Jolly Roger IIΒ 

4.9/5Β (695 reviews)
Β 
Federally permitted
Β 1801 North Roosevelt Boulevard, Key West, FL 33040, United States–

Jolly Roger IIΒ 

Β 
Federally permitted
4.9/5Β (695)
β€’
Β Angler's Choice
map-thumbnail
1801 North Roosevelt Boulevard
Key West, FL, United States
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Exceptional sport fishing experience, exclusively focusing on topwater action. No bottom fishing.

Key West, FL is home to some of the world's most famous fishing grounds – what better way to discover them than alongside a captain who grew up exploring these waters? Captain Joe Mercurio comes from a long line of Floridian fishermen, and can't wait to pass on the knowledge he's inherited. Come aboard Jolly Roger II and get ready to discover plenty of local tips and tricks – you'll be fishing like a native Floridian in no time!

Capt. Joe has been fishing these waters for over 37 years. He bought the 'Jolly Roger II' boat from his father, and his grandfather owned one of the first charters boats in Key West in the 40s – it's safe to say that a passion for angling is a true family tradition for him! He uses his wealth of knowledge to provide a variety of angling adventures that are suitable for guests of all ages and skill levels, all on board a luxurious fishing machine.

The vessel in question is an impressive 39' Chu Chu sportfishing vessel, able to accommodate up to 6 anglers. She's the perfect choice if you're looking for a fun family getaway, or want to tangle lines with some of your best angling buddies. There are 5 fishing chairs on the back deck, a fighting chair for battling big game, and outriggers to cover plenty of ground when trolling.

Speaking of trolling, your captain specializes in putting guests on fish by using his 'reef to bluewater' trolling method. This means that you'll be exploring fishing grounds around the local reefs, as well as up to 25 miles offshore. You'll have the chance to hook Mahi Mahi, a variety of Marlin, Barracuda, Wahoo, Tuna, and more. Don't worry if you've never fished before – your captain and first mate will be on hand to show you the ropes.

Your trip includes rods, reels, bait, tackle, and a fishing license. Your captain will fillet your catch, too. Come aboard Jolly Roger II and learn how to fish like a true Floridia

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Rating

4.9
695 reviews
5
668
4
21
3
3
2
2
1
0
4.9
Boat & equipment
5.0
Captain & crew
4.9
Fishing Experience

Anglers' gallery (1292)

great time
Exactly what we were looking for!
Exactly what we were looking for!
Exactly what we were looking for!
Exactly what we were looking for!
A variety of fish including Mahi Mahi and Tuna laid out on a dock after a successful fishing trip.
+1286

What anglers say

98%
Great experience
94%
Family friendly
100%
Friendly captain
100%
Good boat
99%
Recommended
94%
Caught fish

All reviews (695)

