Offshore Naples runs one of the sharpest small deep sea fishing charters in the port, a new 36 foot Contender called the How Deep on twin 2025 Honda 350 outboards, run by Captain Bill, a licensed captain and a dive master who knows the Naples reefs from the surface and from below. It posts a clear rate for every trip, fuel and fish cleaning included, and it fishes the deep sea bottom for grouper and snapper. For a small group that wants a fast, modern boat and a captain with thousands of marked spots, it is a strong call.
The verdict and where it ranks
At 8.0 Offshore Naples sits third in the ranking, a hair behind the A&B cabin boat and the top six pack Off Her Radar. Its strengths are a standout captain, a new well equipped boat, and posted rates, the transparency the site values. The trade is comfort: a center console is an open boat with no cabin, so a long summer day in the sun and chop is less comfortable than on a cabin boat like A&B. For an affordable shared seat the Pure Florida head boat is the pick, and Tom’s Deep Sea Fishing is the other six pack. See the full Naples ranking.
The boat
The How Deep is a 36 foot Contender, a fast, seaworthy center console on a pair of new 2025 Honda 350 V8 outboards. The speed gets a small group to the offshore reefs quickly, so more of the trip is fishing and less is steaming, which matters on a coast where the good grouper sits a long run out. It is well rigged with quality rods and electronics. What it does not have is a cabin: it is an open boat, so up to 6 anglers who do not mind sun and weather is the right fit, and a comfort first group should look at a cabin boat.
The fishing and what you target
This is a deep sea bottom boat, working the reefs and wrecks for red, black, and gag grouper, mangrove, lane, and red snapper, cobia, amberjack, king and Spanish mackerel, hogfish, permit, and shark. Red grouper is the year round Naples staple; red snapper opens June 1 to October 26, 2026 in federal waters, and Captain Bill runs the 10 hour red snapper trip in summer. Amberjack is closed until September and triggerfish through July. The captain’s thousands of marked spots are the edge on a day when the fish move.
Trips and prices
Offshore Naples posts its rates in full, which counts: $1,000 for a 4 hour half day, $1,700 for a 6 hour reef and wreck trip, and $2,000 for an 8 hour red grouper trip, with a 10 hour red snapper trip in season. Each is for the boat and up to 6 anglers, and fuel, bait, tackle, licenses, and fish cleaning are all included, which makes the price easy to compare. Our cost guide and the walk on versus private guide set those numbers against a shared head boat seat.
The crew
Captain Bill is both a licensed captain and a certified dive master with thousands of logged dives, which is an unusual combination: he knows the reefs the boat fishes from having been down on them. Reviewers describe a captain who puts groups on fish and keeps moving until the bite is on, and the boat draws positive, steady sentiment. The review record is solid rather than huge, which is the one place a newer operation cannot match the port’s longest running boats.
Booking and what to know
Book direct, ahead for summer, and pick the trip length to match the fishing you want, since the longer trips reach the better grouper and the red snapper. Bring sunscreen, layers, food, and a cooler, because the open boat offers little shelter; fuel, gear, the license, and fish cleaning are covered.
How we scored it
Offshore Naples scores 8.0 on a standout dive master captain, a new well equipped boat, and fully posted rates, held just back by the comfort limits of an open center console and a review record that is solid but smaller than the port’s veterans. Captain and crew is its strongest factor. See how we scored this boat and the Naples ranking for the field.