Key West, Florida
Key West holds many superlatives for its extreme southern location: the southernmost city in the United States, the southern end of U.S. 1 and the southern terminus of the Florida East Coast Railway. Closer to Cuba than Miami, Key West is the last of the Florida Keys, connected to the mainland by 42 bridges that make up the Overseas Highway.
Since Europeans came to Key West with the arrival of Ponce de Leon in 1521, it has served as a bridge between Caribbean and North American cultures, playing home and muse to a large artistic community made famous by Ernest Hemingway.
“Start a day trip with the Hemingway House and Museum and the Harry S. Truman Little White House, which served as the summer White House,” said Jack Meyer, group sales manager for the Florida Keys. “When it was decommissioned, the contents were left completely intact. You can rent a private dining space for lunch for up to 20 or utilize the lawn for up to 200.”
To explore the full gamut of Key West’s history in one stop, visit the four-by-five-block cemetery in the center of town. Situated directly at sea level, Key West is an unusual spot for a cemetery because mausoleums must be built above ground; but that hasn’t stopped famous or infamous locals from taking up permanent residence.
“You can find tombs of sailors, all the way back from the USS Maine, who started the Spanish-American War, celebrities and tombs with a sense of humor that say things like ‘I told you I was sick.’ It’s definitely worth a tour,” Meyer said.
“Wrap up the day with the sunset celebration on Mallory Square,” said Meyer. “Every night it’s a different experience because entertainers and vendors, who are all local craftsmen, take turns drawing from a lottery at the beginning of the evening for a spot.”
Though it’s easy for tour groups to arrive by bus, being a small island with an oversized number of residents and visitors, “the town has a delicate pickup and drop-off system,” said Meyer. The city’s website lists commercial routes and designated drop-off spots.
The newly launched travel trade website Key Lime Academy includes sample itineraries and other resources for travel professionals.
Ship Island, Mississippi
Though they’re still referred to collectively as Ship Island, two islands, united until Hurricane Camille divided them in 1969, make up the “island,” which forms an important historic and ecological cornerstone of the Gulf Islands National Seashore.
Today, Ship Island is known for its pristine barrier beaches, but its history is much more colorful. During the French colonial period, Ship Island served as the South’s version of Ellis Island, with immigrants from the Caribbean passing through on their way to the mainland.
Imposing Fort Massachusetts, where NPS rangers give 45-minute tours 15 minutes after each ferry arrival, serves as an unmistakable reminder of the island’s strategic importance. During both the War of 1812 and the Civil War, the British and Union armies rallied their troops on the island before attempting to capture nearby New Orleans.
“There’s really no scheduled activities aside from the fort tour,” said Kevin Buckel, who runs the Ship Island Excursions ferries. “You can take a boat ride to look for dolphins, but most people come just to enjoy the beauty of the island, swim in the clear Gulf surf, shell and fish. One you’re out there, you’re completely away from civilization.”
After the fort tour, many groups opt for a stroll down the boardwalk around the facade of the fort and the western tip of the Gulf of Mexico beaches.
Although the NPS oversees Ship Island, Ship Island Excursions operates ferry services to West Ship Island, the larger of the two islands. In the summer, two ferries per day in each direction operate on weekdays and Sundays; four ferries are scheduled on Saturdays. Groups can also charter a private boat from a list of NPS-approved captains.
There is no restaurant or seated dining service on the island. On the ferry and the island, snack bars serve casual beach fare.