Filter
ShowingΒ 1 – 5Β ofΒ 695Β reviews
Todd Ely
Todd Ely
5.0
Verified
great crew that put us fish quick!!
3/4 Day Trip on November 19, 2025 β€’ 4 adults
We had an amazing experience on the Jolly Roger II with Captain Joe and First Mate Brian. Both of them were incredibly easygoing, informative, and made the entire trip enjoyable from start to finish. Captain Joe got us on the fish quickly β€” we ended up catching 7 mahi-mahi, 2 barracuda, and 2 tuna. Brian worked nonstop the entire time, from setting us up at the start all the way through bringing the lines in as we headed back to shore. He truly goes above and beyond. Brian also recommended taking our fresh catch to Half Shell Raw Bar, and we’re so glad we did. They cooked our fish for just $15.99 per pound, served with two sides. We had half blackened and half fried β€” everything was absolutely delicious. Highly recommend Captain Joe, Brian, and the Jolly Roger II for anyone looking for a fun, successful, and memorable fishing trip!
Two anglers proudly displaying a large Mahi Mahi on a fishing boat during a sunny day at sea.
A group of anglers proudly displaying their catch of Mahi Mahi on the dock after a successful fishing trip.
A young angler and an adult are actively fishing on a boat, with a fish visible in the water, showcasing the excitement of deep-sea fishing.
A young angler watches as an adult casts a line while fishing on a boat in open waters, showcasing an engaging fishing experience.
A young angler and a guide are engaged in reeling in a catch while fishing on a boat in open waters.
Reported catch:
Dolphin (Mahi Mahi)
Great Barracuda
Response from Captain
November 20, 2025
you guys were awesome, enjoyed the fish. Have a safe flight home, see you next time. Thank you so much for choosing us.😎🎣
1
Patrick Fox
Patrick Fox
5.0
Verified
SAILFISH!!
3/4 Day Trip - 12:30 PM on November 25, 2025 β€’ 4 adults
Had an absolutely incredible day aboard the Jolly Roger II with Captain Joe and First Mate Brian! We filled the box with mahi, picked up a king mackerel and a barracuda, and the highlight of the trip was my daughter landing a 6.5-foot sailfishβ€”an unforgettable moment and truly the catch of a lifetime. Captain Joe and Brian were amazing from start to finish: knowledgeable, hardworking, and fun to be around. Couldn’t have asked for a better crew or a better day on the water. Highly recommend the Jolly Roger II for anyone looking for a top-notch fishing experience!
Review media 0
Review media 0
Review media 1
Reported catch:
Dolphin (Mahi Mahi)
King Mackerel (Kingfish)
Sailfish
Response from Captain
December 3, 2025
You guys were awesome, great Charter, beautiful day and a great catch. Have a good one. Take care and hope to see you next time. 😎🎣
0
Ed Young
Ed Young
5.0
Verified
Fantastic Outing!!!
3/4 Day Trip on October 18, 2025 β€’ 2 adults
Booked a 3/4 day trip for my son and I and we couldn't have had a better time! We arrived early but Captain Joe and Brain were ready to go so we got an early start. They were great explaining how the day would go and they got us to the right spots to pull in 10 Mahi-Mahi! We even had to through a couple back along with a barracuda and tuna too! Took our catch to a restaurant to get them cooked up and had one of the best lunches ever. Next time in in Key West, definitely going to book another trip on the Jolly Roger II.
Two anglers proudly displaying their catch of Mahi Mahi while enjoying a day of deep-sea fishing on a charter boat.
Review media 0
A collection of Mahi Mahi laid out on a dock, showcasing a successful fishing trip.
A plate of fried fish and grilled fish garnished with lime, served in a dining setting.
A serene sunset over the ocean, capturing the tranquil beauty of the fishing environment.
Reported catch:
Dolphin (Mahi Mahi)
Great Barracuda
Albacore Tuna
Response from Captain
October 20, 2025
thank you so much for all the kind words beautiful pictures and we really appreciate you, take care and hope to see you again someday, 😎
0
William Langenberg
William Langenberg
5.0
Verified
New
Made life long memories! Great experience.
3/4 Day Trip on March 30, 2026 β€’ 4 adults
Had an amazing time with Joe and his mate Bryan. Would recommend these guys any day of the week!! Top notch knowledge of whats biting at what time. This crew could not have made us feel any more comfortable than they did. Truly made some lifelong memories even in some choppy conditions. Cant wait to be back in Key West and book another trip with Joe.
Review media 0
Review media 0
Review media 0
Review media 1
Review media 2
Reported catch:
Skipjack Tuna
Response from Captain
April 1, 2026
Will, you guys were awesome. Great catch. Hope dinner was awesome and hope to see you again soon. πŸ™πŸ˜Ž
0
Edward Kammerer
Edward Kammerer
5.0
Verified
Wind Blowing 25 knots, but still had a great trip
3/4 Day Trip - 12:30 PM on January 21, 2026 β€’ 6 adults
We went out with Cap Joe and Brian on a less than ideal weather day, but it was the only day we could fish while in KW. The wind had been blowing hard for several days and still blowing the day we went out. Despite the weather, we stiil had a great time. The boat was very comfortable even in rough seas and they even managed to put us on some fish. Definitely recommend these guys even if you think the weather is not ideal. We will be back!
Angler proudly displaying a large fish at the dock during a fishing trip, with a scenic sunset backdrop.
Reported catch:
King Mackerel (Kingfish)
Great Barracuda
Response from Captain
January 23, 2026
thank you for all the kind words, waste every day could be awesome and beautiful weather. It was a pleasure having you and thank you so much.πŸ˜ŽπŸ™
1

