I knew when I visited Key West for the first time two-and-a-half years ago that I would return someday. Between the unforgettable 127-mile drive on the Overseas Highway, the colorful and quaint architecture, and the overall relaxed vibe of the island, I instantly fell in love with the “Conch Republic.” Winter is actually peak season for visiting Key West and I discovered that it’s much more comfortable in February than during the unbearably humid summer months like on my last trip. This time around I was able to take in more of the history and sights too.
Here are a few of the fun activities I enjoyed:
The “World Famous” Conch Tour Train
Operating since 1958, the “trains” are actually open-air trams that make a 14-mile loop around the island, passing the many sights, landmarks, and historic homes that Key West has to offer. The “engineer” narrates the 90-minute tour with colorful anecdotes, describing the history of the island and recounting the many local legends. The tour begins at Front Street Depot and gives access to the Key West Aquarium, The Shipwreck Treasures Museum, The Audubon House, The Harry S. Truman Little White House and Mallory Square, widely regarded as the best place to catch the sunset every evening. The second stop is right around the corner at the Conch Tour Train Station, located on trendy Duval Street where the island’s best bars, restaurants, art galleries, nightlife, and boutiques are centralized. The train then drives clear across the island to the Truman & Duval Depot, where you can hop off to visit the Hemingway House, the Key West Lighthouse, the famous Southernmost Point marker, and the Butterfly & Nature Conservatory. The tour then takes visitors off the beaten path through residential neighborhoods characterized by pastel-colored, gingerbread-trimmed Victorian houses surrounded by lush gardens. The final stop on the loop is back on the north end of the island at Flagler Station Museum. From here you can visit the historic seaport and catch a ferry to Dry Tortugas National Park (something I plan on doing the next time I come to town.) Visitors may disembark at any of the stops and hop back on later to resume the tour.303 Front Street, Key West, FL 33040. Online ticketing prices – Adults: $27.41, Children 12 and under: Free, Seniors 62+ and Military with ID: $24.57. For more information, visit their website by clicking here.
Key West Lighthouse Museum
Poking high above the tropical foliage and peaked Victorian roofs of the city is the Key West lighthouse. Built in 1848 to replace the original wooden structure that was destroyed by a hurricane, the lighthouse helped prevent shipwrecks on the shallow reef located just offshore. Visitors can climb the eighty-eight steps for unbelievable, sweeping panoramic views in all directions. On the grounds you can also tour the Keeper’s Quarters, with displays of nautical artifacts, antique furnishings, maps and vintage photos.938 Whitehead Street, Key West, FL 33040. Adults: $10, Children 6 and up and students with ID: $5, Children under 6: free. $1 off for seniors 62 and over or with a AAA card. For more information, visit their website by clicking here.
Ernest Hemmingway Home & Museum
Renowned as one of America’s greatest authors, Ernest Hemingway lived on Key West from 1931 to 1961 where he wrote many of his acclaimed novels including For Whom the Bell Tolls, The Snows of Kilimanjaro, and Old Man and the Sea. He even used Key West as the setting for To Have and Have Not — his only novel to take place in the United States. Admission includes a guided tour of the two-story home, a peek into Hemingway’s writing studio, and access to the lushly landscaped grounds. The home famously features an in-ground swimming pool that cost the equivalent of over $250,000 in today’s dollars. The house is filled with furniture and other items that were used by Hemingway and his second wife, Pauline Pfeiffer, and their family. The house was built in 1851 and is now also home to more than forty cats, many of which are six-toed (a trait called polydactylism) descendants of Hemingway’s beloved cat, Snowball.907 Whitehead Street, Key West, FL 33040. Adults: $13, Children: $6, 5 and Under: Free. For more information, visit their website by clicking here.
I fell in love even more with Key West on my second visit. I look forward to coming back again sometime to enjoy more of the laid-back island’s picturesque charm and natural beauty. Click here to read about my first visit—Snapshot: Key West.
Here are more photos of Key West. Click on the thumbnails for a closer look.
Have you ever been to Key West? What were your impressions? Feel free to comment in the section below!
Michael Figueiredo is a freelance travel writer based in Los Angeles, California. When he’s not gallivanting around the world, he’s enjoying the laid-back lifestyle and perfect weather of Southern California. So far he’s visited forty countries and territories on five continents. His goal is to see at least one new country every year! . Read more from this author