Pirate Adventure Charters 

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

Pirate Adventure Charters 

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

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Customer reviews

Rating summary

4.8/5
out of 5 stars from 48 reviews
Boat
4.9/5
Crew
4.8/5
Experience
4.8/5

Photos & videos by reviewers (109)

Yellow Tailed Snapper
Half Day Trip
Dolphin, snapper catcher!
+106

Angler rating

44
2
1
1
0

Anglers claimed

Good experience

95%

Appropriate for children

97%

Friendly captain

97%

Satisfied with the boat

100%

Recommend this charter

94%

Caught fish

73%

Showing 1 - 5 of 48 reviews
Showing: 5 of 48 reviews
Colleen Gaughan
Colleen Gaughan
Miami, Florida
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!
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JASON COX
JASON COX
Key West, Florida
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
0
Nick Hagemeister
Nick Hagemeister
New Richmond, WI
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.
Review media 0
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0
Gavin Weyrich
Gavin Weyrich
5.0
Verified
Yellow Tailed Snapper
5 Hour Trip on October 3, 20241 adult
Great day with Captain Sergei, nailed some yellow tailed snappers
Review media 0
0
Jason Schweinsberg
Jason Schweinsberg
Keenesburg, CO
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
Review media 0
Review media 1
Review media 2
Reported catch:
Mangrove Snapper
Jack Crevalle
0

Trip availability and prices

Trip Date:
Days:
Group Size:
Select date to see availability
November 2025
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
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Almost there...
Half Day Trip
Low rate deposit non-refundable
4 Hour Trip, starts at 9:00 AM
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US $700 
Entire boat: up to 6 people
5 Hour Trip
Low rate deposit non-refundable
5 Hour Trip, starts at 9:00 AM
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US $850 
Entire boat: up to 6 people
3/4 Day Trip
Low rate deposit non-refundable
6 Hour Trip, starts at 9:00 AM
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US $900 
Entire boat: up to 6 people
7 Hour Trip
Low rate deposit non-refundable
7 Hour Trip, starts at 9:00 AM
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US $1,150 
Entire boat: up to 6 people
Full Day Trip
Low rate deposit non-refundable
8 Hour Trip, starts at 9:00 AM
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US $1,250 
Entire boat: up to 6 people
There is 1 person looking at this charter.

Customer reviews

Rating summary

4.8/5
out of 5 stars from 48 reviews
Boat
4.9/5
Crew
4.8/5
Experience
4.8/5

Photos & videos by reviewers (109)

Yellow Tailed Snapper
Half Day Trip
Dolphin, snapper catcher!
+106

Angler rating

44
2
1
1
0

Anglers claimed

Good experience

95%

Appropriate for children

97%

Friendly captain

97%

Satisfied with the boat

100%

Recommend this charter

94%

Caught fish

73%

Showing 1 - 5 of 48 reviews
Showing: 5 of 48 reviews
Colleen Gaughan
Colleen Gaughan
Miami, Florida
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!
Review media 0
Review media 1
Review media 2
0
JASON COX
JASON COX
Key West, Florida
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
0
Nick Hagemeister
Nick Hagemeister
New Richmond, WI
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.
Review media 0
Review media 1
Review media 2
Review media 3
0
Gavin Weyrich
Gavin Weyrich
5.0
Verified
Yellow Tailed Snapper
5 Hour Trip on October 3, 20241 adult
Great day with Captain Sergei, nailed some yellow tailed snappers
Review media 0
0
Jason Schweinsberg
Jason Schweinsberg
Keenesburg, CO
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
Review media 0
Review media 1
Review media 2
Reported catch:
Mangrove Snapper
Jack Crevalle
0

FAQs about Pirate Adventure Charters

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The fish you can target

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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
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What’s biting in Stock Island right now

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