Boston & Salem for Halloween

Pilgrims, Pillories and Haunting History

  • Date

    October 25-29, 2020 | Sun / Thu – 5 Days

  • Location

    Boston | Cambridge | Salem | Plymouth


As one of the oldest cities in the United States, Boston boasts nearly 400 years of history since the first Pilgrim’s arrived. Enjoy a historical tour of the city, a visit to the John F. Kennedy Presidential Library and Museum, and free time on your own. Infamous for its witch trials of the 1600s, Salem has embraced its sinister past and transformed October into a month of scary fun. A guided tour of the Witch Trial Memorial and Old Burying Point, along with a visit to Salem Witch Museum will set the ghostly mood. Dive deep into the rich legends of Harvard’s past with a student guide, and spend a day in Plymouth touring Burial Hill and celebrating the 400th anniversary of the Pilgrim’s landing. With Halloween just around the corner, this trip of spooky haunts is sure to delight!


  • Visit Salem at Halloween time
  • Tour the Salem Witch Museum and the House of Seven Gables
  • Haunted tour of Harvard University
  • Plimoth Plantation and tour of Burial Hill
  • Celebratory Pilgrim Harvest Feast
  • Sightseeing tour of Boston
  • Nostalgic dinner in historic downtown Boston
  • Visit the John F. Kennedy Presidential Library and Museum


  • Roundtrip commercial air from Indianapolis to Boston, Massachusetts
  • Escorted
  • 4 nights accommodations
  • Breakfast daily
  • 2 lunches, 2 dinners
  • Sightseeing and admissions per itinerary
  • Ground transportation
  • Hotel baggage handling


This itinerary includes activities where moderate walking, possibly on uneven terrain, is required. Some of the most unique sightseeing can be restrictive to motorcoaches, especially in historic areas.

Sun, Oct 25: Fly to Boston, Massachusetts. Tour Boston with a local guide, and stop for a slice of Boston Cream Pie at the Omni Parker House, the very place where this famous dessert originated in 1856. It was also here in this hotel restaurant that John F. Kennedy proposed to Jackie Onassis. Enjoy free time for lunch at the Boston Public Market, or stroll through Boston Common. Check in to your hotel, The Bostonian, occupying one of the city’s best locations — just steps from Quincy Market and Faneuil Hall Marketplace and a short walk from Boston Harbor and the Freedom Trail.

Mon, Oct 26: This morning, travel to Cambridge, the home of Harvard University. A university with this much history is sure to have some skeletons in its closet! On a guided tour, hear about the impact the school has had on American history, with some interesting folklore woven in as well. Dive deep into the rich legends of Harvard’s past and discover what makes Harvard so unique. Enjoy lunch in the university town before returning to the hotel for the remainder of the day at leisure. (Meals: Breakfast, Lunch)

Tue, Oct 27: Today is all about Salem. See the village come alive around Halloween, as people travel from near and far to celebrate the season in this spooky town. A local guide will take you on a walking tour including the Witch Trial Memorial and Old Burying Point. Visit the Salem Witch Museum and learn about the Salem Witch Trails of 1692, and the interesting phenomenon of witch hunting. See a presentation based on actual trial documents and experience the drama of that dark period. Enjoy free time for lunch at Pickering Wharf and explore the nearby Salem Maritime Historic Site. This afternoon, the House of Seven Gables is sure to catch your attention. Built in 1668 right on Salem Harbor for merchant John Turner, the home’s iconic black shingle siding is in stark contrast to the beautiful gardens on site. Best known today as the setting of world-renowned author Nathaniel Hawthorne’s novel of the same title, the home is a National Historic Landmark. Return to Boston and take in a different view as you travel by ferry to Boston Harbor. Enjoy a group dinner this evening. (B,D)

Wed, Oct 28: In nearby Plymouth a tour of Burial Hill will make your hair stand on end. As the site of one of the first forts built by the Pilgrims, this location claims an interesting history, with many of the first settlers being buried in the cemetery. Enjoy the peace and quiet, away from the bustle of town, and learn about one of America’s oldest and most significant burying grounds. After lunch on your own, tour the Mayflower in Plymouth Harbor and continue to Plimoth Plantation, to visit the Wampanoag Homesite and 17th-century English Village, a re-creation of the original Pilgrim’s colony. At the Wampanoag Homesite, you can see, touch, and experience the history of indigenous people and hear about the relationships between the two peoples. This evening, to celebrate the 400th anniversary of the landing of the Mayflower, enjoy a Wampanoag and Pilgrim inspired Harvest Feast. (B,D)

Thu, Oct 29: After checking out of the hotel, visit the John F. Kennedy Presidential Library and Museum. Engage in the interactive exhibits, presidential artifacts, and video presentations that take you on a journey from JFK’s childhood to the White House. Depart for the airport to return home. (B,L)

The Bostonian, Boston, Massachusetts.  Located central to popular landmarks such as the Boston Harbor, Freedom Trail, and Quincy Market. This beautiful hotel features stunning views, thoughtful furnishings, and modern conveniences. Highlights: in-room coffeemaker and mini-refrigerator • bar/lounge • fitness center • Spa.


  • Package with Air
  • Double P/P – $2,699
  • Triple P/P – $2,489
  • Single – $3,349
  • Land Only
  • Double P/P – $2,129
  • Triple P/P – $1,919
  • Single – $2,779

* Subject to change due to increase in exchange rate or fuel surcharge

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