Private Sailing Tour through the Ten Thousands Islands in Naples
Naples, United States

Private Sailing Tour through the Ten Thousands Islands

Outty Ranking 61 4.9 · 156 traveler reviews2 hoursFrom $400

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September 2026

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Adults

Age 13 and over

2

Children

Age 12 and under

0

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From, per person$400
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Outty Ranking

61/100

Solid Choice. Our proprietary evaluation. How we score

Traveler rating

4.9/5

Based on 156 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Private Sailing Tour through the Ten Thousands Islands worth booking?

Private Sailing Tour through the Ten Thousands Islands is a 2-hour experience in Naples, United States, from $400 per person. It scores 61 out of 100 on the Outty Ranking, which we label “Solid Choice, based on a 4.9/5 rating across 156 reviews. This booking is non-refundable, so pick your date carefully. Same-day spots are currently showing.

Outty Ranking
61 / 100
Rating
4.9/5 (156)
Duration
2 hours
From
$400 per person

If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos where built in the early 80s and are known through out the sailing community as the fastest, driest, beachable catamaran

What you get

    About this experience

    If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos where built in the early 80s and are known through out the sailing community as the fastest, driest, beachable catamaran on the market.

    What's included

    Included

    • Bottled water

    Where it starts and ends

    Meeting point

    Naples

    The captain will be waiting at the ship store. Please arrive 15 to 20 minutes before your departure time to find parking and utilize restrooms. Starting 01/01/2022 The county will be charging $10 for parking

    Hotel pickup

    No pickup: everyone meets at the start point.

    Ends at

    The captain will be waiting at the ship store. Please arrive 15 to 20 minutes before your departure time to find parking and utilize restrooms. Starting 01/01/2022 The county will be charging $10 for parking

    Options you can book

    • Private 2 hour sail

    • Private 1/2day Sail/Beach trip

      Duration: 4 hours

    • Private sunset sailing

    Before you book

    Cancellation
    All sales are final. No refund is available for cancellations.
    Languages
    en
    Ticket
    Mobile Only
    Runs on
    Every day
    Group size
    Up to 15 travelers per booking
    Operated by
    Easy Breezy Charters

    Know before you go

    • Service animals allowed
    • Public transportation options are available nearby
    • Infants are required to sit on an adult’s lap
    • Not recommended for travelers with spinal injuries
    • Not recommended for travelers with poor cardiovascular health
    • Travelers should have at least a moderate level of physical fitness

    Photos

    Private Sailing Tour through the Ten Thousands Islands in Naples, photo 2Private Sailing Tour through the Ten Thousands Islands in Naples, photo 3Private Sailing Tour through the Ten Thousands Islands in Naples, photo 4Private Sailing Tour through the Ten Thousands Islands in Naples, photo 5Private Sailing Tour through the Ten Thousands Islands in Naples, photo 6

    What travelers are saying

    Outty’s summary of the themes that recur across 156 traveler reviews. Written by us, not quoted from reviewers.

    Knowledge and storytelling

    3 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Good for families

    2 mentions

    Reviewers traveling with kids report it landed well with their group.

    Small groups

    2 mentions

    The group size is repeatedly described as intimate rather than packed.

    Traveler reviews

    156 verified traveler reviews for Private Sailing Tour through the Ten Thousands Islands. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    148
    4 star
    3
    3 star
    2
    2 star
    2
    1 star
    1
    Sort
    N1791LAkellyg · June 2026

    Ready for our next trip!

    Our entire family had an absolutely amazing experience with Easy Breezy Charters! From the moment we stepped aboard, we knew we were in for a special day. The boat was beautiful, incredibly comfortable, and perfect for our family. The wildlife sightings were incredible—we were thrilled to see dolphins up close, which was a highlight for both the kids and adults. Captain Nick was outstanding. His knowledge of the area, local wildlife, and waterways made the trip even more enjoyable, and he was friendly, professional, and great with our whole family. Everything about the experience exceeded our expectations. We had such a wonderful time that we’re already planning our next trip—and next time we’ll definitely book for a much longer excursion! If you’re considering a charter, Easy Breezy Charters is the way to go. Highly recommended!

    via Tripadvisor

    407deannb · May 2026

    See you next year Nick!

