Next AvailableJul 01
Book with Sergey Chashchukhin
Pirate Adventures Charters offers one-of-a-kind outdoor water adventures that allow you to design your very own unique getaway. Whether you’re looking forward to having a fun time fishing, sun bar or sunset tour, dolphin watching, snorkeling, or tubing & wakeboarding—Pirate Adventures Charters will make it happen for you! Leave everything behind and disappear into the calm waters surrounding Key West.
Captain Sergey Chashchukhin is a licensed Captain who has 10 years of experience in local waters. With him at the helm, you are assured to have a safe, comfortable, and memorable experience. He will not only share his expertise with you but he will also show you the sugary white sandbars, crystal clear emerald water, palm trees, breathtaking sunsets, mangroves, manatees, dolphins, birds, and other wildlife in the area. He invites anglers of all skill levels as well as families with kids to join to have an amazing time.
Your adventure will start as soon as you hop aboard the brand new 26’ Sea Born center console boat that can comfortably accommodate up to 6 guests. It is powered by 2 200 HP Suzuki engines that run a maximum speed of 55 knots. It features the latest navigational equipment such as GPS and Fishfinder and it has a live bait well and ice box ready for use. It also has snorkeling and spearfishing equipment on board.
There’s a huge variety of fish that reside in Key West. Take advantage of Florida’s amazing fisheries and go after prized species such as Amberjack, Barracuda, Bonefish, Cobia, Mahi Mahi, Goliath Grouper, Crevalle Jack, Tuna, Sheepshead, Snapper, and more! Captain Sergey will make sure you are ready to face these monsters—he will teach you a variety of fishing techniques such as using light tackle, bottom fishing, jigging, drift fishing, and spearfishing.
Pirate Adventure Charters appreciates how valuable vacation and family time is and go all out to make your experience relaxing and enjoyable. Everything you need for your trip will be provided—Rods, reels & tackle, and licenses. The Captain will even offer catch cleaning after the trip. All you have to prepare is some snacks & drinks, your sun protection, and come prepared and full of enthusiasm!
Pirate Adventure Charters is willing to help you to create YOUR OWN SPECIAL DAY in Key West's calm waters. Start picking the dates and booking your today. Make your dream fishing adventure come true!
What's Included
Your Guide has some important details about your trip with them.
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When you book your fishing trip, you will need to first put down a deposit to hold the reservation.
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What's Included
Your Guide has some important details about your trip with them.
Show More
When you book your fishing trip, you will need to first put down a deposit to hold the reservation.
Show More
Fishing
Starting At $1,250
Description:
Fishing
Starting At $900
Description:
Fishing
Starting At $850
Description:
Fishing
Starting At $500
Description:
Fishing
Starting At $900
Description:
Fishing
Starting At $700
Description:
Fishing
Starting At $700
Description:
Fishing
Starting At $900
Description:
Fishing
Starting At $700
Description:
Fishing
Starting At $1,150
Description:
Fishing
Starting At $700
Description:
Fishing
Starting At $900
Description:
Fishing
Starting At $700
Description:
Fishing
Starting At $900
Description:
Sea Born
Boat Type:
Boat Guest Capacity:
6
Boat Length:
26 ft
Manufacturer Name:
Sea Born
Model Year:
2021
Engine Manufacturer Name:
Suzuki
# of Engines:
2
Horsepower Per Engine:
200
Maximum Cruising Speed:
55
Features: Bait Tank Ice-Box GPS
Sea Born
Boat Type:
Boat Guest Capacity:
6
Boat Length:
26 ft
Vehicle Details
Ratings & Reviews Summary
July 1, 2025
Sergey is a top pro in the adventure planning, he knows how to make your trip special. We have enjoyed a lot, catched some waves and fishes, plus discovered beautiful nature of Key West.
July 1, 2025
Hands down the best experience we had in Key west. He took us to the most beautiful places that look just like a Caribbean island, not crowded, crystal clear water. Captain himself is a very friendly and welcoming person, who will explain you everything in details. boat has coolers so you can bring your own food and drinks, we were lucky to enjoy our Prosecco in this beautiful paradise. We are a well travelled couple, but this has been one of the most enjoyable experiences we had! Try it and you won’t regret!
July 1, 2025
Had an awesome time with Captain Sergey! He took us out fishing and then to a private sandbar to cool off and swim. The kids really enjoyed it. I would highly recommend booking a private charter with him.
July 1, 2025
We had an amazing day boating with Captain Sergey. Would definitely recommend him for a charter around Key West. He was a great host and made sure we got to a nice sand bar to relax and enjoy the beautiful beach.
July 1, 2025
We had an amazing stay at the houseboat. We swam and snorkeled right off the boat and adventured around with the kayaks. Sergey is an excellent host.
July 1, 2025
We had a great day with Captain Sergey celebrating our 22nd Anniversary 9/18/2021! He’s super friendly, plays sweet tunes, and is very knowledgeable. The boat is exquisitely clean, comfortable and very well maintained. Had a blast talking about life and the future may hold. We caught barracudas and yellow tails. We will definitely book again with Captain Sergey @ Pirate Adventure Charters and you should too. You won’t be disappointed!