Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach
Clearwater, United States

Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach

Outty Ranking 84 4.9 · 279 traveler reviews2 hoursFrom $80
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Outty Ranking

84/100

Exceptional. Our proprietary evaluation. How we score

Traveler rating

4.9/5

Based on 279 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach worth booking?

Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach is a 2-hour experience in Clearwater, United States, from $80 per person. It scores 84 out of 100 on the Outty Ranking, which we label “Exceptional”, based on a 4.9/5 rating across 279 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
84 / 100
Rating
4.9/5 (279)
Duration
2 hours
From
$80 per person

Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater will be a memorable visit!!! ;) *Children under age 5-not permitted to sail. *Not Suitable for Guests with mobility issues. *Participants must weigh less than 275 pounds - IMPORTANT- plan to arrive 45 minutes before departure time for mandatory check in to collect your boarding passes. -Our USCG credentialed Captain & Crew will welcome you on board like an old friend and treat you to a relaxed sailing excursion. -Expect a 5 Star "True Sailing Experience" on our 52' custom steel Schooner sailing vessel. -Our motto is "We SAIL and We SAIL Well"!

What you get

    About this experience

    Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater will be a memorable visit!!! ;) *Children under age 5-not permitted to sail. *Not Suitable for Guests with mobility issues. *Participants must weigh less than 275 pounds - IMPORTANT- plan to arrive 45 minutes before departure time for mandatory check in to collect your boarding passes. -Our USCG credentialed Captain & Crew will welcome you on board like an old friend and treat you to a relaxed sailing excursion. -Expect a 5 Star "True Sailing Experience" on our 52' custom steel Schooner sailing vessel. -Our motto is "We SAIL and We SAIL Well"!

    What's included

    Included

    • Complimentary Chilled Sparkling Water
    • "A True Sailing Experience"

    Not included

    • Alcoholic beverages
    • It is customary to tip the crew (20%). Our crew are USCG licensed professionals,

    What you'll see and do

    1. Clearwater Beach

      Once you book your tickets, check your email for instructions to ensure a carefree visit with us. Meet at Clearwater Beach Municipal Marina. Check in 45 minutes prior to your scheduled departure at our ticket booth to receive your boarding pass(s). We pre board all passengers for a safety talk and then throw the lines off exactly at departure time! As we motor out of the Marina our First Mate will work on raising our sails. We then navigate Clearwater Pass between the barrier islands of Sand Key and Clearwater Beach to head offshore :) Once outside of the Clearwater Pass the Captain will shut down the engine and we will be completely under sail power. It is a unique and beautiful perspective of Clearwater Beach offshore. You may even catch a glimpse of Bottlenose Dolphins feeding or at play in the wake of our Schooner!

      120 minutes here

    Where it starts and ends

    Meeting point

    Clearwater

    Our ticket booth and dock are located at Clearwater Beach Municipal Marina directly across the parking lot from "Crabby's" restaurant on the West end of the Marina complex. *Look for our ticket booth with the silver sailboat wind vane on the roof*

    Hotel pickup

    No pickup: everyone meets at the start point.

    Ends at

    Our ticket booth and dock are located at Clearwater Beach Municipal Marina directly across the parking lot from "Crabby's" restaurant on the West end of the Marina complex. *Look for our ticket booth with the silver sailboat wind vane on the roof*

    Before you book

    Cancellation
    For a full refund, cancel at least 24 hours before the scheduled departure time.
    Languages
    en
    Ticket
    Mobile Only
    Runs on
    Every day
    Group size
    Up to 4 travelers per booking
    Operated by
    Schooner Clearwater

    Know before you go

    • Public transportation options are available nearby
    • Not recommended for travelers with spinal injuries
    • Not recommended for pregnant travelers
    • Not recommended for travelers with poor cardiovascular health
    • Travelers should have at least a moderate level of physical fitness
    • Weight restrictions of 275 pounds per person will apply. Not recommended for passengers with mobility and or balance issues.
    • NO animals of any kind allowed on sailboat tour
    • Children under the age of 5 are NOT permitted to sail
    • Passengers must be physically able to navigate a long narrow dock and stairs to board the boat. Weight restrictions of 275 pounds per person will apply. Once on board you will need to be able to move about on uneven deck surfaces, climbing down a 2-foot-deep step into our seating area, and then a 2 foot step back up on to the deck. Loose fitting clothing and flat soft soled shoes are best, no heels or hard soled shoes please, you may go barefoot onboard.