Trip availability and prices

Trip Date:
Days:
Group Size:
Select date to see availability
April 2026
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Number of days
1
Group Size
2 adults β€’ 0 children
Change
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Half Day Trip
FREE Cancellation 7 days notice
4 Hour Trip
starts at 7:30 AM
US $950
Entire boat: up to 6 people
Half Day Trip - 12:30 PM
FREE Cancellation 7 days notice
4 Hour Trip
starts at 12:30 PM
US $950
Entire boat: up to 6 people
Half Day Trip - 1:30 PM
FREE Cancellation 7 days notice
4 Hour Trip
starts at 1:30 PM
US $950
Entire boat: up to 6 people
3/4 Day Trip
FREE Cancellation 7 days notice
6 Hour Trip
starts at 7:30 AM
US $1,200
Entire boat: up to 6 people
3/4 Day Trip - 12:30 PM
FREE Cancellation 7 days notice
6 Hour Trip
starts at 12:30 PM
US $1,200
Entire boat: up to 6 people
Full Day Trip
FREE Cancellation 7 days notice
8 Hour Trip
starts at 7:30 AM
US $1,500
Entire boat: up to 6 people
There are 16 people looking at this charter.

Rating

4.9
695 reviews
5
668
4
21
3
3
2
2
1
0
4.9
Boat & equipment
5.0
Captain & crew
4.9
Fishing Experience

Anglers' gallery (1292)

great time
Exactly what we were looking for!
Exactly what we were looking for!
Exactly what we were looking for!
Exactly what we were looking for!
A variety of fish including Mahi Mahi and Tuna laid out on a dock after a successful fishing trip.
+1286

What anglers say

98%
Great experience
94%
Family friendly
100%
Friendly captain
100%
Good boat
99%
Recommended
94%
Caught fish

All reviews (695)

