Private Island & Fishing Charters in Key West 37ft Knotty Cowgirl

Jumping aboard the Knotty Cowgirl, a 37-foot sportfishing boat, offers a chance to combine some serious offshore fishing with tranquil island exploration right here in Key West. The trip, offered by Cowboy Cowgirl Sportfishing Charters, promises a semi-custom experience for up to six travelers that lasts around four hours, focusing on both catching fish and discovering hidden islands. Based on available details and reviews, this appears to be a solid outing especially for groups who crave a blend of adventure and relaxing downtime.

One thing to keep in mind is the price at $1,100 for up to six people, which might sound steep for some, but given the private, tailored nature of the trip, it offers significant value if you’re seeking quality over quantity. It’s worth considering that the trip isn’t just about fishing—although that’s a big part of it—also about personalizing your outdoor experience in the warm waters off Key West. For anyone expecting a structured, all-in, touristy experience, this might feel more like a flexible, intimate boat day suited to your tastes.

What I personally appreciate from the descriptions is how nicely the tour balances offshore fishing with opportunities to relax on secluded islands, sandbars, and crystal-clear waters. Plus, knowing that all tackle, bait, and fishing permits are included, with just a small fuel surcharge of $150, simplifies budgeting. The flexibility to adapt the 4-hour trip is especially appealing—whether you want to chase after mahi-mahi or just unwind in a gentle hammock on a sandbar, you can tailor the day to your mood.

However, a consideration is that this isn’t a packaged “set-it-and-forget-it” tour; it’s a more personalized experience, which, while rewarding, requires some level of flexibility or spontaneity about what you actually want to do that day. Also, marine weather conditions always have the potential to cancel or alter plans—nothing ruins a boat day faster than an unexpected storm.

• Private & Personalized: Only your group shares the boat, giving you a tailored experience.
• Dual Focus: Combining deep-sea fishing with island hopping offers both adrenaline and relaxation.
• All-Equipment Included: No need to bring your own tackle or worry about permits—they’re all provided.
• Customizable Trip Duration: 4 hours gives enough time for both fishing and island exploring, based on your group preferences.
• Breathtaking Views: Expect sweeping ocean vistas, promising memorable scenery throughout.
• Relaxing Escape: The chance to lounge on beaches or sandbars dotted with clear waters makes for lovely downtime.

When considering a private fishing and island tour in Key West, the Knotty Cowgirl presents itself as a well-rounded choice, especially for groups of friends or families of up to six. As a specialized vessel for both offshore fishing and coastal exploration, it provides comfort, access, and flexibility wrapped all in one.

Setting Out: A 4-Hour Customizable Window

The experience kicks off bright and early at 7:00 am from Cowboy Cowgirl Sportfishing’s base located at 1801 N Roosevelt Blvd. Setting off early in the morning makes sense here, mainly because calmer seas tend to make for smoother trips—and prime fishing. You’ll likely spend the initial hours diving into deep-sea pursuits such as mahi-mahi, king mackerel, or sailfish, expertly targeted by experienced captains and crew who know the waters intimately.

Fishing Focus: Catching Big Fish

Expect the crew to take care of all tackle, bait, and permits, removing much of the hassle from your trip. According to some reviews, “we loved the way our captain kept us engaged” and “we caught some impressive mahi-mahi”—signaling that this tour delivers on the fishing front. The guided expertise enhances the chance of a successful catch, making this a good choice for anglers or those just looking to try their luck at the big game species.

While fishing is a core component, it’s worth knowing that you can customize your experience, adjusting the trip to include more leisure or more fishing depending on your mood. The boat’s design makes it easy to switch gears, with plenty of room on deck and straightforward access to prime waters.

Island Hopping: A Tranquil Escape

Once you’ve had your fill of fishing—or perhaps took a while to reel in that one big one—you can pivot toward exploring secluded islands, sandbars, or crystal-clear waters. This part of the experience is not just a break but an intentional reward, giving you scenic vistas, a chance to stretch your legs, or even enjoy a picnic onshore. Since it’s optional, you get to decide whether you want a full day of activity or a more relaxed experience.

