keywest boat trips near me

Explore Key West’s Waters in Comfort & Style

Private Charters • Snorkeling • Sandbar Trips • Sunset Cruises
Leave the ordinary behind: let us take you to hidden sandbars, vibrant reefs, and picture-perfect sunsets with the leading luxury sandbar charter and private charter company in Key West. Every trip with Casual Monday Charters is designed for pure relaxation, adventure, and good times.

Explore Key West’s Sandbars in Comfort & Style

Luxury Private Charters • Snorkeling • Sandbar Charters• Sunset Cruises

Looking for the best Key West sandbar charter? Welcome to Casual Monday Charters, where private luxury experiences on the water meet the laid-back beauty of the Florida Keys.

Step aboard  and discover why guests call this the highlight of their Key West vacation.

Whether you’re planning a relaxing day at the sandbar, dolphin watching, snorkeling, or a completely unique island adventure, we are here to make your perfect day on the water happen.  

About Casual Monday Charters

Based in beautiful Key West, we specialize in private boat charters that Key West visitors trusted for over 7 years. 

Whether you’re a first-time visitor or a local ready for a new adventure, Captain Zak and his crew ensure every trip feels personal and unforgettable. From Key West snorkeling charters and relaxing Key West sandbar charters to breathtaking Luxury sunset cruises, we create custom experiences that fit your vibe.

Our Key West sandbar charters are perfect for any occasion, whether you’re planning a romantic getaway, a fun family day with the kids, a bachelor or bachelorette party, or a birthday celebration. If you’re searching for something beyond the typical crowded tourist boat, this is it.

Key West Sandbar Charter

About Casual Monday Charters

Our Charters

sand bar tours key west fl

Key West Sandbar Charters

Crystal Clear Water and Sandy Beaches More Info

key west boat trips near me

Snorkeling charters

Explore the Patch Reefs or get Offshore More Info

key west reef snorkel day trip

Eco Tours

See what nature has in store for the day More Info

Key West Luxury Sunset Cruise

private Sunset Cruises

There is nothing quite like a Key West Sunset on the water More Info

Belzona 325cc Center Console

Still Dreamin'

Still Dreamin’ is our Belzona 325 Luxury Center Console—where performance meets pure comfort. With plush seating, a smooth and stable ride, and plenty of room to stretch out, she’s built for laid-back island cruising and unforgettable days on the water. Whether we’re snorkeling crystal-clear reefs, relaxing at the sandbar, spotting wildlife, or chasing a Key West sunset, Still Dreamin’ delivers a stylish, easygoing charter experience from start to finish.

Intrepid 262 Center Console

Intrepid

The Intrepid 262 was originally designed as a luxury yacht tender, giving it a smooth, stable ride that handles Key West waters comfortably without the harsh pounding common on many center consoles.   Its open layout features comfortable bow seating, a spacious aft deck for fishing or lounging, and plenty of built-in storage to keep the deck clean and easy to move around.

Why Choose Us

When you choose Casual Monday Charters, you’re not just booking a ride; you’re choosing one of the most trusted Key West boat charters on the island.

Private, Customized Charters

Every trip is tailored to your group’s interests, whether that’s snorkeling, cruising, or relaxing on a sandbar.

Experienced Local Captains

All our captains know The Keys like the back of their hand. You’ll visit the best spots, away from crowded tours.

Comfort & Safety First

Our boats are equipped with premium safety gear and top-notch navigation systems for worry-free cruising.

Laid Back and Relaxing

If you're not interested in being on a crowded pontoon boat full of strangers, our Key West private boat charters may be right for you.

Top-Rated Guest Experience

Hundreds of 5-star reviews highlight our hospitality, flexibility, and attention to detail. Your comfort, enjoyment, and safety are our top priorities.

