Venturing into the waters around Cudjoe Key, you’ll find yourself immersed in some of the most captivating sights the Florida Keys have to offer. For $525 per group (up to 8 people), you can rent a 23-foot Tritoon boat equipped with a Yamaha 150 motor and a 9″ GPS screen, available for anything from one day up to a month. The company offers free delivery to locations between Sugarloaf Key and Summerland, making your aquatic adventure seamless from the start. Whether you’re a seasoned boater or have some experience, this rental promises a flexible, fun, and scenic escape on the water.
What we really appreciate about this service is the customized GPS tracks leading to local hotspots—like Picnic Island and Tarpon Belly Island—ensuring you get the most out of your time on the water without constantly worrying about navigation. Plus, the personalized delivery means you can start your day right at your accommodation or favorite spot, rather than fighting for parking or navigating busy marinas. The well-maintained boats and reliable service are also consistently praised by visitors.
A potential consideration is the boating experience requirement—you must have prior boating skills and a safety card or be born before January 1, 1988. If you’re new to boating, this might be a barrier; however, for those with experience, it ensures safety and smooth sailing.
This experience suits travelers who love exploring at their own pace, enjoy adventurous water outings, and value personalized service. Whether you’re keen on fishing, visiting local bars like Kiki’s Sand Bar Grill, or just relaxing on the water, this rental offers an authentic and well-supported way to enjoy the Florida Keys.
Key Points

- Flexible Duration & Cost Savings: Rent from 1 to 30 days, with discounts for longer rentals.
- GPS-Guided Routes: Pre-planned tracks lead you to popular spots and hidden gems.
- Delivery & Convenience: Boats are delivered to your preferred location, saving time and hassle.
- Experienced Boater Required: Must have prior boating experience and safety credentials.
- Well-Maintained Fleet: The boats are praised for their cleanliness and reliability.
- Customer Satisfaction: All reviews highlight excellent service and trustworthy operation.
A Close Look at Cudjoe Key Boat Rentals

When considering a boat rental in the Florida Keys, the experience should blend scenic beauty, ease of use, and safety. This particular service excels in providing all three, especially if you’ve got some boating skills under your belt. The 23′ Tritoon is a spacious, stable choice perfect for families or small groups. Its Yamaha 150 motor ensures enough power to explore local hotspots comfortably, whether you’re cruising to picnic islands or stopping for a swim.
What makes this rental stand out are the GPS tracks, which are designed to lead you directly to engaging spots without the need for complicated navigation. These routes take you to places like Picnic Island, where boaters relax just within sight of celebrity-studded islands, and Tarpon Belly Island, an intriguing shell of an old shrimping island from the 1970s. The GPS system, paired with a detailed written guide, minimizes the need for guesswork, so you can focus on enjoying your surroundings.
The delivery option offers a significant advantage, especially for visitors unfamiliar with the area or those preferring to start their day stress-free. The company offers free delivery in a broad area, making it convenient to begin your adventure without extra logistical hassle. As one reviewer noted, “We drive all the way from Tampa, FL, and the boats are always in immaculate condition,” highlighting their commitment to quality and reliability.
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What to Expect on Your Day
Starting at 9:00 am, you’ll pick up your boat or have it delivered to your location. Once on the water, you can follow the GPS trails to various local attractions or simply explore your own route. The trails lead to lively hangouts like Kiki’s Sand Bar and Tonio’s Tiki, where you can anchor and enjoy a meal or drinks. The designated areas like Geiger Key Tiki are perfect for a relaxed, laid-back experience if the weather cooperates.
The boat itself offers plenty of space for up to eight people, making it ideal for families or groups of friends. The reviews emphasize its cleanliness and power, with one user describing it as “well powered, with plenty of room for gear and passengers.” The GPS system’s reliability is another highlight, ensuring you reach your destinations safely and easily.
The Experience of Safety and Responsibility
One point to note is the boating experience requirement. The company insists that renters possess a boating safety card or be born before January 1, 1988, which helps ensure everyone onboard is capable of handling the vessel responsibly. This policy, coupled with the company’s emphasis on safety and ecosystem protection—boats are not permitted beyond the barrier reef—helps maintain the area’s delicate environment.
Authenticity and Local Flavor
Many reviewers mention how trustworthy and reliable the service feels, with Tommy receiving special praise for his quick and helpful communication. The boats’ maintenance and cleanliness are clear priorities, ensuring a smooth trip without mechanical worries. This emphasis on quality provides peace of mind, especially for those new to boat rentals, making it a value-driven choice in a competitive market.
Who Would Love This Experience?

