Luxury Boat Charters Key West – Experience Still Dreamin’

Captain TJ was the best! Went on a bachelorette trip to Key West and the private charter with TJ was definitely the highlight of our trip! Being a group of just girls TJ made us feel safe, he engaged with everyone, and was the best captain! Boat was very clean, we got to play our music, and we had the best time! Would recommend this charter to anyone thinking of doing one in Key West.

Fun experience So much fun. Captain Jude and first mate Jordan were great. The kayaking was fun. Happy to get to try my hand at paddle boarding. Just a fun experience.

Amazing experience We had one of the best time ever out on the water with captain Zack. We highly recommend him of anybody going to the keys. No stress and just feel like time just stand still and nothing else matters, beside just relaxing.

Best experience ever. Already booked for next visit. This was an absolutely amazing experience.Zak took his time explaining a lot about Key West and some of its history. We learned a lot and are so excited to come back again. He went out of his way to point out some cool things like snails, sharks, birds, etc. We appreciated that it was laid back and fun. Our favorite parts were spending time at the sandbar (a must see) and floating in the ocean. We ended our night with a beautiful sunset and my 7 year old was so excited to hang out by the captain. We already rebooked for our trips in March and June.

Simply amazing! Was an amazing time! Captain Zak took us to several keys and sandbars with amazing beaches! We ended up at one of the furthest, most remote beaches in the keys. Sun was shining with crystal blue water and sugar like sand! We were so amazed and impressed! We also had a chance to snorkel. Captain Zak knows the area so well and explains the history and important landmarks in the Florida Keys. His attention to detail and stories from the charters as well as his own personal experiences on sailing for years were unmatched! I’d never recommend anyone else for a private charter in Key West! We are already going back tomorrow and are planning trips with Captain Zak in the future. It was well worth the investment! I’d rather invest in Captain Zak and Casual Monday Charters versus buying my own boat. It was one of the best times we’ve had in our lives!!

Great Charter Casual Mondays is the must do charter. Zack made our trip! Friendly, fun, fantastic time. I don’t like crowds so he made sure we were able to experience the keys without a lot of other boats around. We snorkeled, chilled in the water, and were able to see a beautiful sunset. Thank you so much Casual Mondays.

Great Key West Charter Group Captain Zak was an amazing guide out on the water. He was flexible with scheduling and helpful with questions prior to meeting at the dock. We just wanted to get out on the water and explore so he took us to some sand bars where we were able to get in water and chill for a bit. I highly recommend this charter company when in Key West.

A Diamond in the Ruff a truly amazing Experience. Memories for a Lifetime Having recently experienced a private boat charter, I find it difficult to consider returning to a company-operated service. The captain Zack was exceptionally punctual, even arriving ahead of schedule at no additional cost. As a local resident, he possessed extensive knowledge of the island's hidden history, insights that are often overlooked by larger companies.He reached out to me early in the morning to confirm our meeting location and informed me that we could bring a bottle of wine or cans of beer, with the caveat of avoiding glass containers due to safety concerns. He also provided ample water as part of the rental fee and offered the option to snorkel. However, given that it was March and the water temperature was quite cold, we opted not to partake in that activity.The only downside was that his advertisement mentioned the availability of soda, which was not provided. Despite this minor issue, I highly recommend his services and eagerly anticipate my next opportunity to venture out into the open ocean with Causal Monday Carters.

5 Stars – The Perfect Experience Captain Zak from Casual Monday Charters was incredible—truly the best we could’ve asked for. We got engaged on a private key, and he helped make the moment absolutely perfect. From the ride out to Snipes Key to helping set up the proposal and snapping amazing photos, he went above and beyond in every way.Professional, friendly, and easygoing—he made the whole experience feel relaxed but special. Couldn’t be happier with how everything turned out. If you’re looking for a memorable and personal experience in Key West, this is the guy you want at the helm.

Amazing private boat tour! Zak was an amazing captain! He took us around Key West and really knew his stuff! He knew just where to go where we all had fun and a great experience!! Thank you!! A+++

Great time! Our family booked a trip with Zack and Casual Monday Charters on January 28th. Despite the fact a recent storm had brought in colder water to the area and caused poor visibility, Zack made the best of it with taking our family to his favorite spots. He took us to a mangrove forest where my kids got to find starfish in the shallows, swing on an Instagram worthy swing, he showed my boys (9 and 11) how to trap crab, and we wrapped the trip up by going to a beach to find conche shells. Our trip with Zack was by far our best experience in Key West. Thanks Zack!

Captain Zach Rocks! Had a great experience with Captain Zack! Highly recommend the trip to the sandbars with him. This is the second trip we have done

Excellent! Excellent, excellent, excellent! Captain Zak is awesome, and we had a perfect day on the water. Communication was prompt, instructions to meet him very clear, and our time with him was a blast.

Amazing Sand Bar Excursion in Key West! Last week, we finally took our long-awaited trip to Key West, and on Thursday, we went on a sandbar excursion with Casual Monday Charters. It was, without a doubt, the highlight of our trip! Captain Zak was fantastic—friendly, incredibly passionate about what he does, and full of knowledge about Key West and the surrounding areas. He brought us to two absolutely stunning sandbars. My only regret is not booking a second sandbar trip during our stay! It was a perfect day.

