Taking the plunge in Key West

Taking the plunge in Key West

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Marriage equality in Florida could mean a big boost to the state’s economy. Many Southern states that have fought against equality will be losing potential grooms and brides to the Sunshine State. Considering the remoteness of Key West, it may or may not be your best choice for a wedding. So let’s explore the more likely option of Key West first — as a honeymoon destination. 


There’s no doubt that if you’re considering a honeymoon in Key West, you’ve either: a. been there; b. haven’t been but always wanted to; and/or c. already researched all of the gay websites associated with Key West. But a honeymoon shouldn’t necessarily be the same as a vacation. Here are some gay and not-so-gay things to consider.

Once in a lifetime


Dry Tortugas National Park and Fort Jefferson (www.nps.gov/drto/index.htm) is the most remote member of the National Parks System — more than 70 miles off the coast. Whether you charter the more expensive, shorter journey by plane or take the leisurely, longer and cheaper ferry, voyaging off the coast of the already-remote Keys is a thrill. Tortuga means island, by the way (and tortoise), and the “dry” descriptor refers to the lack of fresh water.

Fort Jefferson is an unbelievably large fort and former prison. It’s even more amazing considering the construction materials were all shipped in. It takes time to walk the grounds, enjoy all of the views and soak up the serenity. Historical note: Dr. Mudd (of the “his name is mud” colloquialism) was imprisoned here briefly for his role as the physician who set John Wilkes Booth’s broken leg.


There’s a walkway around the exterior wall, around the moat, along with other spaces to explore outside the walls. Snorkeling is also perfect in the crystal-clear water, and the abundant variety of marine life makes it simple and simply fun. It’s a must-visit for this special occasion.

Even if you’ve been to Key West before, there are other things to do that you never got around to. This is that chance to do them. Take advantage of the pristine waters around the Keys; you’re on an island for god’s sake! Lazy Dog (lazydog.com) has kayak rentals and tours, paddle boats, paddle yoga and guided eco tours. They hold classes for the uninitiated, so dive right in. If you want to see under you as you kayak, hit up Clearly Unique Charters (clearlyuniquecharters.com/).

Key West is synonymous with sunsets. Most people visiting Key West go to Sunset Pier or Mallory Square. Fine and dandy, they’re nice places. But for your special trip, you really want to go on the Wind and Wine Sunset Sail chartered by Danger Charters (dangercharters.com). Sample a variety of wines (or beers) with cheeses, meats and hors d’oeuvres as you tack out from the harbor. Leisurely, intimate and romantic, enjoy the breeze, spray and companionship as the sun melts into the water. Quite honestly one of the best times I’ve ever had.


Speaking of sunsets, you’ll want to have dinner on Sunset Key, just a short boat ride from Key West, at one the top dinner spots around: Latitudes Key West (westinsunsetkeycottages.com/latitudes-key-west). Reservations are required due to popularity, so you’ll want to plan this before arrival. No beach clothes; it’s a collared-shirt-required dining experience.

Menu items change by the seasons and availability and prices reflect that, so be forearmed with that information. Five-star food, an elegant setting, fine wines and spirits and patio seating for some of the most spectacular sunsets in the hemisphere make this an absolute destination-must, so plan accordingly.

Another proper-attire, fine-dining establishment is really a pair: The Commodore Waterfront Restaurant and The Boathouse (commodorekeywest.com). The Commodore is the original seafood and steak house and the Boathouse is the newly added smaller cousin beneath it. The former is on a very large, open second floor with terrific views of the harbor, and the latter is where I hear you’ll want to stop in for a fantastic happy hour.

In either case, the food is exceptional and the atmosphere divine. If you’re in a steak mood, this is the place, and if you’re out for seafood, this is the place also! If you haven’t been before, this is the trip to try conch fritters and conch chowder, among other specialty dishes. And then of course there’s the Key lime pie, which is excellent just about everywhere.


Off the beaten street

Chances are, if you’ve gone to Key West, it was for the glorious weather, Fantasy Fest or maybe a few other reasons. That’s fine. That’s part of why we go, yes. But there are a number of places you’ve probably heard about here that you just never got around to visiting. (Maybe because you slept past their closing times?)


Probably the most well-known yet unvisited place is the Ernest Hemingway House (hemingwayhome.com), mostly because everyone just heads to Sloppy Joe’s (or one of its reincarnations). Easy to find, one block off Duval across from the Key West Lighthouse, this magnificent Southern home is a museum packed with memorabilia, photographs and furniture that belonged to the old man by the sea. They offer interesting and entertaining tours every 20 minutes that include more than just Hemingway facts. (Feel free to ask the names of the more-than 40 cats that live there, all direct descendants of cats Hemingway owned.)


The outdoor space is beautiful and inspirational, allowing for a tree-canopied wedding on one side and open yard on the other for a reception, with two charming walkways connecting them around the house. Accommodations are all over the place in Key West, but the bridal party should consider staying across the street at the Lighthouse Court, 902 Whitehead St. The B&B is a convenient location and the breakfast, pool and mojito bar are valuable assets. You can also climb to the top of the Key West Lighthouse next door for a fantastic view or some wedding photos!

