Next AvailableApr 04
Book with Sergey Chashchukhin
Pirate Adventure Charters
Identity Verified Key West FL
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Sergey Chashchukhin, Captain at Pirate Adventure Charters
Identity Verified
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!
Trips Available with Pirate Adventure Charters
Fishing
Starting At $1,250
Key West, FL 8 Hour Fishing Trip
Fishing: Offshore
Fishing Boat:
Sea Born • 26' Sea Born • Max 6 guests (base trip price includes 6 guests)Description: Spend a productive full-day fishing adventure in the rich waters of Key West where fishing opportunities are endless. Muscle with Cobia, Barracuda, Tuna, Grouper, and more! Snorkeling and spearfishing gears are also available on board. Up to 6 guests can join.
Fishing
Starting At $900
Key West, FL 6 Hour Sandbar Trour
Fishing: Shore
Fishing Boat:
Sea Born • 26' Sea Born • Max 6 guests (base trip price includes 6 guests)Description: Leave the crowds behind and step into “Corona Country”! Experience and relax on the same sandbars and remote beaches Visit Boca Grande, Woman Key, Ballast Key (the true Southernmost spot in the U.S.), or Snipe point. Jump in, cool off, grab a floaty and enjoy your favorite beverage!
Fishing
Starting At $850
Key West, FL 5 Hour Fishing Trip
Fishing: Offshore
Fishing Boat:
Sea Born • 26' Sea Born • Max 6 guests (base trip price includes 6 guests)Description: Discover Florida’s hottest fishing destination and get a chance to hook your next trophy fish with Pirate Adventure Charters. Pack some snacks & drinks, sun protection, and wear weather-appropriate clothing. It's time to have fun fishing out in the waters. Book your trip now.
Fishing
Starting At $500
Sunset and Dolphin Watching Excursion
Fishing: Inshore
Capacity:
Max 8 guests (base trip price includes 8 guests)Description: Enjoy complimentary Soda, beer, wine, or champagne as you relax. Leave your worries behind and go sail into Key West's famous sunset! As the sun gently sets over the horizon, toast the end of another perfect day in paradise. You can contact Captain Sergey if you wish to adjust the start time.
Fishing
Starting At $900
Key West, FL 6 Hour Eco Tour and Dolphon Watching
Fishing: Shore
Fishing Boat:
Sea Born • 26' Sea Born • Max 6 guests (base trip price includes 6 guests)Description: Observe “Safari Style” our resident pods of dolphins that feed, play, and socialize in the shallow waters North and West of Key West. This is a peaceful, no-impact connection with these beautiful animals and a great photo opportunity. Bring the whole gang and enjoy the beautiful scenery & wildlife.
Fishing
Starting At $700
Key West, FL 4 Hour Eco Tour and Dolphon Watching
Fishing: Shore
Fishing Boat:
Sea Born • 26' Sea Born • Max 6 guests (base trip price includes 6 guests)Description: Have you ever dreamed of getting up close and personal with a blue whale or being eye-to-eye with a dolphin? Enjoy a painlessly educational nature experience – birders and naturalists welcome. Up to 6 guests can join the trip.
Fishing
Starting At $700
Key West, FL 4 Hour Tubing or Wakeboarding Trip
Fishing: Shore
Fishing Boat:
Sea Born • 26' Sea Born • Max 6 guests (base trip price includes 6 guests)Description: There’s no doubt that this tour offers one of the best tubing or wakeboarding experiences in Key West. Don’t end your adventures with tubing—go for a swim in one of the many shallow rivers and make the most of your action-packed day.
Fishing
Starting At $900
Key West, FL 6 Hour Fishing Trip
Fishing: Offshore
Fishing Boat:
Sea Born • 26' Sea Born • Max 6 guests (base trip price includes 6 guests)Description: Have an amazing time fishing in Key West, the best in the country! Enjoy all year-round fishing opportunities and get the chance to hook your next trophy fish. Target catching Snapper, Grey Triggerfish, Tuna, Sheephead, Cobia, Mahi Mahi, Barracuda, and more!
Fishing
Starting At $700
Key West, FL 4 Hour Fishing Trip
Fishing: Inshore
Fishing Boat:
Sea Born • 26' Sea Born • Max 6 guests (base trip price includes 6 guests)Description: Enjoy a 4-hour fishing trip as you chase after Florida's most popular species—Sheepshead, Snapper, Triggerfish, Bonefish, and more! All your gear, licenses, and catch cleaning will be provided. This trip accommodates up to 6 guests.
Fishing
Starting At $1,150
Key West, FL 7 Hour Fishing Trip
Fishing: Offshore
Fishing Boat:
Sea Born • 26' Sea Born • Max 6 guests (base trip price includes 6 guests)Description: Have enough time to chase after Florida's mightiest species in this 7-hour offshore fishing trip and practice a variety of fishing techniques with Pirate Adventure Charters. The trip can accommodate up to 6 guests. Your gear, licenses, and catch cleaning are included in the fee.
Fishing
Starting At $700
Key West, FL 4 Hour Sandbar Trour
Fishing: Shore
Fishing Boat:
Sea Born • 26' Sea Born • Max 6 guests (base trip price includes 6 guests)Description: Experience an unforgettable trip to a desert island with amazing sand and clear water. On the way, you can see dolphins and wild animals. Sunbathe. This trip is perfect for groups of family or friends who want to spend a relaxing time enjoying the stunning scenery of Key West, Florida.
Fishing
Starting At $900
Key West, FL 6 Hour Tubing or Wakeboarding Trip
Fishing: Shore
Fishing Boat:
Sea Born • 26' Sea Born • Max 6 guests (base trip price includes 6 guests)Description: Ideal for an active and fun holiday. Try to catch the wave and stay on it. Suitable for both a large company and for entertainment with teenagers. There’s no doubt that this tour offers one of the best tubing or wakeboarding experiences in Key West. Join the fun and book your trip now!
Fishing
Starting At $700
Key West, FL 4 Hour Snorkeling Trip
Fishing: Shore
Fishing Boat:
Sea Born • 26' Sea Born • Max 6 guests (base trip price includes 6 guests)Description: Snorkelers in Key West enjoy views of a variety of sea creatures, including urchins, sea turtles, dolphins, and shovelnose guitarfish. Explore the rich marine life in Key West and spend an awesome and relaxing time with your family and friends. Book now and get ready to be amazed!
Fishing
Starting At $900
Key West, FL 6 Hour Snorkeling Trip
Fishing: Shore
Fishing Boat:
Sea Born • 26' Sea Born • Max 6 guests (base trip price includes 6 guests)Description: Experience the breathtaking snorkeling spots filled with living coral reefs and underwater marine life. You can watch this amazing world. Then explore the tropical island while lounging on the beach to complete your journey. Pick your dates and start packing—your next adventure is here.
FAQs about Pirate Adventure Charters
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Ratings & Reviews Summary
April 4, 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.
April 4, 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!
April 4, 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.
April 4, 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.
April 4, 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.
April 4, 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!
