Kayak and Canoe News

Prices – Caribbean Watersports & Activities

Please Contact us for information and reservations about Parasailing Flights, WaveRunner Tours, Enviro-Tours of the Everglades Florida Bay, Carolina Moon Adventure Sailing Cruises & Sunset Cruises, Hobie Cat Instruction, Private Fishing Charters, Caribbean Cruiser 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!

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

All Rentals are “First Come, First Play”

CWS Beach Opens 9 – 5:30 (last rentals out by 5:05 pm)

Full Moon Rise is 5:19 pm Dec 11, 2019 is Sunset at 6:358 pm (perfect viewing week!)

Activity Menu Sheet


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. Prices: $95 for 2 hours Wave . $105 for 2 hours Getaway Four and more hour rates available!

WAVERUNNERS are the fast and exciting sit on type jet skis that ride one to three persons at a time. And what a time, as you speed along our warm, clear calm waters right off the beach.
Prices: Guided Tour $250 for 1 1/2 hour VIP Tour (one Person) $195 for 2 to 3 skis max $225 for 2 hours

Our 37′ x 22′ USCG Certified for 24 Passengers Stiletto type Sailing Catamaran Really Moves! Join us on our fast cat for a 3 hour Bayside Snorkel/Swim or 2 hour Sunset Champagne Cruise.

SNORKELING in the clean, clear waters of Pennekamp or the Florida Keys National Marine Sanctuary should not be missed. We offer a private snorkel charter on our new 25′ World Cat powered catamaran for up to 6 guests at a time.

If the Reef is a little too windy, we can also go a Bayside Island Snorkel Cruise to the “Wall” (a 4′ to 25′ size drop off on the Bay) or into the Everglades Florida Bay. Or Just Cruise the Waterfront form homes to Saloons on the Bay!

Private Coral Reef Snorkeling Prices: $525 for half day (3 hrs) or $650 for full day (6 hrs).

Public Coral Reef Snorkeling Prices: $45 – $55 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.

Trying to keep cool? Here’s a way to get wild, wet, spilled and thrilled, offer the Wedding Golden Ticket for your guests! Same program as above but with your own custom ticket with the wedding party’s name on it!

Minimum order of 15 CWS Golden Tickets at $62 each. Order 30 at $55 each or 40 at $51 each. Please add 7.5% Sales tax and 18% gratuity.

Pre-dinner Sunset Cruises available or perhaps get dropped off at your favorite waterfront restaurants such as our own Playa Largo Beach Resort’s Sol by the Sea Restaurant and Marina or others like Marker 88, Snooks Bayside or Bayside Grill. Return back by boat or with Limousine. Prices available on a per quote bases.


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 sting rays. Six flights per hour. Flights of 600′ Solo or Tandem or NOW Triple Flyers!

*Most days with winds less than 20 m.p.h. or gusts less than 25 m.p.h. and weights Min. 150#, Max 425#





$49 “I’M ON VACATION” REPEAT FLYER (Fly within previous 7 days)

Private Trips on our Caribbean Cruiser

See the Keys like the natives. Join us on a 1/2 or full day tour and go exploring, shopping, lunch, Enviro-Touring, snorkeling and party back home. Private trips available on the new Caribbean Cruiser Snorkel-Cruise 255 World Cat Catamaran powered with twin Yamaha 4 cycle 150 HP outboards! Got a Party over six? We can add other boats to join in the fun on our Rondezvous Program!

Private Half Day Charter 3.25 hrs for up to six $475. Grecian Rocks tour is 4 hrs $525

Full Day 6 Hours $650 Private Sunset Champagne Cruise $325

All charters plus 7.5% sales tax. 22% gratuity.

Split parties to share boat accepted, but not guaranteed.

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 $650 1/2 Day $500 BC;IS+PU

Captain Brett Greco 24′ – 4* Islamorada Fly, Spin, Live Bait Full Day $700 1/2 Day $600 BC;IS+PU

Captain Larry Sydnor 17′ – 2* Chittum Skiff or 22′ Bay Boat Full Day $700 1/2 Day $600 BC;IS+PU

Captain Frank Juliano 17′ – 2* Maverik or 16′ – 4* PathFinder Full Day $600 1/2 Day $450 BC;IS+PU

Captain Paul Hunt 22′ – 2* Ranger Bay Full Day $650 1/2 Day $550 BC; -PU

Captain Chris Barron 24′ – 4* Everglades Full Day $700 1/2 Day $600 BC; -PU

Captain Kerry Wingo 17′ – 2* Maverick Full Day $600 1/2 Day $600 BC;IS +P

Captain John Baar Mayhem Sport Fishing Full Day $1300 3/4 Day $900 R;BW-PU

Captain Frank Drudi 38′ – 4* Buddy Davis
SportFisher Phoebe II CHELSEA CHARTERS Full Day $1200 3/4 Day $1000 1/2 Day $800 R;BW-PostCardInn

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 Hilton Available




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.

$325 and it’s ALL yours for 2 hours! (With up to 6 friends) + 7.5% tax + gratuity


Check with CWS Beach before 4:00 to join us on our Two Hour Public Sunset Cruise with a Champagne toast.

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

Public Departures: 2 1/2 hr Day Trips $50**, 2 hour Sunset Cruise $60* + 7.5% tax

Private Departures: 2 1/2 hr tour for 1 – 6 passengers $650 (last hour before departure when available) 7 – 14 $1300, 15 – 24 passengers $1800 + 22% Gratuity and 7.5% tax


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!

Public departures: $65 per person $45 children under 13, max of 6

Private departure: $300 for up to six + 7.5% tax

*Special 10% discount off boarding cocktail from Sol by the Sea Bar.

**Qualifies for 10% M.A.D. discount if you have rented from us on the same day!

Recommended Gratuity is 18% to 20% Thank you from our Crew!

An 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 Caribbean Cruiser World Cat 255 powered catamaran boat with a max of six per trip. Can be used with our 24 passenger sailing catamaran “

Carolina Moon

” as a mother vessel and extended tour into the Florida Bay’s Islands!


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 2-6 passengers.

$75 ADULTS $55 CHILDREN UNDER 13, 2 yrs and under Free!


Truly a paddler's paradise, Florida has diverse ecosystems and pristine waters that nature lovers can really appreciate. You can spot abundant wildlife in the lush landscapes as you float through miles of pristine beauty in one of Florida's most picturesque places to go kayaking.