Pirate Adventure Charters 

4.8/5 (48 reviews)
 5130 Overseas Highway, Stock Island, FL 33040, United States

Pirate Adventure Charters 

Stock Island, FL, United States
26 ft
6
4.8/5 (48 reviews)

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Pirate Adventure Charters offers private Key West boat cruises to tourists and locals looking to have an ocean adventure without the crowd. Snorkeling, sandbar, sunset cruises, eco tours, and dolphin watch. From boat proposals and photoshoots to birthdays and weddings or business meetings. We're also able to accommodate a wide range of events on the water.

Come down to Stock Island, Florida, a first-door neighbor to the Key West. There you'll discover amazing beaches and a lot of fishing potential. Pirate Adventure Charter is waiting for you to provide you with a memorable experience and a fishing session. You'll be under the guidance of Captain Sergey, who is more than eager to share with you his great knowledge and enthusiasm for the sea.

You'll be cruising the area on the brand new Sea Born, center console model from 2021. It is 26' and it can accommodate groups of up to 6 guests. The boat is fitted with a double Suzuki engine that can reach top speeds of 55 knots. You'll be zooming to your hot spot in no time! For your maximum fishing experience, fishfinding equipment is available.

The charter covers the inshore region with backcountry, nearshore, and offshore areas which include reef and wreck locations. The fish bites all year round, though some periods are busier than others. You can encounter a variety of pelagic fish like Mahi Mahi and several types of Tuna. You can go after these beauties with several fishing techniques such as light tackle, trolling, and drift fishing. Spearfishing is also an option.

Families with children are welcome, and you'll be happy to know that there's snorkeling equipment available. The charter covers your Florida fishing license, and the crew will set you up with the fishing gear. If you want to freshen up you can use the onboard shower. If you end up catching some fish, you can keep it and the crew will gladly help you with cleaning and bagging.

Creat some life-long memories on fishing trips with Pirate Adventure Charters.

Pirate Adventure Charters offers private Key West boat cruises to tourists and locals looking to have an ocean adventure without the crowd. Snorkeling, sandbar, sunset cruises, eco tours, and dolphin watch. From boat proposals and photoshoots to birthdays and weddings or business meetings. We're also able to accommodate a wide range of events on the water.

Come down to Stock Island, Florida, a first-door neighbor to the Key West. There you'll discover amazing beaches and a lot of fishing potential. Pirate Adventure Charter is waiting for you to provide you with a memorable experience and a fishing session. You'll be under the guidance of Captain Sergey, who is more than eager to share with you his great knowledge and enthusiasm for the sea.

You'll be cruising the area on the brand new Sea Born, center console model from 2021. It is 26' and it can accommodate groups of up to 6 guests. The boat is fitted with a double Suzuki engine that can reach top speeds of 55 knots. You'll be zooming to your hot spot in no time! For your maximum fishing experience, fishfinding equipment is available.

The charter covers the inshore region with backcountry, nearshore, and offshore areas which include reef and wreck locations. The fish bites all year round, though some periods are busier than others. You can encounter a variety of pelagic fish like Mahi Mahi and several types of Tuna. You can go after these beauties with several fishing techniques such as light tackle, trolling, and drift fishing. Spearfishing is also an option.

Families with children are welcome, and you'll be happy to know that there's snorkeling equipment available. The charter covers your Florida fishing license, and the crew will set you up with the fishing gear. If you want to freshen up you can use the onboard shower. If you end up catching some fish, you can keep it and the crew will gladly help you with cleaning and bagging.

Creat some life-long memories on fishing trips with Pirate Adventure Charters.