Filter
ShowingΒ 1 – 5Β ofΒ 695Β reviews
Todd Ely
Todd Ely
5.0
Verified
great crew that put us fish quick!!
3/4 Day Trip on November 19, 2025 β€’ 4 adults
We had an amazing experience on the Jolly Roger II with Captain Joe and First Mate Brian. Both of them were incredibly easygoing, informative, and made the entire trip enjoyable from start to finish. Captain Joe got us on the fish quickly β€” we ended up catching 7 mahi-mahi, 2 barracuda, and 2 tuna. Brian worked nonstop the entire time, from setting us up at the start all the way through bringing the lines in as we headed back to shore. He truly goes above and beyond. Brian also recommended taking our fresh catch to Half Shell Raw Bar, and we’re so glad we did. They cooked our fish for just $15.99 per pound, served with two sides. We had half blackened and half fried β€” everything was absolutely delicious. Highly recommend Captain Joe, Brian, and the Jolly Roger II for anyone looking for a fun, successful, and memorable fishing trip!
Two anglers proudly displaying a large Mahi Mahi on a fishing boat during a sunny day at sea.
A group of anglers proudly displaying their catch of Mahi Mahi on the dock after a successful fishing trip.
A young angler and an adult are actively fishing on a boat, with a fish visible in the water, showcasing the excitement of deep-sea fishing.
A young angler watches as an adult casts a line while fishing on a boat in open waters, showcasing an engaging fishing experience.
A young angler and a guide are engaged in reeling in a catch while fishing on a boat in open waters.
Reported catch:
Dolphin (Mahi Mahi)
Great Barracuda
Response from Captain
November 20, 2025
you guys were awesome, enjoyed the fish. Have a safe flight home, see you next time. Thank you so much for choosing us.😎🎣
1
Patrick Fox
Patrick Fox
5.0
Verified
SAILFISH!!
3/4 Day Trip - 12:30 PM on November 25, 2025 β€’ 4 adults
Had an absolutely incredible day aboard the Jolly Roger II with Captain Joe and First Mate Brian! We filled the box with mahi, picked up a king mackerel and a barracuda, and the highlight of the trip was my daughter landing a 6.5-foot sailfishβ€”an unforgettable moment and truly the catch of a lifetime. Captain Joe and Brian were amazing from start to finish: knowledgeable, hardworking, and fun to be around. Couldn’t have asked for a better crew or a better day on the water. Highly recommend the Jolly Roger II for anyone looking for a top-notch fishing experience!
Review media 0
Review media 0
Review media 1
Reported catch:
Dolphin (Mahi Mahi)
King Mackerel (Kingfish)
Sailfish
Response from Captain
December 3, 2025
You guys were awesome, great Charter, beautiful day and a great catch. Have a good one. Take care and hope to see you next time. 😎🎣
0
Ed Young
Ed Young
5.0
Verified
Fantastic Outing!!!
3/4 Day Trip on October 18, 2025 β€’ 2 adults
Booked a 3/4 day trip for my son and I and we couldn't have had a better time! We arrived early but Captain Joe and Brain were ready to go so we got an early start. They were great explaining how the day would go and they got us to the right spots to pull in 10 Mahi-Mahi! We even had to through a couple back along with a barracuda and tuna too! Took our catch to a restaurant to get them cooked up and had one of the best lunches ever. Next time in in Key West, definitely going to book another trip on the Jolly Roger II.
Two anglers proudly displaying their catch of Mahi Mahi while enjoying a day of deep-sea fishing on a charter boat.
Review media 0
A collection of Mahi Mahi laid out on a dock, showcasing a successful fishing trip.
A plate of fried fish and grilled fish garnished with lime, served in a dining setting.
A serene sunset over the ocean, capturing the tranquil beauty of the fishing environment.
Reported catch:
Dolphin (Mahi Mahi)
Great Barracuda
Albacore Tuna
Response from Captain
October 20, 2025
thank you so much for all the kind words beautiful pictures and we really appreciate you, take care and hope to see you again someday, 😎
0
William Langenberg
William Langenberg
5.0
Verified
New
Made life long memories! Great experience.
3/4 Day Trip on March 30, 2026 β€’ 4 adults
Had an amazing time with Joe and his mate Bryan. Would recommend these guys any day of the week!! Top notch knowledge of whats biting at what time. This crew could not have made us feel any more comfortable than they did. Truly made some lifelong memories even in some choppy conditions. Cant wait to be back in Key West and book another trip with Joe.
Review media 0
Review media 0
Review media 0
Review media 1
Review media 2
Reported catch:
Skipjack Tuna
Response from Captain
April 1, 2026
Will, you guys were awesome. Great catch. Hope dinner was awesome and hope to see you again soon. πŸ™πŸ˜Ž
0
Edward Kammerer
Edward Kammerer
5.0
Verified
Wind Blowing 25 knots, but still had a great trip
3/4 Day Trip - 12:30 PM on January 21, 2026 β€’ 6 adults
We went out with Cap Joe and Brian on a less than ideal weather day, but it was the only day we could fish while in KW. The wind had been blowing hard for several days and still blowing the day we went out. Despite the weather, we stiil had a great time. The boat was very comfortable even in rough seas and they even managed to put us on some fish. Definitely recommend these guys even if you think the weather is not ideal. We will be back!
Angler proudly displaying a large fish at the dock during a fishing trip, with a scenic sunset backdrop.
Reported catch:
King Mackerel (Kingfish)
Great Barracuda
Response from Captain
January 23, 2026
thank you for all the kind words, waste every day could be awesome and beautiful weather. It was a pleasure having you and thank you so much.πŸ˜ŽπŸ™
1

FAQs about Jolly Roger II

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The fish you can target

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What is the boat like?

Boat Image
Boat category
Sportfishing boats
Capacity
6 persons
Boat length
39 ft
Year built
1979
Restored in
2019
Boat manufacturer
Chu Chu
Boat type
Sportfishing

Engine model
3126 Cats
Powered by
2 x 350HP
Max cruising speed
17 knots
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