    Photos

    Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach, photo 2Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach, photo 3Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach, photo 4Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach, photo 5Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach, photo 6Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach, photo 7

    What travelers are saying

    Outty’s summary of the themes that recur across 279 traveler reviews. Written by us, not quoted from reviewers.

    Food and drink

    2 mentions

    The tastings and food stops are a highlight for most reviewers.

    Traveler reviews

    279 verified traveler reviews for Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    271
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    Christina_K · September 2026

    Canceled Trip at 3:39 PM

    This was booked for our anniversary and they canceled due to impending weather when there was not a cloud in site. My guess is they did not have enough people registered so they canceled. We used a Lyft to drive us up from Madeira Beach and arrived at Clearwater around 3:30pm. Received the text message 9 minutes later. Paid a Lyft to take us back and we enjoyed a beautiful sunset from our condo. If you dont mind paying Lyft both ways the drive was beautiful just would not have waisted an important night and would have found someone more reliable. Of note, we did watch other boats out sailing and they could have kept us inland but that was not even am option. Then when you request a refund I got directed to a link that was broken and gave me a number to call which no one answered. It states that if you do nothing they will automatically refund your money in 5-7 days so I am choosing that route instead of wasting more time on the phone dealing with trying to get a refund sooner. So keep that in mind as well.

    Response from the operator: Hello Christine, My name is Tim Penna I am the owner of Schooner Clearwater and I was to be your Captain on your scheduled trip this past Tuesday. I fully understand the disappointment that comes with a cancellation, especially when the trip is for a celebration. Unfortunately, you have provided some inaccurate and ill-informed information on a public review. I will clarify for the benefit of those who read reviews to decide if they will sail with us. We are a small family owned and operated business that operates in nature and currently during the end of a very active weather time in Florida called the “rainy” season where strong storms are usually nearby later in the day and the deciding factor is whether they will strengthen/come our way, fall apart, or stay away. At Schooner Clearwater, when deciding whether a trip will or can proceed we consider 2 main factors: Can we do it safely and can we provide an enjoyable experience in line with what we promise and what you are paying for? When you come aboard our Schooner you do not need any knowledge at all of Sailing or boating/seamanship, nor do you need to even consider the local weather patterns and associate risks for a sailing vessel of this caliber – we do that for you and we always err on the side of safety. There is no benefit at all for our team to cancel a trip. When a trip is cancelled nobody here gets paid that day and the company loses money. When making an operational decision we pull from 30+ years of local knowledge operating vessels in the area and personally from my over 30 years of going to sea as a formerly educated Ship Captain all over the world. We use a multitude of the latest weather predicting tools and models. When possible we try to make the call in a timely manner out of respect for our guests’ time. This advanced notice is not always possible and it is a risk for us, as weather conditions and predictions change rapidly for the worse or for the better. On Tuesday, the decision was made to cancel the trip due to nearby dangerous weather including strong storms and dangerous lightning (which can strike over 6 miles from the producing storm) nearby and the consistent predictions that these storms would expand and be in our immediate area during our sailing time, as they had throughout multiple days prior and following Tuesday – during a very active multi-day weather pattern. The forecasts and warnings, accurate or not, are also seen by potential knowledgeable customers on their devices who usually opt for boating on another day, making it difficult to reach our minimum (break-even) booking requirement. The vast majority of the operators in the marina made the difficult decision to close that evening. You were notified, as were the other guests scheduled for that trip, by email initially at 3:15 that afternoon for a 6PM trip with a check in time of 5:15. We then followed up with text notifications and would further follow up with calls for those who did not respond to make sure they got the message. As we suggest, most of our guests take a flexible approach to sailing and take cancellations in stride, understanding that we do not control the weather or the forecasts. We operate in nature, and we are looking out for YOUR safety. There are many operators who will gladly and knowingly take you out in unpleasant and even dangerous conditions for your money, I see it often. We are not one of them. I would much rather spend my time responding to an ill-informed attack like this than apologizing for putting you in an unpleasant or even dangerous situation on your special day. Finally, you purchased your tickets through Viator/Trip Advisor, instead of directly through our website. Viator/Trip Advisor is a reputable third-party re-seller of our tickets. They receive and they hold your money when you book through them. The trip was cancelled through them following all of their appropriate protocols and timing requirements on our end and it is their responsibly to provide a timely refund to you per your agreement with them. Please reach out to their customer support for any issues with a refund. Thank You.

    via Viator

    lorettasH6631IL · August 2026

    Awesome evening!

