Operating from Charter Boat Row at Docks 19 and 20 (1801 N Roosevelt Blvd) in Key West, Linda D Sportfishing maintains a 4.8-star rating from 245 Google reviews. Running trips from 6:00 AM to 11:00 PM, they offer extended hours that accommodate various scheduling needs.
According to their website at charterboatlindad.com and customer feedback, the operation runs with multiple captains (Tom and Billy are mentioned in recent reviews) and first mate Jesse gets called out by name in numerous reviews for his exceptional work ethic.
You can reach them at (305) 304-8102. Being located on Historic Charter Boat Row means they're part of Key West's established charter community with access to proven fishing grounds.
Exceptional first mate work
First Mate Jesse gets extraordinary praise across multiple reviews. Randy Jones said he "must have some octopus blood - his hands seemed to be everywhere at once" while managing rods, reels, bait, and guiding first-timers through the action. Lauren Pederson noted Jesse "was working constantly - re-baiting lines, swapping lures, and he did it all with a smile."
That level of first mate performance is what separates good trips from great ones.
Patient with first-timers and families
Multiple reviews mention daughters' first deep sea fishing experiences turning into "successes" thanks to crew patience. Randy specifically noted they were "GREAT with the kids (that meant a lot)." Captain Tom and Jesse work well together to make beginners comfortable.
Full catch service and recommendations
Crews fillet your catch at the dock and point you to local restaurants that will cook your fish. Randy's group took their fish to a recommended spot and had it "prepared fried, grill, and blacken along with fries and coleslaw." That complete service matters when you're visitors unfamiliar with the local restaurant scene.
Educational approach
Lauren's review noted the crew "shared details about the ocean currents, grass patches, birds, fish, and anything else we asked about." Good guides teach you to understand what's happening, not just pull your string.
With 245 reviews averaging 4.8 stars on Google, the feedback is consistently strong:
First Mate Jesse is mentioned by name constantly. The volume of specific praise for one crew member is unusual and indicates exceptional skill and work ethic. Multiple reviewers call him "amazing" and note they "can't say enough" about him.
Captains Tom and Billy both get positive mentions. Tom is described as knowing "the exact area to go and depth" for target species, while Billy "knows his spots."
High action days even when conditions aren't ideal. Randy's trip wasn't during favorable season ("time of season was not favorable") but still caught skipjack tuna, barracuda, and yellowfin snapper.
Kid-friendly atmosphere without compromising adult fishing. Parents appreciate crews who can balance keeping children engaged and successful while also delivering quality fishing for the adults.
The main thing to understand is this appears to be primarily an offshore/deep sea operation rather than flats or backcountry. If you're specifically after tarpon, permit, or bonefish, you'll want to confirm they offer those trips.
First-time offshore anglers, especially families - The patient teaching approach and Jesse's exceptional first mate work make this ideal for people new to deep sea fishing.
Groups with mixed experience levels - When you've got beginners and experienced anglers together, you need a crew that can handle everyone effectively. Reviews confirm they excel at this.
Anglers who appreciate educational guiding - If you want to understand what's happening (why we're fishing this depth, what the birds tell us, etc.) rather than just follow instructions, the crew's teaching approach delivers.
Visitors wanting complete service - From catching through filleting through restaurant recommendations, they handle the full experience for people unfamiliar with Key West.
Book early if you want Jesse as your first mate specifically. While he's clearly a core part of the operation, if timing matters and you specifically want him based on reviews, mention that when you call.
Bring kids' Dramamine if you're going offshore with young ones. Even calm days have swells in deeper water. Taking medication an hour before departure helps prevent seasickness from ruining their experience.
Ask the crew questions during slower moments. Multiple reviews mention they're happy to explain ocean patterns, fish behavior, and technique. That knowledge makes you a better angler on future trips.
Follow Jesse's advice on where to have your fish cooked. He's sending people to these restaurants regularly and knows which ones do the best work with different species and preparations.
If you're targeting specific species like mahi, ask about seasonal timing when you book. Even skilled crews have better odds during peak season for particular fish.
Take photos during the action. First-timers especially will want to document their first barracuda or their kids' catches. Jesse's constant movement and work means he may not have time to play photographer, so assign someone in your group to that role.
Bring adequate sun protection for extended trips. Offshore fishing means full sun exposure with intense reflection off the water. Quality sunglasses, sunscreen (applied before and during), and protective clothing matter.
The extended hours (until 11:00 PM) might include sunset trips or night fishing. If that interests you, ask what they target during those times. Some species feed better at dusk or after dark.
Source: Google My Business listing and customer reviews for Linda D Sportfishing, accessed January 2026.