    The four of us had a wonderful sail with Captain Nick. He is well informed, interesting, and funny! He is a very easygoing and a nice person. Nick owns his boat, and his company, so you are guaranteed to get him as your captain. Which is a plus, as we wouldn't want anyone else. I was hoping to see turtles, and didn't, but we saw lots of dolphins, and it was their mating season. Hopefully next year I will see the turtles.

    via Tripadvisor

    megand624 · May 2026

    Perfect Catamaran Sailing

    We have gone out twice with EasyBreezy Charters. Both times were awesome! The captain is super easy going and the boat well equipped and comfy! It's always nice to explore on the water and this catamaran is a perfect way to do it!

    via Tripadvisor

    M5714WRjohns · April 2026

    What a great private sunset sailing experience!

    Captain Nick provided an awesome experience for my wife to celebrate her birthday with our family on a beautiful sunset sail. It was so nice to see the turtles and dolphins! We'll definitely do it again!

    via Tripadvisor

    Carolyn_R · February 2026

    Relaxing Sunset Catamaran Tour

    Bring your drinks and snacks and climb aboard the catamaran for a relaxing ride on the beautiful water off yve coast of Marco Island. If you are lucky, you will see dolphins swimming beside your boat. The sunset is breathtaking. A private boat tour that is more than worth the cost.

    via Viator

    Good to know

    Duration
    2 hours
    Free cancellation
    Non-refundable
    Minimum age to book
    All ages
    Availability
    Bookable today
    Runs on
    Every day
    Price range
    $400 to $875
    Hotel pickup
    No pickup, meet at start point
    Booked in 30 days
    55
    Verdict
    Solid Choice

    Why this scores 61

    The Outty Ranking is a weighted composite. Here is how this experience performed on each component.

    Traveler sentiment (30% weight)93
    Review evidence (18% weight)72
    Booking momentum (14% weight)67
    Value for money (12% weight)0
    Listing quality (10% weight)62
    Local standing (8% weight)53
    Booking flexibility (8% weight)0

    Private Sailing Tour through the Ten Thousands Islands: questions travelers ask

    Practical detail on this experience, plus the wider planning questions for Naples.

    How much does Private Sailing Tour through the Ten Thousands Islands cost?

    +

    Prices start at $400 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Naples usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.

    How long does Private Sailing Tour through the Ten Thousands Islands take?

    +

    Plan for about 2 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Naples is not rushed.

    Is Private Sailing Tour through the Ten Thousands Islands worth it?

    +

    It holds an Outty Ranking of 61 out of 100, which we label "Solid Choice". That score blends traveler sentiment (4.9/5 across 156 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable food & drink in Naples, and how flexible the cancellation terms are.

    Can I cancel or reschedule Private Sailing Tour through the Ten Thousands Islands?

    +

    No. This experience is sold on a non-refundable basis, so only book a date you are confident about. Similar experiences in the city do offer free cancellation if flexibility matters more than price.

    Is Private Sailing Tour through the Ten Thousands Islands suitable for kids and families?

    +

    Yes, all ages are welcome. Families should still weigh the 2-hour running time, and strollers are easier on the earlier, quieter departures.

    How far in advance should I book Private Sailing Tour through the Ten Thousands Islands?

    +

    Around 55 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Naples can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.

    What should I bring or wear?

    +

    Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Naples and add a light layer if any part of the 2-hour experience runs outdoors or after sunset.

    Where does Private Sailing Tour through the Ten Thousands Islands start and how do I get there?

    +

    The exact meeting point and directions are on your voucher once you book, and they sit in central Naples within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.

    What are the best things to do in Naples?

    +

    Naples is the launch point for Everglades airboat rides and Ten Thousand Islands boat tours, along with shelling trips, sunset sails off the pier and small-group food walks downtown. On Outty we rank every Naples experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Marco Island and Naples Pedal or Paddle Kayak Tour, Mangrove Tunnels & Mudflats Kayak Tour - Local Biologist Guides, Manatees and Mangrove Tunnels Small Group Kayak Tour. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.

    When is the best time to visit Naples?

    +

    November to April, the dry season with the best wildlife viewing. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.

    How many days do you need in Naples?

    +

    Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.

    Do I book through Outty or through the operator?

    +

    Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.

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