Bound for Boston featuring Rockport, Gloucester and JFK's 100th Birthday

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Bound For Boston! It's a Presidential Celebration featuring Rockport, Gloucester and Camelot for JFK's 100th Birthday!

Day 1 - Hello Boston (D)
Arrive in the heart of Boston, with a first stop at Quincy Market and Faneuil Hall. Explore these historic landmarks with plenty of time for lunch and shopping on your own.
On a guided tour of the city, span the life of John Fitzgerald Kennedy, first son of Boston. From birth to adulthood, see the many sites with ties to this iconic man and his family, such as Old City Hall, Omni Parker House Hotel, Boston State House and more.

Dinner tonight will be in the historic north end, where you’ll enjoy authentic Italian dishes from Boston’s old neighborhood. After dinner, settle in at the Holiday Inn Express Brockton. Your home for three nights is conveniently located outside the city, central to the highlights of the next three days!

Day 2 – Rockport, Gloucester and Lobstah (B, D)
Today, journey outside the city to the beaches and boulders of the Massachusetts North Shore for a guided tour of Rockport and Gloucester. Hear legends and history at the Famous Fisherman’s Statue, Rocky Neck Art Colony, Eastern Point, Pigeon Cove and more.
Known as one of the prettiest towns in Maine, enjoy Rockport with lunch and shopping on your own. Stroll Bear Skin Neck, where fishermen’s homes have been converted into quaint shops, artist studios and antique stores.
Next stop – Gloucester, America’s oldest seaport, with centuries of seafaring history and stunning ocean scenery.
The perfect finish to your day is a Lobsterbake Dinner at the famous Gloucester House Restaurant.

Land Ho!
Optional Gloucester Harbor Cruise
Leave the wharf and hit the waves! Join us for an optional afternoon cruise of Gloucester Harbor, one of the country’s most beautiful harbors. Enjoy a narrated tour including the famous fishing fleet, Ten Pound Island, Norman’s Woe, and more. It’s a chance to see sights inaccessible from land -- bring your camera!

Day 3 – Happy Birthday, Mr. President (B, D)
Begin your morning 70 stories in the sky, high atop the city at the Prudential Center Skywalk. The city’s only observation deck with a 360 degree panorama, you’ll have a breathtaking, bird’s eye view of Boston and beyond!

Next, relive JFK’s legacy at his Presidential Library and Museum. Relive the powerful Kennedy years in the re-created world of the Kennedy Presidency.

Tonight, it’s a birthday dinner fit for a Commander in Chief!  Don your non-partisan party hat for a Presidential Dinner celebrating JFK’s 100th Birthday. With music, a festive atmosphere, a live show and more, it’s a night of Camelot. Happy Birthday Mr. President, this is a special event honors the ‘High Hopes’ of JFK’s youthful administration, with dinner and dancing to the music of the era and a tribute to the celebrities and songs he liked best.

Day 4 – Goodbye at Galillee (B,L)
Today we leave this City on a Hill, and it’s favorite son, JFK. Finish the trip with a farewell three-course luncheon overlooking Block Island Sound at local favorite George’s of Galilee.

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  • $759 triple
  • $799 double
  • $999 single
  • Travel Protection 10%


  • Faneuil Hall & Quincy Market
  • Rockport and Gloucester Guided Tour
  • Prudential Center Skywalk
  • JFK Museum
  • Lobster Bake Dinner
  • Presidential Dinner Birthday Bash
  • Upper Class Tour Director, Taxes & Gratuities


Sunday June 11th, 2017

  • Yonkers 8:00 am
  • Mamaroneck 9:00 am


Wednesday June 14th, 2017

  • Mamaroneck 5:00 pm
  • Yonkers 5:45 pm