Friendly Professional Crew

Friendly Professional Crew
Florida Keys Charters
Book Now

Islamorada Boat Trip

Captain Jim, and Captain Rebekah, both USCG licensed Captains will ensure you have a wonderful day on the beautiful waters of the Florida Keys.

Island Adventures Team

Exploring the Florida Keys aboard one of our private boat charters here in Islamorada, whether that be a half day relaxing on the Islamorada Sandbar, on a quiet week day with your wife and kids, to an all out party with as many as 800 boats and people from all over the world.
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.
If we had to say what our specialty is here at Island Adventures the answer is simple. We specialize in creating memories on the spectacular waters of the Florida Keys! Our Captains excel at showing new and familiar visitors to the Keys of all ages the waters that we call “Home” every day. We never forget that your vacation is our job. We all strive to create greater memories for everyone onboard our boats.

Pricing and Reservations

Groups of 1 to 6

  • 4-Hour Charters $699

    9:00 AM - 1:00 PM
    1:10 PM - 2:10 PM

  • 6-Hour Charters $899

    11:00 AM - 5:00 PM

Groups of 7 to 12

  • 4-Hour Charters $1,399

    9:00 AM - 1:00 PM
    1:10 PM - 5:10 PM

  • 6-Hour Charters $1,899

    11:00 AM - 5:00 PM

  • 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.

Meet Captain Jim

A Michigan native and 8 year resident of the Florida Keys, with 4 years of service as a United States Air Force, Intelligence Analyst along with over 28 years of professional experience including information technology and digital marketing, Jim brings management and operations expertise to Island Adventures. Through his training in the Air Force and 3 years of service as a licensed Captain, Jim has learned the importance of pride and integrity, as well as the importance of direct and open communications amongst team members. This has led to his interest in helping vacationers discover their dream day on the open waters of the Florida Keys!. With a certification as a licensed boat captain, a certified first responder and advanced open water scuba diver he has a passion for protecting the oceans and maintaining species sustainability. The environment and integrity in business are on top of Jim’s priority list. As a father the future of our environment is critical to Jim. He will be a corner stone in our relationship assisting you with building your vision for you and your families Florida Keys adventure!

Meet Rebekah

Rebekah moved to the Keys from Ohio in 1999. She is an English Teacher at Coral Shores High School and loves animals. She has a couple dozen chickens for their fresh eggs, sugar gliders, and bunnies. She plays several instruments including the piano in a band called Generation Gap, which plays regularly at the Island Grill in Islamorada.  Rebekah also likes writing, reading, painting, photography, backcountry fishing, kayaking/paddle boarding, yoga, and exercise. She serves on Islamorada’s Achievable Housing Committee and is active in local government.

Islamorada Boat Trip Schedule

Groups of 1-6

Groups of 7-12

If your group has 12 or more, please call so we can find crew and vessels to accommodate your group: 305-394-1436

Florida Keys Boat Tour Gallery

Book Direct Online

Featured Activities