Pirate Adventure Charters 

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

Pirate Adventure Charters 

Stock Island, FL, United States
–
26 ft
6
4.8
(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

Select date to see availability

Trip availability and prices

Trip date:
Group Size:
September 2026
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Group Size
2 adults • 0 children
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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
There are 5 people looking at this charter.

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

Reviews (48)

  • 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, 2023 • 3 adults • 1 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!

  • 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, 2021 • 2 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, 2024 • 1 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, 2023 • 4 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

  • Jason Molinet
    Jason Molinet
    us
    New York, US
    •
    Member since 2023
    5.0
    Verified

    Dolphin, snapper catcher!

    Half Day Trip on June 22, 2023 • 1 adult

    Capt. Sergey is knowledgeable, considerate and fun. He put me on fish out in the deep blue water and closer to shore where the snappers are biting. And his boat is tip top. Highly recommended.

  • John Pratt
    John Pratt
    Repeat angler
    us
    Ohio, US
    •
    Member since 2022
    •
    5 trips
    5.0
    Verified

    Half Day Fishing & Sandbar Trip

    Half Day Trip on July 6, 2022 • 4 adults • 2 children

    We had a great day with Sergey. He’s extremely friendly and knowledgeable about the area. He took us to one of the most beautiful beaches I’ve ever seen. Drove the boat right through this tight mangrove right up to the sandbar. I’ve been to a lot of amazing places in my life and this experience was surely top 5.

  • Jeff Yarnall
    Jeff Yarnall
    Repeat angler
    us
    Idaho, US
    •
    Member since 2021
    •
    2 trips
    5.0
    Verified

    22nd Anniversary Fishing Trip

    5 Hour Trip on September 18, 2021 • 2 adults

    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!

  • Sonny Hennis
    Sonny Hennis
    Repeat angler
    us
    Mississippi, US
    •
    Member since 2021
    •
    2 trips
    5.0
    Verified

    Half Day Trip

    3/4 Day Trip on June 24, 2023 • 6 adults

    It was a great time. The captain put us on some yellow fins and we did the rest

  • Matthew Musolino
    Matthew Musolino
    us
    Virginia, US
    •
    Member since 2022
    5.0
    Verified

    Captain Sergey

    5 Hour Trip on August 19, 2022 • 2 adults

    What a wonderful trip, I am hard-pressed to remember a boating experience that was more accommodating, We were made to feel as if we have known Sergey for many years. What an experience we cannot thank you enough!

  • Sarah Nunley
    Sarah Nunley
    us
    California, US
    •
    Member since 2022
    5.0
    Verified

    Half day trip with Cpt Sergey

    Half Day Trip on July 12, 2022 • 5 adults

    So much fun! From the boat to the Captain it was a wonderful experience. Easy to onboard and communication was great. We fished, scuba-dived the reef and enjoyed every minute. We will be back!!

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
Showing 1 – 5 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, 2023 • 2 adults • 1 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, 2023 • 3 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, 2021 • 2 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, 2024 • 1 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, 2023 • 4 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

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.

Sergey Chashchukhin
Sergey Chashchukhin
48
reviews
2019
member since
~1h
response
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)

Real catches by this captain

  • Yellow Tailed Snapper
    Gavin W.
    Gavin W.
  • Dolphin, snapper catcher!
    Jason M.
    Jason M.
  • Full day!
    Cody S.
    Cody S.

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)

Compare similar fishing charters

Current
Pirate Adventure Charters
Pirate Adventure Charters
4.8
(48)
26 ft
Group size 1 - 6
1 - 6
Fish 1
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+10
4 hour trip • 6 persons
US $700