Jolly Roger II 

4.9
(741 reviews)
 
Federally permitted
 1801 North Roosevelt Boulevard, Key West, FL 33040, United States–

Jolly Roger II 

Key West, FL, United States
–
39 ft
6
4.9
(741 reviews)

Booked with us before? You may qualify for a Loyalty Discount. Sign in to check.

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

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

Joe Mercurio III
Captain
Joe Mercurio III
35 years of experience
ID & credentials verified
responds within an hour

Select date to see availability

Trip date:
Group Size:
October 2026
SuMoTuWeThFrSa
Loading...
Group Size
2 adults • 0 children
Change
Almost there...
Half Day Trip
FREE Cancellation 7 days notice
4 hour trip multiple starting times (7:30 AM, 12:30 PM, 1:30 PM)
US $1,000
Entire boat: up to 6 people
3/4 Day Trip
FREE Cancellation 7 days notice
6 hour trip multiple starting times (7:30 AM, 12:30 PM)
US $1,250
Entire boat: up to 6 people
Full Day Trip
FREE Cancellation 7 days notice
8 hour trip starts at 7:30 AM
US $1,600
Entire boat: up to 6 people
There are 14 people looking at this charter.

Customer reviews

Loading...

Rating

4.9
741 reviews
4.9
Boat & equipment
5.0
Captain & crew
4.9
Fishing Experience

Anglers' gallery (1384)

What anglers say

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

Reviews (741)

  • Kevin Pozdol
    Kevin Pozdol
    Repeat angler
    us
    Washington D.C., US
    Member since 2022
    4 trips
    5.0
    Verified

    Amazing experience and crew!!

    3/4 Day Trip on June 17, 2026 • 4 adults • 1 child

    This is our family’s first fishing trip in Key West and Capt Joe and Brian were nothing less than awesome!! Capt Joe called the day before and explained everything about the boat and trip. I am very thankful because we had no idea about sport fishing! We were the first boat off the dock in the morning and within an hour he put us on some Mahi Mahi. Brian, mate, was fantastic. He worked his tail off all day, taught us about where they find the fish, helped everyone reel in a mahi. I cannot say enough good things about him. They said fishing had been up/down this week, but we caught 15 fish, a bunch of keepers, and a 24 pound Mahi. Catching fish is never guaranteed, but you can tell Capt Joe and Brian love what they do! It was an epic trip and I highly recommend the Jolly Roger II for anyone. Thanks for a memorable experience!

  • Randall Sonderhouse
    Randall Sonderhouse
    Repeat angler
    us
    Illinois, US
    Member since 2020
    4 trips
    5.0
    Verified
    New

    Awesome 60th Birthday!!!

    Half Day Trip on September 15, 2026 • 4 adults

    Excellent communication from the time of booking, at the dock before boarding, and while fishing! We had a party of 4 to celebrate my 60th Birthday. We explained to the Captain that we wanted fresh fish for dinner and some excitement. With that in mind, we went offshore for Dorado (Mahi-Mahi). 45 minutes in, we landed a 12-15 lbs fish. The Captain worked hard to find fish. In total, we caught 4 Dorado. The first mate cleaned the fish and did a stellar job. We will book with this Captain again.

  • Gregory Lewis
    Gregory Lewis
    us
    Texas, US
    Member since 2026
    5.0
    Verified

    You want to fish on the Jolly Roger with Captain Joe

    3/4 Day Trip on August 14, 2026 • 2 adults

    Absolutely incredible experience. If you want to go fishing in Key West, look no further. Captain Joe and his first mate, Brain, not only delivered an incredibly successful fishing trip but their knowledge of the area and the science and art of deep sea fishing really shows. They took care of everything. Boat was super clean, equipment was excellent and they truly cared about delivering the best experience possible. Incredible ¾ day trip. Would do it again in a heartbeat.

  • Gary Kelley
    Gary Kelley
    Repeat angler
    us
    Ohio, US
    Member since 2023
    4 trips
    5.0
    Verified

    beautiful key west day and charter!

    Full Day Trip on May 5, 2026 • 2 adults

    Captain Joe and first mate Adam were fantastic. It was a beautiful day on the water in Key West! Our first bite was a sailfish, got to see him but he spit the hook. then we caught 2 blackfin tuna which was on our bucketlist. Then to end the day my brother in law landed a beast of a mahi on a day when fish were not biting very frequently. Great crew whom actually cared that we were there and treated us like friends right from the start. Will definitely be booking them again!

  • Windy Jansen
    Windy Jansen
    Repeat angler
    us
    Connecticut, US
    Member since 2025
    2 trips
    5.0
    Verified

    Incredible Trip!

