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Welcome to Dream Vacations, a lifestyle column on travelling to amazing destinations with practical advice and my revelations about locales from years of personal experience. Winter is coming. In fact, in most of the northern US, it has arrived. Want to get away from the dreary sun-less expanse and snow-covered areas that you call home? Why not visit the charming, historical and most southern point in the contiguous United States: Key West.


A Bit of History

If you like a touch of culture in your travels, a winter visit to the sunny warm waters of Key West provides a plethora of options. The once Spanish-Cuban isle was sold to American businessman John W. Simonton, which was contested by another deed of sale to another prominent American, General John Geddes, former Governor of South Carolina. Simonton eventually won control of the island.

The island was home to Calusa and Tequesta Native Americans before the US gained control of Florida from Spain in 1821. Cubans and Bahamians also used the island for fishing and other commercial uses, but it was not regularly inhabited until the US took control of it.


Historical Sites

Any trip to Key West would not be complete without visiting some of the historical monuments and places that have made it a cultural icon including:

  • Little White House – used by President’s Taft, FDR, Truman, Eisenhower, Kennedy and Carter as a winter retreat, and it acted as a ‘second’ White House for some of them.
  • Ernest Hemingway House – home to the infamous writer, where portions of many of his novels were written.
  • Tennessee Williams House – is where A Streetcar Named Desire was originally written by the famous playwright.
  • Old Town – the area where many tourist sites are including Mallory Square, Duval Street, the Truman Annex and Fort Zachary Taylor.


Sun and Sand

Of course, with the warmest ocean waters on the mainland, Key West provides some of the best wintertime swimming without having to travel to Hawaii or other tropical locales. Some beaches that offer great views, swims and amenities include:

  • Smathers Beach
  • Fort Zachary Taylor Beach
  • Higgs Beach
  • Rest Beach

A major tourist and tropical location, you can experience many of the same great watersports and beach activities you would find in other tropical locales such as scuba diving, deep-sea fishing, snorkelling, yachting, parasailing, watercraft rentals and more.


Make it Conch Salad

The best Conch Fritters in Key West

Key West offers a wide and varied food scene, but its fresh seafood offerings are hard to beat anywhere in the US. One of its specialties, Conch (pronounced ‘kaanck’), is served up in a delicious tropical salad or as a fried fritter.  Of course, Conch is not the only local food specialty. Here is a great run-down on the best places to eat in Key West, including a wide range of local favourites.

Looking for top-notch accommodations in Key West? Try the Hyatt Residence Club Key West, Sunset Harbor right in the heart of Old Town, Key West. Dream Vacations even has limited availability!

Feel free to call me about any of our Resort rentals in Key West for January and February 2020.


*NOTE: I want to clarify, that none of the business operators included in my posts are affiliated with Dream Vacations in any way. I highlight those businesses that I have generally heard good things about, had good experiences directly with, or are generally known to have good industry reputations. Of course, your experience may differ.


Tags: winter getaway, Key West, Florida, United States, US, family vacation, beach vacation, family vacation