Jolly Roger II

4.9/5 (679 reviews)

Federally permitted

1801 North Roosevelt Boulevard, Key West, FL 33040, United States–

Jolly Roger II

Federally permitted

4.9/5 (679)

•

Angler's Choice

1801 North Roosevelt Boulevard

Key West, FL, United States

Trips & prices Targeted species Boat info What's biting What's included Contact captain

Trips & prices What's included Targeted species Boat info Reviews Contact captain

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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

Rating

4.9

679 reviews

652

5.0

Boat & equipment

4.9

Captain & crew

4.9

Fishing Experience

Anglers' gallery (1269)

+1263

What anglers say

98%

Great experience

94%

Family friendly

100%

Friendly captain

100%

Good boat

99%

Recommended

94%

Caught fish

All reviews (679)

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Showing 1 – 5 of 679 reviews

Todd Ely

5.0

Verified

great crew that put us fish quick!!

3/4 Day Trip on November 19, 2025 • 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 — 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 — 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!

Reported catch:

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.😎🎣

Ed Saurusaitis

5.0

Verified

Great Crew, Great Effort—Still a Memorable Day Offshore

3/4 Day Trip on October 8, 2025 • 2 adults

Even though the fish weren’t biting, our 6-hour offshore trip aboard the Jolly Roger II was still a fantastic experience. Captain Joe and First Mate Brian were top-notch—professional, friendly, and clearly passionate about what they do. They worked tirelessly to find the fish, adjusting tactics and locations throughout the day. Their dedication and upbeat attitude made all the difference. The boat was clean and comfortable, and the atmosphere was relaxed but focused. Sometimes the ocean has its own plans, but thanks to Joe and Brian, we still came back with great memories and a deep appreciation for the effort behind every charter. Would absolutely book again!

Response from Captain

October 13, 2025

Thank you for understanding. Thank you for all the kind words. See you next time.😎🎣🙏

Jenell Keiser

5.0

Verified

Fishing Frenzy

3/4 Day Trip on September 14, 2025 • 2 adults

Started the morning with a couple small Black Fin Tuna, a very toothy barracuda, and finished the trip with a fishing frenzy of 9 Mahi. One after another were hitting our baits. It was bc of experienced Captain Joe and First Mate Bryan the fish were all landed and made it into the fish box. The communication was great, location easy to find and the boat is set up to catch fish. Clean, comfortable and great gear. Thanks to Captain Joe and First mate Bryan for a super fun day! (Ps- Bryan recd we take our catch to Thai Island where they would prepare our fresh catch. Our dinner was fantastic! Green curry and mixed vegetables in ginger sauce, both Included our Mahi and Tuna. What a special option for our fresh catch!). See you all again soon! Love from Michigan LETZFSH

Response from Captain

September 15, 2025

thank you so much, really appreciate you guys. Thanks for having patience of course and it paid off. Great catch. See you next time. 😎🎣

Peter Abramson

5.0

Verified

Book this boat !!!

3/4 Day Trip on August 31, 2025 • 2 adults

We did a lot of searching. We have been on many deep sea fishing excursions before and this was the BEST!! First of all we had the most amazing captain Joseph II . This is a multigenerational group of experienced Captains and Brian was the first mate who worked harder than we’ve ever seen anyone work before- literally NONSTOP while smiling and making sure the bait was always always fresh on the line, changing up, based on the way, the fish were biting . He is also has years of incredible experience. Everything was absolutely perfect. Unlike most boats, this boat has FOUR fighting chairs instead of two and is super clean. We opted not to go out for the sailfish, but remain inland and caught multiple fish right away and during the trip . It was a perfect day. Don’t look any further than Captain Joseph II and Brian ! We are coming back with our adult sons and wouldn’t book with anyone else.

Response from Captain

September 2, 2025

thank you so much for the great review and glad you had had a good time, 😎🎣

Jeffrey Prowse

5.0

Verified

Phenomenal!

Full Day Trip on July 28, 2025 • 6 adults

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

Response from Captain

July 29, 2025

Thank you so much for all the kind words, you guys were awesome and it was a great day! 😎🙏❤️

Trip availability and prices

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January 2026

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Group Size

2 adults • 0 children

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Half Day Trip (AM)

FREE Cancellation 7 days notice

4 Hour Trip

starts at 7:30 AM

US $950