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High Stakes Charters

Features Animals
Oceanside Marina, 5950 Peninsular Ave Slip #659, Key West, FL 33040
+1 305-294-8040
Review Highlights
Tuna for days!

We had a great day of fishing with Heath and Capt Jason! Caught so much tuna we couldn’t bring it... read more

Reviewed 4 days ago
William H
via mobile
Awesome fishing

My first fishing trip, the crew was on it. They put us on the fish when no other boat s caught... read more

Reviewed 6 days ago
Mike H
via mobile
Read all 214 reviews
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Treat yourself to a one of a kind fishing experience in Key West Florida. High Stakes Charters offers a 53' Striker Sportfishing vessel. A/C, twin engines, tournament grade tackle, 2 staterooms, 2 bathrooms, full service galley and a spacious lounge area with leather couches. High Stakes is located at Oceanside Marina which is on the south side of the island. This means we are closer to the fishing grounds allowing you more time fishing the beautiful crystal clear blue water of the Gulf Stream. Our professional crew with 35 years combined fishing experience work extremely hard to catch Blue Marlin, Sailfish, Wahoo, Mahi Mahi, Black fin Tuna, Yellowtail Snapper, Grouper, a vast variety of sharks and much, much more.
  • Excellent98%
  • Very good1%
  • Average0%
  • Poor1%
  • Terrible0%
Travelers talk about
“captain jason” (45 reviews)
“wahoo” (23 reviews)
“tuna” (20 reviews)
Oceanside Marina, 5950 Peninsular Ave Slip #659, Key West, FL 33040
+1 305-294-8040

Similar Things to Do in Key West

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1 - 10 of 214 reviews

Reviewed 4 days ago via mobile

We had a great day of fishing with Heath and Capt Jason! Caught so much tuna we couldn’t bring it all back after giving some to the crew! Excellent service throughout the day and A+ sashimi 😋Would definitely recommend for anyone wanting to fish out...More

Thank William H
Reviewed 6 days ago via mobile

My first fishing trip, the crew was on it. They put us on the fish when no other boat s caught anything, all three of us got fish. 5 stars. Thank you Jason and heath.

Thank Mike H
Reviewed 1 week ago via mobile

We spent a short time with Jason and Heath and had such a good time. The fishing was good and the fellowship was great. I would highly recommend spending time with High Stakes charters. You will not be disappointed.

Thank David P
Reviewed 1 week ago via mobile

Amazing fishing, great crew, seven other charters out we were the only ones who caught anything, awesome hospitality. I wouldn’t choose any other than these guys

Thank 841codyw
Reviewed January 7, 2018 via mobile

We normally fish Islamorada light tackle, and thought we’d give big water, and big fish a shot. Start to finish, Jason & Sean were very nice, professional, and real knew their stuff. Great boat, and tournament grade tackle - all first rate. You can tell...More

Thank David T
Reviewed September 2, 2017

The Captain and the First Mate are so nice and funny! We have seen them working hard and returning to Oceans Edge Marina with a boat full of fish, but this was our first time joining. I couldn't believe how they knew exactly where to...More

Thank SarahSnorkel
Reviewed August 23, 2017 via mobile

Most awesome experience ever we had the best time caught so many fish, Great guys and made my husbands birthday the best one. Thank you for your great hospitality and made our vacation the best one ever!!!

Thank paulapollnow
Reviewed August 22, 2017 via mobile

We went to key west for a fun filled fishing weekend for my husband's 50th bday and after a thorough review of all of the charters in the area we selected "High Stakes Charters" and are very happy that we made the choice. Captain Jason...More

Thank rkousaleos7
Reviewed August 4, 2017 via mobile

What a great day fishing with Captain Jason and First Mate Heath. They were so much fun to fish with and we caught Dolphin Fish which are great to catch and yummy to eat. The boat was clean and nice AC since it was 95...More

Thank 874donna
Reviewed August 3, 2017 via mobile

I cannot say enough good stuff about Jason and his mate, Heath. Number one, we caught a lot of fish, 4 dolphin fish (one large enough to mount), 2 barracuda, and I know, a fish story, hooked a 60 lb. wahoo - the one that...More

Thank NatTataRat
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