Island Hopping

NEW Key West, FL 1 - 6 People 4 - 8 Hours From $800 Trip #10608
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin

About Your Trip

Skill Levels

Beginner, Intermediate, Advanced

Weather

You won’t lose your deposit if the trip is canceled due to weather.

Set out on a private 4, 6, or 8-hour island hopping adventure, exploring the many unique islands scattered around Key West. With more time spent cruising, this trip offers a wider variety of sights and a greater chance of spotting wildlife such as dolphins, turtles, stingrays, and even manatees. Each route is flexible, so you’ll get to experience both the journey and the hidden gems along the way.

On board, you’ll have storage, and a...

About Your Trip

Set out on a private 4, 6, or 8-hour island hopping adventure, exploring the many unique islands scattered around Key West. With more time spent cruising, this trip offers a wider variety of sights and a greater chance of spotting wildlife such as dolphins, turtles, stingrays, and even manatees. Each route is flexible, so you’ll get to experience both the journey and the hidden gems along the way.

On board, you’ll have storage, and a cooler stocked with ice and water. Guests are welcome to bring their own food and drinks—alcoholic or non—and I recommend packing towels and reef-safe sunscreen. While we’ll spend more time exploring by boat, there’s always the option to stop at a sandbar, hop off for a swim, or wade in the shallows if you’d like to add a break into the day.

Every trip is customizable—you can choose the length, the islands, and the pace that fits your style. Some groups prefer more cruising and sightseeing, while others like to combine the ride with time relaxing in the water. Either way, you’ll get a personal, local perspective from someone who has spent over 11 years navigating these waters.

The highlights of this charter include diverse island scenery, wide-open turquoise waters, abundant marine life, and the freedom to shape the day around your group’s interests. It’s the perfect choice for those who want to see more of Key West’s natural beauty while enjoying a private, flexible experience on the water.
Amenities

Skill Levels

Beginner, Intermediate, Advanced

Beer

Feel free to enjoy responsibly, but please no glass.

Music

You can play your own bluetooth music.

Location

This guide can be flexible with the departure location.

Weather

You won’t lose your deposit if the trip is canceled due to weather.

Kid Friendly

This trip can cater to small children.

Flexible Cancelation

This trip can be canceled up to 7 days before the trip.

Physicality

This trip requires an easy level of physical activity.

Disability Friendly

This trip is not suited for those with disabilities.

Lunch

Please provide your own food / snacks.

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Pricing Matrix

4 hours 6 hours 8 hours
1 Person
$800.00
$1,000.00
$1,200.00
2 People
$800.00
$1,000.00
$1,200.00
3 People
$800.00
$1,000.00
$1,200.00
4 People
$800.00
$1,000.00
$1,200.00
5 People
$800.00
$1,000.00
$1,200.00
6 People
$800.00
$1,000.00
$1,200.00
Pay 20% of the price as a deposit today, with the balance due on the day of the trip.
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About Your Guide

Profile photo of Captain Experiences guide Zdravko

Zdravko B.

Independent Guide
Laid-back
Adventurous
Quality
Beginner Oriented
Instructional
Hey there, I’m Capt ZD! With over 11 years of experience sailing the waters around Key West, I’ve built a deep knowledge of the area’s hidden gems, wildlife, and best-kept secrets. My goal is to share the beauty of the Keys in a way that’s personal, laid-back, and unforgettable. Whether we’re hopping between islands, anchoring at a sandbar, or spotting dolphins along the ride, I enjoy creating experiences that feel more like spending a day...

About Your Guide

Profile photo of Captain Experiences guide Zdravko

Zdravko B.

Independent Guide
Hey there, I’m Capt ZD! With over 11 years of experience sailing the waters around Key West, I’ve built a deep knowledge of the area’s hidden gems, wildlife, and best-kept secrets. My goal is to share the beauty of the Keys in a way that’s personal, laid-back, and unforgettable. Whether we’re hopping between islands, anchoring at a sandbar, or spotting dolphins along the ride, I enjoy creating experiences that feel more like spending a day on the water with a friend than taking a tour. My goal at the end of the day is to make some lasting memories and build a relationship with my guests so that if they’re ever back in the keys again, they’ll want to come back out and make some more unforgettable memories.

