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Key West Watersports w/BobbyB

All Key West Tourist Watersports Private Charter Agent "There is magic in Key West...if you believe..."
201 William Street B, Key West, FL
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Key West is a World Wide Famous Fishing hole and we have our finger on the pulse of Key West's vast fishing fleet and what is possible. Text me BobbyB for live personalized service. I will take all the time it takes to hear you say, "Yes! That is what I want"

Key West Party Boat Fishing
We now have not one not two but 3 Party Boats for all your Key West Party Boat Fishing Fun.
Come one come all just 1 angler or the whole family, office, church group, wedding parties, bachelor parties. We have the right boat at the right price for you.
"Your Fr...

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Gay Men Gay Men Gay Men

Jun 14, 2022 – Dec 31, 2022

All Male All Male All Male

🏳️‍🌈May through October 🏳️‍🌈 Sandbar and Snorkel All Male Clothing Optional Trips🏳️‍🌈 November through April 🏳️‍🌈 Kayak and Snorkel All Male Clothing Optional Trips

 Key West's Home on the Water for Gay Men since 1996!


🏳️‍🌈 All Male Day Trips (Cl...

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Live Personalized Key West Watersport Information and Reservations.

We give you choices!

Published on February 1 2022

Hello, My friends call me Bobby B.
I am an independent information and reservations agent. What that means is I have all Key West's Water Sports an...

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Key West Sunset Sails

May 11, 2022 – Aug 31, 2022

Known for spectacular sunsets, Key West Watersports with BobbyB has the right sunset sail for you.

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2 weeks ago
If you are not taking a shuttle from your hotel to BobbyB @ 201 Williams Street, use the parking garage at the corner of Caroline and Grinnell streets and allow 15 minuets.
- Bobby B
8 months 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
6 months ago
We booked a private cruise around the Island. The Captain was excellent and made it special. Gave us lots of information on sights and the boat was clean & comfortable. The boat left on the agreed schedule and the price was as agreed. Can’t think of any negatives or improvements to suggest. Highly recommend this booking service.
- Bob G

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


Get directions
201 William Street B
Key West, FL 33040
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