Underwater Cowboy
4.9/5 (118 reviews)
State licensed
Caribbean Drive 522, Key Largo, FL 33037, United States–
Underwater Cowboy
State licensed
Key Largo, FL, United States
–36 ft
6
4.9/5 (118 reviews)
Angler's Choice
Running angling trips out of Key Largo, Underwater Cowboy invites you to check out the local fishery in style.
Come on aboard with Capt. Dan, whose main priority is to get you on some fish. Expect to use techniques like light tackle, heavy tackle, bottom fishing, trolling, big game fishing, drift fishing, jigging, kite fishing, spearfishing, based on the species you're targeting. Speaking of which, you have the option of 4 to 8-hour trips, where you'll be fishing for the likes of Dolphin, Snapper, Sailfish, Wahoo, Amberjack, Swordfish, depending on the specific season and the day's weather.
Your private boat for the day will be a 36' Contender that fits up to 6 anglers at any one time. The boat comes with an ice box and flushing bathroom in center console.
When it comes to rods, reels, and terminal tackle, everything you need is included in the price.
The captain will supply all the needed fishing licenses for your trip.
You're welcome to keep all legal species caught during the trip.
Here to help you with anything you need, the first mate will be on hand during the trip. Leaving a tip for a job well done is much appreciated.
You'll find water, ice and cooler space and you are always welcome to pack your own drinks and snacks.
Children are welcome aboard so you're good to get the young ones started early.
Book your trip now and hit the water with Underwater Cowboy.
Running angling trips out of Key Largo, Underwater Cowboy invites you to check out the local fishery in style.
Come on aboard with Capt. Dan, whose main priority is to get you on some fish. Expect to use techniques like light tackle, heavy tackle, bottom fishing, trolling, big game fishing, drift fishing, jigging, kite fishing, spearfishing, based on the species you're targeting. Speaking of which, you have the option of 4 to 8-hour trips, where you'll be fishing for the likes of Dolphin, Snapper, Sailfish, Wahoo, Amberjack, Swordfish, depending on the specific season and the day's weather.
Your private boat for the day will be a 36' Contender that fits up to 6 anglers at any one time. The boat comes with an ice box and flushing bathroom in center console.
When it comes to rods, reels, and terminal tackle, everything you need is included in the price.
The captain will supply all the needed fishing licenses for your trip.
You're welcome to keep all legal species caught during the trip.
Here to help you with anything you need, the first mate will be on hand during the trip. Leaving a tip for a job well done is much appreciated.
You'll find water, ice and cooler space and you are always welcome to pack your own drinks and snacks.
Children are welcome aboard so you're good to get the young ones started early.
Book your trip now and hit the water with Underwater Cowboy.
Popular features
Fishing license
Live bait
You keep catch
Catch cleaning & filleting
Drinks
Popular features
Fishing license
Live bait
You keep catch
Catch cleaning & filleting
Drinks
Customer reviews
Rating
4.9
118 reviews
5.0
Boat & equipment
4.9
Captain & crew
4.9
Fishing Experience
Anglers' gallery (201)
What anglers say
96%
Great experience
96%
Family friendly
99%
Friendly captain
100%
Good boat
97%
Recommended
98%
Caught fish
All reviews (118)
Filter
Sort by: Featured
Frequently mentioned
Showing 1 – 5 of 118 reviews
Sam Steck
Florida, US
•
Member since 2025
0
5.0
Verified
New
Hell Yeah to Capt Dan
Full Day Trip on May 23, 2026 • 6 adults
Capt Dan was the recommendation from a few different friends that we have down in the Keys, and he definitely did not disappoint. It was easy to book the charter, and he was very communicative after booking. He was on time and ready to roll right at 7:00 am the day of our trip.
We went out and conditions were a little rough. Despite the choppy seas, we quickly got some lines in the water. While I bet most boats did not catch fish, we ended up having a pretty damn good day and had a ton of fun with my buddies and Capt Dan. He fit right in with the group, and we appreciated him getting us out there and putting us on some fish. Already looking forward to the next trip with him. Thanks, Capt Dan. Appreciate ya! 10/10 would recommend!
Response from Captain
June 3, 2026
you guys were great. hope to have you back soon.
Daniel Nigri
Ohio, US
•
Member since 2024
0
5.0
Verified
Amazing Private Fishing Experience
3/4 Day Trip on February 18, 2026 • 2 adults
Yesterday we went on a 6-hour private fishing trip with Captain Dan, and it was an awesome experience from start to finish.
We caught tuna and wahoo and had an incredible time on the water. Captain Dan is extremely professional, clearly knows what he’s doing, and uses different fishing techniques to make sure you have the best possible chance of success.
Beyond the fishing itself, he was great to spend the day with — very friendly, knowledgeable, and easy to talk to. The trip never felt rushed, and you can tell he truly cares about giving his guests a great experience.
At the end of the trip, he filleted and vacuum-sealed all of our fish so we could easily take it back home, which was all included in the price — a huge bonus.
Highly recommend Captain Dan to anyone looking for a top-quality fishing trip. I would definitely come back again.
