quincy Court

    Quincy Court, Boston, MA

  • Sights

    House of Seven Gables

    The House of the Seven Gables, Salem, MA

  • Sights

    Salem Witch Trials Memorial

    Salem Witch Trials Memorial, Salem, MA

  • Food

    Anna's Taqueria

    Anna's Taqueria, Boston, MA

  • Food

    Legal Sea Foods

    Legal Sea Foods, Boston, MA

  • Food

    The Hotel Salem

    The Hotel Salem, Salem, MA

  • Sights

    Long Point Lighthouse

    Long Point Light, Provincetown, MA

  • Sights

    Scenic Route 6A Drive

    Route 6A, Cape Cod, MA

  • Sights

    Flying Horses Carousel

    Flying Horses Carousel, Oak Bluffs, MA

  • Sights

    Isabella Stewart Gardner Museum

    Isabella Stewart Gardner Museum, Boston, MA

  • Sights

    The Satanic Temple

    The Satanic Temple, Salem, MA

  • Sights

    Count Orlok's Nightmare Gallery

    Count Orlok's Nightmare Gallery, Salem, MA

  • Sights

    Halloween Museum

    Salem, MA

  • Sights

    Essex Street

    Essex Street, Salem, MA

  • Food

    Odd Meter Coffee Co

    Odd Meter Coffee, Salem, MA

  • Food

    Ugly Mug Diner

    Ugly Mug Diner, Salem, MA

  • Food

    Ledger Restaurant

    Ledger Restaurant, Salem, MA

  • Tour

    Ghost Tour

    Salem, MA

  • Tour

    Hocus Pocus Tour

    Salem, MA

  • Sights

    Old Burying Point Cemetery

    Old Burying Point Cemetery, Salem, MA

  • Sights

    Salem Maritime National Historic Site

    Salem Maritime National Historic Site, Salem, MA

  • Sights

    Witch Board Museum

    Witch Board Museum, Salem, MA

  • Sights

    Witch Dungeon Museum

    Witch Dungeon Museum, Salem, MA

  • Food

    Dungerians

    Boston, MA

  • Sights

    Salem Witch House

    Salem Witch House, Salem, MA

  • Sights

    Portland Head Lighthouse

    Portland Head Light, Cape Elizabeth, ME

  • Sights

    Old Port

    Old Port, Portland, ME

  • Sights

    Salem Witch Museum

    Salem Witch Museum, Salem, MA

  • Sights

    Gingerbread Houses

    Oak Bluffs Campground Cottages, Oak Bluffs, MA

  • Food

    Chef Chow's House

    Chef Chow's House, Boston, MA

Make this plan your own — every place, in order, on your dates. Nothing personal comes with it.