If you’re considering a boat trip in Naples, Florida, you’re in luck. Perrydise Charters offers a private sailing experience that combines the beauty of the Gulf Coast with personalized service. With a perfect 5-star rating based on nine reviews, this tour appeals to those seeking an intimate, flexible, and authentic way to enjoy Naples’ natural and architectural splendors. Whether you’re after a relaxing sunset cruise or a fun-filled beach adventure, this experience might just become the highlight of your trip.
What makes this tour special? First, you get to skip the crowded, touristy boats packed with strangers. Instead, you’re on a private vessel with your own family and friends, allowing for a customized experience. Second, the opportunity to see dolphins, visit secluded beaches, and admire some of the most luxurious homes in Port Royal makes this a well-rounded, memorable outing.
One thing to consider is the price—at $425 for up to six people, it’s not the cheapest option for a day on the water, but the exclusivity, flexibility, and personalized service could easily justify the cost. This tour suits travelers who value privacy, personalized attention, and a chance to see Naples from the water in a relaxed, unhurried setting. If you’re looking for a special way to celebrate or just want to enjoy a peaceful day on the Gulf, this could be a perfect choice.
Key Points

- Private experience: Perfect for families or small groups wanting exclusivity.
- Flexible options: Sunset cruises or beach excursions tailored to your interests.
- Scenic sights: Gorgeous mansions, dolphins, and secluded beaches.
- Customizable trips: Possibility to add stops like Marco Island or waterfront dining.
- Value: All essentials like bottled water, sunscreen, and private transportation included.
- Advance booking: Typically booked 16 days ahead, so plan early.
What to Expect from Your Naples Boat Tour
This tour is designed around your preferences—whether you’re craving a romantic sunset, a playful dolphin watch, or a beach day on Keewaydin Island. For the sunset cruise, you’ll start by gliding past some of Naples’ most exclusive mansions in Port Royal. Imagine cruising past opulent waterfront estates, some of which are likely to be familiar from the glossy magazines. The first part of the 2.5-hour trip is all about soaking in the stunning views and enjoying the warm breeze.
As the sun begins to set, the sky transforms into a canvas painted with oranges, reds, and blues. You’ll be comfortably seated, sipping a cool tropical drink, feeling the gentle Gulf breeze on your skin. It’s a calm, scenic way to unwind and appreciate Naples’ natural beauty in a quiet, private setting. The reviews sing praises about this part, with one traveler calling it “hands down the best part of my trip to Naples.”
For those opting for the beach excursion, the journey starts in Naples’ backwaters—quiet, less developed, and bursting with natural charm. Your boat will take you to Keewaydin Island, a private, secluded spot accessible only by water. Expect to see dolphins swimming alongside the boat, and once on the island, you’re free to hunt for shells, take a swim, or just relax on the pristine sands. One reviewer exclaimed, “Walk the beach for shells. Sit and watch the dolphins play,” capturing the essence of this tranquil escape.
You can also read our reviews of more boat tours in Naples
The Itinerary – What You’ll Cover
Keewaydin Island:
This stop is the highlight for beach lovers. The boat journey itself offers picturesque views of Naples’ backwaters—calm, lush, and perfect for spotting wildlife. Once on Keewaydin, you’ll find soft sands and shells galore. If you love dolphins, you’ll be thrilled; multiple reviews mention dolphin sightings as a favorite part. You have the option to swim, walk, or simply soak up the sun while observing the natural beauty.
Port Royal:
For sunset cruisers, the trip begins with a tour of Naples’ most luxurious homes. The variety of mansion sizes and styles paints a picture of affluence and style along Florida’s west coast. The first hour is dedicated to sightseeing from the water, giving you ample chances to admire architectural grandeur. One reviewer mentioned how easy and fun Captain Perry was, responding quickly to weather changes and making adjustments for perfect timing.
Optional Extra Stops:
If you’re feeling adventurous, the tour can be customized—adding stops like Marco Island or a waterfront lunch. This flexibility makes the experience more than just a generic cruise; it becomes uniquely tailored to your interests.
Comfort and Convenience
The tour includes bottled water, a cooler filled with ice, and sunscreen, so you’re well prepared. The boat is private for your group of up to six people, which means no need to share your space or worry about strangers. Transportation to and from the meeting point at 1600 Danford St is included, simplifying logistics.
Travelers have noted that exiting the boat might require entering thigh-deep water or using a small step ladder, so it’s good to be prepared for some light water activity if you wish to get ashore. One reviewer highlighted how Captain Perry was accommodating, making sure everyone felt comfortable during the trip.
Duration and Booking
The sunset cruise lasts roughly 2.5 hours, making it a manageable outing for most travelers. The beach trip can extend up to 4 hours, allowing plenty of time to enjoy the water and scenery. Booking is usually done about 16 days in advance, so plan ahead, especially during peak season. The flexible cancellation policy—free up to 24 hours before—adds reassurance should your plans change.
Value for Money
At $425 per group, the price might seem steep at first glance, but it’s important to consider what you’re getting: a private, customizable experience that includes all the essentials. Considering the exclusivity, personalized service, and the chance to see dolphins, mansions, and secluded beaches from the comfort of your own boat, many travelers might find it a fair value. One review highlighted how responsive Captain Perry was, making sure their experience was “perfect,” which adds to the perceived value.
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Who Will Love This Tour?