Reported catch:
Response from Captain
February 19, 2026
it was a great time. cannot wait for your next trip.
Neil Quinlan
Repeat angler
Kentucky, US
•
Member since 2019
•
5 trips
0
5.0
Verified
Blackfin, Mahi, Wahoo… and a Whole Lot of Laughs
Full Day Trip on February 13, 2026 • 2 adults
We fished today with Underwater Cowboy (Cptn Dan), and it was an awesome experience. The conditions weren’t easy, but he worked nonstop to get us on fish. We ended up catching blackfin tuna, mahi, and a really nice wahoo.
Even when things slowed down, he kept us entertained with great stories and made the whole trip fun and memorable. It felt like fishing with someone who genuinely cares about your experience, not just the catch.
If you’re heading to the Keys, don’t hesitate — book with Underwater Cowboy. We’ll definitely be back.
Reported catch:
Response from Captain
February 14, 2026
You guys were great. Get back down here and we will go get some swordfish to knock them off your list. Until next time.
Adryanna Galarce
Repeat angler
Florida, US
•
Member since 2025
•
2 trips
0
5.0
Verified
Unforgettable Fishing Experience!
Half Day Trip on June 15, 2025 • 2 adults
I’ve been on two trips with Underwater Cowboy, and both were nothing short of amazing. Captain Dan and his first mate are a dynamic duo—friendly, knowledgeable, and completely dedicated to making the day fun, relaxing, and seamless. They work as a team and make sure everyone on board is well taken care of from start to finish.
The boat ride itself is incredibly peaceful—perfect for someone like me who’s constantly on the go and needs a moment to hit pause. And while the ride alone is worth it, catching fish is the icing on the cake! Captain Dan cleans your catch at the end, so you can take home a fresh reward from your day at sea.
The boat is spotless and clearly well cared for. I was especially impressed with how the crew constantly cleaned up after each catch—no fishy mess to worry about! There’s also thoughtful storage for your snacks, drinks, and even a secure spot for your phone so you’re not stressing about it getting wet or going overboard.
If you’re looking for a relaxing day on the water with the bonus of fishing and amazing company, Underwater Cowboy is it. Can’t wait for trip #3! 🎣🚤
Response from Captain
June 30, 2025
Thanks for the review. We work hard to Kell the equipment in tip top shape. I try to make our trips the same way I would want them if I were on vacation. I hope to see you guys back soon.
Bric Garrett
Texas, US
•
Member since 2025
1
5.0
Verified
WHAT A GREAT DAY OF CATCHING !!!
Full Day Trip on November 15, 2025 • 2 adults
WOW!!! What a great day of CATCHING fish and not jus fishing!!!!
We got started early laying into the Blakfin Tuna while trolling for a wahoo. After all most no tome at all, we had nearly met our limit of blackfin.. Then it happened, a slam of of a top water jig, and the wahoo fight was on.. He definitely did not want to conw into the boat but after a couple good runs of the reel that is where he ended up.
It was an amazing day of fishing and the 51 inch wahoo is going to look great on the wall.. and yes it was excellent eating as well !!!!
Reported catch:
Response from Captain
November 23, 2025
you guys were great. had a good day with alot of fun and got fish.
Trip availability and prices
Trip Date:
Group Size:
Select date to see availability
June 2026
| Su | Mo | Tu | We | Th | Fr | Sa | |
|---|---|---|---|---|---|---|---|
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Number of days
1
Almost there...
Yellowtail Fishing
FREE Cancellation 3 days notice
3 hour trip starts at 7:00 AM
US $900
Entire boat: up to 6 people
US $900
Entire boat: up to 6 people
Half Day Trip
FREE Cancellation 3 days notice
4 hour trip starts at 7:00 AM
US $1,000
Entire boat: up to 6 people
US $1,000
Entire boat: up to 6 people
3/4 Day Trip
FREE Cancellation 3 days notice
6 hour trip starts at 7:00 AM
US $1,200
Entire boat: up to 6 people
US $1,200
Entire boat: up to 6 people
Full Day Trip
FREE Cancellation 3 days notice
8 hour trip starts at 7:00 AM
US $1,400
Entire boat: up to 6 people
US $1,400
Entire boat: up to 6 people
Full Day Trip – Swordfish
FREE Cancellation 3 days notice
8 hour trip starts at 7:00 AM
US $2,100
Entire boat: up to 6 people
US $2,100
Entire boat: up to 6 people
There are 3 people looking at this charter.
Customer reviews
Rating
4.9
118 reviews
5.0
Boat & equipment
4.9
Captain & crew
4.9
Fishing Experience
Anglers' gallery (201)
What anglers say
96%
Great experience
96%
Family friendly
99%
Friendly captain
100%
Good boat
97%
Recommended
98%
Caught fish
All reviews (118)
Filter
Sort by: Featured
Frequently mentioned
Showing 1 – 5 of 118 reviews
Sam Steck
Florida, US
Member since 2025
0
5.0
Verified
New
Hell Yeah to Capt Dan
Full Day Trip on May 23, 2026 • 6 adults
Capt Dan was the recommendation from a few different friends that we have down in the Keys, and he definitely did not disappoint. It was easy to book the charter, and he was very communicative after booking. He was on time and ready to roll right at 7:00 am the day of our trip.
