High Stakes Charters — Local services in Stock Island

When I 1st started looking for charters in Keywest I spoke to several different Captains telling me the same thing that they would get me on whatever fish I was after, I then called High Stakes and had a long conversation with Captain Jason who spoke the truth and stated he would do his best to get us on some fish but there was no guarantee unlike all the others charters promised. I am a life long Fisherman and Hunter and have spent many hours weather it be in the woods hunting game, on a stream, lake or on the big seas after fish, the one thing I have learned in all my years is there is no guarantees and it's called fishing not catching. I have been fishing with Highstakes for several years now and would never even think about going anywhere else, the boat and accommodations are 1st class and have all the comforts one could ask for, Captain Jason knowledge has always put us on fish no matter the conditions, some trips we have done better than others but he has always put forth 110% effort. I have also had the opportunity to fish with Big Don who always makes it a special day by adding all his experience and sharing his wisdom and techniques along with great stories and a lot of laughs with us. The 1st Mates ( Matt & Heath ) have always worked there tails off the entire time making sure everything is perfect and provide instruction every step of the way to bring in every fish, they never rest until the day is done. Highstakes is the perfect charter for all ages. I am fortunate enough to say the entire Highstakes crew is more than a charter they have become part of our family always going out of there way to provide us with the best possible experience you can ask for. I highly recommend if your looking for a charter in Keywest look no further book...

TL/DR: If you're looking for a Charter, go with a company that has a young and hungry team. This captain (Don) is an old guy who just doesn't care about his client experience anymore after however many decades he's been at this. If you do end up going with High Stakes, I strongly suggest requesting to go out with Jason as Captain.

8-hour trip in early December. This was our first deep-sea trip, so I asked for guidance when booking on what we should do for the highest probability of success and if this was the right time of year. We were told to book the 8 hours and we should be able to get some good fish on the line

We had 1 mahi on for maybe 15 seconds for the entire day. The deck-hand worked hard making sure all the lines were always freshly baited, but the captain and owner just could not have cared less that we were getting nothing. We drove in circles in the same area for 8 hours. No attempt was made to try a substantially different area, and he was dismissive when we asked if there were any other options.

At the end of the trip, we were told "sorry for the slow day" and sent on our way with a $1,760 ticket. The captain even added on the $60 fee he should have incurred from Stripe without even asking us.

Plenty of Charter options in Key West. I'd suggest...

My wife and I live in south Florida and brought some customers down to Key West to relax. Decided to fish with Captain Jason and his first mate Matt for two days. We had a great time even though the fishing was slow. We did, however, do better than the rest of the fleet both days!

My wife and I do a lot of chartered fishing, usually up north a little, so we’ve seen about everything you can see in south Florida. The difference with this team is the high level of professionalism and skill. Matt even served up a plate of wahoo sashimi from my wife’s catch the day before.

They were very patient with the novices on the boat and literally coached them to land every fish we hooked, which is critical when the fishing is slow. Matt was good about keeping the seaweed off the lines and they always had 6-7 lines in the water. Some boats barely get 4 lines in the water consistently.

Captain Jason and Matt keep the boat clean, and because of its size, you can even sit out front and get some sun.

You can’t swing a dead cat anywhere around South Florida without hitting 50 charter fishing boats, so finding the right one is hit or miss if you don’t know what you’re looking for. Make the effort to book with...