Had a sunset cruise last night. What an amazing experience. The captain and crew were friendly,…read moreprofessional and just when you thought they couldn't be any better at sailing, they started making drinks and appetizers! Can't wait to do it again !

We have sailed the sunset cruise 3 years in a row. Top notch…read moreboat and crew. Great night

My husband booked us on this sunset cruise. We wanted a lower keyed experience and it was perfect…read more This tall ship does not serve alcohol or food only water and snacks. The positive side is you get to bring your own alcohol and food if you want. We chose to eat dinner at the Conch Republic seafood house before we boarded. And of course I brought my wine on board. We boarded at 6:15 pm and were greeted by a crew of three. Captain and two mates. They were all awesome full of knowledge answering all our questions while tending to the boat. They are known for their cannon which is fired at other ships veering too close lol. We had a quiet group of 18 souls on board but it was my first time on an actual sail boat so I totally enjoyed it. I highly recommend this as your option if want to avoid the huge boats.

What a fantastic sailing cruise and sunset!!! The Jolly Roger captain and staff made the sailing…read moreinteractive with ALL guests with cheerful conversations, letting guests help lift the sails, sitting at the helm, and handing out snacks and water!! The cruise was a gentle and smooth sail of the area ending with a great sunset!!!! Highly recommend for an enjoyable couple or family group.

We had so much fun! Brian was respectful and helped us enjoy the excursion fully. We cant wait to…read morereturn!

This is my second adventure with Cruisin Tikis Key West which rents dock space from Macs…read morerestaurant. Very laid back reservation system directly with the owner Johna. Arrived thirty minutes early to blow up our rafts and register online with an ipod. Brought our snacks and liquor onto the tiki boat with our charismatic captain, Kathy who provided mixers and a quick safety drill. We were off right on time and headed out to the sandbar in the Gulf of Mexico. Light drizzle for the first ten minutes then pure sun for the entire two hours. Loved every minute and would do it again and again. Price is $430 for two hours with a max of six people.

If you are lucky enough to catch the Top Sail Schooner Wolf in town, do whatever you can get on…read moreboard! We got extremely lucky to go out on a familiarization sunset sail the day they got back into town from Jamaica, and we'll never forget it! While the other crazy tourists in Key West were doing the sunset booze cruises on the big noisy yachts, we had an awesome sail right in front of Mallory Square. Its amazing being on a pirate ship, sitting back and cracking open a cold can of ale while an entire dock of people ooh and awe and take pictures. Then for the best part; our captain fired the black powder 'canon' (that thing is small but LOUD!) and just about scared the pants off of everyone. Awesome. The crew was young but very experienced. They had a good time, but were dead serious and masterful when it came to operating and sailing their ship. This was an experience we will never forget. The only regret? No green flash. I guess we'll just have to go out again next time we meet up with the Wolf!

When you're asking your guests to travel over 1000 miles to attend your destination wedding, you…read morewant them to have the best time possible. Getting married on the water is great, but if you really want to set your celebration apart charter the Schooner Wolf! Planning our sail was easy, even from a distance. Julie made sure everything was in order and always responded to my emails promptly. I must have asked a million silly questions, but she patiently answered every one of them and went out of her way to offer assistance in a variety of ways, like offering hotel and restaurant recommendations and procuring a cd player so we could play music on board. Since we'd already planned a wedding on the beach before we found out about the Wolf, we declined the chance to get married by Admiral Finbar and chose to use the ship as a sort of cocktail hour. It's BYOB, and we were able to drop off alcohol and plastic champagne flutes the day before so we didn't have to worry about remembering it the day of. I was a bit worried about getting sea sick, especially after I ended up over the side of a boat during a snorkeling trip two days prior! I would have felt terrible if any of our guests would have gotten sick, but we made sure the Bonine, ginger gum, and Dramamine were flowing as freely as the champagne, and didn't have any problems. Everyone had a great time, including my 3 year old nephew. He was the only kid at our wedding and I was afraid he would get restless, but Murphy kept him entertained when she brought him below deck so he could seek out the hidden treasure chest. He went into shy mode, but with a little prodding from his dad and me he found and opened the chest. The look on his face was priceless, and proudly displayed the pieces of "treasure" she let him take for the rest of the trip! The whole experience was wonderful. The crew was really personable and so much fun- they definitely provided a flair to the evening that you wouldn't get most other places! Toasting our new marriage on the open sea was lovely, and sailing right out toward the beautiful Key West sunset was unforgettable.

