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Key West Watersports

Schooner Sails*All Key West Watersports* ....and Private Charter Agent***** "There is magic in Key West...if you believe...
201 William St, B, Key West, FL
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Christmas Season in Key West
A unique time on our Island
Book watersport here for Live Personalized Service
We will make sure you have all you need to know to have a Jolly time.
( Little tips like; Allow 20 minutes for parking if you are not using a shuttle.) And other important little details yo...

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Key West Schooner Sailing
The air is crisp, the winds are up, a sea of green and sky's of blue. The traditional wooden schooners are ready for you to sail away....
Text BobbyB
"Your Friend In Key West"

Key West Parasailing
The most relaxing Xtreme Sport!
Text us to reserve your seats.
Boats leave every hour on the hour.
"Your Friend In Key West"

You Have Found The Keys

Sep 28, 2021 – Dec 31, 2021

Mention seeing this on this site when you book a watersport and you get a Key from the Keys

Show this code at the store: I found the πŸ”‘

We are following CDC guidelines at Key West Watersports with BobbyB.
I have been vaccinated to protect myself and others.
I respect others' decisions.
I keep my work area clean and disinfected.
I mask up on occasion, social distance when it is appropriate and I wash my hands frequently.
I offer h...

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a month ago
I was in a bind because my original sunset cruise was cancelled less than 24 hours before it was suppose to happen. Key West Watersports with Bobby G. came through. Their customer service and follow through was excellent. We thoroughly enjoyed the sunset sailing cruise. The sailing crew was responsive; the snacks delicious and overall it was amazing. Thank you! I highly recommend them.
- Kathy L
3 months ago
Bobby is my best wingman for my trip in Key west. I planned to propose my girlfriend during my trip and when I was searching online I found him. I reached out to him and he gave me the best options and within my budget. No professional planner would have made it. I was referred to a sunset Cruise with Blue ice.. and they were the best. He checked on weather, got some flowers upon my request and did the best he could ! We also booked our tours through him ! Common Folks! Let's not use big tech companies to book for local adventures and help bobby who stays on site and gets the best deals.
- Muthu R
2 months ago
Bobby B set us up with a snorkel / sunset cruise to celebrate a birthday. Working with him made the experience smooth with zero stress. Contact and communication was a breeze! 100% recommend Bobby B!!
- Marie A

Live Personalized Attention To You

Personal live service for all your Key West Vacation Watersports under one umbrella ⛱️.

Contact Us


Call now
  • (305) 923-9533


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201 William St
Key West, FL 33040
United States
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