About Us

Who We Are
Florida Keys Private Boat Charters
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About Island Adventures

Are you ready for an unforgettable adventure in the Florida Keys? Look no further than Island Adventures! There’s no difference in any of our trips except sandbar only.  On any of our trips we can do anything listed here on our website, time and weather permitting.  Other than the sandbar only trip, snorkeling, site seeing, sandbar, bar hopping, and dolphin watch are always available to you!  Our commitment to personalized and high-quality experiences sets us apart from the rest. Our expert captains will work closely with you to design a customized itinerary tailored to your interests and preferences. Trust us to provide exceptional service and create memories that will last a lifetime. Let Island Adventures show you the true beauty of the Keys in a way you’ll never forget!

Charters can be a tandem of two boats for up to 12 people exploring the waters of the Florida Bay or a quiet sunset tour with cocktails. The locals are all here, the choice is yours! The nearby flats that surround the Upper Keys hold quiet nooks and crannies, 10 million dollar homes, and some of the most epic sunsets in the world. Each of these spots is ready for you to explore with us one one of our private boat charters.

“Get ready for a once-in-a-lifetime experience in the Florida Keys!” exclaims Captain Jim, proud owner of Island Adventures. Having called this place home for 8 years, there’s nothing he’s more passionate about than sharing its breathtaking beauty with visitors. Trust us, the memories you’ll create here will be ones you’ll cherish forever. Let’s go!”

Get ready for a wild ride with Island Adventures! We’re all about crafting incredible memories on the water that you won’t be able to stop talking about. Whether you’re sipping cocktails on one of our sunset tours or discovering every corner of Florida Bay, every second spent with us will be an adventure you’ll cherish for a lifetime. Don’t miss out on the excitement – book your Island Adventures experience today!

Pricing and Reservations
(Deposit is 100% Refundable up to 48 hrs in Advance.)

Groups of 1 to 6

Groups of 7 to 12

  • 4-Hour Charters $1199
    (Deposit $399)
  • Bluetooth Speaker, and onboard music
  • Cooler with Ice
  • Inflatable Paddleboard
  • Floating Foam Mat
  • Inner Tube Floats
  • Snorkel Gear
  • Football, Badminton Gear and a Frisbee
  • Ice and a cooler if you’re mixing drinks
  • Lunch and your favorite snacks
  • Life jackets for very small children

We pickup at Island Grill or Islamarina on Snake Creek in Islamorada. We will send you specific parking and pick up instructions, via text the day before your trip. You can plan ahead by checking out the pick up locations link in our website to determine how long it will take to get there from where you are staying. Both locations are within just a few hundred yards of each other.

We offer 4 and 6 hour trips. Your trip duration will depend on the day and time that you’ve booked. If you’d like to extend your trip we offer that service for an extra fee that can be negotiated on the day of your trip if our scheduling allows for additional time.

If you have small children you will want to bring your own snorkel gear as we have 6 adult sets of snorkel equipment but it is not suitable for very small children under the age of 10. You’ll want to bring your own cooler with ice for mixed drinks as our cooler is suited for cans, bottles and pre-packaged food.

Our Team

Meet Captain Jim

Ahoy there, mates! Let’s give a hearty “Arrr!” for the legend himself, Captain Jim, the fearless leader of Island Adventures! 🏴‍☠️ This isn’t just a captain, this is the pirate-king of the Florida Keys, guiding you through azure waters and past coral kingdoms like only he can. With years of maritime experience and a passion for the open sea, Captain Jim is the go-to guy for all things adventure in Islamorada. Whether it’s a snorkeling escapade, a chill sandbar trip, or a mesmerizing sunset tour, he knows how to dial up the fun to 11! And let’s not forget that infectious enthusiasm of his—it’s as contagious as the laughter that erupts aboard his ship. One sail with Captain Jim and you’ll find out why we can’t help but love the guy! From his sea-salty wisdom to his uncanny ability to spot dolphins, manatees, and even the occasional treasure chest (okay, maybe not that last one), a trip with Captain Jim feels less like a tour and more like an epic tale you’ll be recounting for years! 🌊🦜⚓🌅

Islamorada Boat Trip Schedule

If your group has 12 or more, or for any other inquiries, reach out to us by text, or call 305-394-1436.   

Florida Keys Boat Tour Gallery

Discover Unrivaled Vacation Bliss with Island Adventures: Your Five-Star Boat Charter Experience in the Florida Keys!

Embark on an unforgettable journey with Island Adventures, where the best day of your vacation awaits. Picture yourself on a luxurious private boat charter, surrounded by the pristine beauty of the Florida Keys. As you step onto our dock, an oasis of VIP treatment welcomes you – from before, during, and even after your trip. Begin your adventure by indulging in our heated pool and tiki bar, setting the stage for an unparalleled experience. With private parking and a relaxed atmosphere at the dock, every moment is designed to be stress-free and remarkable. And that’s just the start. Dive into the vibrant world beneath the waves as you explore snorkeling, feel the golden glow of stunning sunsets on our tours, and unwind on serene sandbar trips. Make every moment count – reserve your voyage with Island Adventures now and let the magic of the Florida Keys captivate your senses. 🚤🌴🌅 

Get ready to embark on an amazing day amidst the breathtaking waters of the Florida Keys. Our multi-activity sandbar trips promise an unforgettable fusion of adventure and relaxation. Immerse yourself in the wonders of snorkeling and sightseeing, each moment designed to create cherished memories. And what better way to cap off your day than by lounging on the world-renowned Islamorada Sandbar, where the sun’s glow meets crystal-clear waters? At Island Adventures, your vacation is our mission – we’re dedicated to crafting seamless, unparalleled experiences that leave you rejuvenated and amazed. Join us and let the magic of the Florida Keys unfold before you. 🚤🏝️🌅🐠

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Full refund is granted if cancellation request is confirmed more than 48 hour in advance of the charter time by phone or text. Weather conditions to be determined the morning of the charter, with full refund if we cancel due to dangerous weather. Please understand the reason for our cancellation policy: Within 48 hours prior to your charter, we will not likely re-book the date you had chosen, your food/drink purchases have already been made, and we owe the captain/mate at least a portion of their lost wages. Thanks for your understanding. Cancel by phone/text at 305-394-1436

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