Welcome Aboard Lady May

    Boat Charters & Tours in
    Grand Cayman

    Explore Grand Cayman in the Cayman Islands with Captain Anthony. Choose Stingray City tours, reef fishing, night fishing or fishing-and-snorkeling trips.

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    Our Tours & Charters

    Choose Your Adventure

    From thrilling fishing expeditions to magical encounters with stingrays, we offer unforgettable experiences in the crystal-clear waters of the Cayman Islands.

    Captain Anthony with a southern stingray at Stingray City in Grand Cayman
    Popular Experience

    Stingray City Tours

    Swim with friendly southern stingrays in their natural habitat

    Lady May guest with a reef fishing catch in Grand Cayman
    Adventure Awaits

    Reef Fishing Trips

    Catch Snappers, Barracuda, Yellowtails and more

    Stingray City Tours

    Swim with stingrays in crystal-clear waters

    4 Stops Stingray City Tour – 4 Hour tour in Grand Cayman
    Stingray City

    4 Stops Stingray City Tour – 4 Hour

    4 hours

    Embark on an immersive 4-hour adventure through the stunning waters of the Cayman Islands with 4 incredible stops.

    $850Up to 8 Persons

    +$60/additional person

    Maximum 25 Persons

    2 Stops Stingray City Tour – 2½ Hour tour in Grand Cayman
    Stingray City

    2 Stops Stingray City Tour – 2½ Hour

    2.5 hours

    Experience the magic of Stingray City and Coral Gardens on this perfect 2½ hour adventure.

    $45Per Person

    Minimum 15 Persons & Maximum 25 Persons

    Fishing Charters

    Experience world-class reef fishing

    Reef Fishing – 4 Hour tour in Grand Cayman
    Fishing

    Reef Fishing – 4 Hour

    4 hours

    Experience the thrill of the catch on our half-day reef fishing tour, perfect for both beginners and seasoned anglers.

    $7501-4 Persons

    +$75/additional person

    Reef Fishing – Full Day tour in Grand Cayman
    Fishing

    Reef Fishing – Full Day

    8 hours

    Spend a full day on the water with our ultimate fishing adventure in the Cayman Islands.

    $14001-4 Persons

    +$75/additional person

    Night Fishing tour in Grand Cayman
    Fishing

    Night Fishing

    4 hours

    Experience the excitement of the Cayman Islands under the stars with our unique night fishing adventure.

    $8501-4 Persons

    +$75/additional person

    Combo Adventures

    Best of both worlds - fishing and snorkeling

    Reef Fishing + Snorkeling – 6 Hour tour in Grand Cayman
    Combo Tour

    Reef Fishing + Snorkeling – 6 Hour

    6 hours

    Combine the thrill of fishing with the beauty of underwater exploration on this exciting combo tour.

    $10501-4 Persons

    +$75/additional person

    Our Vessel

    The Lady May

    Your home on the water for unforgettable Cayman Islands adventures

    Lady May charter boat

    Built for Comfort & Adventure

    The Lady May is a well-maintained charter vessel designed to provide you with a safe, comfortable, and memorable experience on the beautiful Caribbean waters. Whether you're heading out for a fishing adventure or a snorkeling trip to Stingray City, you'll enjoy spacious decks, modern amenities, and all the equipment you need for an amazing day.

    Custom Built

    Purpose-built for Cayman waters

    Comfortable Capacity

    Up to 25 passengers

    Spacious Deck

    Plenty of room to move around

    Safety First

    Full safety equipment on board

    Onboard Amenities

    Toilet facilitiesShaded seating areasIce box & coolerDrinking waterSoda & refreshmentsHand basinRod holdersFish cleaning station

    The Experience

    Meet Captain Anthony & Lady May

    Born and raised in the Cayman Islands, Captain Anthony has spent his entire life on these waters. With over 20 years of professional experience, he knows every hidden reef, fishing hot spot, and secluded beach.

    Lady May is a 34-foot Crusader with an onboard restroom. Explore our fishing, snorkeling and Stingray City tours to see each itinerary and what’s included.

    Local Caymanian Captain
    34-foot Crusader
    Family Friendly & Safe
    Fishing Gear
    Private Restroom Onboard
    Customizable Itineraries
    Learn More About The Boat
    Lady May 34-foot charter boat in Grand Cayman
    20+Years Experience

    Guest Reviews

    What Our Guests Say

    5.0 on Google

    Had an amazing experience with us?

    Review us on Google

    Book Your Trip

    Ready for an Adventure?

    Fill out the form to book your charter. Full payment is required to confirm your reservation.

    Call or WhatsApp

    +1 345-525-0678

    Email Us

    ladymaycharters@gmail.com

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