
Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach
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September 2026
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Who is going?
Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
4.9/5
Based on 278 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 278 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 (278)
- 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
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
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






What travelers are saying
Outty’s summary of the themes that recur across 277 traveler reviews. Written by us, not quoted from reviewers.
Photo opportunities
2 mentionsThe views and photo stops come up again and again.
Value for money
2 mentionsTravelers feel they got more than they paid for.
Food and drink
2 mentionsThe tastings and food stops are a highlight for most reviewers.
Traveler reviews
277 verified traveler reviews for Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach. Ratings and reviews provided by Viator and Tripadvisor.
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
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
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
Fantastic experience!!
This was an excellent first time experience on a sail boat combined with a sunset cruise. Tim was knowledgeable and friendly Captain, while Jack was a fantastic first mate! Absolute enjoyed the entire experience and highly recommend it to everyone!
via Viator
Relaxing sunset.
Captain Tim and Frist Mate Christopher were excellent: good communicators, friendly, competent and engaging. There was a relaxed vibe which was perfect for a sunset cruise.
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 $89
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 97
- Verdict
- Exceptional
Why this scores 84
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
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 278 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute 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 97 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.
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