    Highly recommend! Capt. Steve and first mate Chris were professional & friendly. Made sure everyone felt safe and comfortable. Schooner was spotless and in great shape. Lovely evening watching the sunset, listening to music and seeing dolphins. Definitely will book again!

    via Tripadvisor

    Jessica_M · August 2026

    Highly recommend!

    My husband and I had a wonderful time on the evening sunset cruise - Schooner Clearwater. Captain Steve and Christian were outstanding and made our sail even more enjoyable. They only allow a limited number of passengers which made it very intimate.

    via Viator

    279gladiem · August 2026

    Schooner Sunset Cruise!

    It was a beautiful experience sailing with Captain Tim and first mate Jack. Initially I spotted this classic schooner while on Sand Key Beach during sunset and I told my husband, we had to do this! The weather was perfect although a little choppy at the bay but all was calm once we sailed the gulf. We spotted dolphins along the way, enjoyed the majestic sunset, and relaxed the rest of the time. We appreciated that Jack chilled our Sangria and cheese. Also kudos to first mate Jack since we were his first official group that he would take on first mate responsibilities! He did a fantastic job! He was such a pleasant young man and Captain Tim was just so chill and funny. We highly recommend!

    via Tripadvisor

    irinamI4554QL · August 2026

    Sooner sailing cruise

    Excellent, if you haven't been on sailing yacht this is highly recommended. Had a fantastic time, Jack and the Captain were very entertaining. Will definitely be back.

    via Tripadvisor

    Good to know

    Duration
    2 hours
    Free cancellation
    Up to 24h before
    Minimum age to book
    All ages
    Availability
    Bookable today
    Runs on
    Every day
    Price range
    $80 to $85
    Hotel pickup
    No pickup, meet at start point
    Booked in 30 days
    98
    Verdict
    Exceptional

    Why this scores 84

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

    Traveler sentiment (30% weight)92
    Review evidence (18% weight)73
    Booking momentum (14% weight)69
    Value for money (12% weight)100
    Listing quality (10% weight)82
    Local standing (8% weight)62
    Booking flexibility (8% weight)100

    Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach: questions travelers ask

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

    How much does Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach cost?

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    Prices start at $80 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Clearwater usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.

    How long does Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach take?

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    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 Clearwater is not rushed.

    Is Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach worth it?

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    It holds an Outty Ranking of 84 out of 100, which we label "Exceptional". That score blends traveler sentiment (4.9/5 across 279 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable most popular in Clearwater, and how flexible the cancellation terms are.

    Can I cancel or reschedule Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach?

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    Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.

    Is Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach suitable for kids and families?

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    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 Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach?

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    Around 98 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 Clearwater 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?

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

    Where does Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach start and how do I get there?

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    The exact meeting point and directions are on your voucher once you book, and they sit in central Clearwater 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 Clearwater?

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    Clearwater Beach fills its calendar with dolphin cruises, pirate-themed family sails, parasailing, jet ski tours around Caladesi Island and sunset trips off Pier 60. On Outty we rank every Clearwater experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Little Toot Dolphin Adventure at Clearwater Beach, Clearwater Encounters with Dolphins Tour, Clearwater Beach Parasailing Experience. 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 Clearwater?

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    March to May and October to November for warm water without peak crowds. 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 Clearwater?

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    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?

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    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.

    What is included in Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach?

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    Included: Complimentary Chilled Sparkling Water; and "A True Sailing Experience". Not included: Alcoholic beverages; and It is customary to tip the crew (20%). Our crew are USCG licensed professionals,. Always check the voucher for the final list before you travel.

    Where is the meeting point for Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach?

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    Our ticket booth and dock are located at Clearwater Beach Municipal Marina directly across the parking lot from "Crabby's" restaurant on the West end of the Marina complex. Hotel pickup is not included, so plan your own transport and arrive 15 minutes early.

    What languages is Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach offered in?

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    It runs in English. Pick your language when choosing a date and time, as not every departure runs in every language.

    Will I get instant confirmation and a mobile ticket for Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach?

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    Confirmation is sent by the operator after booking, usually within 48 hours; if it is not confirmed you are not charged. Mobile tickets are accepted, so you can show the voucher on your phone.

    Is Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach wheelchair or stroller accessible?

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    The operator notes: Not recommended for pregnant travelers; and Weight restrictions of 275 pounds per person will apply. Not recommended for passengers wi. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.

    What happens to Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach if the weather is bad?

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    This experience depends on good weather. If it is canceled because of poor weather, you are offered a different date or a full refund.

    What do travelers say about Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach?

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    Across 279 reviews averaging 4.9 out of 5, recurring themes include food and drink. The tastings and food stops are a highlight for most reviewers.

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