REVIEW · KEY WEST
Key West: Private Fishing Charter with Experienced Captain
Book on Viator →Operated by Drop Off Sportfishing · Bookable on Viator
Sailfish days start fast. This is a true private Key West offshore charter built around getting you on the bite, with your own captain and first mate. I love that it’s limited to up to six people (so nobody else is piling in), and I also like that Captain Craig and his crew will tailor the plan and clean and filet whatever you choose to keep. One consideration: you’re going 6–16 miles offshore, and the water can get choppy.
Your day can center on mahi-mahi, snapper, grouper, king mackerel, wahoo, sailfish, and other species, depending on what’s biting that season and day. You can expect an active approach too, using techniques like trolling, bottom fishing, live baiting, wreck fishing, and deep dropping. If you’re sensitive to rough water, this is the main thing to think through.
You’ll board from the Perry Hotel & Marina Key West area and head back to the same meeting point when the charter ends (about 4 hours, with 6- and 8-hour options). It runs low-key in a good way, with an experienced team on the boat and an emphasis on safety, quality gear, and helping you make decisions out there on the water.
In This Review
- Key Highlights at a Glance
- Boarding at Perry Hotel & Marina: A Simple Start
- Captain Craig, First Mate Brett and Riley: The Crew That Pushes for Results
- How 6 to 16 Miles Offshore Changes Your Chances
- Target Species and the “Bite-First” Fishing Plan
- Techniques You’ll Use: From Trolling to Deep Drop
- Staying Comfortable at Sea: Snacks, Cooler, Sun, and Motion
- When You Land Fish: Cleaning and Fileting That Saves a Weekend
- Price and Value: What $900 Per Group Really Buys
- Timing: How a 4-Hour Trip Feels vs. 6 or 8
- Where This Charter Fits Best (And Who Might Want Something Else)
- Quick Practical Tips Before You Go
- So, Should You Book This Private Fishing Charter?
- FAQ
- Where does the charter start and end?
- How many people can go on this private charter?
- How long is the fishing charter?
- What does the $900 price include?
- What fish might we catch?
- Do we need to bring equipment?
- Can we bring food and drinks?
- What is the cancellation policy?
Key Highlights at a Glance

- Private charter for up to 6 people: you won’t share the boat with strangers.
- Captain Craig with 15+ years of commercial fishing experience: big focus on putting you on fish.
- Offshore range of 6–16 miles from shore: helps match the day’s fishing conditions.
- Techniques match the bite: trolling, bottom fishing, live baiting, wreck fishing, and deep dropping.
- Fish cleaning and fileting help: crew can clean and filet what you keep.
- Bring your own snacks and drinks: stored in the cooler you’ll have access to onboard.
Boarding at Perry Hotel & Marina: A Simple Start
The experience starts at the Perry Hotel & Marina Key West (7001 Shrimp Rd). That’s a big deal because Key West days can be chaotic if you’re trying to coordinate transport and timing. Having a clear, central marina start helps you get on the boat with minimal fuss.
The return is back to the same meeting point. That makes your day easier to plan—no awkward “end somewhere else” logistics. You’re also booking a private setup, so your captain and first mate can focus on your group from the moment you step aboard.
The boat is called Double Wrap, and you’ll be working with a captain plus a first mate during your charter. In the real world, that matters: one person can manage line work and baiting while the other helps you position correctly, handle gear, and adjust when the fish are changing their behavior.
You can also read our reviews of more private tours in Key West
Captain Craig, First Mate Brett and Riley: The Crew That Pushes for Results
You’ll be dealing with an experienced fishing team. The captain brings over 15 years of commercial fishing experience, and the goal is straightforward: put you on fish. That doesn’t just mean casting harder. It means reading water conditions, matching a technique to what’s happening that day, and shifting when the bite moves.
The crew also shows up as genuinely helpful. The standout theme across the experience is that the captain and first mate keep working nonstop from departure until you’re back. In practical terms, it’s about finding productive spots and staying on task rather than running a slow “tour” pace.