An Amazing Day on the water with Captain Zach!! Best Day!! First and foremost, Captain Zach is responsible, knowledgeable and safe. We went snorkeling off the protected reef in the Atlantic, for 2 hours then he took us to a beautiful, relaxing sandbar on the Gulf side. We selected the PRIVATE charter and were not disappointed!!! While diving, we saw sea turtles, stingray, dolphins, Goliath grouper, and lots of tropical fish. Bring subs, sunscreen, towels and your drinks. He has nice snorkel gear, waters and ice. His boat is clean, a great size, would accommodate 4-6 comfortably, has 2 engines, and rode smooth. He's takes his job extremely serious and knows the waterways. Zach is salt of the earth, fun & very easy and enjoyable to talk to. We felt very comfortable with him. Thanks for making our diving/sandbar day great. See you on our next visit to Key West!!

Sandbars, sun, and great fun with Zak! Zak helped us have a wonderful experience out on the water and on the sandbar. He was easy to coordinate with before the trip and selected spots on the water based on our interests. His friendly personality and easy- going spirit made us all feel like we were with a great friend (who happens to be an expert on the area and waterways) for an awesome afternoon. Trust him when he encourages you to use the bean bag chairs- best afternoon!

Excellent Captain, fantastic day tour Captain Zak was outstanding, knowledgeable , friendly and easy going. A great value. Highly recommend. We did the 6 hour day and it was money well spent . He found us a secluded beach , dolphins, two great snorkeling areas, and a really cool sandwich. It was beautiful and he was especially with our kids included one of which has special needs (autism). Definitely recommend ! Looking at all the mega snorkeling trips , I enjoyed the seclusion of your own charter, thanks zak!

A great day with a great captain!!! If your in the Keys you must go on a sandbar tour with Zach from "Casual Mondays". Aside from being a great captain and knowing the waterways like the back of his hand, he bought us to a beautiful sandbar to swim and hang out. He also bought us to other places to see things like stone claw crabs, and a place where the dolphins swim, even an old military waterway where the jets fly right over your head. He's super knowledgeable and laid back. He'll do whatever you ask and was so enjoyable to spend the day with. Get a bunch of friends and go!

A charter that will not disappoint! "This trip was an amazing time! Captain Zak was professional and laid-back and truly made our day over the top. With his relaxed demeanor and extensive knowledge, we were able to do everything we wanted and more. We are definitely planning to use Casual Monday Charters again, and we highly recommend them to you as well. You won't be disappointed!"

Take This Trip --- Zak's Your Man! Wanna spend 4 sublime hours on --- and in --- the blue-green salt-water enveloping Key West? Learn a thing --- or 300 --- about the crazy Conch Republic? Have a damn fine time you'll remember for years to come? Zak's your guy. On our trip, he just happened to run us near a big pod of dolphins (they tend to make your spirit soar!); introduced us to some feisty stone crabs (their claws grow back!); and got us up close --- but not too personal --- with a majestic Great White Heron (5-foot wingspan!). Many thanks again, Z-man. We'll be back!

A must book! Captain Zak is friendly, knowledgeable, and all around awesome. He made our private excursion so fun and memorable. He took us to some amazing secluded spots for snorkeling and swimming and he provided tons of useful and interesting historical tid-bits about Key West. We will definitely charter with him again next time we visit Key West.

Best part of our Key West trip Zak is the best! We booked a sandbar and sunset cruise. This was our second time to book with Casual Monday. He is full of information about the history of the area. He makes it a point to make sure everyone, of every age, has a great time. We visited a sandbar and the Key West swing. He shared facts about the tiny crabs we saw and how the scenery changes with the tides. He then took us to the dolphin playground where we saw several groups of dolphins playing. Last but not least, the amazing Key West sunset. Book with Zak @ Casual Monday and you will not be disappointed!

BEST Key West Experience!! Our excursion with Captain Zak was the BEST part of our Key West trip. We got to see so much wildlife and so many areas that can only be explored by boat. Captain Zak was extremely knowledgeable and personable. There is no better way to learn about and experience Key West than an excursion with Captain Zak!

Fantastic and fun What a fabulous day! I can’t say enough positive things about Zak and his business, Casual Mondays. Zak was warm, friendly and easy to spend a day with. While very safety oriented, he made our trip a lot of fun. He had great local knowledge of not only great snorkeling spots and sand bars, but also restaurants bars, sunset spots and even where we could take our dogs on Key West. The boat was spotless and provided a smooth ride even on a blustery day! We truly enjoyed our experience with Zak and can easily recommend a booking.

Awesome Key West Day on the Water I decided to skip the big snorkel Tours, and instead offer something more private and personal. This was a great choice. Our entire day with Zak was amazing. He took us to the best snorkel spots given the conditions of the day as well as a super awesome sandbar. I would highly recommend to anyone wanting to get out on the water and stay safe and have a great day.

Great day on the water. We had a great day on the water with Zak. He took us to a snorkeling spot and then we went to a beautiful sandbar. He was willing to do whatever we wanted to do and we enjoyed hanging out with him for the day.

Awesome Charters! We had a great trip with Zak and Casual Monday Charters. I highly recommend this trip. We cant wait to do it again! I we would have know it was going to be this good of an experience we would have booked a second trip.

Key West Sunset Cruise with Captain Zak Zak made my family's sunset cruise around Key West a terrific experience. He shared with us really interesting facts about Key West and its history. Zak was super polite and engaging and was the difference between my family having a pleasant vs. a wonderful experience. Highly recommend.

Outstanding trip Zack is very knowledgeable, honest, and adapts the trip based off of conditions. Will seek out his charter next time we are in the Keys.

Awesome Charter! We had a wonderful experience with Zak and Casual Monday Charters. This is the perfect option if you’re looking for a laidback, but knowledgeable captain who knows a lot about the area, history, and the spots where locals frequent (i.e. not packed and super touristy). We did a 4-hour morning trip and highly recommend it!