Jolly Roger II
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
Customer reviews
Rating summary
Photos & videos by reviewers (1188)
+1185Angler rating
Anglers claimed
Good experience
98%
Appropriate for children
94%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
99%
Caught fish
94%
Jul 28, 2025
Full Day Trip
Phenomenal!
Joe and Jameson were top notch pros! We were targeting dorado by my request, and these fellas had a wealth of info about the species, tactics, as well as a variety of other species and related topics. In between the waves of action, we had enjoyable conversations which only added to the experience. The boat is solid and comfortable even for people that aren’t accustomed to big water. 12 beautiful keepers were boated, as well as a few sublegal sized fish and some bycatch which were returned. We wound up the day feeding scraps to the tame tarpon and nurse sharks at the dock - which was a hoot! It was a day our family will remember! While I haven’t sampled the other charters, when I book again in the future I’ll stay with what I know wins: Jolly Roger II
Joe and Jameson were top notch pros! We were targeting dorado by my request, and these fellas had a wealth of info about the species,...
Captain replied
Jun 16, 2025
Full Day Trip
Excellent 2 days out on the water.
My father and I decided to visit Key West and fish with the Jolly Roger II. Last time we did was April 2004, over 20 year years ago. Capt. Joe is one of the most experienced charter boat captains in Zoey West. Keep in mind that he specializes in trolling so you will be targeting most pelagic species. Both days were a tough bite but Capt. Joe and his first mate Brian worked their asses off and kept us on the fish. We limited out the first day on Mahi and caught a barracuda in addition. Second day was a bit tougher but we still cameout with a full cooler of Mahi. We will be coming back hopefully next April to target some different species.
My father and I decided to visit Key West and fish with the Jolly Roger II. Last time we did was April 2004, over 20 year years...
Captain replied
Jun 11, 2025
Full Day Trip
I Took My Wife Deep Sea Fishing for Our 20th Anniversary… and Somehow She Still Likes Me
Most guys take their wives to Paris or a fancy resort for their 20th wedding anniversary. You know — massages, room service, wine with weird names. Not me. I booked us a deep sea fishing trip with Captain Joe and First Mate Brian on the Jolly Roger II. Because nothing says “I love you, babe” like the smell of bait, fish guts, and sunscreen SPF 100. And it turned out to be the best anniversary idea I’ve had in two decades. No joke. The night before the trip, Captain Joe gave me the most honest pep talk ever: “I’m not God. I can’t make the fish bite or the weather behave.” Fair enough. I appreciated the warning — figured I’d probably be spending six hours on a boat, burning to a crisp while holding an empty fishing rod and trying to act like this was totally worth it. Turns out… he was lying. Or at least being modest. Because the weather? Absolutely perfect. Blue skies, calm seas, warm breeze. No storm clouds, no squalls, not even a seagull that looked at me funny. The ocean practically rolled out the red carpet. And the fish? They wouldn’t leave us alone. We pulled in 19 Mahi Mahi and 4 barracuda like we were running some kind of underwater fast food drive-thru. Captain Joe runs the show like a guy who’s seen everything — funny, laid back, and patient enough to deal with first-timers who have no idea which end of the rod is up (that would be me). His jokes were sharp, his advice was spot-on, and I only tangled the lines twice. Maybe three times. Brian probably untangled them before I noticed. Speaking of Brian — the first mate might be part human, part fishing robot. The man never stops. He’s baiting hooks, setting lines, clearing decks, handing out tips, and telling ridiculous boat stories — all while acting like the circus going on behind him (me) is completely normal. Even my wife — who originally thought this anniversary idea meant I’d forgotten a dinner reservation — was hauling in fish and grinning like a kid on Christmas. And she caught more than me, which she will remind me of for the next 20 years. Possibly longer. By the time we got back to the dock, my arms were spaghetti, my face was sunburned in weird shapes, and I had the biggest grin I’ve worn since the wedding. Best day ever — and way cheaper than jewelry. So if you want a fishing trip that feels like part comedy show, part National Geographic episode, and 100% worth it, book with Captain Joe and Brian on the Jolly Roger II. These guys are the real deal — and apparently, Captain Joe is God after all, because the fish sure listened to him.
Most guys take their wives to Paris or a fancy resort for their 20th wedding anniversary. You know — massages, room service, wine...
