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This all-inclusive trip offers a unique juxtaposition of historic inns, fine dining, and modern and contemporary art all set within the scenery of the Berkshire Mountains. Beginning at the historic Red Lion Inn in Stockbridge, this six-day, five-night trip will take you to major Berkshires landmarks including Tanglewood, the Norman Rockwell Museum, the Clark Art Institute, Jacob's Pillow and the Williamstown Theatre Festival as well as newer gems like MASS MoCA and the Barrington Stage Company. Experience the quintessential Berkshires vacation with towns such as Lenox, Stockbridge, Great Barrington and Williamstown and connect with one of the most unique areas of the world. This 15-20 person group tour is a high-end experience with three tour guides throughout the week. Each stop on the trip includes a private guided tour and inside access including talkbacks with actors, docents and more. Transportation for the week is in luxury Mercedes vans.

Enjoy complimentary shuttle service from the Albany International Airport and begin the trip with a welcome lunch at the famed Red Lion Inn where you'll meet your three tour guides and the other guests on the trip. Parking for the week is also available for those driving. You'll kick off the trip with a private tour and performance at Jacob's Pillow, the acclaimed modern dance festival. Following the performance you'll dine at the Old Inn on the Green overlooking the Ted Shawn Theatre. You'll return to the Red Lion Inn for evening entertainment in the Lion's Den and return to your room for the evening.

On Monday, you'll enjoy breakfast at the Red Lion Inn before visiting the Norman Rockwell Museum for a private guided tour. Following the tour there will be time to explore the scenic grounds of the museum and enjoy lunch on the patio. In the afternoon, you'll have the option to visit the Berkshire Botanical Gardens or Chesterwood, the home of Daniel Chester French. There will be time to relax at the Birchwood Inn in the evening, where your bags will be waiting for you. You'll dine at a lovely French bistro followed by a performance of the Boston Symphony Orchestra at Tanglewood.

On Tuesday, you'll enjoy breakfast at the inn and then visit Edith Wharton's home, "The Mount." You'll take a private guided tour, have time to explore the gardens and enjoy a lunch on the patio overlooking the gardens. In the afternoon you can choose to shop in the quaint Berkshires town of Lenox and visit the many artisan shops or visit the Frelinghuysen Morris Studio for a private guided tour of some of Picasso's works. The evening will include a dinner at an American Bistro followed by a play at the Barrington Stage Company. Accommodations for the night will be at the Birchwood Inn.

On Wednesday, you'll enjoy breakfast at the inn and then visit MASS MoCA for a private guided tour of the contemporary art museum. Following the tour there will be time to explore the museum, take a guided hike or enjoy a round of golf. Luggage will be awaiting you at the nearby Porches Inn, where you'll relax before dining at Loom, a brand new restaurant by James Beard-award winning chef Cortney Burns. To cap off the day, you'll have top-notch seats at the Williamstown Theatre Festival's Nikos Stage production. 

On Thursday, after breakfast, you'll visit the Clark Art Institute for a private guided tour and time to explore the vast museum grounds on your own. Then you'll take in a matinee of the Williamstown Theatre Festival's mainstage production. After a dinner at Mezze Bistro, you'll enjoy raucous late night cabaret put on by the actors from the theatre festival. 

On Friday, you'll enjoy breakfast followed by a private guided tour of the Williams College Museum of Art and time to explore shops in WIlliamstown. You will say goodbyes to the group and be returned to the airport or to you car after a wonderful week!


    Location: Massachusetts, United States

    Duration: 6 days

    Voucher Redemption: You can present either a paper or an electronic voucher for this activity. 

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    Additional Information

      Operates: See Availability

      Departure Point:
      Stockbridge, MA

      Departure Time: 12:00 PM

    • Inclusions:
      • 5 nights accommodation
      • 3 expert trip leaders
      • All breakfasts and dinners including curated 3-course menus each night, plus 3 lunches
      • Snacks and beverages between meals
      • Luxury van transportation
      • Exclusive access to behind the scenes meet ups, talkbacks and visits
      • Comprehensive travel planner with detailed pre-trip information
      • All gratuities at hotels and restaurants
      • Baggage transfer and porterage
      • Complimentary shuttle service from local airports
      • Breakfast
      • Lunch
      • Dinner
      • Snacks
      • Bottled water
      • Coffee and/or Tea

    • Exclusions:
      • Airfare
      • Three "explore on your own lunches"
      • All alcoholic beverages are to be purchased by the guest

    • Other Information:
      • Confirmation will be received at time of booking
      • Not wheelchair accessible
      • Travelers should have a moderate physical fitness level
      • Children must be accompanied by an adult
      • You will receive a detailed pre-trip package with a recommended packing list
      • Please advise any specific dietary requirements at time of booking
      • Performance details will be announced at least 3 months prior to the trip
      • This tour/activity will have a maximum of 20 travelers

    Travel Voucher
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