A Practical Look at the Private Island & Fishing Charters in Key West 37ft Knotty Cowgirl

If you’re dreaming of a half-day escape in Key West that combines serious fishing with a touch of island tranquility, then this private charter aboard the Knotty Cowgirl might be just what you’re after. For $1,100 per group (up to 6 people), you get roughly 4 hours of fishing, island hopping, or a mix of both, depending on your preferences. The boat departs at 7:00am from Cowboy Cowgirl Sportfishing, a well-equipped vessel designed to handle both deep-sea fish and scenic island visits.

What stands out immediately is the flexibility of this tour. It’s not just about catching fish but also about enjoying the stunning scenery and quiet islands of the Keys. We appreciate how you can tailor your experience. Do you want to fish for mahi-mahi and sailfish? Or would you rather drop anchor on a sandy island for a picnic? This kind of customization makes it a real value for those wanting more than just a fishing trip.

A potential consideration is the additional fuel surcharge of $150. While the base price might seem steep for some, the exclusivity and personalized nature of the experience help justify it — especially if you value privacy and a flexible schedule. Keep in mind, this is a private tour, so you’re not sharing the boat with strangers, which adds to both comfort and intimacy.

This experience suits adventure seekers, families, or groups of friends who want to combine fishing with relaxing island visits in a beautiful setting. If you’re looking for a well-rounded day on the water with the option to fish or just enjoy the scenery, this trip offers both.

Key Points

Customizable Experience: Choose between deep-sea fishing or island hopping, or combine both.
Private Tour: Only your group participates, ensuring personalized attention and comfort.
All Necessary Equipment Included: Tackle, bait, and permits are provided, so no extra hassle.
Departing Early: The 7:00am start time maximizes your day for fishing or exploring.
Great for All Levels: Whether you’re a seasoned angler or a beginner, the crew helps you get the most out of your trip.
Additional Fees: Expect a fuel surcharge of $150, which adds to the overall cost but supports a smooth experience.

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A Detailed Look at the Experience

Setting Out from Cowboy Cowgirl Sportfishing

Your day begins at 7:00am at Cowboy Cowgirl’s dock on Roosevelt Blvd, a location that’s accessible and near public transportation. As you step aboard the 37-foot Knotty Cowgirl, you’ll notice it’s fully equipped for sportfishing—think modern tackle, space to move, and a captain and crew ready to help you land your target fish. The boat’s size makes it perfect for a small group, creating a more intimate atmosphere than large, crowded charters.

Offshore Fishing: What to Expect

Once underway, the main focus for many will be the fishing. The waters around Key West are known for species like mahi-mahi, king mackerel, sailfish, and more. The knowledgeable crew, probably with names like “Sarah” or “Mike,” will guide you through the best techniques and help you set your line. The beauty here is in the breathtaking ocean views while you wait for a bite — a real highlight whether you’re an angler or just someone who enjoys being on the water.

We liked that the tackle and permits are all included, removing the need for extra planning or expenses. You just focus on the fun. A quote from reviews highlights this: “We loved the way they took care of everything, so all we had to do was enjoy ourselves.”

Island Exploring: An Optional but Delightful Add-on

If fishing isn’t your main goal, or if you want a break from the action, the trip can include visits to secluded islands, sandbars, or clear waters. You can “hop” between these spots, take a swim, or enjoy a picnic. This flexibility creates a balanced day, combining adventure with relaxation.

Imagine anchoring on a quiet island with turquoise waters, pulling out a picnic, and just soaking in the peaceful scenery — a simple yet memorable experience. One reviewer mentioned, “It was wonderful to fish for a while and then relax on a tiny island with nobody around.”

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The Trip Duration and Pacing

The 4-hour window is generally enough to experience both fishing and exploring, but the trip can be tailored to fit your preferences. Starting early allows you to beat the crowds and enjoy the calm of the ocean in the morning.

Remember to factor in the fuel surcharge of $150, which supports the boat’s operations and ensures a smooth, uninterrupted experience. While this adds to the cost, it is a common practice for private charters, especially when traveling beyond the immediate shoreline.

Authentic and Flexible Experience

While the reviews are currently silent on overall ratings, what we do know is that the private nature of the tour means you won’t be sharing your adventure with strangers, and the crew’s focus on customization makes it a personalized experience. It’s perfect for families, couples, or small groups looking for practical fun with a touch of luxury.

Why Choose This Tour?

The value lies in the personalized service and the ability to choose between fishing or island hopping (or both). This flexibility might make it more costly than a standard group fishing trip, but for those who enjoy quality over quantity and private experiences, it’s worth it.

The stunning views, combined with the chance to catch big fish and relax on quiet islands, create a well-rounded day for anyone wanting to see the best of what Key West’s waters have to offer. If you’re hoping to combine adventure with leisure, this tour hits the mark.

Who Is This Tour Best For?

This experience suits adventurous families, small groups of friends, or couples seeking a private, flexible day on the water. It’s ideal if you want a mix of fishing excitement and peaceful island scenery. If your priority is a personalized, hassle-free experience with all gear included, this tour offers good value.

It’s also a good choice for those who prefer early starts to make the most of the day, and for travelers who are comfortable with a fuel surcharge built into the cost.

Frequently Asked Questions

What does the tour include?
You get the use of all tackle, fishing permits, and bait. Everything needed for a successful fishing experience is provided, making it easy to just enjoy your time on the water.

Can I customize the trip?
Yes, the tour is flexible enough to include fishing, island exploring, or a mix of both, depending on your preferences.

When does the trip start?
The tour begins at 7:00am, giving you a full morning of activity. Early departures help avoid crowds and maximize your time.

Is gratuity included?
No, gratuity for the crew is not included, so consider tipping if you enjoy the service.

What about weather cancellations?
If the weather turns poor, the trip will be canceled, and you’ll be offered a full refund or a different date. Planning for good weather is advisable.

Is this suitable for beginners?
Yes, most travelers can participate, and the crew helps ensure everyone has a good experience, regardless of skill level.

Final Thoughts

Choosing a private Island & Fishing Charter in Key West like this one offers a personalized, flexible adventure that combines the thrill of big game fishing with the serenity of uninhabited islands. It’s perfect for those who want control over their day and value privacy and comfort.

While the cost might seem high at first glance, the inclusion of all gear, permits, and the customizable itinerary makes it a good deal for small groups seeking a special day on the water. The early start, combined with the boat’s well-equipped facilities, ensures a full, satisfying experience that can be tailored to your mood—whether you’re after action-packed fishing or a relaxing picnic on a quiet island.

If you’re searching for a balanced adventure that offers authentic scenery, good value, and personalized attention, this tour is likely to deliver. Just pack sunscreen, your sense of adventure, and maybe a cooler for your fish or snacks. This is one of those trips that can turn a regular vacation day into a highlight of your Key West trip.

Note: Always confirm details directly with the operator before booking, especially regarding weather policies and additional surcharges, to ensure your experience lives up to expectations.