Sergey Chashchukhin
Captain
Sergey Chashchukhin
9 years of experience
responds within an hour

Trip availability and prices

Trip Date:
Group Size:
Select date to see availability
July 2026
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
Change
Almost there...
Half Day Trip
FREE Cancellation 7 days notice
4 hour trip starts at 9:00 AM
US $700
Entire boat: up to 6 people
5 Hour Trip
FREE Cancellation 7 days notice
5 hour trip starts at 9:00 AM
US $850
Entire boat: up to 6 people
3/4 Day Trip
FREE Cancellation 7 days notice
6 hour trip starts at 9:00 AM
US $900
Entire boat: up to 6 people
7 Hour Trip
FREE Cancellation 7 days notice
7 hour trip starts at 9:00 AM
US $1,150
Entire boat: up to 6 people
Full Day Trip
FREE Cancellation 7 days notice
8 hour trip starts at 9:00 AM
US $1,250
Entire boat: up to 6 people

Customer reviews

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Rating

4.8
48 reviews
4.9
Boat & equipment
4.8
Captain & crew
4.8
Fishing Experience

Anglers' gallery (107)

What anglers say

95%
Great experience
97%
Family friendly
97%
Friendly captain
100%
Good boat
94%
Recommended
73%
Caught fish

All reviews (48)

Frequently mentioned
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Showing 15 of 48 reviews
Colleen Gaughan
Colleen Gaughan
Repeat angler
us
Pennsylvania, US
Member since 2023
2 trips
5.0
Verified
9-2 trip—great time!
5 Hour Trip on March 12, 20232 adults1 child

My preteen does not like to get up early, but I wanted to get him excited about Keys fishing! This time slot was great! Got some great time on a close reef and everyone caught fish! Lots of fish and good variety! When I got a little too hot for the fishing on the reef, we broke for lunch and went to a good snorkeling spot. Very refreshing after a day on the water! Our captain Sergey was very knowledgeable and a good teacher! It was our son’s first trip out fishing and he really enjoyed it—thanks, Sergey!

JASON COX
JASON COX
us
Georgia, US
Member since 2023
5.0
Verified
Sergey is great
3/4 Day Trip on July 10, 20233 adults

A hard working Russian immigrant who is determined to give you a great experience. He was very accommodating and polite. We had a great time. Everyone in our group had a great time, and it’s not everyday you can say that.

Reported catch:
Mangrove Snapper
Great Barracuda
Nick Hagemeister
Nick Hagemeister
Repeat angler
us
Minnesota, US
Member since 2021
3 trips
5.0
Verified
Half day trip with Captain Sergey!
Half Day Trip on July 1, 20212 adults

Very nice, clean boat. Captain Sergey is a very awesome and friendly guy. Our goals today were to catch a Mahi plus a variety of other fish. He succeeded right away and got us our Mahi! Then he brought us in to catch some other fish off the reefs. My wife lost a BIG shark and we caught several smaller fish. Then we went snorkeling for a bit. When we came in he fileted our fish. Then recommended where to have them cooked. Mahi is delicious! Very high recommendation. He's a very happy guy who brings out the joy in his clients.

Gavin Weyrich
Gavin Weyrich
Repeat angler
us
Wyoming, US
Member since 2024
2 trips
5.0
Verified
Yellow Tailed Snapper
5 Hour Trip on October 3, 20241 adult

Great day with Captain Sergei, nailed some yellow tailed snappers

Jason Schweinsberg
Jason Schweinsberg
us
Colorado, US
Member since 2023
5.0
Verified
3/4 day trip with Sergey
3/4 Day Trip on June 11, 20234 adults

Was an absolute great trip was able to not only catch fish the whole time but was also able to do a few other things the group wanted to do and Sergey was extremely helpful in showing and explaining any questions we had

Reported catch:
Mangrove Snapper
Jack Crevalle

FAQs about Pirate Adventure Charters

Pirate Adventure Charters offers the following trips to customers:
  • US $700 per group - Half Day Trip (4 hours)
  • US $850 per group - 5 Hour Trip (5 hours)
  • US $900 per group - 3/4 Day Trip (6 hours)
  • US $1,150 per group - 7 Hour Trip (7 hours)
  • US $1,250 per group - Full Day Trip (8 hours)
When you book a trip with Pirate Adventure Charters, you can expect the following amenities onboard:
  • GPS
  • Fishfinder
  • Snorkeling equipment
  • Live bait well
  • Spearfishing equipment
  • Ice box
Trips booked with Pirate Adventure Charters include:
  • Rods, reels & tackle
  • Catch cleaning & filleting
  • Fishing license
Pirate Adventure Charters offers the following types of fishing:
  • Inshore fishing
  • Nearshore fishing
  • Offshore fishing
  • Reef fishing
  • Wreck fishing
  • Backcountry fishing
Pirate Adventure Charters offers the following fishing techniques:
  • Light tackle
  • Bottom fishing
  • Trolling
  • Jigging
  • Drift fishing
  • Spearfishing
Top targeted fish species with Pirate Adventure Charters include:
  • Amberjack
  • Barracuda (Great)
  • Bonefish
  • Cobia
  • Dolphin (Mahi Mahi)
  • Grouper (Goliath)
  • Jack Crevalle
  • Sheepshead
  • Snapper (Mangrove)
  • Triggerfish (Gray)
  • Tuna (Blackfin)
  • Tuna (Skipjack)