    3/4 Day Trip on April 20, 2026 • 6 adults • 2 children

    We had an incredible time out on the water with Captain Joe and Brian. In the days leading up to the charter, Captain Joe shared that the fishing report offshore had been very poor with very few fish being caught. Knowing this, he helped us create a revised plan which would still allow us to catch a large quantity of fish. The plan worked perfectly, and we started the day with dozens of good sized cero mackerel and a couple false albacore. Thanks to the transperency of Captain Joe, we were able to change plans and have an extremely successful day that otherwise would not have happened. We then headed offshore, knowing the chaces of us catching would be very poor. Despite this, we managed to still bring in a blackfin tuna before heading back in for the day. The skill and knowledge of both Capatin Joe and his first mate Brian absolutely made this day as successful as possible. They helped us outfish most if not all the surrounding boats and shared their invaluable local knowledge and tips. The trip was the best experience we have had on a charter and I would only want to fish with him here in the future.

  • Todd Ely
    Todd Ely
    us
    Pennsylvania, US
    Member since 2025
    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!

  • Patrick Fox
    Patrick Fox
    Repeat angler
    us
    New Mexico, US
    Member since 2021
    2 trips
    5.0
    Verified

    SAILFISH!!

    3/4 Day Trip - 12:30 PM on November 25, 2025 • 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 sailfish—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!

  • Mike Jobgen
    Mike Jobgen
    us
    Illinois, US
    Member since 2026
    5.0
    Verified

    Amazing trip!!

    3/4 Day Trip on August 8, 2026 • 5 adults

    Captain Joe and Brian were amazing! They were professional and knowledgeable!! They had us on fish the whole time. The 3/4 day was perfect. Let me tell you Brian was working his butt off and made our day effortless so we could focus on reeling in the Mahi! Highly recommend and will be coming back and booking with Captain Joe on the Jolley Roger II again!

  • Tyler Griffin
    Tyler Griffin
    us
    Arkansas, US
    Member since 2026
    5.0
    Verified
    New

    Hard Working and Personable

    3/4 Day Trip on October 16, 2026 • 2 adults

    Joe and Brian worked hard for us today and were great to share a boat with. Fishing was tough but they kept working, ended up with 2 nice Mahi, a Wahoo, Bonito, and released 3 Barracuda.

  • Pete Karahalis
    Pete Karahalis
    Repeat angler
    us
    Pennsylvania, US
    Member since 2025
    2 trips
    5.0
    Verified
    New

    3 for 3

    Full Day Trip on October 7, 2026 • 4 adults

    Put a lot of miles on the Gulf, came away with 3 beauties! Captain Joe and first mate Brian did an excellent job of navigating us through 3 really nice fish all on at the same time.

Rating

4.9
741 reviews
4.9
Boat & equipment
5.0
Captain & crew
4.9
Fishing Experience

Anglers' gallery (1384)

What anglers say

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

All reviews (741)

Frequently mentioned
Showing 1 – 5 of 741 reviews
Kevin Pozdol
Kevin Pozdol
Repeat angler
us
Washington D.C., US
Member since 2022
4 trips
5.0
Verified
Amazing experience and crew!!
3/4 Day Trip on June 17, 2026 • 3 adults • 1 child

This is our family’s first fishing trip in Key West and Capt Joe and Brian were nothing less than awesome!! Capt Joe called the day before and explained everything about the boat and trip. I am very thankful because we had no idea about sport fishing! We were the first boat off the dock in the morning and within an hour he put us on some Mahi Mahi. Brian, mate, was fantastic. He worked his tail off all day, taught us about where they find the fish, helped everyone reel in a mahi. I cannot say enough good things about him. They said fishing had been up/down this week, but we caught 15 fish, a bunch of keepers, and a 24 pound Mahi. Catching fish is never guaranteed, but you can tell Capt Joe and Brian love what they do! It was an epic trip and I highly recommend the Jolly Roger II for anyone. Thanks for a memorable experience!

Reported catch:
Dolphin (Mahi Mahi)
Joe Mercurio III
Response from Captain

thank you so much for the kind words you guys were awesome and what a great day. See you next time. 😎🙏

Randall Sonderhouse
Randall Sonderhouse
Repeat angler
us
Illinois, US
Member since 2020
4 trips
5.0
Verified
Awesome 60th Birthday!!!
Half Day Trip on September 15, 2026 • 4 adults

Excellent communication from the time of booking, at the dock before boarding, and while fishing! We had a party of 4 to celebrate my 60th Birthday. We explained to the Captain that we wanted fresh fish for dinner and some excitement. With that in mind, we went offshore for Dorado (Mahi-Mahi). 45 minutes in, we landed a 12-15 lbs fish. The Captain worked hard to find fish. In total, we caught 4 Dorado. The first mate cleaned the fish and did a stellar job. We will book with this Captain again.

