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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
Awesome Team!

The Captain and the First Mate are so nice and funny! We have seen them working hard and returning... read more

Reviewed 3 weeks ago

Most awesome experience ever we had the best time caught so many fish, Great guys and made my... read more

Reviewed 4 weeks ago
Benton, Kentucky
via mobile
Read all 209 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” (21 reviews)
Oceanside Marina, 5950 Peninsular Ave Slip #659, Key West, FL 33040
+1 305-294-8040

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Reviews (209)
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1 - 10 of 209 reviews

Reviewed 3 weeks ago

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 4 weeks ago 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 5 weeks ago 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
A TripAdvisor Member
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 A TripAdvisor Member
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
Reviewed July 16, 2017 via mobile

Great trip with Jason and Heath. These guys will do everything to put you on the fish. We caught Mahi and Sailfish We will be back on our next trip down to the Keys.

Thank Michael T
Reviewed July 10, 2017 via mobile

Wow! The entire trip from start to finish was absolutely incredible! Top notch boat and equipment, from my initial inquiry to Capt Jason he was completely honest and straight forward about the trip and there was no gurantee about landing a nice catch, once on...More

Thank Jferet
Reviewed July 8, 2017 via mobile

What a day!! At two separate occasions we had 4 fish on and the whole family was working together reeling and trying not to cross lines ! We pulled in barracudas, mahi mahi and some other fish..! We took the fish after the charter to...More

Thank MikeGuev
Reviewed July 7, 2017 via mobile

Captain Jason and Heath were incredible! Hard working. Trip of a lifetime! Caught a monster Yellow Fin and a 40 lb Mahi Mahi amongst others. Can't say enough about these guys, they were great! I will definitely be back next year!!!

Thank lferet
Reviewed June 12, 2017 via mobile

Last year monster sailfish! This year a monster Mahi and about 30 or so of his friends and cousins of different species! Probably a $40 k fish if tourney sponsor wouldn't have pulled out and they cancelled! Oh well! Jason and Jarrett find the fish...More

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