07 Oct Sunset Sail in Key West: Schooner Jolly II Rover
Sunsets in Key West are a big deal–every evening Mallory Square hosts a sunset celebration where thousands of people gather to watch the sun dip below the horizon. With gorgeous colors and the elusive green flair, more often than not, you will catch a great sunset in the midst of street performers, vendors and visitors clamoring to watch and celebrate the beginning of the evenings likely debauchery.
We have seen many a sunset from the west-facing Mallory Square, but this time we opted for a sunset sail since we were celebrating our anniversary and all. I have always wanted to take a sunset cruise in the keys, but the typical sunset cruise is jam-packed with people looking to party like crazy with blaring music or the other option of an expensive, upscale wine and cheese sail–neither are my ideal conditions for sitting on a boat. There is enough craziness to participate in on Duval street, so when I’m on the water, I want to relax, and not for a price tag of over $100 per person. After some online browsing, I came across the perfect option for us and I couldn’t have been more excited! I booked our tickets on the Schooner Jolly II Rover Sailboat for a price of $40 per person with a coupon ($45 original price, and although not exactly cheap, much more affordable than the other sailboat options).
The cruise departs from the Historic Seaport area of Key West and lasts for about 2 hours. Unlike all of the other sunset cruises, the Jolly II Rover does not serve any food or drinks, but they do supply water bottles. You can bring your own snack, picnic and beverages, which honestly, I prefer as it keeps the ticket cost down and you are able to bring what you actually prefer to drink or snack on.
The captain and crew could not have been nicer–this boat actually gets out and sails around the waters and passengers can help with the ropes and steering if they want. Of course, we had to try our hand at being the captain and both took a turn at the wheel.
We also set out in search of dolphins and actually found some! They weren’t feeling like playing much, but we did get to stop and watch the dolphins swim around for a bit. Another fun feature on the Jolly II Rover is the cannon–we got to fire at the noisy party cruises when sailing by which was fun, but beware, it is loud! I didn’t heed the warnings too well and my ears were ringing for quite some time afterwards! We also listened to stories about the pirates and rum runners who roamed the Florida straights and waters around Key West.
After playing with the cannons, dolphins and hearing pirate stories of the 1800’s, it was time for the famous sunset. We sailed over toward Mallory Square and watched the sun disappear before our eyes, but not before putting on a beautiful, golden show.
Sailings are only available on the weekends, as during the week the boat sets out on weeklong Boy Scout trips where the boys can live like pirates by walking the plank, jumping into the water and shooting off cannons. I can only imagine it would be quite the exciting week!
We loved our sunset cruise and would definitely consider trying one of the day cruises as well–if you are looking for something a little different from the traditional sunset cruise, the Jolly II Rover has you covered!