If you’re seeking an intimate, flexible way to explore Naples’ waterways, this tour hits the mark. It’s ideal for small groups, families, or couples who want to avoid crowded boats and enjoy a tailored experience. Nature lovers will appreciate the dolphin sightings and scenic vistas. Those interested in architecture will enjoy cruising past opulent mansions. Plus, if you’re craving a sunset that paints the sky with vivid colors, this tour delivers.
Conversely, travelers on a tighter budget might find slightly cheaper boat tours, but they likely won’t match the private, personalized vibe. If you’re looking to combine luxury with authentic natural encounters, this experience is worth considering.
FAQ

Is this tour suitable for children?
Yes, most travelers can participate, but be aware that exiting the boat might require entering thigh-deep water or using a small step ladder if you don’t want to get wet.
How many people can join the tour?
Up to six people per group, ensuring plenty of space for everyone to relax comfortably.
What should I bring?
Aside from the provided bottled water and sunscreen, you might want to bring snacks, additional drinks, or a camera to capture the stunning scenery.
Can I customize my trip?
Absolutely. You can add stops like Marco Island or plan for lunch at a waterfront restaurant, making it a fully tailored experience.
How far in advance should I book?
Most bookings are made about 16 days ahead of time, especially during busy seasons.
What is included in the price?
The price covers private transportation, bottled water, a cooler with ice, and sunscreen. Alcoholic beverages or additional snacks are not included but can be brought along.
What happens if the weather is bad?
The tour requires good weather; if canceled due to poor conditions, you’ll be offered a reschedule or a full refund.
Final Thoughts

This private boat tour in Naples, Florida, offers a peaceful, personalized way to experience the area’s natural beauty and luxurious architecture. Whether you’re watching a breathtaking sunset or hunting for shells on a secluded island, you’ll enjoy the comfort of a private vessel and the flexibility to tailor your trip. The presence of dolphins, the chance to see famed waterfront mansions, and the quiet comfort of a small group make this a standout choice for those who appreciate quality over quantity.
If you’re after an elegant, low-key way to enjoy Naples from the water with friends or family, this tour deserves strong consideration. It balances value with intimacy, offering a memorable day that’s more about meaningful moments than ticking off tourist spots.
Final Recommendations

This experience is best suited for travelers who prioritize privacy and personalized service. If you love wildlife—especially dolphins—or have a fascination with luxury homes along the coast, you’ll find plenty to enjoy here. The flexibility to customize the itinerary makes it ideal for special occasions or just a relaxing escape.
While the price may seem high, the exclusive nature of the trip and the opportunity for authentic, unobstructed views make it a worthwhile investment for those wanting a more meaningful way to explore Naples. It’s perfect for small groups looking for a balance of adventure, relaxation, and luxury—all wrapped into one memorable boat trip.
More Boat Tours & Cruises in Naples
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