We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

High Stakes Charters

#41 of 237 Boat Tours & Water Sports in Key West Features Animals
Oceanside Marina, 5950 Peninsular Ave Slip #659, Key West, FL 33040
+1 305-294-8040
Review Highlights
Another EPIC trip! My 20th! At least!

Last year monster sailfish! This year a monster Mahi and about 30 or so of his friends and cousins... read more

Reviewed 1 week ago
via mobile
Graduation gift for boys

Couldn't wait to get out after reading all the great reviews. True pros, went beyond expectations... read more

Reviewed 1 week ago
West Palm Beach, Florida
via mobile
Read all 200 reviews
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
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%
Travellers talk about
“captain jason” (43 reviews)
“wahoo” (22 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

Write a Review
Reviews (200)
Traveller rating
Traveller type
Time of year

1 - 10 of 200 reviews

Reviewed 1 week ago 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

Reviewed 1 week ago via mobile

Couldn't wait to get out after reading all the great reviews. True pros, went beyond expectations. They spent extra time with the boys explaining how everything works. These kids had a blast. Plus if you get hot the cabin has plenty of places to sit...More

Thank footballville
Reviewed 2 weeks ago

We knew the odds were against us with the nice weather, but we went out anyways. Heath was a really friendly Deck Hand and Jason the Captain/owner was really accommodating!! They treated us like family and let us do whatever we wanted on their boat....More

Thank Krullsie
Reviewed 4 weeks ago via mobile

Capt Jason and firstmate Heath were awesome!! They wasted no time getting us off the dock and out in the open water. Within 30 minutes the lines were in the water and we were off. 3 decent mahi within the hour but that was just...More

Thank kwmike2017
Reviewed 4 weeks ago via mobile

Just got off of the high stakes charter and I have to say it was an awesome time. Jason and Heath did a great job. We caught so many fish we and threw 9 young ones back . They knew exactly what to do and...More

1  Thank markmoncayo
Reviewed 18 May 2017 via mobile

Not enough kind words for the amazing Captain Jason and 1st Mate Heath. One of the most kindest, honest and enjoyable guys to take you out fishing. The boat was great, great equipment very informative. If you are really looking into fishing these guys are...More

Thank Adventures68
Reviewed 12 May 2017 via mobile

Myself, my father and one of our family friends flew out to key west for 3 days of deep sea fishing with Jason and his crew. We'd booked in for the first day fishing for 6 hours in the afternoon, the next day being a...More

Thank OllieSexton
Reviewed 20 April 2017 via mobile

BEST charter we ever booked! If you plan on visiting the Keys...go with Captain Jason and Heath. They were amazing and so patient with our boys. Looking forward to booking with them again next year!

Thank Kimberly R
Reviewed 28 February 2017

This was the best fishing trip we have had! Captain Don and first mate Heath were amazing! They had great stories, taught us so much and made us feel at home. We caught amazing tuna and ate it right on the boat!! Incredible!! We saw...More

Thank rlister124
Reviewed 26 February 2017

Fulfilled every expectation and then some. Everything was great from the boat to the crew. We caught plenty of fish. We will definitely pick the High Stakes Charters again in the future and would recommend to everyone.

Thank Tero U
Nearby Restaurants
Hogfish Bar & Grill
3,145 reviews
.49 km away
Roostica Wood-Fire Pizzeria
662 reviews
1.24 km away
Yellowfin Bar & Grill
44 reviews
.21 km away
El Mocho Restaurant
49 reviews
1.03 km away
Nearby Attractions
Stock Island Marina Village
19 reviews
.76 km away
Wild About Dolphins
455 reviews
.26 km away
Footloose Excursions
225 reviews
.14 km away
Questions & Answers
Get quick answers from High Stakes Charters staff and past visitors.
Note: your question will be posted publicly on the Questions & Answers page.
Posting guidelines