If you're going to do ANYTHING on your bucket list in Key West other than tattoos, piercings or…read morefishnets (that was a joke, honest), find a Barefoot Billy's outlet at one of the resorts on the island and have fun! We went to the Reach Resort and did the Jet Ski Tour and it was great! Our tour guides were Dakota and Mateus (I'm sure I spelled that incorrectly). They did a super job and REALLY knew their way around the Keys! Ask for them by name and enjoy the tour! Oh, and tip big! They will have earned it!

Ok, first things first (full transparency) both my wife and I had/have no business being on jet…read moreskis. The phrase 'monkey humping a football' is not wildly inappropriate. That said, the crew at Barefoot Billy's were patient and knowledgeable, and helped us through the ~2 hour jet ski tour, without causing massive inconvenience to the other guests (we think - we were too embarrassed to take a vote). Was there profanity? Yes Are the jet skis kept in good order? Yes? Do we recommend? Yes, but with a caveat, that being if your party includes someone 30ish years younger than you (ie 8-12 years old) and they seem better equipped to handle a jet ski solo then your 40ish year old ass does, then like...opt in for the Old Folks Jet Ski and Sundowning Tour, coming soon. Great people, highly recommend. Tip them accordingly.

Nice find! You want to take a boat trip for two this is an awesome experience. We traveled for 30…read moreminutes or so through mangroves and then open sea to an isolated area where you can adventure for 45 minutes on an private Island. We found this spot where they have a swing and man made hammocks that you can climb on. Also private sandbar. Sunset Watersports have it all but this trip was great! They are professional and friendly. Thank you guys!

We had a good time. Came in May 2025…read more We did the 6 hour cruise with Watersports. Snorkeling Banana boat Paddleboard Kayak Parasailing Jet ski Water Slide The lunch they gave us was pretty good. Hot dogs Chicken nuggets Fruit Veggie tray We got a military discount Cost was $135. So a great deal. The staff on the boat were super friendly and well organized. We had about a hundred and five people on the boat that day. Some people were late to the boat and we were thirty minutes late sailing. The weather was beautiful that day. I would do this again. Cons: They tell you you will get free beer and drinks with your ticket. What they don't tell you is... As soon as you have a alcohol beverage, you can no longer get in the water. The captain said we could not even put our toe in the water. Haha. So basically You will probably only get one or two beers With this ticket. The alcohol drinks are extra the cost is $4 each. They also ask for extra tip money when you get off the boat. That tip is optional.

We absolutely loved our experience with Sun Surf and Sand Charters! The great experience started…read morebefore we even arrived. I spoke with Captain Shane prior to booking, and he answered all of my questions--even some I didn't know I should be asking. He was incredibly personable and made us feel comfortable about our choice from the beginning. The trip itself was smooth and relaxing. We visited three stunning, very private locations and were able to simply enjoy being there without feeling rushed. One thing we especially appreciated was Captain Shane taking so many pictures of us throughout the trip. It allowed us to put our phones down, be present in the moment, and enjoy the experience. He captured some wonderful memories for us. We also asked for recommendations while we were out, and Captain Shane shared suggestions for restaurants and nightlife all the way from Key Largo to Key West, which was incredibly helpful. Looking back on our vacation, this experience was truly the highlight of our time in the Keys. Thank you, Captain Shane, for giving us such a memorable day on the water and for making the entire experience so enjoyable from beginning to end!

Shane and scruffy were awesome. We had a bunch o ladies and we went to a few sandbars. He served…read moreus our drinks while we floated, played the music for us, provided floaties and snorkel gear. A fantastic ladies boat day! We had ten people and two boats. Best part of our trip. Bring your drinks and snacks!!

We are soooo happy we booked a sunset Sail with Hindu! Oh my gosh...the ALL FEMALE CREW was…read moreamazing. My husband volunteered to help raise some sails.....he could not believe how strong they were! Very attentive crew...just a beautiful night. Sparkling Cava and appetizers. No screaming music (although some days I would be up for that) just a peaceful, gorgeous sail. My favorite thing we did all week. Thank you! Susie & TJ

This was the most amazing experience!! my wife and I had a wonderful time onboard the Argo Navis!…read moreThe captain and crew were sensational hosts, and we thoroughly enjoyed the drinks, the hors d'oeuvres, and the spectacular view of the sunset that we were fortunate to experience.