Top Florida Cruises & Sailing

Went on St Augustine sunset boat tour with friends. Capt Evan, guide McKenzie and crew Kelly were awesome with handling the boat, interacting with the group. First let’s talk about the boat: new, clean and spacious. We were not crowded and had open space to walk around. Cash bar and fun music made for great trip. We took off from pier and immediately saw a pod of dolphins frolicking and fishing for their dinner. Guide McKenzie was very knowledgeable and shared details about dolphins, wildlife and best of all…St Augustine. The trip was a perfect 1.5-2 hr length to tour the harbor, pier and bridges. Timing was perfect to see a beautiful sunset. We got great pictures. The cost was affordable and I recommend this to anyone interested in waterfront touring. Thanks for a perfect sunset trip.

Still thinking about this private boat tour. From the moment we stepped on board, everything was smooth, relaxing, and unforgettable. Captain Leo was professional, welcoming, and made the whole experience feel personal instead of rushed. The views were absolutely beautiful, the vibe was peaceful, and every detail was handled with care. Whether you want a fun day out, a romantic moment, or just time to unwind on the water, this is 1000% worth it. One of the best experiences I’ve had in a long time — can’t wait to book again

Great views! Capt Anna and the crew were great! The musician was awesome and played great music. We really enjoyed the tour.The tour was fantastic! We had great views and the captain and crew were incredibly friendly. The musician was also awesome and played some great music. We thoroughly enjoyed the tour.

Enjoyed beautiful views of Clearwater & the amazing sunset. The captain was very informative & talked about the different landscapes we passed by. Also had the pleasure of watching dolphins swim right alongside of our boat. Be sure to sit on the top deck to enjoy the full skyline views!

We treated our adult ‘kids’ to a dinner cruise on the Calypso Queen on a gorgeous Wednesday evening. Every aspect was very pleasant ~ from being greeted on the gangway by the Captain, being served by Kim who treated us like family, the efficiency of the buffet, special acknowledgments of our son’s & daughter-in-law’s 2nd wedding anniversary, the music, friendly all-age group passengers, the amazing water and sunset views, and the phenomenal weather!!! Things we were concerned about like traffic delays due to active construction, limited parking, and long walks to and from the parking lot to the marina never materialized! Can’t ask for better than what we experienced!! Thank you for a wonderful evening!

The upper deck definitely has better views so get in line early. We were below and could only see the sites the guide was talking about on our side. For the money, this is a great excursion. Cash bar which we didn’t use so not sure the prices. I read other reviews that it’s cheaper to buy tickets in person not online and that seemed true. We saw the paper ticket of the couple in front of us and they paid $60. We paid $70 but our paper ticket said we paid $220. As far as being a sunset cruise, we didn’t pull out of port until the sun had set which was a bit disappointing. We definitely enjoyed the gorgeous Miami skyline all lit up. Overall we’d go again.

I had an incredible time and the staff was amazing. They were all super friendly, informational and even thru in some jokes. I really enjoyed myself and the prices was very reasonable for the experience! Highly recommend if you’re on a vacation alone or with your family! I’ve been spreading the word with folks at the hotel I’m staying at

The check-in was easy and the service was exceptional. We were surprised to find a gorgeous sailboat, not some plastic tourist vessel. It was equipped with standard, padded boat seating and beanbag style bags on the deck under the sails that, duh… we chose. Perfect for tanning and lounging with flexible BYOB policies. Upon check-in, your beverages are checked and iced where they are waiting for you wonderfully on board. The staff was incredible. Captain Tim was fun, entertaining and knowledgeable, while his first mate not only looked like a runway model from France, but had the professionalism and poise of someone who had worked on a yacht. We came on board as Tampa locals for a proposal. We had been on multiple dinner cruises, catamarans and others, and found this activity to be posh and relaxing. They graciously accommodated our quick proposal and we brought chilled Rosè and champagne flutes for the guests. The vessel sailed throughout the Clearwater channels and briefly out into the golf along the Clearwater Beach Shoreline. It was a perfect way to view not only the golf, including Clearwater Beach and Sand Key with the Treasure Island shoreline filled with dolphins and sometimes manatees, but to get firsthand views of multimillion dollar homes including of Tom Brady, Hulk, Hogan, Tom Cruise and others. Sunset sailings at an even more magical touch to this already luxurious sailboat cruise. We’d highly recommend this to any tourist or Florida local. The views from the boat are exceptional and the amount of time is just right.