Miss Chief Charters is an owner operated boat with a long Upper Keys record, run by Captain Dan Matthews, who has fished the Keys since 2002. It earns its place in our Key Largo field on a clear, fair, all included price and a deep review trail, more than 200 reviews on TripAdvisor over the years, with the recurring praise a fun, skilled crew that teaches newer anglers. It lands in the mixed tier rather than higher for two honest reasons: the boat is the oldest and slowest in the ranked field, and the otherwise positive record carries at least one unresolved complaint about the owner that is worth reading before you book.
The verdict and where it ranks
At 6.9 Miss Chief is a mixed pick: book it with caveats, depending on the trip. The case for it is the owner and the value, a hands on captain with a long Keys record and one of the clearer, more affordable all included prices in the port. The caveats are real, though, which is why it sits below the strong tier. The 34 foot Crusader is a 1979 hull with a single engine, the oldest and slowest boat we rank in Key Largo, so a fast or comfortable ride is not what you are booking. And under a mostly positive trail sits a critical review or two about the owner’s conduct that we could not fully resolve, the kind of flag a reader should weigh for themselves. Book it for a straightforward reef or offshore half day with a hands on owner. The Key Largo ranking sets the field side by side.
The boat
The Miss Chief is a 34 foot Crusader sportfisher on a 1979 hull, powered by a single 400 horsepower Cummins diesel that cruises at around 20 knots. That is the honest weak point: it is the oldest and slowest boat in our ranked field, so the run out to the grounds eats more of the trip and the ride is less comfortable than the newer Contenders and rebuilt flybridges around it. It takes up to 6 anglers, the Coast Guard limit on a six pack boat. It is a capable enough boat for a reef or a nearshore offshore day in fair weather, but it does not have the speed or the comfort to make the most of a rough one.
The fishing and what you target
Miss Chief fishes the reef and the Gulf Stream off Key Largo. Offshore the boat works sailfish in the cooler months, mahi mahi from spring into fall, and blackfin tuna and wahoo through the year, with swordfish on the longer runs, while the reef and wreck trips drop for grouper and snapper. Captain Matthews has fished these waters since 2002, and reviewers credit the crew with finding fish and, in particular, with teaching first timers and kids, which is a genuine strength on a boat at this price.
Trips and prices
Miss Chief sells by the whole boat for up to 6 anglers, private only, with posted rates of $900 for a 4 hour half day, morning or afternoon, $1,200 for a three quarter day, and $1,500 for a full day. The tackle, live bait, lures, fishing license, catch cleaning, ice, and bottled water are all included, which is a clear and fair package and one of the better value private prices in the port. The transparency is a real point in its favor against the boats here that hide a rate or list two. Our cost guide puts those numbers against a shared seat and the bigger boats.
The crew
Captain Dan Matthews owns and runs the boat, and most of the record is positive: a fun, skilled crew, good with families and patient with newer anglers, and a captain who knows the local water after two decades. The honest qualifier is that the same record carries a critical review or two centered on the owner rather than the fishing, including an owner conduct complaint on TripAdvisor whose substance we could not verify. It is one flag against a deep, mostly positive trail, not a pattern, but it is the kind of thing to read in full before you book, since it touches the person you will be dealing with.
Booking and what to know
Book through the operator’s site or its FishingBooker listing. The boat leaves from 400 Ocean Drive, mile marker 100 on the ocean side of Key Largo. No fishing license is needed, the boat covers it, and the crew cleans your catch and provides ice and bottled water. Allow extra time on the water for the slower run to the grounds, and pick a calmer day if comfort matters, since this is not a fast or modern hull. For a newer boat at a similar price, the value pick Lock It Up is worth a look.
How we scored it
Miss Chief scores 6.9: an owner operated boat with a long record and clear, fair pricing, held in the mixed tier by the oldest and slowest hull in the ranked field and an unresolved owner conduct complaint under an otherwise positive trail. Value and transparency is its strongest factor; boat and equipment is where the aging hull costs it. See how we scored this boat, and weigh it against the rest of the Key Largo fleet.