Boston to New York by the Beaches
DAY 1: Boston
Arrive Boston and transfer to your hotel. Evening on own to stroll Boston’s lively neighborhoods and discover some of the city’s great restaurants.

DAY 2: Boston – Hyannis - Cape Cod / Yarmouth (76mi/122km)
This morning, depart for Cape Cod. In Hyannis, take a leisurely one hour cruise on Lewis Bay and Hyannis Harbor. The accompanying commentary points out the highlights and interesting anecdotes as you sail past vistas of historical interest, scenic islands and beaches, even two presidential summer homes. Then travel to the neighboring village of Yarmouth. Centrally located on Cape Cod, it’s a short drive to all that Cape Cod has to offer; beaches, shopping, golf, biking and hiking trails, and fine dining.

DAY 3: Yarmouth – Provincetown – Yarmouth (93mi/150km)
Today, visit the Cape Cod National Seashore to explore lighthouses, quaint coastal communities, and natural scenic beauty. Stroll the charming and upscale village of Chatham before visiting the lively artist colony of Provincetown. Here one can take a whale watch or shop its many eclectic art galleries and shops; or spend the day relaxing at your hotel’s sandy beach. Don’t leave New England without feasting on Lobster, steamers, corn-on-the- cob and all the trimmings!

DAY 4: Yarmouth – Woods Hole/Martha’s Vineyard Ferry – Martha’s Vineyard (28mi/45km)
Car and passengers drive on board the ferry in Woods Hole for the short, 45-minute ride to Martha’s Vineyard. Take the remainder of the afternoon to relax and familiarize yourself with the area before checking in to your island hotel.

DAY 5: Martha’s Vineyard
Today, take a tour of the Vineyard to see a variety of landscapes in the six independent towns whose separate histories form a composite tale of the island’s past. Tour “downisland”, the busy, fashionable eastern half of the Vineyard where Oak Bluffs, Edgartown, and Vineyard Haven lure the rich and famous; and up-island, the sparsely populated and sleepy towns to the west. Aquinnah is known for its beautiful clay cliffs and quiet natural serenity and the beach is one of the few nude beaches left in the U.S. Or explore the island on own and discover one of the island’s many hidden beaches.

DAY 6: Martha’s Vineyard - Woods Hole/Martha’s Vineyard Ferry – Mystic - Old Saybrook (147mi/237km)
Depart the Vineyard for Connecticut. This afternoon, visit Mystic Seaport, the museum of America and the Sea. Set on 17 acres, it depicts 19th c. seafaring life. This evening, visit Foxwoods or Mohegan Sun, the country’s two largest casinos under one roof. Try your luck at gambling or enjoy a show. Overnight in Old Saybrook, a charming, historical, coastal community.

DAY 7: Old Saybrook – New London / Orient Point Ferry – Riverhead, NY (108 mi/174 km)
It’s a short ride to the Orient Point Ferry where car and passengers board for the short 40 minute trip to the tip of Long Island. Upon arrival visit the North Fork to visit wineries and explore the region. Then, travel to Riverhead and check-in to your hotel at the west end of the Hampton’s South Fork

DAY 8: The Hamptons
Today one can stroll the charming villages filled with boutique shops and art galleries, have a picnic at an outdoor concert, tour the historic mansions, or just relax on the beach.

DAY 9: Riverhead– New York City (124mi/200km)
This morning, travel west toward New York City. If departing the country today, JFK International Airport is en route, or add on nights in this most iconic of all cities.


Hilton Back Bay


Blue Water on the Ocean

Martha\'s Vineyard

Mansion House

Old Saybrook

Saybrook Point Inn


Hyatt Place Riverhead

Package includes:
  • Accommodation
  • Passenger and vehicle fare for the Orient Point ferry and Martha\'s Vineyard Ferry
  • Taxes
  • Fly - Drive directions and information packet at hotel upon arrival