
Spend a private day on the water in Islamorada with Island Adventures, a fully restored 19 ft Hurricane deck boat perfect for up to 6 guests. This isn’t a crowded party boat or a rigid group tour. It’s your own small-group trip built around what you want to do: snorkel calm, beginner-friendly reefs, hang out at the famous Islamorada sandbar, look for dolphins and other wildlife, or just cruise with music and a drink in hand.
Powered by a reliable 150 HP Yamaha and restored in 2024, the boat has shade, comfortable seating, easy water access, quality snorkel gear, and all required safety equipment on board. You tell Captain Jim what kind of day you want, and he’ll match the plan to your group and the conditions so you get the best spots for that specific day.
A standard, fully refundable security deposit is listed by the platform, but in most cases there are no surprise charges beyond what you see here, as long as there is no damage. Safety is always the priority, and if weather or conditions aren’t right, Captain Jim will work with you on options.
If you’re looking for a relaxed, safe, and memorable day on the water that becomes the highlight of your Keys trip, book your Island Adventures charter and we’ll take care of the rest.
Rating summary
Photos & videos by reviewers (16)


+13Customer rating
Customers claimed
Good experience
100%
Appropriate for children
100%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
90%
Mar 14, 2026
Exclusive Sunset Charter
Captain Jim was amazing and the sunset cruise we experienced with Island Adventures was breathtaking! We enjoyed every moment of our time. Wonderful conversation and a breathtaking sunset that only the Keys could provide. If you have the opportunity take the Sunset Cruise with Captain Jim, you will not be disappointed.
Captain Jim was amazing and the sunset cruise we experienced with Island Adventures was breathtaking! We enjoyed every moment...
Mar 15, 2026
4 Hour – Snorkel & Sandbar (PM)
We booked two trips with Captain Jim and had a great time despite some persistent winds! We had us a couple in our later years and a pair of 23 year olds, and everyone had fun!
We booked two trips with Captain Jim and had a great time despite some persistent winds! We had us a couple in our later years...





Feb 14, 2026
4 Hour – Snorkel & Sandbar (AM)
Captain and mate were great. Would highly recommend!
Captain and mate were great. Would highly recommend!


Dec 25, 2025
The charter operator canceled on trip date. This is an automated posting.
May 30, 2025
4 Hour – Sandbar Adventure (PM)
My friend and I booked a 4 hour sandbar trip, had a wonderful time. Captain was knowledgeable and very kind. Would book again!
My friend and I booked a 4 hour sandbar trip, had a wonderful time. Captain was knowledgeable and very kind. Would book again!...

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Rating summary
Photos & videos by reviewers (16)


+13Customer rating
Customers claimed
Good experience
100%
Appropriate for children
100%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
90%

Experience:
Equipment
Crew
Overall
Exclusive Sunset Charter on March 14, 2026
Captain Jim was amazing and the sunset cruise we experienced with Island Adventures was breathtaking! We enjoyed every moment of our time. Wonderful conversation and a breathtaking sunset that only the Keys could provide. If you have the opportunity take the Sunset Cruise with Captain Jim, you will not be disappointed.
Captain Jim was amazing and the sunset cruise we experienced with Island Adventures was breathtaking! We enjoyed every moment of our time. Wonderful conversation and a breathtaking sunset that only the Keys could provide. If you have the opportunity take the Sunset Cruise with Captain Jim, you will not be disappointed.

Experience:
Equipment
Crew
Overall
4 Hour – Snorkel & Sandbar (PM) on March 15, 2026
We booked two trips with Captain Jim and had a great time despite some persistent winds! We had us a couple in our later years and a pair of 23 year olds, and everyone had fun!
We booked two trips with Captain Jim and had a great time despite some persistent winds! We had us a couple in our later years and a pair of 23 year olds, and everyone had fun!





Experience:
Equipment
Crew
Overall
4 Hour – Snorkel & Sandbar (AM) on February 14, 2026
Captain and mate were great. Would highly recommend!
Captain and mate were great. Would highly recommend!


Trip was supposed to happen on December 25, 2025
The charter operator canceled on trip date. This is an automated posting.
Experience:
Equipment
Crew
Overall
4 Hour – Sandbar Adventure (PM) on May 30, 2025
My friend and I booked a 4 hour sandbar trip, had a wonderful time. Captain was knowledgeable and very kind. Would book again!
My friend and I booked a 4 hour sandbar trip, had a wonderful time. Captain was knowledgeable and very kind. Would book again!
