Friendly Professional Crew

Friendly Professional Crew
Florida Keys Charters
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Islamorada Boat Trip

Get ready for an unforgettable day on the stunning waters of the Florida Keys with not one, but two licensed USCG Captains!   Captain Jim and Captain Rebekah are here to guarantee you a fantastic experience that you’ll never forget.  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!

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
(Deposit is 100% Refundable up to 48 hrs in Advance)

Groups of 1 to 6

  • 4-Hour Charters $599
    ($199 Deposit)

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

  • 6-Hour Charters $799
    ($299 Deposit)

    11:00 AM - 5:00 PM

Groups of 7 to 12

  • 4-Hour Charters $1199
    ($399 Deposit)

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

  • 6-Hour Charters $1399
    ($399 Deposit)

    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 Anglers House Marina which is bay side at MM 80.5.  The entrance is across the highway from Midway Cafe.  The address is 80500 Overseas Hwy, Islamorada.

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

Captain Jim, a Michigan native and 8-year resident of the Florida Keys, founded Island Adventures. His passion for the waters of the Florida Keys and his commitment to environmental conservation and business integrity inspired him to start Island Adventures and share his love for the area with others. Today, the company provides unforgettable private boat charters for visitors seeking adventure and memories in the Florida Keys.  With a certification as a licensed boat captain, a certified first responder, and an advanced open-water scuba diver, Captain Jim is committed to ensuring the safety and enjoyment of all those who embark on an Island Adventures charter. He is also dedicated to preserving the oceans and maintaining species sustainability.

Islamorada Boat Trip Schedule

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

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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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