This boat rental service is perfect for experienced boaters who want to explore the Florida Keys on their own terms. It’s especially suitable for those who appreciate guided GPS routes and want the convenience of delivered vessels. Families or groups of friends will find the spacious Tritoon comfortable and accommodating. If you’re interested in visiting popular spots like Picnic Island or Geiger Key, or simply enjoying a day of fishing or relaxing, this rental offers a practical and enjoyable way to do it.
However, if you’re a first-time boater or don’t have a boating safety card, you might want to consider other options or ensure you obtain the required credentials beforehand.
Final Considerations
This boat rental service in Cudjoe Key combines reliability, convenience, and local expertise to deliver a memorable Florida Keys experience. The GPS-guided routes are a standout feature, helping you discover the best spots without the hassle of navigation. The well-maintained boats and excellent customer reviews indicate that you’re likely to enjoy a smooth, safe, and fun day on the water.
The flexible rental periods and delivery options make it a versatile choice for both short getaways and longer explorations. While the boating experience requirement might limit some, for seasoned boaters, this offers a great balance of freedom and guidance—your chance to create personalized adventures in one of America’s most beautiful coastal regions.
Whether you’re after a fishing trip, a scenic cruise, or just a relaxing day at a sandbar, this service offers authentic, hassle-free access to the stunning waters of the Florida Keys.
FAQ

Do I need a boating license or safety card to rent the boat?
Yes, you must have a boating safety card or be born before January 1, 1988, to rent the boat. This ensures you have the necessary skills to operate it safely.
Can I rent the boat for a single day?
Absolutely. Rentals are available from one day up to 30 days, with discounts for longer periods.
Is fuel included in the rental price?
No, fuel is not included. You’ll need to budget additional for fuel, depending on how much you plan to use the boat.
What areas are off-limits for boating?
Boats are not permitted to go past the barrier reef, which helps protect the delicate ecosystem and keeps navigation safe.
How is the boat delivered?
The company offers free delivery to locations between Sugarloaf Key and Summerland, making it very convenient to start your day.
What kind of GPS system is used?
A 9″ GPS with pre-set tracks guides you to local hotspots, helping you find interesting spots without the stress of navigation.
Can I bring small children or pets?
Yes, most travelers, including families with children and service animals, can participate. Always check with the provider if you have specific concerns.
What if the weather turns bad?
Since this experience relies on good weather, cancellations due to poor conditions are fully refundable or can be rescheduled.
In sum, if you’re seeking a reliable, guided, and flexible way to explore the waters of Cudjoe Key, this boat rental service delivers on all fronts—especially if you value personalized routes, quality gear, and excellent service.
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- Private Historic Harbor Cruise
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- Half Day Luxury Boat Tour in Key West with Snorkeling
- Day Sailing Adventure in the Florida Marine Sanctuary
- Key West Sunset Sail with Live Music, Drinks and Appetizers
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More Key West experiences we've covered
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- Half Day Luxury Boat Tour in Key West with Snorkeling
- Day Sailing Adventure in the Florida Marine Sanctuary
- Key West Sunset Sail with Live Music, Drinks and Appetizers
- Key West: Private Fishing Charter with Experienced Captain
- Private Key West National Wildlife Refuge Eco Trip
- Exploring and Walking Food Tour of Cayo Hueso
- 8 Hours Pontoon Rental in Key West
- Key West Stand Up Paddleboard Rental
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