One named crew combination you may see is Captain Craig with first mates Brett and Riley. The important takeaway for you is not just the names—it’s the teamwork. Two sets of hands, two brains, and constant attention to your fishing lines is exactly what makes a half-day charters feel more like a real outing and less like a casual cruise.
How 6 to 16 Miles Offshore Changes Your Chances
This charter typically runs around 6–16 miles from shore. That range is key because it gives the crew room to find fish where they’re feeding. In Key West, you can have a bright, calm shoreline one minute and a totally different story offshore—temperatures, currents, and structure all shift.
The distance you go can also depend on the trip length you choose (4, 6, or 8 hours) and the season. Even if you’ve fished before, it helps to have someone decide how far to run based on the day’s bite. That removes a lot of guessing.
The tradeoff is motion. Reviews highlight choppy conditions at times, but the experience is described as smooth overall. Still, go in with the expectation that offshore can get rough. If seasickness is a concern, plan ahead with the usual remedies and dress in layers so you can stay comfortable while moving.
Target Species and the “Bite-First” Fishing Plan
The species list is where this charter gets interesting for anglers who want variety, not just one target. Depending on the day and season, you may see action for:
- Mahi-mahi
- Snapper
- Grouper
- King mackerel
- Wahoo
- Sailfish
- And other species that show up with the right conditions
What I like about the way this is framed is the flexibility. The crew isn’t locked into one “script.” They’ll travel and fish in a way that matches what’s actually biting.
A detail worth noting: the captain will tailor the trip to your preferences. That can mean different priorities, like focusing on faster, aggressive species versus taking a slower approach if you’re with beginners. If you want a certain kind of fishing (or you want to learn), this style of charter is set up to adapt.
Techniques You’ll Use: From Trolling to Deep Drop
This charter can use multiple fishing techniques to maximize your chances. You might see:
- Trolling: great when fish are moving and you want to cover water.
- Bottom fishing: often used when the bite is tied to structure.
- Live baiting: helps when fish want something natural and active.
- Wreck fishing: targets areas where fish stack around underwater structure.
- Deep dropping: used when fish are holding at depth.
For you, the value here is simple: technique switching beats stubbornness. If one method slows down, the crew can change gears instead of wasting time. That’s also why these charters tend to feel “busy” in a good way—your gear gets worked, and you’re actively fishing rather than passively waiting.
If you’re new to fishing, don’t worry. The captain and crew will accommodate both first-timers and experienced anglers. That’s the kind of balance that makes a private charter work for families and mixed-skill groups.
You can also read our reviews of more tours and experiences in Key West
Staying Comfortable at Sea: Snacks, Cooler, Sun, and Motion
A good fishing day needs more than hooks. You’ll want to think about comfort because you’ll be out there long enough for the sun and the wind to matter.
The charter encourages you to bring snacks and drinks that you can store in the cooler. It’s also smart to pack sunscreen and hats. Offshore sun in Key West can be intense, and you’ll feel it even if the water looks calm from shore.
Then there’s the “what you can’t control” part: sea state. One experience mentions choppy seas but a smooth experience overall. That suggests the boat handling and crew focus help, but the ocean still drives the vibe. Dress for layers, keep valuables secure, and if you’re prone to motion sickness, handle that before you leave.
When You Land Fish: Cleaning and Fileting That Saves a Weekend
One of the practical wins here is what happens after you catch. The crew will clean and filet fish you wish to keep, and they’ll help with everything you need during your time onboard.
That’s a big deal if you’re traveling. It turns the day’s catch into something usable at home instead of a chore. It also reduces the stress of trying to find a place later to process the fish.
You should still think of it as a “you bring the cooler, they handle the work” situation. If you’re planning to take fish back, ask the crew what they recommend for storage so you get the best results. The charter is designed to take care of the processing side, but your travel setup matters too.
Price and Value: What $900 Per Group Really Buys
The listed price is $900 per group for up to six people. That’s not “cheap,” but it can be good value when you look at what’s included and what private means in the real world.
