Florida Keys Boat Rentals: Exploring the Beautiful Backwaters on Your Own

Not everyone has their own boat (we don’t) so finding ways to get out on the water can sometimes be a challenge. When you’re visiting Islamorada and the Middle Keys there is actually a great option for renting your own boat for exploring the sandbars and small islands around the area. Driving a boat through beautiful turquoise waters, watching for dolphins and rays or maybe fishing is a blast, and it’s pretty easy to add to your trip.

Have you rented a boat before or been out in the backwaters of the Florida Keys? If not, don’t worry, because we’ve got all the info you need to determine if renting a boat is a good idea for your trip plan. There are several things to consider as you think about doing a boat rental, so if you have any questions we don’t answer, please leave a comment or send us a note. We’re always happy to share more and help you make a great plan for a Florida Keys vacation.

Rob Taylor driving Carolina Skiff from Florida Keys Boat Rentals at Robbies of Islamorada Florida Keys 1

Highlights of Renting a Boat in Islamorada

What I love about doing a Florida Keys boat rental is that the destination and stops are 100% up to us as the renter/captain. Don’t get me wrong, I absolutely love when we get to have a day doing a sandbar charter or when we’re out on a snorkeling trip, but the freedom of being on our own is great. And it’s kind of fun. Driving a boat through the turquoise waters surrounding Islamorada, you can just decide that it’s time to jump in, so you turn off the engine and go for a swim. If you’re driving along and you want to stop and take photos of birds, great, you can.

While not everyone is going to feel comfortable doing Florida Keys boat rentals, either because they don’t have boating experience or they aren’t familiar with the waters, if it’s something you can add to your trip, I think it’s worth it. We rented an 18 foot skiff from Florida Keys Boat Rentals out of Robbie’s of Islamorada and had four hours of freedom on the water.

Even though I hadn’t driven a boat in this specific area before, the boating dude who did our safety talk and completed our rental process was very helpful showing us some good spots to head off to. When you’re boating out of Robbie’s you’ve got lots of options for where you can go, whether it’s a sandbar you want to hang out on or just beautiful stretches of water to explore. It was good to have personal recommendations for our Florida Keys boat rental day instead of just wandering the backwaters aimlessly.

Swimming while boating in backwaters from Florida Keys Boat Rentals at Robbies of Islamorada Florida Keys 1

Tips for a Great Florida Keys Boat Rental Experience

I know that renting a boat seems like a fun, easy sort of thing to do when you’re in the Florida Keys, and it kind of is, but there are some things to know before you go. First off, you don’t just get to pay for your rental and take off, but you need to fully understand where you’re allowed to drive and what sort of areas you cannot cross into. The Florida Keys have very shallow water all around them and much of that is covered with protected seagrass beds. YOU CANNOT CROSS THESE. If you’re doing a Florida Keys boat rental, the vendor has the ability to track the boat with GPS and knows if you carry on into the seagrass beds, which comes with a heavy fine.

You have to pay attention to the navigation system as you go, keeping to designated channels and open water so the seagrass areas can stay healthy. If you scar the seagrass or get caught out there, you’ll be in big trouble, both with the vendor AND Florida State F&W. The best way to stay within acceptable boating areas is to keep your eyes on the GPS and follow the channel markers to where you want to go. There is plenty of room to have fun, but be smart about it.

Boating Map at Florida Keys Boat Rentals at Robbies of Islamorada Florida Keys 1

Where to Visit with a Keys Boat Rental

Doing Florida Keys Boat Rentals from Islamorada more takes you into great swimming and sandbar waters than snorkeling waters. I do enjoy snorkeling near sandbars and around the edges of the grasses, as there are some cool fish and rays that hang out here, but what you’ll see isn’t nearly as good as if you’re snorkeling at one of the reefs off Key Largo (I love Horizon Divers for this) or if you go out to Sombrero Reef or Looe Key Reef.

Instead of planning on snorkeling, bring your reef-safe sunblock and beach towel and enjoy the boundless water for swimming or ever changing sandbar areas. If you’re stopping at a sandbar, use your sand-spike/anchor to keep from drifting when you turn off the motor. Plan your time so you can spend as much of the day as you want either playing in the water or cruising around. Don’t forget to bring lots of water and your polarized sunglasses too.

Note: you can do boat rentals in Islamorada, Key Largo, Key West and other small marinas. Wherever you choose to do it, be sure to talk to the rental desk and get SOLID RECOMMENDATIONS for routes and sights.