Few tours offer such a personalized island-hopping experience in conjunction with fishing, making it stand out for those who love diversity in their day out on the water. Reviewers have noted the sight of small islands and sandbars, perfect places to unwind and soak in the scenery.

Practicalities and Value

All essentials—tackle, permits, bait—are included in the $1,100 price (up to 6 people). Our perspective is that for a private, tailored adventure, this pricing gives good bang for your buck. The $150 fuel surcharge is an extra, but in the grand scheme, it’s a small fee for covering the variable costs of a private boat trip.

Timing and group size are important: the 4-hour window works well for those wanting a quick, intense outing without committing to longer days. Starting at 7:00 am maximizes daylight (Ideal in summer months), but adjusting timings can possibly be arranged by calling ahead.

Comfort and Convenience

On the boat itself, you’ll find fully equipped with all necessary tackle and bait, so no need to pack gear or worry about permits—everything is set up beforehand. The vessel, being a 37-foot Knotty Cowgirl, appears to be designed for comfort and safety, with enough space to move around and plenty of seating for your small group.

Accessibility-wise, the location is near public transportation, which is a plus for those staying elsewhere in Key West and needing easy access. The tour also supports service animals, making it accessible for guests with special needs.

While reviews are currently limited, what’s clear is that participants appreciated the flexibility and professionalism of the crew. One reviewer mentioned, “The crew kept us engaged and crowded free,” which speaks to their focus on delivering a personalized experience. Several said the scenery was breathtaking, particularly the views while fishing and on the islands.

The key highlight for many is the combination of active fishing with serene island sitting, offering a well-rounded outing. Some mentioned that catches like mahi-mahi made the day especially memorable, while others enjoyed the tranquil waters and quiet beaches for their relaxing aspect.

Summary of the Experience

This tour is best suited for groups who value privacy, flexibility, and a blend of adventure and chill moments. If catching fish is your main goal, the knowledgeable crew increases your likelihood. If simply soaking up coastal scenery and basking in warm sun sounds more appealing, the tour’s offered island stops will meet those expectations.

This private charter fits travelers seeking a customized, intimate outdoor experience in Key West. It’s ideal if you are a group of up to 6, eager for guided fishing and scenic island stops. No doubt, the professional crew’s expertise elevates the outing, making it suitable for seasoned anglers or curious beginners.

While it’s a pricier option, the personalized nature and inclusive gear support justify the cost, especially for families or friends celebrating a special occasion. The flexible day starts early, making it perfect for maximizing daylight hours.

If you’re looking for a private, flexible, and engaging water experience in Key West, the Knotty Cowgirl tour offers an excellent value. Its combination of fishing, island exploring, and personalized service makes it stand out from mass-market tours. The scenery is stunning, and the chance to reel in a sizable fish is compelling for anglers.

The option to relax on secluded islands paired with the thrill of offshore fishing could be a highlight of any trip to the Keys. The price reflects the exclusivity and customization of the experience but consider it an investment into a memorable, tailored day on the water.

Bottom line: this tour is best for small groups looking for a blend of adventure and relaxation, who appreciate personalized service, and want to make the most of their time on the water in Key West. For those wanting a straightforward fishing trip or a simple sightseeing cruise, other options might be more suitable, but for a balanced, elegant adventure, the Knotty Cowgirl delivers.

What is included in the cost of the tour?
All tackle, fishing permits, and bait are included. You won’t need to bring gear or worry about permits because they’re provided.

How many people can participate?
Up to six participants can join, making it a good option for small groups or family outings.

What time does the tour start?
The tour begins at 7:00 am, which is ideal for catching fish and enjoying ample daylight.

Is the tour customizable?
Yes, you can tailor the trip depending on whether you want more fishing or island exploration or a mix of both.

Are meals or drinks provided?
No, food and beverages are not included; you might want to bring your own snacks or plan to purchase onshore or bring a picnic.

What happens if the weather is poor?
The tour requires good weather. If canceled due to weather conditions, you’ll be offered an alternate date or a full refund.

This adventure is a chance to treat yourself to a personalized day of sportfishing and island lounging in Key West that can be as energetic or relaxing as you want. Whether caught up in the thrill of fishing, or simply marveling at the tranquil waters, it’s one experience that’s worth considering for your Keys trip.