Here’s the value math that matters:
- Private access means you’re not competing for attention. Your captain can focus on your group.
- Gear and fishing setup are provided, including lures, bait, and a fishing license.
- The crew handles safety and equipment onboard and can help you stay efficient while fishing.
- Cleaning and fileting are included for fish you keep.
If you compare this to paying for a shared trip plus rentals plus licensing plus the hassle of getting your catch processed, $900 can start to look reasonable—especially for families or small groups that want action and instruction rather than just a ride.
Also, booking timing can be in your favor. This kind of charter is commonly reserved about 48 days in advance on average, so if you’re targeting a specific week, plan sooner rather than later.
Timing: How a 4-Hour Trip Feels vs. 6 or 8
The charter runs about 4 hours as the standard duration, with 6- and 8-hour options. A 4-hour trip is great if you want offshore fishing without burning your whole vacation day.
In practice, longer charters usually give the crew more flexibility to find the right bite. If the fish move or the weather shifts, extra hours can make the difference between a good day and a great one—especially for species that can be finicky about timing.
If you’re aiming for multiple species and want time for different techniques, consider stretching the day. If you’re traveling with kids, a shorter outing can also be kinder. The “best” option depends on your group’s energy level and how serious your fishing goals are.
Where This Charter Fits Best (And Who Might Want Something Else)
This private charter is a strong match for:
- Small groups up to six who want your own boat and crew
- Families with mixed experience levels
- Anglers who want a serious shot at multiple offshore species
- People who want the catch cleaned and filleted without extra hassle
It may be less ideal if:
- You’re highly sensitive to motion and rough seas
- You only want a low-effort, scenic cruise (this is built around actively fishing)
- You’re trying to keep costs ultra-tight per person, since private charters price by group, not by solo bargain deals
The key is that you’re not signing up for a one-note day. You’re choosing a captain-led fishing plan with changing techniques and a focus on results.
Quick Practical Tips Before You Go
These are the small things that help a lot on the day:
- Bring snacks and drinks you like, and plan to use the cooler onboard.
- Pack sunscreen and a hat; offshore sun adds up fast.
- Dress in layers for wind and spray.
- If you get seasick, prepare before you board.
- Tell the captain what you want most: certain species, learning, or simply maximizing action.
The crew is set up to tailor the trip. Your input helps them target your ideal day.
So, Should You Book This Private Fishing Charter?
If your goal is a private, captain-led offshore fishing day with a serious push to land fish—and you appreciate that gear, license, and processing are handled—you should book. The standout strengths are the team’s focus on results, the private setup for up to six, and the way the crew adapts techniques as the bite changes.
I’d especially recommend it if you’re visiting Key West for a short time and want one high-impact activity that feels worth your money. Just go in expecting offshore conditions and dress for comfort. If you do that, this is the kind of charter that turns into a story you’ll keep telling.
FAQ
Where does the charter start and end?
The meeting point is the Perry Hotel & Marina Key West at 7001 Shrimp Rd, Key West, FL 33040, USA. The experience ends back at the same meeting point.
How many people can go on this private charter?
The private charter can take up to 6 passengers, and only your group participates.
How long is the fishing charter?
The trip duration is approximately 4 hours, with options for 6 hours or 8 hours.
What does the $900 price include?
The information provided says the charter provides all necessary gear, lures, bait, and a fishing license. The crew will also clean and filet the fish you wish to keep.
What fish might we catch?
Depending on season and the bite that day, the target species include Mahi Mahi, Snapper, Grouper, King Mackerel, Wahoo, Sailfish, and many other species.
Do we need to bring equipment?
No. The charter provides the necessary gear, lures, and bait, along with the fishing license.
Can we bring food and drinks?
Yes. You can bring snacks and drinks, and they can be stored in the cooler. You’re also encouraged to bring sunscreen and hats.
What is the cancellation policy?
Cancellation is free up to 24 hours in advance for a full refund. If canceled due to poor weather, you’ll be offered a different date or a full refund.































