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

Features Animals

High Stakes Charters
Booking unavailable on TripAdvisor

Want other options you can book now?
All photos (338)
Full view
Certificate of Excellence
Traveler Overview
  • Excellent98%
  • Very good1%
  • Average0%
  • Poor1%
  • Terrible0%
Travelers talk about
“captain jason”(46 reviews)
“wahoo”(23 reviews)
“tuna”(23 reviews)
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...more
Oceanside Marina, 5950 Peninsular Ave Slip #659, Key West, FL 33040
+1 305-294-8040
Improve This Listing
Recommended experiences in and around Key West
from $72.50
More Info
from $63.00
More Info
from $145.00
More Info
from $112.00
More Info
Reviews (222)
Filter reviews
222 results
Traveler rating
Traveler type
Time of year
Show reviews that mention
All reviews captain jason wahoo tuna deep sea fishing fishing trip these guys great fishing caught fish big fish great trip go fishing highly recommend this charter sea sickness the florida keys mate trolling boat
Updating list...
1 - 10 of 222 reviews
Reviewed July 10, 2018 via mobile

Can’t thank Jason and Heath enough for making an unforgetable memory. If your looking for a top notch charter look no further. Can’t miss with High Stakes.

Date of experience: July 2018
1  Thank shawnmoore05
Reviewed July 10, 2018 via mobile

Once again a fantastic day out with Capt. Jason and Heath plenty of Mahi Mahi which made a great meal and then some! Can't say enough about High Stakes and the experience they go out of their way to make it special and get you...More

Date of experience: July 2018
1  Thank jeff f
Reviewed June 21, 2018

Six of us on a family get away in Key West spent the day with Captain Jason and Heath on the MV High Stakes. High Stakes is a very comfortable, well maintained boat and it was a great experience, Jason and Heath are excellent at...More

Date of experience: June 2018
Thank Frederick R
Reviewed June 5, 2018

Jason and Jarret (yes the one from the Hot Tuna), thank you for a great time with our two boys back in 2016. You were patient with them and my wife and all of their fishing, sightseeing, and boat questions. You guys do a fabulous...More

Date of experience: July 2017
Thank Zane131
Reviewed May 16, 2018 via mobile

We had an awesome time! We were three generations together on a family trip. They couldn’t have been nicer and more accommodating. We caught a really nice sailfish and also a pretty good size barracuda! I would highly recommend this charter if you are looking...More

Date of experience: May 2018
Thank lynn m
Reviewed March 29, 2018 via mobile

What a great time fishing with the High Stakes charter team. The weather wasn’t great and the quality fish escaped us but Captain Don and mate Heath never once gave up on us. The boat is awesome, the crew professional and they provided us with...More

Date of experience: March 2018
Thank Spyke W
Reviewed March 27, 2018 via mobile

Our crew was great for our first time deep sea fishing! I rode out on the bow and got some amazing sunrise pictures. Within about a half hour my husband and I were catching fish. Unfortunately, I forgot to take Dramamine or Benadryl and a...More

Date of experience: March 2018
Thank angnott
Reviewed March 16, 2018

My two college aged kids and I went out on a 3/4 day afternoon trip on Wednesday March 14th - upshot excellent trip! Jason put us on fish in really tough conditions. Details below. First, I'd like to say that I spoke with 3 charter...More

Date of experience: March 2018
Thank NewRocMom
Reviewed February 16, 2018 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

Date of experience: February 2018
Thank William H
Reviewed February 14, 2018 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.

Date of experience: February 2018
Thank Mike H
View more reviews
Nearby HotelsSee all 51 nearby hotels
Oceans Edge Key West Hotel & Marina
1,319 reviews
.12 miles away
The Perry Hotel Key West
648 reviews
.65 miles away
Best Western Key Ambassador Resort Inn
2,084 reviews
1.41 miles away
DoubleTree by Hilton Hotel Grand Key Resort - Key West
4,067 reviews
1.41 miles away
Nearby RestaurantsSee all 479 nearby restaurants
El Siboney Restaurant Stock Island
22 reviews
.73 miles away
Matt's Stock Island Kitchen & Bar
246 reviews
.64 miles away
Hogfish Bar & Grill
3,721 reviews
.33 miles away
Roostica Wood-Fire Pizzeria
815 reviews
.82 miles away
Nearby AttractionsSee all 738 nearby attractions
Sea Monkey Ocean Adventures
23 reviews
.16 miles away
Stock Island Marina Village
37 reviews
.47 miles away
Collections Key West
16 reviews
.39 miles 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