Upper Keys

Upper Keys Trips & Tours

From Long Key all the way up to North Key Largo, you’ll find world class fishing, both backcountry and offshore, great dining options, incredible snorkeling, and of the course the world famous Islamorada Sandbar! Classy, quiet, and packed with things to do, the Upper Keys are a great choice for your Florida Keys vacation.

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Mangroves & Manatees Guided Eco-Tour

With PADDLE! the Florida Keys
In the Upper Keys
You choose: single kayaks or double? Either way, our pro guides are there to give you a memorable experience! Each guide shares their unique enthusiasm and extensive local knowledge of the mangrove and marine environments, and island-life perspective!
Duration: 2 Hours
Starting from: $60

¾ Day Fishing - 42' Liberty

With DirtyBoat Charters LLC
In the Upper Keys
What we call our “Dinner and a Show” package: 6 action-packed hours of fishing just a few miles off the coast. We start on the reef catching live bait and some good-eating Snapper and Grouper. Once dinner is in the cooler, we head further offshore to close by wrecks, on the hunt for bigger fish, including Sailfish, Wahoo, Tuna, Amberjack or even Sharks!
Duration: 6 Hours
Starting from: $1400

19' Wellcraft Center Console Half Day Rental

With Sand Dollar Boat Rentals - Islamorada
In the Upper Keys
Enjoy our beautiful waters on your own schedule with our boat rentals! From as short as 4 hours to multiple days, we have the perfect boat for you and your crew!
Duration: 4 Hours
Starting from: $250

20' Hyrda-Sport Dual Console Half Day Rental

With Sand Dollar Boat Rentals - Islamorada
In the Upper Keys
Enjoy our beautiful waters on your own schedule with our boat rentals! From as short as 4 hours to multiple days, we have the perfect boat for you and your crew!
Duration: 4 Hours
Starting from: $295

21’ Sea Born - Center Console Multi Day Rental

With Sand Dollar Boat Rentals - Islamorada
In the Upper Keys
Enjoy our beautiful waters on your own schedule with our boat rentals! From as short as 4 hours to multiple days, we have the perfect boat for you and your crew!
Duration: 2+ days
Starting from: $700

Half Day Fishing - 42' Liberty

With DirtyBoat Charters LLC
In the Upper Keys
A half-day trip is the shortest offered: 4 hours of fishing on the reef OR wrecks, depending on what you want to catch.The trip starts with catching live bait. Then we collaborate to make a decision: “swing for the fences” and try our luck catching something big on the wrecks or heading to the reef to anchor up and catch Snapper and Grouper.
Duration: 4 Hours
Starting from: $1000

21’ FunDeck Full Day Rental

With Sand Dollar Boat Rentals - Islamorada
In the Upper Keys
Enjoy our beautiful waters on your own schedule with our boat rentals! From as short as 4 hours to multiple days, we have the perfect boat for you and your crew!
Duration: 8 Hours
Starting from: $395

Kayak/SUP Rental - 1 Day

With PADDLE! the Florida Keys
In the Upper Keys
We never run out of gear…. Please call us if you want to rent today! Free delivery from mm 100 to mm 80. Or we will strap to the top of your car or truck. We will lend you the straps and padding at no extra cost.
Duration: 1 Day
Starting from: $100

22.5’ Hurricane SunDeck Half Day Rental

With Sand Dollar Boat Rentals - Islamorada
In the Upper Keys
Enjoy our beautiful waters on your own schedule with our boat rentals! From as short as 4 hours to multiple days, we have the perfect boat for you and your crew!
Duration: 4 Hours
Starting from: $295

Kayak/SUP Rental - 7 Days

With PADDLE! the Florida Keys
In the Upper Keys
We never run out of gear…. Please call us if you want to rent today! Free delivery from mm 100 to mm 80. Or we will strap to the top of your car or truck. We will lend you the straps and padding at no extra cost.
Duration: 7 Days
Starting from: $100
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