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.

Captain Brandon was awesome! He made our sandbar trip so much fun. He was friendly,…read moreknowledgeable, and very accommodating. This was our favorite day of our Key West trip. Highly recommend booking here! We'll definitely be back!

What an amazing experience! I recommend this to anyone who is planning on coming to key west. Boat…read moreride was awesome, our captain Dante, super cool guy. This was our first time doing a sandbar trip and we plan on making another reservation before we leave next week. Absolutely epic! You won't regret this!!

We had a good time. We did the sail, snorkel, and kayak adventure. It was a fun trip and the crew…read morewas very nice. The food wasn't bad either and cocktails were included.

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.

Absolute highlight of our trip! The captain and crew were amazing and the whole excursion was…read morewonderful! Our excursion included rum swizzles and chocolate chip cookies, which was just a bonus to the snorkeling we got to do! The entire experience was something we'll never forget and will definitely do again the next time we visit Bermuda!

My friends and I went Key West for a bachelorette party. We decided to spend a whole day out in the…read moresea with Restless Native. Unfortunately the chef was not able to work that day, our captain, Brad, was also the chef! Brad was a trooper for handling six crazy girls. He took us out to the dolphin playground and to the reefs where the girls could choose to snorkel. We ended the day with a beautiful sunset where he took us right in front of Mallory Square.

Party of two. Called to book a four hour dive trip and indicated we were interested in lobster…read more Captain Rick said we would have to book a six hour for lobster. We were taken to the reef, given a ten minute oral lesson on mask and snorkel and left on our own while captain and mate dive on their own for lobster. We were left on our own in the water for 90 minutes. No one checked in us or gave us any dive assistance. No one offered us any assistance in identifying, finding, poking or netting lobster. Hmm. $900 private charter to catch lobster yet no help. Did we just hire a Captain-and no services? Came in for lunch - a basic meat and tomato sandwich with a handful of chips. Captain and mate got eight lobster was they swam off while leaving us all on our own. We Went back in for a second dive and we located two lobster which the first mate bagged for us. At the end of charter we asked about taking home the lobster and the captain stated that he kept what he caught. We were not offered lobster gear or offered any instruction I felt that since we paid $900.00 for a charter for only two people (same price as six) and paid for their time and gas and expenses, the catch should go with us. He said no way. I've never taken any fishing charter before that did not send the customers home with the catch- cleaned and bagged. What a disappointment. $900 doesn't get you much on this one - keep on looking.

Chartering boats can always be a little bit of a scary experience if you've never met the crew. We…read morewere pleasantly surprised in every way possible with the Tortuga Sailing staff. A few friends and I chartered the boat last weekend for a day trip and we had a great 8+ hour adventure visiting the reef, watching the boat races, and seeing Key West from the water. Even though the weather was a bit off they made every effort to make sure we had a great time and we did have a blast.

Amazing Captain, boat, and conversation. We were well taken care of. 11/10. We've found our new…read morego-to!

We booked Captain Anthony and his 1st mate Mystic for a 1/2 day sandbar excursion. What a blast!…read more Will definitely do it again next trip. He was very accommodating and friendly. This was the best part of our trip!

So knowledgeable I highly recommend you're definitely gonna have a great time! Best keys, boat tour…read moreever!

Brian was amazing! We had a little trouble getting in the gate to the RV park but thankfully we…read morecalled him. We rented a two person kayak & set out on our adventure. The kayak was more comfortable than we expected & we stayed out for four hours. I have attached a photo of our route with some pictures. They loaned us a waterproof phone case which was essential. We had a pretty significant downpour which added excitement. This was definitely a highlight of our trip to the Keys. The price is right and Brian & his assistant really set us up well. Remember to call if they turn you away at the gate. I would also call a day ahead to let them know when you are coming.