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As longtime captain Lenn Verreau prepares the 130-foot wooden Schooner Western Union for departure on a glorious April evening, his crew informs the passengers that help from some of them will be needed to hoist the majestic sails.
"You get great benefits, like priority on the life boats," one crew member announces.
The schooner has a storied history dating to 1939, when it was launched in Key West to lay the first of more than 30,000 miles of underseas telegraph cable in the Caribbean, including to Cuba.
For 35 years it served Western Union. Its next mission was to help troubled adolescents in a program called Vision Quest.
Now, it's owned by the nonprofit Schooner Western Union Preservation Society, which raised $1 million for a stem-to-stern makeover. In April, it was back in its slip next to the Schooner Wharf Bar in the Historic Seaport of Key West.
The two-hour sunset cruises leave the dock at 7 p.m. and once out of the busy marina, despite light winds of less than 10 mph, the crew and volunteer passengers hoist the sails. The motor is turned off.
As the boat sails past Mallory Square and Fort Zachary Taylor State Park, a musician plays traditional music, sometimes on a harp or hammered dulcimer. Cindy the bartender serves complimentary beer, wine, soda, water and champagne and dishes out conch chowder and crackers.
On this evening, the sun cooperates and displays a colorful orange and red show before disappearing beyond the horizon, seemingly into the sea.
If booze cruises are more your thing, there are plenty of options to get your groove on. But realize that sunsets are the thing in Key West — where else can you see the sun sink into the ocean? — so the majority of cruises will take place at the end of the day.
Whether it's a catamaran or a schooner sailboat, the biggest difference between the sunset cruises will be your drink options. Some are all-inclusive with a selection of wine, beer, cocktails and champagne. Most of the time the choices are on the lower end — we're not talking top shelf here. The other option is BYOB — bring your own bottle, or drink, or cooler full of drinks. This option is great for families with various levels of imbibers to consider. Or creative groups of friends who get into Jell-o shots, high-end spirits or even some liquor-infused fruit (think peaches with vodka).
Some cruises may feature music, while others feature a spread of food. Otherwise most cruises are the same — and with great photo opportunities. Buy tickets early, even reserving online several days in advance, to get a discount and ensure a seat. These cruises fill up fast, because the sunsets are among the best things going for Key West, and how you experience it is important.
The schooner Jolly II Rover, an 80-foot Caribbean coastal sailing ship, is one of the more popular sunset cruises in Key West that allows you to bring your own food and drink.
The crew takes the pirate theme seriously, with staff dressed the part. Guests have a chance to steer the schooner, raise and lower the sails, and even fire a cannon at other sunset boats.
Fury Water Adventures offers a daily sunset sail on a 360-foot catamaran. There are two versions of this sunset sail, and both are equally fun. The first features complimentary beer, wine and champagne. The second, called Commotion on the Ocean, provides complimentary beer, wine, margaritas and a spread of appetizers along with live music.
Both sails are great for large groups, with plenty of standing areas for views of the sunset from the upper deck. Seating is limited, so get aboard early if you prefer not to stand.
Cheeca Lodge in Islamorada has a sunset sail that leaves from the dock behind the hotel. There are complimentary beer and wine, as well as nonalcoholic beverages, or you can bring aboard a small cooler of your favorites.
The sunset sail is very intimate with a limited number of spots available. Bring a light jacket or a blanket as the trip will get breezy.