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
    US $700
    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
    US $850
    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
    US $900
    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
    US $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
    US $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.
There are 4 people looking at this charter.

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)

Meet the Captain

Sergey Chashchukhin
Stock Island, Florida, United States
ID & license verified
46 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 46 reviews
Boat
Excellent
4.9 / 5
Crew
Excellent
4.9 / 5
Experience
Excellent
4.8 / 5
Photos & videos by reviewers (108)
Half Day Trip
Dolphin, snapper catcher!
Dolphin, snapper catcher!
+105
Angler rating
43
2
0
1
0
Anglers claimed
Good experience
95%
Friendly captain
97%
Recommend this charter
96%
Appropriate for children
97%
Satisfied with the boat
100%
Caught fish
71%
Sort by:
Featured  
Showing:
5 of 46 reviews
JASON C.
Key West, Florida
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Sergey is great

VERIFIED   3/4 Day Trip on July 10, 2023
A hard working Russian immigrant who is determined to give you a great experience. He was very accommodating and polite. We...
JASON C. recommends Pirate Adventure Charters
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JASON C. recommends Pirate Adventure Charters
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Jason S.
Keenesburg, CO
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

3/4 day trip with Sergey

VERIFIED   3/4 Day Trip on June 11, 2023
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...
Jason S. recommends Pirate Adventure Charters
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Jason S. recommends Pirate Adventure Charters
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Tre G.
United States
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

July fishing trip

VERIFIED   5 Hour Trip on July 4, 2023
Had a great charter. Very cool guy good fishing and good conversation. Had lots of knowledge besides just fishing and water/boats....
Tre G. recommends Pirate Adventure Charters
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Tre G. recommends Pirate Adventure Charters
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Jason M.
Northport, NY
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Dolphin, snapper catcher!

VERIFIED   Half Day Trip on June 22, 2023
Capt. Sergey is knowledgeable, considerate and fun. He put me on fish out in the deep blue water and closer to shore where...
Jason M. recommends Pirate Adventure Charters
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Jason M. recommends Pirate Adventure Charters
Mark review as helpful
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Sonny H.
Beaufort, SC
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Half Day Trip

VERIFIED   3/4 Day Trip on June 24, 2023
It was a great time. The captain put us on some yellow fins and we did the rest
Sonny H. recommends Pirate Adventure Charters
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Sonny H. recommends Pirate Adventure Charters
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You found this review helpful