I’m passionate about helping guests truly connect with the unique environment of the Keys while keeping things simple, flexible, and fun. I went to school to be a teacher so I love seeing people learn or ask questions peaked from general curiosity. You have questions, I have answers! So from the clear turquoise waters, to the incredible marine life, or maybe swapping stories of keys type activities, every charter is an opportunity to make lasting memories.

Can’t wait to meet you!

Captain Zdravko (Zak/ZD)
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Rapid Fire Guide Q & A

What’s the biggest fish you’ve caught?
My Wife
If you were cooking for all your friends what would you cook?
Thanks Giving

Rapid Fire Guide Q & A

What’s the biggest fish you’ve caught?
My Wife
If you were cooking for all your friends what would you cook?
Thanks Giving
What’s your favorite band?
Rubber
What’s your favorite movie?
Ones with color and sound
What’s your favorite sports team?
Eagles 🦅
What’s your drink of choice?
Orange lemonade
How did you get started guiding?
It all started when I was answering phones at a pizza shop when I was 15….
What makes you different from other guides?
Personable and easy to get along with. I pick up on social cues
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Start Location & Lodging Options

Your guide can be flexible with your start location.
You can work with your guide after booking to set a more specific start location in the area.
Key West, Florida

About Your Boat

Boat photo for Island Hopping
Boat Type
Center Console
Boat Manufacturer
Proline
Boat Length
24'
Boat Restroom
No

About Your Boat

Boat Type
Center Console
Boat Manufacturer
Proline
Boat Length
24'
Boat Restroom
No
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Trip Details & Amenities

Skill Levels

Beginner, Intermediate, Advanced

Beer

Feel free to enjoy responsibly, but please no glass.

Music

You can play your own bluetooth music.

Location

This guide can be flexible with the departure location.

Weather

You won't lose your deposit if the trip is canceled due to weather.

Kid Friendly

This trip can cater to small children.

Flexible Cancelation

This trip can be canceled up to 7 days before the trip.

Physicality

This trip requires an easy level of physical activity.

Disability Friendly

This trip is not suited for those with disabilities.

Lunch

Please provide your own food / snacks.

Everything Else to Know

Everything is included, but we also recommend bringing sunglasses, sunscreen, weather-appropriate clothing, and anything else you might want on the trip.
We use a cashless autopay system. We'll send you a boarding pass, and on the day of the trip, your guide will scan your boarding pass to automatically transfer the remaining balance. The only cash needed is to tip your guide (we recommend 20%).
Cancel for free up to 7 days before the trip and receive credit back to your account. Cancelling within 7 of the trip will forfeit your deposit to the guide. Day-of cancellations and no-shows will be charged the full balance of the trip to their card.
In the event of inclement weather you'll be covered by out 100% Weather Guarantee and will not lose your deposit.

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First Time Booking with Us?

Captain Experiences is home to thousands of quality, vetted fishing, hunting, and other outdoor sports guides across the US and beyond. Our mission is to Unlock the Outdoors by making it quick and easy to book the trip of a lifetime every time with our Damn Good Guides.
We vet our guides and only partner with the best of the best. Our guides do their very best to keep you safe, show you a great time, and send you home with a memorable experience shared with family and friends.
Once you've paid your deposit at checkout, we'll send you a QR Code boarding pass. Just show your guide your boarding pass on the day of the trip, they'll scan it, the remaining balance will transfer automatically, and you'll be all set to get out there. Just make sure you bring a cash tip for the guide!
In the event of inclement weather, our guides will check the conditions and make the final call on whether its safe to go on the trip. If they decide the trip needs to be postponed, we'll work closely with you to reschedule or provide a credit for the full deposit, which can be applied to any of our trips in the US and beyond.
Each trip's price is determined by the guide and reflects all associated costs. A significant factor in pricing is often the type of boat and the corresponding fuel expenses. Additional costs may include leases, marina or slip fees, and the expenses involved in providing and maintaining the necessary gear for your trip.
After booking your trip, we'll connect you directly with your guide to discuss additional details. In the meantime, our team is here to answer any questions via email, text, or phone.
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