Please Contact us for information and reservations about Parasailing Flights, Enviro-Tours of the Everglades Florida Bay, Carolina Moon Adventure Sailing Cruises & Sunset Cruises, Hobie Cat Instruction , Private Fishing Charters,  Private Snorkeling , Island Tours & Sunset Cruises, Group and Family Rates & Special Events

All Rentals & Tours are subject to weather conditions, Prices subject to change without notice. Florida Sales tax is 7.5%.  Gratuity recommended 18% – 22% and is always Appreciated!

ALL Private Tours – Trips – Instruction Needs Reservations – See our Schedules page

All Rentals are “First Reserve, First Play” #PlaySafeTogether #StaySafeTogether

CWS Beach Opens 9:00 am – 6:30 pm (last rentals out by 6:05 pm)

Full Moon Rise is 8:16 pm July 23, 2021 is Sunset at 8:12 pm (perfect viewing week for Sunset and Moon Rise Cruises before then!)

PRIVATE CHARTERS FOR GROUPS, WEDDINGS, FAMILIES AND SCHOOLS REUNIONS SEE ACTIVITY MENU SHEET BELOW

Activity Menu Sheet

Activity Menu Printable PDF

  • Adventure Mimosa Sip-n-Splash Cruise
  • Carolina Moon
    Carolina Moon Champagne Sunsets Cruise
JPEG Activities

The Ultimate Sailing Adventure on Florida Bay!

Our 37' x 22.5' USCG Certified for 24 Passengers Stiletto style Sailing Catamaran is the Perfect Answer to Fun on the Waters for Families and Groups!  Join us on this fast cat for a 3 hour Bayside Adventure Snorkel/Swim or 2 hour Sunset Champagne Cruise. Available for Private Guaranteed or limited to 18 ppl with min. of 8 guests on Public Charters.

Sip-n-Splash Mimosa Adventure Cruise Mornings or Afternoons or Sunsets or Champagne Sunset Sailing Cruises.

PARASAILING is as close as you can get to flying! Forget the meetings and the deadlines as you fly solo or with a partner above the spectacular turquoise waters of the Florida Bay or Atlantic Coral Reefs. Be on the lookout for dolphins and stingrays. 1/2 hour Flights of 600' Solo or Tandem or NOW Triple Flyers and 3/4 hours or one hour to 1.5 hour Private Charters Available! Bring your Phones and Camera for breathtaking 25 mile views from 500 feet in the AIR! *Most days with winds less than 20 m.p.h. or gusts less than 25 m.p.h. and weights Min. 150#, Max 475#

Dreams of a Real Wedding with #Microwedding Flair.

Private Charter our 37' x 22' Classic Sailing Catamaran for guests up to 24 guests, including a Mimosa's Or Champagne Toast to the Bride and Groom.

Add More fun and friends with our 6 passenger Private Charter Parasailing boat for multiple flyers to see the beauty of 25 mile views while under way. OR Add our 6 Passenger Enviro-Tour Boat to seek out dolphins, manatees and local wildlife on the shallow, pristine waters of Florida Bay!

CWS Cancellation Policy

Reservations with Credit Card or Guest Reservation (Room) Number are required on all tours / trips. Due to the limited amount of seats available on our trips, and in order to avoid disappointments, Caribbean Watersports adopts a Cancellation Policy. You may cancel with CWS Tours BEFORE 3 business hours of activity without cancellation fee (3 days if Private Charter, 4 weeks for Fishing Charter). Cancellation Fee is 100% of charter. Re-schedule fee is $25 if within that period. No Fee is charged if tour is cancelled because of weather call by Captain. Call or Text our  Beach Desk 305-852-4707 or 305-619-7844 for more info.

Private Fishing Charters from the Best of the Upper Keys Fishing Captains

Contact  Victoria or Hannah, our Watersports Concierge Fishing experts, 305-852-4707 or text via cell to 305-619-7844 for inquiries.
Captain Randy Stallings  17' - 2* Hell's Bay     Spin, Fly, Live Bait      Full Day  $call     1/2 Day  $600  
Captain Brett Greco          24' - 4* Islamorada  Fly, Spin, Live Bait      Full Day  $call     1/2 Day  $700 
Captain Larry Sydnor       17' - 2* Chittum Skiff  or 22' Bay Boat         Full Day  $call      1/2 Day  $700 
Captain Frank Juliano     17' - 2* Maverik  or 16' - 4* PathFinder       Full Day $call       1/2 Day   $650  
Captain Paul Hunt             22' - 2* Ranger Bay                                             Full Day  $call      1/2 Day   $750  
Captain Chris Barron      24' - 4* Everglades                                               Full Day  $call      1/2 Day   $700    Captain Kerry Wingo      17' - 2* Maverick                                                    Full Day  $call       1/2 Day  $700  
Captain John Baar          Mayhem Sport Fishing                                        Full Day $call       3/4 Day $1200 
Captain Frank Drudi    38' - 4* Buddy Davis SportFisher Phoebe II   CHELSEA CHARTERS                                     Full Day  $call  3/4 Day $1200 1/2 Day $900 R;BW-
Captain Skip Bradeen  48 Guthrie S/F New BlueChip II"                  Call for Availability & Price
Captain Ron Moore .    44' - 4* Marlago SF                                        Call for Availability & Price