Captain replied
Apr 11, 2025
Half Day Trip (AM)
April fishing trip
We had the BEST time with Jolly Roger Fishing Charter! From the moment we stepped on the boat, the crew was super friendly, fun, and incredibly helpful—especially for our group of 6 girls who were clueless haha. They made sure we were comfortable and helped us catch a ton of fish! They cleaned and filleted all the fish for us, and even recommended a local restaurant where we could bring our catch to have it cooked up fresh. It was such a cool experience from start to finish. Highly recommend!
We had the BEST time with Jolly Roger Fishing Charter! From the moment we stepped on the boat, the crew was super friendly, fun,...
Captain replied
Mar 22, 2025
3/4 Day Trip (AM)
Captain Joe, first mate Brian - are outstanding!
We had the pleasure of being out on the water w/one of Key West's most experienced fishing families. Joe (captain) and his family have been fishing Key West waters for decades. And first mate Brian - has a ton of experience as well - both were v friendly and gracious hosts. The boat was hand built by the family - specially designed for fishing the waters around Key West. Cannot recommend them enough. Every time I'm back in Key West, I'll be out on the Jolly Roger II w/Joe & Co. Thx again guys - great times.
We had the pleasure of being out on the water w/one of Key West's most experienced fishing families. Joe (captain) and his family...
Captain repliedTrip availability and prices
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Customer reviews
Rating summary
Photos & videos by reviewers (1188)
+1185Angler rating
Anglers claimed
Good experience
98%
Appropriate for children
94%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
99%
Caught fish
94%
Experience:
Boat
Crew
Overall
Phenomenal!
Full Day Trip on July 28, 2025
Joe and Jameson were top notch pros! We were targeting dorado by my request, and these fellas had a wealth of info about the species, tactics, as well as a variety of other species and related topics. In between the waves of action, we had enjoyable conversations which only added to the experience. The boat is solid and comfortable even for people that aren’t accustomed to big water. 12 beautiful keepers were boated, as well as a few sublegal sized fish and some bycatch which were returned. We wound up the day feeding scraps to the tame tarpon and nurse sharks at the dock - which was a hoot! It was a day our family will remember! While I haven’t sampled the other charters, when I book again in the future I’ll stay with what I know wins: Jolly Roger II
Joe and Jameson were top notch pros! We were targeting dorado by my request, and these fellas had a wealth of info about the species, tactics, as well as a variety of other species and related topics. In between the waves of action, we had enjoyable conversations which only added to the experience. The boat is solid and comfortable even for people that aren’t accustomed to big water. 12 beautiful keepers were boated, as well as a few sublegal sized fish and some bycatch which were returned....
Experience:
Boat
Crew
Overall
Excellent 2 days out on the water.
Full Day Trip on June 16, 2025
My father and I decided to visit Key West and fish with the Jolly Roger II. Last time we did was April 2004, over 20 year years ago. Capt. Joe is one of the most experienced charter boat captains in Zoey West. Keep in mind that he specializes in trolling so you will be targeting most pelagic species. Both days were a tough bite but Capt. Joe and his first mate Brian worked their asses off and kept us on the fish. We limited out the first day on Mahi and caught a barracuda in addition. Second day was a bit tougher but we still cameout with a full cooler of Mahi. We will be coming back hopefully next April to target some different species.
My father and I decided to visit Key West and fish with the Jolly Roger II. Last time we did was April 2004, over 20 year years ago. Capt. Joe is one of the most experienced charter boat captains in Zoey West. Keep in mind that he specializes in trolling so you will be targeting most pelagic species. Both days were a tough bite but Capt. Joe and his first mate Brian worked their asses off and kept us on the fish. We limited out the first day on Mahi and caught a barracuda in addition. Second...