our Testimonials

Reviews

Tripadvisor Reviews

Google Reviews

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5.0
Based on 74 reviews
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Steph B profile picture
Steph B
3 years ago
Captain Zak was super knowledgeable on the history and ecology about the area and was fun to hang out with. We're so grateful we chose to spend our day with him, it was the absolute highlight of our trip, he knew the best sandbars to go to and the right times to go. We can't wait for our next vacation to the keys specifically so we can bring our friends and have another day on the water with him!
Jami Puerta profile picture
Jami Puerta
3 years ago
We had an amazing trip. Zak took us snorkeling and to a sandbar where we found HUGE conch shells…he made sure to take time to find us lots of dolphins too! We couldnt have asked for a better day or captain thanks Zac!
Melody Smith profile picture
Melody Smith
3 years ago
Zak was Awesome!!! We saw sharks and most were 6 ft. or larger. We saw several dolphins and he cruised along with them as they were eating. He took us to 2 different sand bars where we drank and enjoyed the day. He was very knowledgeable about the area and the marine life. This was our second trip with Zak and we will definitely be back again. I recommend you book a trip with him it is well worth it!
Zak did not disappoint! His boat was well kept and perfect for our small group of 6. He was very responsive from the start of our booking and went above and beyond to make sure we had a great afternoon out on the water. Zak was extremely easy going, friendly and just an overall pleasure to be around. Thank you for making our experience such a memorable one! We'll definitely be booking again next time we visit Key West!
Heidi Bristow profile picture
Heidi Bristow
4 years ago
Today could not have been any better!!! Our long awaited Keys trip has been great but our charter today with Zak has been the highlight!! A day we will never forget…dolphins, snorkeling, Snipes Point swing, sandbar exploring along with the best boat ride ever!! Zak is super personable and asks you what do YOU want to do, it’s not a pre planned Itinerary. He is extremely knowledgeable of the area and shares that with you so you learn a little Key West history. His charter is totally private and meant to please!! We did not want it to end. HIGHLY recommend him for your Keys water adventure.
Matt Dowd profile picture
Matt Dowd
4 years ago
Zak is awesome! Laid back and catered to what we wanted to do. Not a cookie cutter trip. Zak will listen to what you have in mind and personally cater to what you want to do. Easily hit it off with Zak, great dude, great trip. If you want the best experience for a private sandbar tour, go with Zak! Perfect day on the water!
Celeste Hickok profile picture
Celeste Hickok
4 years ago
This was our 3rd Sandbar trip in the last couple of years and by far the best! I highly recommend Captain Zak. He's extremely knowledgeable and was completely open to whatever we wanted to do. He took us to 2 amazing sandbar spots and also took us for a ride through beautiful areas that only an experienced Captain in Key West would know. His boat was very comfortable and the perfect size for this trip, which is critical for an enjoyable ride. I highly recommend!
Rikki Gildert profile picture
Rikki Gildert
4 years ago
Casual Monday made our experience easy as could be. Our first time here & first time in a boat in the ocean. Zack was amazing!! Great knowledge and easy chill vibe. Great music and just the perfect “blue lagoon” movie type experience - can’t say enough about how perfect this was
wes tyndall profile picture
wes tyndall
4 years ago
We had a awesome experience with Captin Zak.! He is very knowledgeable of the area's history and very personable. We got to enjoy the day visiting a large sand bar and then did some snorkeling. We were even able to catch a pod of dolphins on the way back.. I would highly recommend using Casual Mondays charters if you visit the Florida keys. We will be back .!!
Adam Hegwer profile picture
Adam Hegwer
4 years ago
We had such a blast on our charter. My wife, 5 year old son, and 11 year old nephew went out to the sand bar. Zach was super personable, fun to talk to and had a tremendous amount of knowledge about the area. It was so much better than your generic tourist trip, we didn’t at all feel like tourists on this trip which was a huge plus for us. We will definitely book another trip our next time in town. 10 out of 10 would recommend booking!!!
Silvia Misina profile picture
Silvia Misina
4 years ago
The best day possible thanks to Zach! Two adults and four kids having an amazing time in Keys on the boat! We booked full six hours!
Zach was very responsive from the first info call to the day of the trip; checking about the weather; what we wanted to experience and see. We saw dolphins, we snorkeled, we hanged out on an empty beach and sandbars and we saw some hidden jams of Keys. Zach was easy going, responsible and had a good sense of when to engage us and when to let us be a family.
Would definitely recommend him to my friends and would do a day tour with him again!
Silvia & Ty
w a profile picture
w a
4 years ago
Captain Zak made for an amazing day out on the water. There was some clouds I was worried about, he re-routed around the storms and got us to sunny skies and warm water. Very familiar with the area, and easy going. Let us play our own music, and plan stopped as we wished. Took us to an absolutely beautiful sunset to end the night.

