Day One: The Olde King’s Highway
Drive the length of scenic Route 6A, the Old King’s Highway, designated one of the most scenic byways in America. Browse antique shops, art galleries, boutiques, and one-of-a-kind gift shops along the way. Have lunch at the Brewster Fish House. Visit the Natural History Museum and walk the nature trails across the marsh to the Brewster Flats at Paines Creek. Catch the sunset along the boardwalk at Gray’s Beach in Yarmouthport. Stop for a soft serve at Captain Frosty’s.
Day Two: The National Seashore
Head east to the National Seashore. Take a side trip to Fort Hill for a view of Nauset Beach and the Penniman House and a walk along the nature trails. Continue on to the Salt Pond Visitors Center at the start of the National Seashore in Eastham. See the Coast Guard Station at Coast Guard Beach, the Nauset Beach Lighthouse, and the Marconi Wireless Station site. Drive down Lecount Hollow Road to Ocean View Drive, past Cahoon Hollow to Newcomb Hollow. Stop at Arnold’s on Route 6 for onion rings and fried clams. Catch a movie at the Wellfleet Drive-In.
Day Three: Provincetown
Hop on Route 6, the mid-Cape Highway, and make a bee-line for Provincetown. Along the way you can detour for a tour of Truro Vineyards and the Atlantic Spice Company. Climb the Pilgrim Monument for a spectacular view. Take a one-of-a-kind tour of the dunes with Art’s Dune Tours. Alternatively take a whale watching excursion to Stellwagen Bank. Have lunch at the Lobster Pot, then stroll the shops and galleries along Commercial Street. Drive to the Province Lands Visitors Center and watch the sunset over Race Point.
Day Four: Cape Cod Rail Trail
Grab your bike and ride the 26-mile Cape Cod Rail Trail. Pack a lunch for a picnic along the trail. Take a detour into Nickerson State Park and have a swim in the one of the lovely ponds. Return via 6A through Dennis on 6A and stop at the Sesuit Harbor Café for a lobster roll or perhaps a sunset cruise in the harbor.
Day Five: Sandwich
Spend the day in Sandwich, the oldest town on Cape Cod. Tour the Sandwich Glass Museum and visit the Dexter Grist Mill. Have tea at the Dunbar Tea House. Walk the boardwalk out to Cape Cod Bay or stroll along the 6-mile trail that lines the Cape Cod Canal. Grab a bite to eat at Seafood Sam’s or order a steamed lobster from Joe’s Seafood Market and dine at a picnic table along the canal. Then spend the afternoon at the Heritage Museum and Gardens. Stroll acres of perennial gardens, visit the historic Shaker round barn with its spectacular classic car collection, and the exhibits of military miniatures, antique toys and Native American artifacts in the American History Museum. Take a ride on the working carousel and stay for an evening concert at the amphitheater.
Day Six: Boston
Take a day trip to Boston (one hour by car) to walk the Freedom Trail, or take a Duck Mobile or Beantown Trolley tour of the city. Visit the New England Aquarium, Old Ironsides, Bunker Hill Monument, Quincy Market, and Faneuil Hall. Dine on fresh seafood at Legal Seafood or the Union Oyster House.
Day Seven: Chatham
Travel to Chatham, the “elbow” of Cape Cod to see the Chatham Lighthouse. Browse the shops along Main Street. Drive out to the Chatham Fish Pier to see the day boats unload their catch. Take Shore Road past Chatham Bars Inn to Morris Island and the Monomoy National Wildlife Refuge. Take a seal cruise aboard the Rip Ryder or have them drop you off for an afternoon at the beach on South Monomoy. Dine at The Impudent Oyster.
Day Eight: Newport
Venture to Newport, R.I. (90 minutes by car) and tour the mansions that were the summer homes of the Vanderbilts and Astors. Take a leisurely drive along the 10-mile Ocean Drive, walk the Cliff Walk in front of The Breakers, Marble House and Chateau Sur Mer. End your day with a bowl of steaming clam chowder at the Black Pearl on the water.
Day Nine: Cape Cod at Play
Spend the day at any one of Cape Cod’s beautiful beaches soaking up the sun, reading the latest novel, walking the coastline in search of treasures from the sea, or frolicking in the waves. Alternately, take a kayak trip in Pleasant Bay or Nauset Marsh with Osprey Sea Kayak Adventures or golf at any of our championship golf courses. After dinner, catch a play at the Cape Cod Playhouse, America's oldest professional summer theatre (in season).
Day Ten: Nantucket
Take the high speed ferry (one hour) to Nantucket for the day. Visit the Whaling Museum. Rent a moped or bicycle and ride the Polpis Road out to ‘Sconset to see the rose-covered fishing cottages. Walk the cobblestone streets of Nantucket Town, climb to the top of the First Congregational Church bell tower on Center St. for a beautiful view of the harbor. Have lunch at the Brotherhood of Thieves or Le Languedoc. Be sure to throw a penny off the stern of the ferry as you pass Brant Point Lighthouse to ensure your return trip to the island one day.
Day Eleven: Falmouth and Woods Hole
Drive to Falmouth and Woods Hole via Route 28A, which will take you through the lovely community of West Falmouth with its many antique shops. Stop for lunch at Dana’s Kitchen for unusual sandwiches, homemade soups and salads. Turn right on Palmer Ave in downtown Falmouth for shopping. Follow Sippewissett Road, a windy 8-mile route that takes you past beautiful homes with great views of the water into Woods Hole, home to the Woods Hole Oceanographic Institution. Alternately you can ride your bike along the Shining Sea Bike Trail. On the return trip have dinner at the Chapoquoit Grill, then catch the sunset from Chapoquoit Beach near the restaurant.
Day Twelve: Plimoth Plantation
Spend the day at Plimoth Plantation in nearby Plymouth, MA (45 minutes by car). Plimoth was the first permanent European settlement in the “New World“. Today it is a living history museum dedicated to recreating the 17th century lifestyle. Tour the Mayflower II, a recreation of the original, and learn about the perils of the 1620 journey. Stop to see Plymouth Rock, located on the waterfront in downtown Plymouth, close to where Mayflower II is anchored.
Day Thirteen: Martha’s Vineyard
Take the Island Queen ferry (35 minutes) from Falmouth Harbor to Oak Bluffs on the island of Martha’s Vineyard for the day. Rent a bike or moped and ride into Edgartown via the designated bike path. Take the 5-minute ferry trip to Chappaquiddick and take the lighthouse tour or visit Mytoi Japanese Garden. Return to Edgartown for lunch at Alchemy. Then ride down to Katama Beach for fine surfing. Alternatively, drive out to see the fishing village of Menemsha, Aquinnah, and the cliffs at Gay Head. Return to Oak Bluffs and ride the Flying Horses carousel before returning to the mainland via ferry.
Day Fourteen: Rail and Sail
Ride the rails on the Cape Cod Scenic Train, a 2-hour journey through beautiful cranberry bogs, natural woodlands, lush marshes and more as you make your way between Hyannis and the Cape Cod Canal. Stop for lunch at Baxter’s Boat House on the harbor then set sail for a leisurely one-hour harbor cruise aboard the Maine coastal steamer replica, Prudence, which will take you on a journey of Lewis Bay and Hyannis Harbor. You can visit the shops along the harbor, then head down Main Street to the JFK Museum. End you day with a concert at the Cape Cod Melody Tent (in season) or stop for a nightcap and some jazz at Harry’s Blues Bar.
