14 Trips Available

from

$500

Pirate Adventure Charters

5 10 reviews

Identity Verified

Key West FL

Reeled In Plenty of Fish in Key West, FL

1 / 5

Pirate Adventure Charters

Key West FL

5 10 reviews

Your Captain

Sergey Chashchukhin

Identity Verified

Sergey Chashchukhin, Captain at Pirate Adventure Charters

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!

Upcoming Availability

July 2025

August 2025

Expertise & Attributes

fishing

Deep Sea Fishing

Good with Families

Good with Kids

Good with New Anglers

Master Guide

Saltwater Fishing

Fishing Techniques

JiggingTrolling FishingLight TackleSpear FishingDeep Sea / Bottom FishingDrift Boat Fishing

What's Included

Good to Knows

Your Guide has some important details about your trip with them.

Cancellation Policy

When you book your fishing trip, you will need to first put down a deposit to hold the reservation.

What's Included

Good to Knows

Your Guide has some important details about your trip with them.

Cancellation Policy

When you book your fishing trip, you will need to first put down a deposit to hold the reservation.

Trips Available with Pirate Adventure Charters

Top-Rated

Instant Booking

Fishing - Offshore

Sea Born26'Sea Born Max 6 guests (base trip price includes 6 guests)

Key West, FL 8 Hour Fishing Trip

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.

Full Day Trip

Maximum 6 persons allowed
(base trip price includes 6 guests)

8 Hours

9:00 AM

$1,250

Pick Your Date

Top-Rated

Instant Booking

Fishing - Shore

Sea Born26'Sea Born Max 6 guests (base trip price includes 6 guests)

Key West, FL 6 Hour Sandbar Trour

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!

Morning Trip

Maximum 6 persons allowed
(base trip price includes 6 guests)

6 Hours

9:00 AM

$900

Pick Your Date

Top-Rated

Instant Booking

Fishing - Offshore

Sea Born26'Sea Born Max 6 guests (base trip price includes 6 guests)

Key West, FL 5 Hour Fishing Trip

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.

Morning Trip

Maximum 6 persons allowed
(base trip price includes 6 guests)

5 Hours

9:00 AM

$850

Pick Your Date

Best Price Guarantee

Top-Rated

Instant Booking

Fishing - Inshore

Sunset and Dolphin Watching Excursion

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.

Evening Trip

Maximum 8 persons allowed
(base trip price includes 8 guests)

2 Hours

6:00 PM

$500

Pick Your Date

Key West, FL 6 Hour Eco Tour and Dolphon Watching

Top-Rated

Instant Booking

Fishing - Shore

Sea Born26'Sea Born Max 6 guests (base trip price includes 6 guests)

Key West, FL 6 Hour Eco Tour and Dolphon Watching

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.

Morning Trip

Maximum 6 persons allowed
(base trip price includes 6 guests)

6 Hours

9:00 AM

$900

Pick Your Date

Key West, FL 4 Hour Eco Tour and Dolphon Watching

Top-Rated

Instant Booking

Fishing - Shore

Sea Born26'Sea Born Max 6 guests (base trip price includes 6 guests)

Key West, FL 4 Hour Eco Tour and Dolphon Watching

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.

Morning Trip

Maximum 6 persons allowed
(base trip price includes 6 guests)

4 Hours

9:00 AM

$700

Pick Your Date

Key West, FL 4 Hour Tubing or Wakeboarding Trip

Top-Rated

Instant Booking

Fishing - Shore

Sea Born26'Sea Born Max 6 guests (base trip price includes 6 guests)

Key West, FL 4 Hour Tubing or Wakeboarding Trip

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.

Morning Trip

Maximum 6 persons allowed
(base trip price includes 6 guests)

4 Hours

9:00 AM

$700

Pick Your Date

Top-Rated

Instant Booking

Fishing - Offshore

Sea Born26'Sea Born Max 6 guests (base trip price includes 6 guests)

Key West, FL 6 Hour Fishing Trip

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!

Morning Trip

Maximum 6 persons allowed
(base trip price includes 6 guests)

6 Hours

9:00 AM

$900

Pick Your Date

Top-Rated

Instant Booking

Fishing - Inshore

Sea Born26'Sea Born Max 6 guests (base trip price includes 6 guests)

Key West, FL 4 Hour Fishing Trip

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.

Morning Trip

Maximum 6 persons allowed
(base trip price includes 6 guests)

4 Hours

9:00 AM

$700

Pick Your Date

Top-Rated

Instant Booking

Fishing - Offshore

Sea Born26'Sea Born Max 6 guests (base trip price includes 6 guests)

Key West, FL 7 Hour Fishing Trip

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.

Trip

Maximum 6 persons allowed
(base trip price includes 6 guests)

7 Hours

9:00 AM

$1,150

Pick Your Date

Top-Rated

Instant Booking

Fishing - Shore

Sea Born26'Sea Born Max 6 guests (base trip price includes 6 guests)

Key West, FL 4 Hour Sandbar Trour

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.

Morning Trip

Maximum 6 persons allowed
(base trip price includes 6 guests)

4 Hours

9:00 AM

$700

Pick Your Date

Key West, FL 6 Hour Tubing or Wakeboarding Trip

Top-Rated

Instant Booking

Fishing - Shore

Sea Born26'Sea Born Max 6 guests (base trip price includes 6 guests)

Key West, FL 6 Hour Tubing or Wakeboarding Trip

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!

Morning Trip

Maximum 6 persons allowed
(base trip price includes 6 guests)

6 Hours

9:00 AM

$900

Pick Your Date

Top-Rated

Instant Booking

Fishing - Shore

Sea Born26'Sea Born Max 6 guests (base trip price includes 6 guests)

Key West, FL 4 Hour Snorkeling Trip

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!

Morning Trip

Maximum 6 persons allowed
(base trip price includes 6 guests)

4 Hours

9:00 AM

$700

Pick Your Date

Top-Rated

Instant Booking

Fishing - Shore

Sea Born26'Sea Born Max 6 guests (base trip price includes 6 guests)

Key West, FL 6 Hour Snorkeling Trip

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.

Morning Trip

Maximum 6 persons allowed
(base trip price includes 6 guests)

6 Hours

9:00 AM

$900

Pick Your Date

Vehicle

Sea Born

Boat Type:

Boat Guest Capacity:

Boat Length:

26 ft

Manufacturer Name:

Sea Born

Model Year:

2021

Engine Manufacturer Name:

Suzuki

# of Engines:

Horsepower Per Engine:

200

Maximum Cruising Speed:

Features: Bait Tank Ice-Box GPS

Boat

Sea Born

Boat Type:

Boat Guest Capacity:

Boat Length:

26 ft

Vehicle Details

FAQs about Pirate Adventure Charters

What are the trip rates for Pirate Adventure Charters?

What's included in the trip price with Pirate Adventure Charters?

What types of fishing does Pirate Adventure Charters offer?

What fishing techniques does Pirate Adventure Charters offer?

Which fishing species can I catch with Pirate Adventure Charters?

What is the cancellation policy for Pirate Adventure Charters?

Ratings & Reviews Summary

out of 5

Based on 10 ratings

recommended

Based on 10 recommendations

July 13, 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 13, 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 13, 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 13, 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 13, 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 13, 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!