Just a few blocks down Whitehead Street and over to Duval is a somewhat well-kept secret, the Key West Butterfly and Nature Conservatory (keywestbutterfly.com).


An intimate venue with 50-60 species of butterflies and over a dozen exotic birds, this beautiful and spiritual space that can be a stunning wedding site for a small party or a glorious get-away destination one afternoon. Consider a visit here on a rainy day, which is not that uncommon. Take the time to check out the “nursery,” where you may see a butterfly emerge from its cocoon. 


Harry S. Truman — atomic bombs, United Nations, New Deal civil rights, NATO, the Korean War; he was president as the Soviet Union went on the offensive — had a lot on his desk. It was first thought that he came to Key West to unwind, but after researchers dug into travel logs, it became clear that he worked as hard there as in Washington, D.C.


The country was being led from the Little White House (trumanlittlewhitehouse.com/) during the 11 trips Truman and staff made over the years, and it’s still occasionally used for government functions. Open 365 days of the year, it is not only a fascinating museum with Truman memorabilia and of the era, it was also a significant site used during the Cold War.  

The sprawling lawn with a smattering of shade trees is another charming place for weddings and receptions. Rental is not inexpensive, as it is a privately funded site now belonging to the state of Florida, but it does include use of the living room, dining room, a suite, porches and house tours for your guests. By the way, did you know the “S” in Truman’s name doesn’t stand for anything?


On a side note, during a visit to Key West during Bill Clinton’s presidency, Hillary Clinton said she would love this site as a Southern White House given the chance, so locals are excited thinking about Clinton 45 and some face time.

A wedding on the beach is not original, true, but in Key West it’s a lot more than just standing in the surf off the boardwalk. Bump it up a notch with one of these unique locations. The Casa Marina Resort (casamarinaresort.com) has enough beach, recreation and ballroom space to host two weddings simultaneously, so any gathering here wouldn’t be a problem. You can even have the reception on the beach. The resort is part of Waldorf-Astoria, as is the adjoining Reach Resort (reachresort.com/). The original buildings, conceived by local Henry Flagler, opened New Year’s Eve 1920. Book your event well ahead of time, as they tend to fill up every weekend.


Southernmost on the Beach Hotel (southernmostresorts.com) is another option for vows in the sand. Located on the south side of the island, one of its claims to fame is that it is located at the southernmost point of the United States, which makes your day just that much more unique. Amenities besides the sand and water include some of the most spectacular views from recently renovated suites.

But wait, there’s more!

Of course the options for museums, dining, sightseeing, drinking and exploring are near-endless, but I would be remiss if I did not point out a few places I was introduced to last trip. There are a lot of funky art, architecture and characters on this island. Take a little time to stroll, rather than scooter around because then you can pay attention to your surroundings and soak it all in.

Need a gourmet chocolate fix? Try Lush (lushkw.com). Organic chocolates from around the world can be found here, and they are dynamite. A fine selection of teas, wines and beers are also available, and wine-tasting and chocolate-pairing is a nice way to spend an hour. Reservations are highly recommended for those.

Just a block away from the Key West Butterfly and Nature Conservatory and the Southernmost Point is Banana Café (bananacafekw.com). This is a delightful locals-place that serves all three meals and has a great selection of crepes for breakfast and lunch. Happy hour also gets a crowd on the second-floor outdoor deck.


Key West Museum of Art and History (kwahs.org) on Mallory Square is part of the Key West Art and Historical Society’s purview, as are the Key West Lighthouse and Fort East Martello. The museum is in the restored Customs House and isn’t large, but it does have some fascinating images, artifacts and stories of the USS Maine, the connecting of the island to the mainland, construction and restoration of the Customs House and the building (and rebuilding) of Key West itself.

Mallory Square is touristy but, from the museum, wander up Greene Street and you’ll find Amigo’s Tortilla Bar (amigoskeywest.com), where there’s some yummy authentic Mexican fare for every time of day. The huevos rancheros is especially good, as in “especially” when accompanied by a bloody mary or mimosa.


And across the street from Amigo’s is Capt. Tony’s Saloon (capttonyssaloon.com/), site of the “first and original Sloppy Joe’s Bar 1933-1937,” according to its signage. Go in, ask for the special shot of the day, toast Ernest Hemingway, sign a dollar bill and staple it to a wall, beam or the ceiling. (It’s what you do.)




Finally, wander into the LGBT Key West Business Guild (gaykeywestfla.com/) and check out the Tennessee Williams exhibit. Yeah, there’s more fame than just Hemingway and Truman on this island. Plus, you can get the scoop on what’s LGBT-special during your stay.

Honeymoon in Key West? Don’t mind if I do. 

But I’ll have to wait until there’s a proposal before I start planning that trip.



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