Key West Private Sunset Charter

In Key West, we celebrate each and every sunset. Sure, we know another one is only 24 hours away, but each one is unique and beautiful. So we take a moment every day to appreciate the simple things, celebrate being alive in one of the most beautiful spots on earth, and toast the end of another day. It’s a quirky tradition that makes Key West a special place.


All About Your Key West Sunset Cruise


Why are sunsets such a big deal in Key West? Maybe it’s our location at the “end of the road.” Or maybe it’s just lucky geography—Key West is a fun East Coast port with an unobscured view of the western horizon. Or perhaps it’s because this island is a great place to catch a glimpse of the elusive Green Flash.


What’s the Green Flash, you ask? No, it’s not the latest Marvel superhero—it’s way better than that. The Green Flash occurs when just the right atmospheric conditions occur at sunset, and you have an unobscured view of the horizon. It only lasts a second or two, so look quick and stay sober! Or not. Either way, Key West is a great place to see it happen.


You may or may not see a Green Flash. And, of course, you can see the sunset with the crowd and street performers in Mallory Square—something everyone should do at least once. But seeing the sunset from the water on a private boat charter is a memorable experience—a relaxed and laid-back private show that will take you back to a quieter time on the island.


A few notes about Casual Mondays’ Key West sunset charters:


• All charters leave from Hurricane Hole Marina on Stock Island
• View the sunset from Key West Man-O-War Harbor
• Sights along the way include Sunset Key, Fort Zachary Taylor State Park (a Civil War fort), Key West Channel, and the Coast Guard and Navy bases.
• Interested in creating a custom sunset cruise package? Combine multiple activities into one charter boat trip (i.e., afternoon reef snorkeling + sunset, or Key West sandbar tour + sunset boat charter)
• We often see dolphins in the harbor, so remember your camera
• The exact route we take may change based on the wind direction
• All ages are welcome
• We are pet friendly



Itinerary — Sunset Cruise Trips, Key West FL


Sunset charters in Key West typically stick to Key West Harbor on the island’s western side. However, we leave from Stock Island on the west, so you’ll get an excellent tour of the island along the way.

• Leave Hurricane Hole Marina, Stock Island
• Head out to Key West Harbor (about 20 mins)
• Cruise around the harbor for an hour or so
• Head back in (20 min)
• The entire trip is around two hours


Captain Zak on the Casual Monday is a Keys history buff, so if you have any questions about Key West, her quirks, or characters, just ask. He’s a bastion of useless information that will help you win trivia night every time.


Booking your own private sunset cruise in Key West means you have complete control over the experience. If you’re thinking about also booking a snorkel or sandbar boat trip, let us know. We can create a custom trip for you and your group based precisely on what you’d like to do.


We’ll pick where we go based on the weather that day. Captain Zak will set a course for the best views and smoothest ride every time. For example, one of Captain Zak’s favorite routes is to head south of the island and view the sunset from the Atlantic, so long as it isn’t rough out.



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