Logo for Perrywise Charters features a boat on the water at sunset with a flying bird in the sky, and text reading 'Perrywise Charters est. 2024'.

Perrydise Charters

Offering Private Sunset Cruises, Boat Charters and Beach Trips in Naples, Florida

Naples Florida Sunset Cruises

At Perrydise Charter we offer private sunset cruises, dolphin tours and custom boat charters in Naples, Fl. Cruise Naples Bay, Port Royal, Keewaydin Island and the Gulf of Mexico ( America) aboard a comfortable private boat with an experienced local captain. Perfect for couples, groups of friends and families looking for a relaxed, unforgettable sunset on the water

Our story is built on creating memorable days on the water and a commitment to our customers. We strive to ensure that your journey with us is as seamless and enjoyable as possible. Embrace the Gulf’s charm while we take care of the details, allowing you to create lasting memories without the hassle.

Whether you want a beautiful sunset trip or private beach to wonder down, let us get you out on the water for a relaxing day.

No Crowds. No Rush. Just your group, the water and a Naples sunset.

Sunset over the ocean with a colorful sky, sailboats in the water, and silhouetted palm trees on the shore.
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A man taking a selfie on a boat, smiling, wearing sunglasses and a black cap, with two outboard motors and the wake behind the boat on the open water under a partly cloudy sky.

Meet Captain Perry

I’ve been a Florida resident for over 50 years, with the last 36 here in Naples. For 25 years, I’ve worked daily on the waters from Naples Bay to the Ten Thousand Islands and have maintained my USCG Captain’s license throughout.

I’m passionate about the water and proud to share my local knowledge to create a private charter experience you won’t forget.

About

Our Services

  • A group of six people smiling and posing on a boat during sunset over the ocean.

    Sunset Cruises

    Cruise through Naples Bay and into the Gulf as the sun sets on a fully private charter. Calm waters, coastal views, and a peaceful evening await.
    Personalized, private, peaceful, and perfect for couples, families, and special occasions.

    $425/ approximately 2.5 hrs
    (up to 6 guests)

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  • Sea shells and coral on sandy beach with ocean in background

    Beach and Shelling Trips

    Explore the quiet beaches of Keewaydin island only accessible by boat. Great for shelling, swimming, beach walks, or lounging in the sand under the sun.

    $550/ approximately 4 hrs
    +$100 / additional hr
    (up to 6 guests)

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  • A dolphin leaping out of the water near a green, forested shoreline.

    Dolphin & Wildlife Tours

    Naples is well known for its dolphins-and we know where to usually find them. An occasional Manatee sighting is possible as well as Bald Eagles and Osprey.

    $550/ approximately 4 hrs
    +$100 / additional hr
    (up to 6 guests)

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  • A white Sea Pro boat floating on the water under a blue sky.

    Boat Operation Instruction and Boat Delivery Service

    Learn to run your boat with confidence through private, one-on-one instruction tailored to your vessel and experience level. From trailering to docking and navigation, these courses build real-world skills on the water.

    $100 / hr (2 hr Minimum)

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Client Reviews

  • I recently had the pleasure of booking with Captain Perry Mapes of Perrydise Charters of Naples and I must say, the experience was exceptional! From the moment I inquired about his services, his customer support team was prompt, friendly, and incredibly helpful. The booking process was seamless, and Captain Perry made sure all of our needs were taken care of. The charter itself was top-notch—immaculate, comfortable, and well-equipped with everything we needed for a smooth journey. Captain Perry was professional, attentive, and made sure we felt safe and well-cared for throughout the entire trip. The attention to detail and commitment to providing a first-class experience truly stood out. I highly recommend Perrydise Charters for anyone looking for a reliable, relaxed, and worry free charter service. Whether it’s for business or leisure, Captain Perry goes above and beyond to ensure a memorable experience. I can’t wait to book with Captain Perry again!

    —Scott G

  • Perry was wonderful! We booked a 3-hour boat ride with him and he allowed our dog to come with! Perry was very friendly and easy to communicate with. He brought us to a beach that was totally private so our dog could run around. Also, we cruised and checked out the waterfront mansions and saw some dolphins. Highly recommend! Thanks, Perry!

    —Heidi B.

  • This sunset tour with Perry was truly unforgettable. From collecting seashells on Keewaydin Island to admiring the beautiful homes of Port Royal and ending with a breathtaking sunset over the Gulf surrounded by dolphins and pelicans—it was simply magical. Captain Perry is kind, patient, and full of great stories. Thank you for an amazing three hours we’ll always remember.

    - Pe H.

Two dolphins jumping out of the water during a cloudy day.

 Have a question?
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Group of six people enjoying sunset on a boat during a tropical vacation, with water and palm trees in the background.

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Policies

*Once your deposit is received, your trip is confirmed and you will receive email or text confirmation.

*The Deposit is partially refundable . I will gladly do my best to rebook your trip. If you fail to show up or cancel within 12 hours of your trip, you will lose half of your deposit.

*If the weather turns for the worse last minute and we are unable to complete your charter, then obviously accommodations will be made. If you have a weather question, text me and we can discuss it. I will have the final decision and will always keep your safety in mind.

*Your trip begins at the agreed upon time in your email confirmation. If YOU are late, time will not be added onto the end of the trip as I have other commitments. However, if you are having a blast and want more time and I can accommodate it, we can add additional hours at a rate of $100/hr.

If you are running late and still want to go, please don’t hesitate to text or call me! I understand there are certain things out of your control and I will always do my best to make this as painless as possible. Communication is KEY.

  • **** I do not have a restroom onboard so please use one prior to your trip.****

  • **** A cooler with ice and water will be on board, bring anything you wish to snack on or drink****** Adult Beverages are allowed*** Charcuterie Boards are also available but must be ordered in advance and paid in advance***

  • Remember that it takes a lot of planning and preparation behind the scenes so please be courteous.

  • Balance of the trip, minus deposit is due day of. PREFERABLY PAY CASH DAY OF FOR REMAINING BALANCE

    *Deposit amounts vary at times due to type of trip booked and also if a holiday is booked*

  • If poor weather arises, your deposit is transferable to another trip in the future. As a local captain for 25 plus years, I am able to judge summer showers and weather forecast more accurately than out of town guests and most weathermen. lol
    Decision is made an hour or two before your trip as our weather forecast changes often.
    ​Please don't look at the weather a week before or even days. It changes daily and usually is predictable the day of trip.

  • The remaining balance minus your deposit is due at the end of your trip. ( CASH preferred ) I also have Zelle, Cash App and Venmo, just ask.

  • As stated, I will do my best to understand complications that arise but this is still my livelihood and cancellations or no shows will be charged the full deposit amount.

If you want to skip the tourist boats and enjoy a private sunset or special occasion cruise, give us a call or text and set up your next trip. Naples has some of the most ultra-luxurious homes in southwest Florida and beautiful sunsets. Bring a bottle of wine or your favorite beverage and sit back and relax while we explore the area by water.

Contact below!

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