We went out and conditions were a little rough. Despite the choppy seas, we quickly got some lines in the water. While I bet most boats did not catch fish, we ended up having a pretty damn good day and had a ton of fun with my buddies and Capt Dan. He fit right in with the group, and we appreciated him getting us out there and putting us on some fish. Already looking forward to the next trip with him. Thanks, Capt Dan. Appreciate ya! 10/10 would recommend!
Response from Captain
June 3, 2026
you guys were great. hope to have you back soon.
Daniel Nigri
Ohio, US
Member since 2024
0
5.0
Verified
Amazing Private Fishing Experience
3/4 Day Trip on February 18, 2026 • 2 adults
Yesterday we went on a 6-hour private fishing trip with Captain Dan, and it was an awesome experience from start to finish.
We caught tuna and wahoo and had an incredible time on the water. Captain Dan is extremely professional, clearly knows what he’s doing, and uses different fishing techniques to make sure you have the best possible chance of success.
Beyond the fishing itself, he was great to spend the day with — very friendly, knowledgeable, and easy to talk to. The trip never felt rushed, and you can tell he truly cares about giving his guests a great experience.
At the end of the trip, he filleted and vacuum-sealed all of our fish so we could easily take it back home, which was all included in the price — a huge bonus.
Highly recommend Captain Dan to anyone looking for a top-quality fishing trip. I would definitely come back again.
Reported catch:
Response from Captain
February 19, 2026
it was a great time. cannot wait for your next trip.
Neil Quinlan
Repeat angler
Kentucky, US
Member since 2019
5 trips
0
5.0
Verified
Blackfin, Mahi, Wahoo… and a Whole Lot of Laughs
Full Day Trip on February 13, 2026 • 2 adults
We fished today with Underwater Cowboy (Cptn Dan), and it was an awesome experience. The conditions weren’t easy, but he worked nonstop to get us on fish. We ended up catching blackfin tuna, mahi, and a really nice wahoo.
Even when things slowed down, he kept us entertained with great stories and made the whole trip fun and memorable. It felt like fishing with someone who genuinely cares about your experience, not just the catch.
If you’re heading to the Keys, don’t hesitate — book with Underwater Cowboy. We’ll definitely be back.
Reported catch:
Response from Captain
February 14, 2026
You guys were great. Get back down here and we will go get some swordfish to knock them off your list. Until next time.
Adryanna Galarce
Repeat angler
Florida, US
Member since 2025
2 trips
0
5.0
Verified
Unforgettable Fishing Experience!
Half Day Trip on June 15, 2025 • 2 adults
I’ve been on two trips with Underwater Cowboy, and both were nothing short of amazing. Captain Dan and his first mate are a dynamic duo—friendly, knowledgeable, and completely dedicated to making the day fun, relaxing, and seamless. They work as a team and make sure everyone on board is well taken care of from start to finish.
The boat ride itself is incredibly peaceful—perfect for someone like me who’s constantly on the go and needs a moment to hit pause. And while the ride alone is worth it, catching fish is the icing on the cake! Captain Dan cleans your catch at the end, so you can take home a fresh reward from your day at sea.
The boat is spotless and clearly well cared for. I was especially impressed with how the crew constantly cleaned up after each catch—no fishy mess to worry about! There’s also thoughtful storage for your snacks, drinks, and even a secure spot for your phone so you’re not stressing about it getting wet or going overboard.
If you’re looking for a relaxing day on the water with the bonus of fishing and amazing company, Underwater Cowboy is it. Can’t wait for trip #3! 🎣🚤
Response from Captain
June 30, 2025
Thanks for the review. We work hard to Kell the equipment in tip top shape. I try to make our trips the same way I would want them if I were on vacation. I hope to see you guys back soon.
Bric Garrett
Texas, US
Member since 2025
1
5.0
Verified
WHAT A GREAT DAY OF CATCHING !!!
Full Day Trip on November 15, 2025 • 2 adults
WOW!!! What a great day of CATCHING fish and not jus fishing!!!!
We got started early laying into the Blakfin Tuna while trolling for a wahoo. After all most no tome at all, we had nearly met our limit of blackfin.. Then it happened, a slam of of a top water jig, and the wahoo fight was on.. He definitely did not want to conw into the boat but after a couple good runs of the reel that is where he ended up.
It was an amazing day of fishing and the 51 inch wahoo is going to look great on the wall.. and yes it was excellent eating as well !!!!
Reported catch:
Response from Captain
November 23, 2025
you guys were great. had a good day with alot of fun and got fish.
FAQs about Underwater Cowboy
The fish you can target
What is the boat like?
Boat category
Center console boats
Capacity
6 persons
Boat length
36 ft
Year built
2018
Boat manufacturer
Contender
Boat type
Center console
Engine model
Yamaha
Powered by
2 x 350HP
Max cruising speed
50 knots