Experience:
Boat
Crew
Overall
I Took My Wife Deep Sea Fishing for Our 20th Anniversary… and Somehow She Still Likes Me
Full Day Trip on June 11, 2025
Most guys take their wives to Paris or a fancy resort for their 20th wedding anniversary. You know — massages, room service, wine with weird names. Not me. I booked us a deep sea fishing trip with Captain Joe and First Mate Brian on the Jolly Roger II. Because nothing says “I love you, babe” like the smell of bait, fish guts, and sunscreen SPF 100. And it turned out to be the best anniversary idea I’ve had in two decades. No joke. The night before the trip, Captain Joe gave me the most honest pep talk ever: “I’m not God. I can’t make the fish bite or the weather behave.” Fair enough. I appreciated the warning — figured I’d probably be spending six hours on a boat, burning to a crisp while holding an empty fishing rod and trying to act like this was totally worth it. Turns out… he was lying. Or at least being modest. Because the weather? Absolutely perfect. Blue skies, calm seas, warm breeze. No storm clouds, no squalls, not even a seagull that looked at me funny. The ocean practically rolled out the red carpet. And the fish? They wouldn’t leave us alone. We pulled in 19 Mahi Mahi and 4 barracuda like we were running some kind of underwater fast food drive-thru. Captain Joe runs the show like a guy who’s seen everything — funny, laid back, and patient enough to deal with first-timers who have no idea which end of the rod is up (that would be me). His jokes were sharp, his advice was spot-on, and I only tangled the lines twice. Maybe three times. Brian probably untangled them before I noticed. Speaking of Brian — the first mate might be part human, part fishing robot. The man never stops. He’s baiting hooks, setting lines, clearing decks, handing out tips, and telling ridiculous boat stories — all while acting like the circus going on behind him (me) is completely normal. Even my wife — who originally thought this anniversary idea meant I’d forgotten a dinner reservation — was hauling in fish and grinning like a kid on Christmas. And she caught more than me, which she will remind me of for the next 20 years. Possibly longer. By the time we got back to the dock, my arms were spaghetti, my face was sunburned in weird shapes, and I had the biggest grin I’ve worn since the wedding. Best day ever — and way cheaper than jewelry. So if you want a fishing trip that feels like part comedy show, part National Geographic episode, and 100% worth it, book with Captain Joe and Brian on the Jolly Roger II. These guys are the real deal — and apparently, Captain Joe is God after all, because the fish sure listened to him.
Most guys take their wives to Paris or a fancy resort for their 20th wedding anniversary. You know — massages, room service, wine with weird names. Not me. I booked us a deep sea fishing trip with Captain Joe and First Mate Brian on the Jolly Roger II. Because nothing says “I love you, babe” like the smell of bait, fish guts, and sunscreen SPF 100. And it turned out to be the best anniversary idea I’ve had in two decades. No joke. The night before the trip, Captain Joe gave me the most honest...
Experience:
Boat
Crew
Overall
April fishing trip
Half Day Trip (AM) on April 11, 2025
We had the BEST time with Jolly Roger Fishing Charter! From the moment we stepped on the boat, the crew was super friendly, fun, and incredibly helpful—especially for our group of 6 girls who were clueless haha. They made sure we were comfortable and helped us catch a ton of fish! They cleaned and filleted all the fish for us, and even recommended a local restaurant where we could bring our catch to have it cooked up fresh. It was such a cool experience from start to finish. Highly recommend!
We had the BEST time with Jolly Roger Fishing Charter! From the moment we stepped on the boat, the crew was super friendly, fun, and incredibly helpful—especially for our group of 6 girls who were clueless haha. They made sure we were comfortable and helped us catch a ton of fish! They cleaned and filleted all the fish for us, and even recommended a local restaurant where we could bring our catch to have it cooked up fresh. It was such a cool experience from start to finish. Highly recommend!...
Experience:
Boat
Crew
Overall
Captain Joe, first mate Brian - are outstanding!
3/4 Day Trip (AM) on March 22, 2025
We had the pleasure of being out on the water w/one of Key West's most experienced fishing families. Joe (captain) and his family have been fishing Key West waters for decades. And first mate Brian - has a ton of experience as well - both were v friendly and gracious hosts. The boat was hand built by the family - specially designed for fishing the waters around Key West. Cannot recommend them enough. Every time I'm back in Key West, I'll be out on the Jolly Roger II w/Joe & Co. Thx again guys - great times.
We had the pleasure of being out on the water w/one of Key West's most experienced fishing families. Joe (captain) and his family have been fishing Key West waters for decades. And first mate Brian - has a ton of experience as well - both were v friendly and gracious hosts. The boat was hand built by the family - specially designed for fishing the waters around Key West. Cannot recommend them enough. Every time I'm back in Key West, I'll be out on the Jolly Roger II w/Joe & Co. Thx again guys...
FAQs about Jolly Roger II
The fish you can target
What is the boat like?
