+1 305 988 1179 CasualMondayCharters@gmail.com
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    • Bareboat Charters

    Key West Bareboat Charters - Perfect for up to 13 guests

    As a bareboat charter, you have the flexibility to choose your own itinerary and hire your own captain, making it a truly personalized adventure. Whether you’re exploring the backcountry, visiting sandbars, or heading offshore.

    Key West Charter Boat

    What is a Bareboat Charter?

    A bareboat charter offers the ultimate freedom to explore Key West waters on your own terms. When you book a bareboat charter, you are renting the vessel itself, giving you full control over your experience.  These charters allow for up to 12 Guests + Crew. 

    • Choose Your Own Captain – We will provide you a list of recommended captains which you can chose from or you can bring your own qualified captain aboard.
    • Select & Pay Your Crew – While the vessel owner may require a general level of proficiency for crew members, you have full control over who joins your trip.
    • Customizable Itinerary – Plan your adventure your way—whether it’s island hopping, fishing, snorkeling, or just cruising the open water.  
    • Pack your own Provisions – With this type of charter Ice, Water, Snacks are not included so be sure to plan ahead or Hire a Provisioner to handle this for you.

    It is important to remember when hiring a bareboat charter that you as the Charterer are responsible for hiring the captain, provisioning the boat.  Ice, Water, Snacks, Fuel and Captain are not included.

    Vessels Available for Charter

    Still Dreamin'

    2017 Belzona 325cc – Twin Mercury 300’s

    Meet the flagship of Casual Monday Charters — the Still Dreamin’. Built for comfortable days on the water, Still Dreamin’ combines the ride quality of an offshore boat with the feel of a luxury day yacht. Guests enjoy plush seating throughout, deep shaded lounge areas, a private bathroom, premium sound system, and a smooth, stable ride perfect for sandbar trips, snorkeling, sunset cruises, and custom adventures around Key West. Ride In Style — Play In Luxury.

    Owners Restrictions: No Spray Sunscreen, No Glass 

    This vessel requires a qualified Captain to operate.   See our list of pre-qualified captains.

    Luxury Charter Florida Keys

    Cobia 296 Center Console

    This well equipped 2017 Cobia 296 Center Console is available now for charter.

    Up To 10 Passengers

    Twin Yamaha 300’s 
    Onboard Head (bathroom)
    Comfortable Seating
    Dual Simrad chartplotters

    Owners Restrictions: No Spray Sunscreen, No Glass, No Pets.

    This vessel requires a qualified Captain to operate.   See our list of pre-qualified captains.

    Charter Itineraries

    sailing charter key west

    What To Bring On A Key West Bareboat Charter

    Here’s a list of a few items you’ll want to make sure you grab before setting off on your Key West Bareboat charter.
    • Hats
    • Beach towels
    • Sunscreen (please no spray on)
    • Sunglasses
    • Cameras (make sure they’re waterproof or safely in a secure case!)
    • Food and Drink (ask us about provisioning)
    – All Documents provided by the Charter Broker
    – Contact info for your Captain and Crew

    A Note From Captain Zak

    I’m just a guy with a boat. I love Key West and having a good time on the water— whether sandbar hopping, diving, fishing, or just enjoying one of those famous Key West sunset cruises. So let me know what you’d like to do during your stay here, and we’ll put together a sandbar cruise in Key West that you and your crew will never forget. So come on down and let me show you my backyard playground — the Fabulous Florida Keys.
    Captain Zak
    From somewhere warm —and yet really cool— aboard the Casual Monday

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