Relaxing on Carolina Skiff from Florida Keys Boat Rentals at Robbies of Islamorada Florida Keys 1

Need to Know for Renting a Boat in the Keys

There are a few Florida Keys boat rentals, but the easiest for both activities and navigation is, I think, going from Robbie’s of Islamorada. The actual business is indeed called Florida Keys Boat Rentals and they have quite a few options for the size and type of boat to rent. I like doing a skiff because it’s small, easy to maneuver and doesn’t encourage you to get wild on the water.

With a small skiff you’ve got enough power to hit your plane and move, but it’s also not a muscle boat. If you need something more powerful, that’s an option too. Keep in mind that boats are rented for the number of people you have with your and your intentions on the water. If you have five people with you, a tiny skiff won’t cut it so you’ll be set up with a bigger boat, and the price will match that. When you’re reserving your Florida Keys boat rental be sure that you’re planning properly.

Carolina Skiff Boat at Florida Keys Boat Rentals at Robbies of Islamorada Florida Keys 1

Do I need a Boating License to Rent a Boat in the Keys?

Kind of, you do need either a Boating Safety Education Identification Card or grandfathered experience. I have a boating license from Washington State and have done the online course here in Florida, but not everyone has that amount of experience. If you were born January 1, 1988 or after, you MUST have completed a Florida Fish and Wildlife approved boater safety course and have your proof or certificate of completion.

From Florida Highway Safety & Motor Vehicles: “anyone born on or after January 1, 1988 is required to either have successfully completed a National Association of State Boating Law Administrators (NASBLA) approved boating education course or have passed an equivalent course or temporary certificate examination. Additionally, they must have in their possession a boating education ID card and a photo identification card before operating a vessel with a motor of ten horsepower or more in Florida.” – THIS APPLIES TO OUT OF STATE VISITORS TOO.

Rob Taylor driving Carolina Skiff from Florida Keys Boat Rentals at Robbies of Islamorada Florida Keys 2

Florida Keys Boat Rentals Operating Information

To be sure you have the best experience when you rent a boat in Islamorada, here’s the operating information for the Florida Keys Boat Rentals shop:

  • Operating Dates/Season: year round, 7:00 am to 9:00 pm (services vary throughout the day)
  • Marina Office phone number: 305-664-5533
  • Company website:  Islamorada rental recommendation
  • Marina/hub address: 77522 Overseas Highway, Islamorada FL 33036
  • Rental booking: book a skiff here
Florida Keys boat rentals can be a great way to explore the waters and have fun with friends and family. We've got the scoop on renting a boat out of Islamorada with suggestions for activities and information about what license or boating experience is required to rent a boat in the Keys.

Ideas for Enjoying the Middle Keys

Whenever I get to talk about my favorite places for history or snorkeling in the Keys, I always try to mention a few places in the Middle Keys that have been wonderful. I love the railroad history and the vintage imagery of the Middle Keys. The old Seven Mile Bridge, Pigeon Key, Windley Key Fossil Reef Geological State Park…

And then the snorkeling and swimming in the Middle Keys is wonderful too. When it comes to planning a trip through the Keys, I think setting aside time right here in the Middle is a great way to mix quiet downtime with the fun of Key West and the adventures of Key Largo.

Where to Stay in the Middle Keys

Whether you’re working your way all the way to Key West or you just want to try out a new destination within the Keys, staying in the Middle Keys is really nice. It’s more quiet than Key West and much less busy than Key Largo. I like the resort hotels in the Middle Keys because so many of them have leaned into this mindset: quiet relaxation. Yes, there are lots of fun things to do and adventures to have, but the lodging options in this area really are the places where I get the best mental reset and fully sink into vacation mode.

Check out Middle Keys lodging options on the map below.

Here are some of our reviews of the many resorts and accommodations we’ve enjoyed in the Middle Keys, primarily Marathon and up into Islamorada (which is more of the Upper Keys). If you have questions about any of our recommendations, reach out!

I hope you’ll consider renting a boat for some fun when you’re in the Keys. It really can be a great activity if you’re comfortable on the water and want to explore on your own. If you have any questions about renting a boat in the Keys or need additional recommendations, please leave a comment or send us a note. We’re always happy to share more and help plan awesome Florida Keys trips!

Florida Keys boat rentals can be a great way to explore the waters and have fun with friends and family. We've got the scoop on renting a boat out of Islamorada with suggestions for activities and information about what license or boating experience is required to rent a boat in the Keys.

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