Two things are guaranteed each day on the island: 1. There's an ocean surrounding it, and 2. The sun will set each and every night. So take advantage of those two things and get out on a boat for a sunset cruise. Hundreds of people flock to Mallory Square to watch the sunset from land, but nothing beats an uninhibited view from a boat on the water.
I nabbed that shot on a sunset cruise aboard a Fury Water Adventures catamaran, which departs on the Gulf side of the island behind the Westin resort. For $37 ($33 if you book online in advance), the catamaran shoves off, taking you on a two-hour cruise near the harbor. Free beer and wine are served during the sail by a friendly, competent staff of (mostly) young guys who act like they love what they do. There may well have been 75 people on the boat, but the deck space is so large, it didn't feel crowded at all.
The downside of a large cruise like this is that you never really get "out on the ocean." In fact, here was our view much of the time, looking back at the harbor and at other big boats from similar companies taking tourists on a similar cruise:
A better option--but also a more expensive one--is to pay for a private sunset expedition. Take a walk through the Historic Seaport one afternoon, and you'll see plenty of captains offering private sunset sails for two to 10 people. Prices range anywhere from $400 to $1,200, and dinner and drink options are endless. Some cruises offer champagne and dessert while others serve a full dinner.
My sister got married in Key West in January, and we took a private sunset sail with Southernmost Sailing, which departs from the key just north of Key West, Stock Island. Captain Dave Griner and his staff were great. We called last minute, on a Friday, to book a Saturday sail, and because he didn't have anyone else scheduled, he cut us a deal for half price. We set out on a 42' Fountaine Pajot catamaran, which had more than enough room for the dozen or so people on board. The boat even picked us up at the Hyatt Resort and Spa, where my sister was staying, which has a private dock. This time, we really got out on the ocean for what was supposed to be a two-hour cruise, but ended up being more like three. They even let us stock the ice chest with our drinks of choice and fire up the grill for a post-wedding bratwurst fest.
There are plenty of companies that offer a two-hour, no-nonsense, all-you-can-drink cruise for less than $40, and a few dozen private sailing charters that give you privacy and a view that's picture perfect. Either way, if you choose a cruise with a bunch of strangers or an intimate sail with your spouse, a Key West sunset cruise is a must see, must do.
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