A Midwinter Cultural Getaway to Key West

A Midwinter Cultural Getaway to Key West



An escape to Key West is always tonic for the soul, especially when your Key West experience is created by the National Trust for lovers of architecture, art and history. Key West’s historic Old Town boasts a splendid architectural heritage, from colorful gingerbread Victorians to Bahamian-style houses to Art Deco masterpieces. In the arc of 100 years, Key West was both the wealthiest city in the United States and the most indigent, resulting in a beautiful city that stayed remarkably “as it was.”

Pricing from


Trip Type
Closer to Home, Group Travel Tour
Departure Dates
Feb 27, 2022 - Mar 3, 2022


Our home for the tour is the newly opened Kimpton property Fitch Lodge, a charming grouping of old-Key West-style houses that provide a relaxed garden setting and brand new guest rooms offering quiet comfort. We’ve booked upgraded King and Two Queen rooms, providing a bit of extra space. The hotel’s location on the east end of the historic district offers many great neighborhood restaurants, cafes, and bakeries close by. Key West Bight is only a 5 minute walk away and Mallory Square is a delightful, shady stroll of just over 15 minutes.


Cancellation by participant must be made in writing to ISDI and is effective only upon acknowledged receipt by ISDI. There is a non-refundable registration and planning fee of $500 per person regardless of cancellation date. Written cancellation  received by ISDI on or before October 18, 2021: full refund minus $500 per person registration and planning fee. Written cancellation received, via email, by ISDI between October 19, 2021 and January 10, 2022: full refund minus $1,800 per person cancellation fee (includes registration and planning fee). Written cancellation received by ISDI on or after January 11, 2022: no refund. Tour registration is non-transferable. In the case of cancellation, substitutions are not allowed. After the tour has commenced, no refunds will be issued for any reason including, but not limited to, unused portions of tour. If the tour is cancelled by ISDI or National Trust Tours due to low enrollment, active registrants will receive a full refund of all tour payments.


  • day 1

    Welcome to Key West

    Independent arrivals at Kimpton Fitch Lodge, one of the finest new B&B style properties in the Florida Keys. The tour begins with a late afternoon guided walk through lower Duval Street and Mallory Square, introducing the history, personalities, and architectural heritage of Key West’s historic core. Tonight, meet fellow travelers over dinner at a great local restaurant.

  • day 2

    History & Beauty in Key West

    Spend the morning learning about the earliest days of Key West with visits to two historic properties. Meet the director of the Key West Art and History Society’s impressive Custom House Museum before viewing the museum’s excellent exhibitions. Nearby, tour Audubon House, where the great artist and illustrator spent a winter in Key West discovering the many rare and beautiful birds of the Florida Keys. Lunch on a shaded restaurant terrace offers a welcome midday break. The afternoon is free allowing you to experience Key West at your own pace, do some shopping, or enjoy our hotel’s pool. Later, gather for a special sunset cruise on a chartered boat, a chance to relax and admire Key West as all early visitors did – from the
    water. Dinner is on your own.

  • day 3

    Architectural Gems & Garden Retreats

    The town of Key West is one of the country’s hot spots for preservation. Take a firsthand look during a leisurely morning walking tour with a local expert who will point out historic theaters, charming gingerbread houses, and hidden gems that abound in Key West. A morning highlight will be a visit to a lovely historic private home. After stopping for lunch at a favorite local spot, spend the afternoon exploring some of Key West’s enchanting gardens. First, as guests of the Key West Garden Club, we’ll explore the beautiful West Martello Tower gardens – a favorite hangout for local conchs laid out in a historic setting. Later, be invited into one of the island’s prettiest backyard gardens, for an intimate look at the rare tropical plants and flowers that thrive in the Keys. The evening is at leisure.

  • day 4

    Authors & Presidents

    Board our privately chartered island trolley for a leisurely journey around the more far-flung corners of old Key West before stopping at the Ernest Hemingway House for a private tour and a chance to see the descendants of the great author’s legendary cats. Cap off the morning with an expert-led tour of Harry Truman’s “Little White House” and Annex, an unexpected part of Key West history. Free time will be given for lunch and the afternoon. Tonight, celebrate your Key West adventure with an elegant farewell dinner at an award winning restaurant.

  • day 5

    Farewell to Florida

    Independent transfers to Key West airport for return flights home.

Everything you need to know about the tour

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