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.



Select date to see available trips and rates:

  • Private trip
    Half Day Trip
    Low rate deposit non-refundable
    4 Hour Trip, starts at 9:00 AM
    $850
    This 4-hour trip is perfect for groups and families who want to have some fun time on the water and still have the rest of the day for enjoying the beach.
  • Private trip
    5 Hour Trip
    Low rate deposit non-refundable
    5 Hour Trip, starts at 9:00 AM
    $950
    Get some extra time with this 5-hour trip and set off on the fishing adventure.
  • Private trip
    3/4 Day Trip
    Low rate deposit non-refundable
    6 Hour Trip, starts at 9:00 AM
    $1,050
    With this 6-hour fishing trip, you get enough time to cover several locations and you can concentrate on getting that big catch.
  • Private trip
    7 Hour Trip
    Low rate deposit non-refundable
    7 Hour Trip, starts at 9:00 AM
    $1,150
    Help yourself to some additional time with this 7-hour trip. You get almost a whole day on the water targeting the big fish.
  • Private trip
    Full Day Trip
    Low rate deposit non-refundable
    8 Hour Trip, starts at 9:00 AM
    $1,250
    With this 8 hour trip, you get to spend a full day on the water. You can turn your fishing trip into a real adventure and snorkeling breaks are also an option.

About the Captain

Sergey Chashchukhin
Stock Island, Florida, United States
Angler's Choice
ID & License verified
35 Customer reviews
Response time 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.

About this listing

Targeted species

Amberjack Amberjack
Barracuda (Great) Great Barracuda
Bonefish Bonefish
Cobia Cobia

Boat specs

Sea Born (Center console) originally built in 2021. Powered by 2 200HP Suzuki engines, with a maximum cruising speed of 55 knots.

Length
26 ft
Capacity
6 persons

Types of fishing

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

Fishing techniques

Light Tackle
Bottom Fishing
Trolling
Jigging
Drift Fishing
Spearfishing

Amenities

GPS
Fishfinder
Snorkeling Equipment
Live Bait Well
Spearfishing Equipment
Ice Box

Trip includes

Rods, reels & tackle
Catch cleaning & filleting
Fishing License

Cancellation policy

Deposit non-refundable

If it is unsafe to travel, you may still cancel free of charge or change the date(s) of your booking.

Listing policies

Pickup not included
Transfer to/from departure site is not included in trip rates.
Child Friendly
You Keep Catch
Catch and Release Allowed

Payment

Book with 20% deposit, pay rest to captain

When the captain confirms your trip, FishingBooker charges your credit card a 20% 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.

Stock Island Fishing Calendar

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Customer reviews

Rating Summary
Excellent
4.9 / 5
out of 5 stars from 35 reviews
Boat
Excellent
5.0 / 5
Crew
Excellent
4.9 / 5
Experience
Excellent
4.9 / 5
Photos & videos by reviewers (95)
Fishing with Sergey
Half day trip with Cpt Sergey
Half day trip with Cpt Sergey
+92
Angler Rating
34
0
0
1
0
Anglers Claimed
Good experience
96%
Friendly captain
97%
Recommend this charter
97%
Appropriate for children
97%
Satisfied with the boat
100%
Catch intended fish
70%
Sort By:
Featured  
Showing:
5 of 35 reviews
Sarah N.
Hernando Beach, FL
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Half day trip with Cpt Sergey

VERIFIED   NEW  Half Day Trip on July 12, 2022
So much fun! From the boat to the Captain it was a wonderful experience. Easy to onboard and communication was great. We fished,...
Sarah N. recommends Pirate Adventure Charters
Mark review as helpful
You found this review helpful
  Sergey Chashchukhin Captain replied

John P.
New York, New York
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Half Day Fishing & Sandbar Trip

VERIFIED   Half Day Trip on July 6, 2022
We had a great day with Sergey.  He’s extremely friendly and knowledgeable about the area.  He took us to one of the most...
John P. recommends Pirate Adventure Charters
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You found this review helpful
  Sergey Chashchukhin Captain replied

Mark S.
Billerica, MA
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

3/4 day fishing snorkeling with Captain Sergey

VERIFIED   3/4 Day Trip on March 6, 2022
Had a fantastic day with my family. High winds prevented us from going to open waters. Captain did a great job and was knowledgeable...
Mark S. recommends Pirate Adventure Charters
Mark review as helpful
You found this review helpful
  Sergey Chashchukhin Captain replied

Jeff Y.
Eagle, ID
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

22nd Anniversary Fishing Trip

VERIFIED   5 Hour Trip on September 18, 2021
We had a great day with Captain Sergey celebrating our 22nd Anniversary 9/18/2021! He’s super friendly, plays sweet tunes,...
Jeff Y. recommends Pirate Adventure Charters
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Jeff Y. recommends Pirate Adventure Charters
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You found this review helpful

Dan M.
United States
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Fishing and snorkeling with Captain Sergey

VERIFIED   Half Day Trip on June 25, 2022
My family and I had a great day fishing and snorkeling with Captain Sergey!  He was extremely friendly and knowledgable as...
Dan M. recommends Pirate Adventure Charters
Mark review as helpful
You found this review helpful
  Sergey Chashchukhin Captain replied

FAQs about Pirate Adventure Charters

Pirate Adventure Charters offers the following trips to customers:
  • $850 per group - Half Day Trip (4 hours)
  • $950 per group - 5 Hour Trip (5 hours)
  • $1,050 per group - 3/4 Day Trip (6 hours)
  • $1,150 per group - 7 Hour Trip (7 hours)
  • $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)