Tours/Clearwater/Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach
Viator · group up to 20 pax

Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach

4.9(273)Clearwater1 hour
VIATOR4.9(97)TRIPADVISOR4.9(176)

Description

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"!

Tour Options

Schooner Clearwater Cruise

Itinerary

120 min

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!

Highlights

Complimentary Chilled Sparkling Water
"A True Sailing Experience"

What's included

Included
Complimentary Chilled Sparkling Water
"A True Sailing Experience"
Not included
If you are 21 or older you may bring a couple of canned beers or a bottle of wine. We provide disposable cups and a corkscrew upon checkin. No coolers please
It is customary to tip the crew (20%). Our crew are USCG licensed professionals,

Traveller Ratings

4.9
273 reviews
5
266
4
3
3
1
2
0
1
3

Important Information

  • 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.

Reviews(273)

I
irinamI4554QL
August 19, 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.

B
Brian_P
August 19, 2026
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!

U
U3000VOstevec
August 11, 2026
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.

F
Farin_S
July 29, 2026
Their last minute cancelation worked out well for us.

I would avoid this company. We booked a sailing trip and the operator canceled while we were in the Uber on the way to the dock! They claimed bad weather. Fortunately for us, the weather was great, like no bad weather at all, and we were able to hop on another sunset cruise after they abruptly canceled on us. The other cruise was much cheaper, had better communication and provided drinks and entertainment. It actually worked out very well. We feel we avoided a bad trip by their last minute cancelation. The sailboat looked dated and appeared to have very little room. I wouldn't try them again next time.

Operator response

Thank you for taking the time to write a review of our business. We are glad that you and your family went on to have an enjoyable evening on Clearwater Beach and we hope you enjoyed/are enjoying the rest of your vacation. We understand the disappointment that comes when a trip is cancelled but our decisions are not made lightly and are based on being able to provide a Safe and enjoyable experience for our guests in a very dynamic environment on a large Sailing Vessel – the only one of its kind in the area. Unfortunately, much of the information you provided is not accurate so I will take the time to clarify for the sake of customers reading reviews while considering sailing with us. Florida's weather changes rapidly, especially during this time of year (Summer Rainy Season). On this particular day there was unsettled weather and storms in the area most of the day. As we approached our sailing time there were rapidly forming and expanding storms including strong thunderstorms, Several Marine Warnings and Statements from the National Weather Service in the area during the day, and predictions of more of the same. More than half of the operators in the marina actually made the difficult decision to close their operations for the day. The decision was made to cancel (2 hours prior to the trip) our sunset trip based on this and a multitude of factors (including timely notification to passengers). Notifications were then sent out from our booking system. As per protocol Viator was also notified at the time of the cancellation which set in motion additional notifications and options to you, from Viator, based on your preferences at the time of booking. In short, you received numerous timely notifications from multiple sources, despite your initial assertion that you were not notified at all. The trip had several groups booked for that evening, all notified in the same way, and nobody else had an issue. Most rebooked for another time and have since sailed and had a great time. We take absolutely no joy or benefit in cancelling a trip – our small family owned and operated company loses money and the crew does not get paid. Despite this we will always err on the side of Safety and quality of the customer experience to make our decisions. As the owner and the Captain for that day, I would much rather spend my time replying to an attack like this than apologizing for putting you and your family in harm’s way unnecessarily, or worse. Finally, you attack our business, encouraging others not to come, promoting another business, and even attack the boat itself - A modern, custom built 52 foot Steel USCG certified Sailing Vessel– again, a small family owned and operated business who was looking out for the safety of Your family, including a child, having to make difficult business decisions based on a multitude of operational factors for a vessel of this type that you don’t understand or even begin to consider. Absolutely shameful. -Tim Penna Captain/Owner Schooner Clearwater

J
J2121UWsteved
July 29, 2026
Best excursion for Clearwater Beach sunsets!

This sailing cruise was excellent and so worth the cost. The captain and his crew were very talented and provided a safe and enjoyable experience. The sunsets in this area are spectacular and to experience one from a beautiful schooner was special. I highly recommend this. I’ve also included some pics of the schooner from our resort to give perspective. Nice Job!

A
Andy_M
July 27, 2026
Relaxing

They should be ready to be totally taken care of with drinks and relaxation. Awesome crew, Steve is an expert in sailing, more people should get to know him!

P
Pamela_P
July 25, 2026
Best Sunset Cruise on Clearwater Beach

This is a beautiful schooner and not overly packed with guests. Only about 15 I believe, making it very comfortable and a great way to get on the water for a sunset cruise and a view of the shores of Clearwater Beach. Capt. Steve and first mate Christian are top notch! Great sailors! I am a local and I 100% recommend! Great evening! Well worth every penny.

J
Jill_S
July 16, 2026
We had an amazing time on...

We had an amazing time on this sunset cruise! The crew was friendly, the views were absolutely beautiful, and watching the sun set over the water was unforgettable. It was the perfect mix of relaxation and fun, making for a memorable evening. Highly recommend this cruise to anyone looking for a great experience on the water! We had an amazing time on this sunset cruise! The crew was friendly, the views were absolutely beautiful, and watching the sun set over the water was unforgettable. It was the perfect mix of relaxation and fun, making for a memorable evening. Highly recommend this cruise to anyone looking for a great experience on the water!

V
Voyage36618989938
July 15, 2026
Great experience

The trip was professional, great ship, nice people. The caption and first mate were great and very helpful. It is highly recommended for a great boat ride in Clearwater!!!!!!

K
K8542BTerikad
July 13, 2026
Amazing Experience and customer service!

This was such a nice experience! We got lucky and got great weather! We had captain Steve and First Mate Christian, who were amazing!! Definitely recommend.

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