Your captain

Sergey Chashchukhin
Sergey Chashchukhin
Sergey Chashchukhin

Stock Island, Florida, United States

48 Customer reviews
Typical response within an hour
Member since October 2019

A commercial fisherman since 2008, Captain Sergey has always loved getting on the water. He maintained his own boat on the side as a hobby while living in Massachusetts, and eventually decided to leave the business to pursue his dream of being a full time captain. He loves sharing his passion with others and hopes to show you why the ocean is the best office in the world.

48 Customer reviews
Typical response within an hour
Member since October 2019

A commercial fisherman since 2008, Captain Sergey has always loved getting on the water. He maintained his own boat on the side as a hobby while living in Massachusetts, and eventually decided to leave the business to pursue his dream of being a full time captain. He loves sharing his passion with others and hopes to show you why the ocean is the best office in the world.

The fish you can target

Amberjack
Amberjack
Great Barracuda
Great Barracuda
Bonefish
Bonefish
Cobia
Cobia
Dolphin (Mahi Mahi)
Dolphin (Mahi Mahi)
Goliath Grouper
Goliath Grouper
Jack Crevalle
Jack Crevalle
Sheepshead
Sheepshead
Mangrove Snapper
Mangrove Snapper
Gray Triggerfish
Gray Triggerfish
Blackfin Tuna
Blackfin Tuna
Skipjack Tuna
Skipjack Tuna
Amberjack
Amberjack
Great Barracuda
Great Barracuda
Bonefish
Bonefish
Cobia
Cobia
Dolphin (Mahi Mahi)
Dolphin (Mahi Mahi)

What is the boat like?

Boat image
Boat category
Center console boats
Capacity
6 persons
Boat length
26 ft
Year built
2021
Boat manufacturer
Sea Born
Boat type
Center console
Engine model
Suzuki
Powered by
2 x 200HP
Max cruising speed
55 knots

What kind of fishing will you do?

Inshore Fishing
Nearshore Fishing
Offshore Fishing
Reef Fishing
Wreck Fishing
Backcountry Fishing

Which fishing techniques you can try

Light Tackle
Bottom Fishing
Trolling
Jigging
Drift Fishing
Spearfishing

Which amenities are available onboard

GPS
Fishfinder
Snorkeling equipment
Live bait well
Spearfishing equipment
Ice box

What's included in the trip price

Rods, reels & tackle
Catch cleaning & filleting
Fishing license

How cancellations work

Free cancellation up to 7 days prior to trip

You can cancel or modify your booking up to 7 days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.

More details

What the listing policies are

Pickup not included

Transfer to/from departure site is not included in trip rates.

Child friendly
You keep catch
Catch and release allowed

How you can pay

Pay online in full

Pay online in full through FishingBooker and save on credit card fees at the dock.

No additional fees.

Book with 50% deposit, pay rest to captain

When the captain confirms your trip, FishingBooker charges your credit card a 50% deposit to guarantee your reservation.

The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:

 Cash

 Visa

 Mastercard

 American Express

 PayPal

When paying the remaining balance with a credit card, an additional 3% charge will apply.

What’s biting in Stock Island right now

AmberjackAmberjack
Barracuda (Great)Barracuda (Great)
BonefishBonefish
CobiaCobia
Dolphin (Mahi Mahi)Dolphin (Mahi Mahi)
Jack CrevalleJack Crevalle
Snapper (Mangrove)Snapper (Mangrove)
Tuna (Blackfin)Tuna (Blackfin)
Tuna (Skipjack)Tuna (Skipjack)

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