Reported catch:
Dolphin (Mahi Mahi)
Joe Mercurio III
Response from Captain

thank you guys, great trip. Hope to see you again, happy birthday. 🙏🙏

Gregory Lewis
Gregory Lewis
us
Texas, US
Member since 2026
5.0
Verified
You want to fish on the Jolly Roger with Captain Joe
3/4 Day Trip on August 14, 2026 • 2 adults

Absolutely incredible experience. If you want to go fishing in Key West, look no further. Captain Joe and his first mate, Brain, not only delivered an incredibly successful fishing trip but their knowledge of the area and the science and art of deep sea fishing really shows. They took care of everything. Boat was super clean, equipment was excellent and they truly cared about delivering the best experience possible. Incredible ¾ day trip. Would do it again in a heartbeat.

Reported catch:
Dolphin (Mahi Mahi)
Great Barracuda
Joe Mercurio III
Response from Captain

you guys were awesome. What a great day, absolutely awesome. Hope to see you again, 😎🎣

Gary Kelley
Gary Kelley
Repeat angler
us
Ohio, US
Member since 2023
4 trips
5.0
Verified
beautiful key west day and charter!
Full Day Trip on May 5, 2026 • 2 adults

Captain Joe and first mate Adam were fantastic. It was a beautiful day on the water in Key West! Our first bite was a sailfish, got to see him but he spit the hook. then we caught 2 blackfin tuna which was on our bucketlist. Then to end the day my brother in law landed a beast of a mahi on a day when fish were not biting very frequently. Great crew whom actually cared that we were there and treated us like friends right from the start. Will definitely be booking them again!

Reported catch:
Dolphin (Mahi Mahi)
Joe Mercurio III
Response from Captain

thank you so much for the review, glad you guys had a good time. Sorry it was slow but a beautiful day, enjoy the Fish. Hope dinner is awesome. 😎🎣🙏

Windy Jansen
Windy Jansen
Repeat angler
us
Connecticut, US
Member since 2025
2 trips
5.0
Verified
Incredible Trip!
3/4 Day Trip on April 20, 2026 • 4 adults • 2 children

We had an incredible time out on the water with Captain Joe and Brian. In the days leading up to the charter, Captain Joe shared that the fishing report offshore had been very poor with very few fish being caught. Knowing this, he helped us create a revised plan which would still allow us to catch a large quantity of fish. The plan worked perfectly, and we started the day with dozens of good sized cero mackerel and a couple false albacore. Thanks to the transperency of Captain Joe, we were able to change plans and have an extremely successful day that otherwise would not have happened. We then headed offshore, knowing the chaces of us catching would be very poor. Despite this, we managed to still bring in a blackfin tuna before heading back in for the day. The skill and knowledge of both Capatin Joe and his first mate Brian absolutely made this day as successful as possible. They helped us outfish most if not all the surrounding boats and shared their invaluable local knowledge and tips. The trip was the best experience we have had on a charter and I would only want to fish with him here in the future.

Joe Mercurio III
Response from Captain

you guys were awesome. The boys were awesome. Can’t wait to take you again someday. It was and did work out very well as planned. Hope dinner was awesome. Take care. See you next time. 😎💕 thank you for all the kind words.🎣

FAQs about Jolly Roger II

Jolly Roger II offers the following trips to customers:
  • US $1,000 per group - Half Day Trip (4 hours)
  • US $1,000 per group - Half Day Trip - 1:30 PM (4 hours)
  • US $1,000 per group - Half Day Trip - 12:30 PM (4 hours)
  • US $1,250 per group - 3/4 Day Trip (6 hours)
  • US $1,250 per group - 3/4 Day Trip - 12:30 PM (6 hours)
  • US $1,600 per group - Full Day Trip (8 hours)
When you book a trip with Jolly Roger II, you can expect the following amenities onboard:
  • Toilet Full, enclosed
  • Fighting chair
  • GPS
  • Fishfinder
  • Flybridge
  • Live bait well
  • Outriggers
  • Ice box
Trips booked with Jolly Roger II include:
  • Rods, reels & tackle
  • Lures
  • Catch cleaning & filleting (After the trip)
  • First mate
  • Fishing license
Jolly Roger II offers the following types of fishing:
  • Inshore fishing
  • Offshore fishing
  • Reef fishing
  • Wreck fishing
Jolly Roger II offers the following fishing techniques:
  • Light tackle
  • Heavy tackle
  • Trolling
Top targeted fish species with Jolly Roger II include:
  • Amberjack
  • Barracuda (Great)
  • Cobia
  • Dolphin (Mahi Mahi)
  • Grouper (Goliath)
  • King Mackerel (Kingfish)
  • Marlin (Blue)
  • Marlin (White)
  • Sailfish
  • Tuna (Albacore)
  • Tuna (Skipjack)
  • Wahoo