Notes: Full Day (8 hrs) 3/4 Day (6 hrs) - 1/2 Day (4 hrs) - Night (3 hrs) (BC) Back Country - (IS) In Shore - (R) Reef - (BW) Blue Water

Rates shown are with Fishing Parties of 2 and are subject to change w/o notice! *Add Extra Chg of $100 Per Angler. Boats 22'+ Max of 4 Anglers Vessels from 17' to 32' (+PU) Pick Up Available at Playa Available

Private Fishing Charters have NO FLORIDA SALES TAX! Recommended Gratuity is 20% ALL PRICES SUBJECT TO CHANGE WITHOUT NOTICE TILL DEPOSIT IS RECEIVED!

SAIL from the whitest, sandiest beach in the Upper Keys! On Florida Bay, 5'-8' ocean bottom with no current and best winds!  As a former Florida Keys Hobie Cat dealer, Caribbean Watersports has the top of the line Hobie Cats for the novice or the advanced sailor. Raise hull in Keys while you cruise the Florida Bay on a Hobie Wave, or Hobie Getaway. All levels of instruction are available for sailing. Hobie rentals with or without Captain, half or full day. Sailboats have 3-4 person maximum. Private Charters on the Hobie Cat Getaway!
OUR ENVIRO-TOUR will take you on a two-hour journey into time and history. Our AB rigid inflatable boat offers you the thrill of rafting while you explore the quiet mangrove islands of the Everglades National Park and watch for dolphins, manatees, bald eagles, and great white herons. Maximum of six guests per voyage. Sunset Enviro-Tours available.  Also Available to be combined tour with our 24 passenger sailing catamaran "Carolina Moon"  as a mother vessel and extended tour into the Florida Bay's Islands!

PRIVATE CHARTER ENVIRO-TOURS

Come explore the Everglades Florida Bay on our 17’ Zodiac style,

Rigid-Inflatable. This personalized environmental tour through the

shallow waters of the Florida Bay can accommodate 1-6 passengers.

FOUR CHOICES ON OUR PRIVATE SUNSET CHARTERS

Private CARIBBEAN FLYER - OUR 30' COMERCIAL WATERSPORTS PARASAIL BOAT!

Like to Toast the end of a Perfect Day with Champagne? And be dropped off at one of four fine restaurants, such as... Bayside Grill, Snooks, Sol or perhaps Marker 88 on the Bay? You can return via local cab or limo.

Private CAROLINA MOON A 37' X 21' SAILING CATAMARAN SUNSET CRUISE WITH CHAMPAGNE TOAST:

Catch the Breeze on our 37', 24 passenger Sailing Catamaran on Florida Bay, departing from our dock.

Private HOBIE CAT GETAWAY SAIL FOR TWO

Let our Captain steer you and your companion to pristeen waters and islands of Florida Bay on our 16' Hobie Cat with wings!

Private ENVIRO-TOUR

Enjoy the Pristine Wilderness from our AB Inflatable as we approach Bird Island in the Florida Bay for sunset, with a bottle of Champagne for a sunset toast to the birds, dolphins or many of the wildlife! *Special 10% discount off boarding cocktail from Sol by the Sea Bar. Recommended Gratuity is 18% to 22% Thank you from our Crew!

SNORKELING in the clean, clear waters of the Florida Keys National Marine Sanctuary should not be missed. We offer Private Snorkel charters on our Carolina Moon 37'x 22' 24 passenger Sailing Catamaran

Florida Bay Islands our main trip but can also go a Bayside Snorkel Cruise to the "Wall" (a 4' to 25' size drop off on the Bay) or into the Everglades Florida Bay. Or Just Cruise along the Million Dollar Waterfront homes to Waterfront Saloons on the Bay!

Off Property Coral Reef Vessels:

Private Coral Reef Snorkeling Prices: Off Property $625 - $725 per 6 passenger vessel

Public Coral Reef Snorkeling Prices: Off Property $55 - $85 per person.

Larger Group prices are available upon request. We have Private Coral Reef Snorkel Charters who can handle 40 - 46 passengers. Check with us for current pricing and availability.