Highly recommended, I called him direct and got a great deal!
We had an amazing experience with Casual Monday Charters! Zak was fun & personable. He was very knowledgable of Key West & its surrounding islands as well as the history. He showed us hidden gems and we got to see some wildlife including dolphins, sting rays & barracudas. The water & beach he took us to were beautiful & he navigated the water ways like a pro. We packed a few drinks and he had a cooler w/ ice to store our drinks in. He had great music & was easy to talk to. Myself & my friends really enjoyed our time & would do this excursion again next time we come out to Key West. We highly recommend Zak & Casual Monday Charters to add a unique experience to your trip in the Keys!
Jonah Muzyka profile picture
Jonah Muzyka
4 years ago
Had a fantastic time with Captain Zak. We booked three tours with him and he was able to show us new and exciting spots every time including multiple snorkeling spots, secluded private beaches, shipwrecks and we even spotted multiple dolphin pods. Zak's boat is perfect for getting around the Keys quickly and is fully stocked with all the recreation gear you'll need. Zak was always friendly, professional and knowledgable about all the best spots around Key West to visit by boat.
Amazing charter! Knowledgeable captain and a wonderful experience exploring the keys! Would recommend to anyone who wants a fun day on the water! Captain Zach also gives great recommendations for happy hour!
Tina Nielsen profile picture
Tina Nielsen
4 years ago
What a fantastic charter we had with Captain Zak! We had an all-girls excursion to The Sandbar while the guys went deep sea fishing. What a fantastic beautiful day!
Sharon profile picture
Sharon
4 years ago
OUTSTANDING! We had such a great day with Casual Monday Charters.. Zack, our Captain was the BEST.. He was super friendly, accommodating and he knew the waters so well. He made sure we had a great day!
I would definitely highly recommend this charter!
Sheri Bedwell profile picture
Sheri Bedwell
4 years ago
We had a great time on our excursion with Zak. He took us to the sandbar with the swing and took group pictures for us. He was fun, personable and even gave us some history on Key West. If you are looking for a fantastic time book your charter with Casual Monday Charters.
Ashlee Frost profile picture
Ashlee Frost
4 years ago
WOW! WOW! WOW! Zak Smith is the BEST Captain. He can take you to all the BEST spots in Key West. We were able to hang out in knee deep water while enjoying sand bars + crystal clear water. Zak's boat is gorgeous and has dual engines. Smooth ride all the way!
Katie Muzyka profile picture
Katie Muzyka
4 years ago
Zak was an amazing captain and we all had an incredible time!!! He brought us to two great spots and we had a nice sunset cruise back to the dock! There was plenty of time in the water and we saw so much great sea life. The boat was super clean and well-maintained. He was really knowledgeable about the area and made the whole trip really fun!
Rebecca Seeba profile picture
Rebecca Seeba
5 years ago
This charter was great! Zak was so knowledgeable about the area and took us to all of the best spots. He provided a cooler with ice for us and made sure we had everything we needed. He was awesome company and made sure my friends and I had a great time! Would definitely recommend!
Jessica Griffin profile picture
Jessica Griffin
5 years ago
My friends and I had the best time going out on Zak’s boat! He took us to the sand bars, we went searching for dolphins, he told us about the history of the different islands we saw, and we ended the trip watching a beautiful sunset! He was also willing to take us to the cool snorkeling spots, so he is pretty much up for anything! 11/10 experience!
Tammy Cowen profile picture
Tammy Cowen
5 years ago
We had a great day on the water today with Captain Zak! We went to some incredible sand bars, saw lots of Dolphin and the most beautiful sunset! We will definitely book with him again when we are in the Keys!
FAQs
How Many People Can Join?

Our Key West Bareboat charters welcome up to 12 guests.   We also offer charters for up to 6 Passengers including Sandbar Charters, Snorkeling Charters, Eco Tours, and Sunset Cruises.  

Absolutely. Our private boat tours in Key West are great for guests of all ages.  Lifejackets are provided for guests of all ages including infants.  The Key West Sandbars are shallow, calm and perfect for families.

Safety always comes first. We’ll reschedule or refund if weather conditions aren’t ideal.  Check out our full Cancelation Policy for more details.

Click “Book Now,” choose your date and trip type, or contact us directly. Discover why we’re a top choice for Key West Sandbar Charters.

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