If there were a heaven strictly for boaters and anglers, it would look something like the Florida Keys. The way the islands string together, the water—clear, warm, and always moving—and the time-slowing vibe create a paradise for water-lovers. Now imagine threading your way through that stretch of island life, wind in your face and sun on your back. Cruising the Florida Keys on personal watercraft is not your average beach-vacation activity. It’s a way above average beach-vacation activity. Maybe one of the best.
Motorcyclists claim that a more immersive sense of freedom comes from fewer wheels on a road trip. If that’s the case, PWC enthusiasts may have a stronger argument.
Sure, plenty of folks will rent a PWC for an hour to rip donuts in the nearby shallows. But a mini-expedition that hops from one island to the next calls for a different kind of devotion. If you fall into the latter camp, there’s a right way to approach this journey, where you can hug the coastline, veer off into mangrove tunnels, and refuel along the way.
For first-timers or folks who would rather follow than lead, guided PWC tours are a great way to get a feel for cruising the Florida Keys. Outfitters in Key Largo, Islamorada, and Key West offer everything from two-hour rides to full-day adventures. These tours usually adhere to scenic routes and stop at sandbars, historic landmarks, and snorkeling spots. You will definitely learn a lot from the guide. It’s also a good way to understand local water conditions and boating etiquette before you venture out on your own.

If you already have some experience on a PWC and want a little more freedom, cruising the Florida Keys on a self-guided trip is where the real magic happens. The stretch from Key Largo to Key West measures about 100 miles by water, if you want to cruise the entire distance. You can easily break it up into manageable legs over two or three days.
You likely want to launch from Key Largo and stop in Islamorada, then hop down to Marathon, and then ultimately down to Key West. Each stop offers a unique experience, plenty of places to fuel up, and dockside establishments at which to rest.
Range typically isn’t an issue with modern PWCs, especially if you plan ahead. Most machines can run 60 to 100 miles on a full tank, but it’s always smart to top off when you can. Marinas are common, but not every dock is PWC-friendly, so call ahead. If you want to play it safe, pack a small auxiliary tank.
It’s possible, but not exactly the norm. Most rental companies are set up for hourly or full-day use and require that you stick close to home base. You could have some luck with a smaller, more flexible operation, maybe. Your best bet for a multi-day trip is to bring your own PWC. Doing that gives you the freedom to go at your own pace. You can build in time for all the stops on your list without the hassle of a lease agreement.

Whether you’re circling one island or packing for a multi-day trip—cruising the Florida Keys in their entirety—you need a number of essentials. For starters, get a waterproof dry bag, a dock line, water, and sunscreen. For longer trips, take more, obviously. Definitely include a small cooler for snacks and hydration. To avoid navigational guesswork, pack a waterproof GPS or an app such as Navionics. If you want to make some underwater sightseeing stops, pack a snorkel and a mask.
Don’t forget to follow the rules. In Florida, anyone born after January 1, 1988, must pass a boater safety course and carry their Boater Education ID card. Additionally, you can operate PWCs only during the daytime, and you must wear life jackets. And don’t feed the stereotype about PWC operators. Respect all idle-speed, no-wake zones around marinas and manatee habitats. Safety is paramount.
Cruising the Florida Keys, the entire route is packed with gems. You can’t go wrong choosing any one destination or single leg. And since you can make an extended trek as laid-back or adventurous as you want, visit any or all of these locations:

Cruising the Florida Keys on a PWC probably isn’t for everyone. But for the right person or group of people, it can be the journey of a lifetime. Plan ahead, know your fuel stops, respect the rules, and have an amazing time.