Your captain

Joe Mercurio III
Joe Mercurio III
Key West, Florida, United States
ID & license verified
741 Customer reviews
Typical response within an hour
Member since January 2019
Angler's Choice
The Angler's Choice Award is given to listings that consistently deliver a high-quality service and earn great reviews from customers.
Capt. Joe has been fishing for the past 37 years, and has been a licensed captain for 27 of then. He was born and raised in Key West, so it's safe to say he knows these waters like the back of his hand. When it comes to the boat you'll be fishing from, it's pretty much a piece of Key West history – Capt. Joe's father owned the boat before him. This family's tradition of fishing doesn't stop there, though. Capt. Joe's grandfather had one of the first charterboats in Key West in the late 40's. Come aboard and make yourself a part of Floridian fishing history!
Joe Mercurio III
Joe Mercurio III
Fully verified
Angler's Choice
741
reviews
2019
member since
~1h
response
Capt. Joe has been fishing for the past 37 years, and has been a licensed captain for 27 of then. He was born and raised in Key West, so it's safe to say he knows these waters like the back of his hand. When it comes to the boat you'll be fishing from, it's pretty much a piece of Key West history – Capt. Joe's father owned the boat before him. This family's tradition of fishing doesn't stop there, though. Capt. Joe's grandfather had one of the first charterboats in Key West in the late 40's. Come aboard and make yourself a part of Floridian fishing history!

The fish you can target

Amberjack
Amberjack
Great Barracuda
Great Barracuda
Cobia
Cobia
Dolphin (Mahi Mahi)
Dolphin (Mahi Mahi)
Goliath Grouper
Goliath Grouper
King Mackerel (Kingfish)
King Mackerel (Kingfish)
Blue Marlin
Blue Marlin
White Marlin
White Marlin
Sailfish
Sailfish
Albacore Tuna
Albacore Tuna
Skipjack Tuna
Skipjack Tuna
Wahoo
Wahoo
Amberjack
Amberjack
Great Barracuda
Great Barracuda
Cobia
Cobia
Dolphin (Mahi Mahi)
Dolphin (Mahi Mahi)
Goliath Grouper
Goliath Grouper

Real catches by this captain

  • Hard Working and Personable
    Tyler G.
    Tyler G.
  • 3 for 3
    Pete K.
    Pete K.
  • We caught fish in minutes
    Thomas S.
    Thomas S.
  • Awesome 60th Birthday!!!
    Randall S.
    Randall S.
  • 1st time and it was awesome
    Brenda P.
    Brenda P.
  • You want to fish on the Jolly Roger with Captain Joe
    Gregory L.
    Gregory L.
  • Great Trip. Great crew
    Pat T.
    Pat T.
  • Amazing trip!!
    Mike J.
    Mike J.
  • Great trip
    Brian C.
    Brian C.
  • Great day on the water!
    Renita J.
    Renita J.

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

What kind of fishing will you do?

Inshore Fishing
Offshore Fishing
Reef Fishing
Wreck Fishing

Which fishing techniques you can try

Light Tackle
Heavy Tackle
Trolling

Which amenities are available onboard

Toilet
Full, enclosed
Fighting chair
GPS
Fishfinder
Flybridge
Live bait well
Outriggers
Ice box
What's included in the trip price
Rods, reels & tackle
Lures
Catch cleaning & filleting
After the trip
First mate
Fishing license

How cancellations work

Free cancellation up to 7 days prior to trip
You can cancel or modify your booking up to 7 days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.
More details

What the listing policies are

Pickup not included
Transfer to/from departure site is not included in trip rates.
Child friendly
No minimum age
You keep catch
Catch and release allowed

How you can pay

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
When paying the remaining balance with a credit card, an additional 3% charge will apply.

What’s biting in Key West right now

AmberjackAmberjack
Barracuda (Great)Barracuda (Great)
CobiaCobia
Dolphin (Mahi Mahi)Dolphin (Mahi Mahi)
Grouper (Goliath)Grouper (Goliath)
King Mackerel (Kingfish)King Mackerel (Kingfish)
Marlin (Blue)Marlin (Blue)
Marlin (White)Marlin (White)
SailfishSailfish
Tuna (Skipjack)Tuna (Skipjack)
WahooWahoo

Compare similar fishing charters

Current
Jolly Roger II
Jolly Roger II
Federally permitted
4.9
(741)
39 ft
Group size 1 - 6
1 - 6
Fish 1
Fish 2
+10
4 hour trip • 6 persons
US $1,000