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Old 13-06-2020, 09:15   #1
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Chartering in the FL Keys

We (6 guys) usually charter a 40-45-foot cat in the Caribbean for 7-10 days. This year we are thinking of not traveling outside the US and looking into chartering in the FL Keys or elsewhere in south FL. We however no nothing about the Keys. Can you recommend a charter company, suggest an itinerary (we will also ask the charter cos 0, places to avoid, places not to miss etc.? We are competent sailors but would prefer areas with few jet skis, and speed boats going in circles. We would also prefer to pick up a mooring rather than anchor.
About a year ago someone posted web address where individuals were interested in chartering their cats. Does anyone know the web sites? Thanks.
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Old 14-06-2020, 07:31   #2
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I can't help with the charter companies because I have never chartered a boat in this area. However, I have cruised my personal boat in the Keys several times and been up and down the west coast of Florida more times than I can count.

The first thing to mention is that there are not many places to pick up a mooring in the Keys or even the west coast of Florida. In the Keys, Boot Key Harbor, in Marathon and Garrison Bight mooring field in Key West are about it. Although, I think I read that there are some moorings at John Pennekamp State Park, I have never been to it. On the west coast, the only mooring fields I'm aware of are Fort Myers Beach, Marina Jack in Sarasota and St Petersburg Municipal Marina in Tampa Bay. Every place else you will need to anchor out or head to a marina. There are, however, plenty of places to anchor, in a protected area, in the Keys and the west coast.

For shore side attractions and water activities this show, sums up the keys very well:


The "How To Do Florida" series has a lot of tips on places to go and things to do in Florida:
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Old 14-06-2020, 07:48   #3
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What month of the year? If summer in the Keys, hope you like heat & lightning!
You can choose from sail charters in Miami, St Petersburg, Fort Myers. Or fly to Miami, rent car and do day charters of power or sail depending upon weather.
Or fly to Nassau and charter there.
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Old 14-06-2020, 08:47   #4
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Thanks for the info. Planning to charter in Jan or Feb 2021.
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Old 14-06-2020, 09:11   #5
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I chartered a sailboat for a week 2 years ago from a Florida keys Sailing in marathon, fl.the guy who owns it goes by G Dub and was fantastic. He can fill you in one all of the places to anchor and see. He was a wealth of knowledge and I had a great time.
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Old 14-06-2020, 09:29   #6
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Could try Fun in the Sun out of Ft Lauderdale. We did the Northern Keys for 1 week then bounced over to Bimini for the second week. We didn't have anything planned for the 1st week and Scott had some recommendations for things to do and excellent areas for anchoring.
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Old 14-06-2020, 11:56   #7
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I guess you have to decide whether to do the upper, middle, or lower keys as well as Atlantic of bay side. There are rentals in Miami, Marathon, and key west.
Upper keys have tons of reef in the Atlantic side and you can moor at John Pennekamp Park. If you like bar hoping the. The upper keys has tons of them on the bay side.
Middle keys have also access to some reef, but the bay side is very interesting. Is quieter
Key west of course has a lot to offer and you can go the the marquesas and look up the fort.
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Old 14-06-2020, 12:01   #8
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Key Lime Sailing club is connected with a charter company. Their main business is cottage rentals but they are associated with a sailboat charter and a sailboat only marina. Paul is a good guy and all the folks we met were super. Disclaimer, we did not charter just stayed in one of the cottages some time ago.
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Old 14-06-2020, 14:07   #9
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Isola Catamaran | Catamaran Rentals Florida | Florida Keys Catamaran Charter | Calypso Sailing
Try this Cat . They are in Key West Bight Marina. Nice people ,

Nice Catamaran and your right in the heart of everything . Dry Tortugas are a must ....allow at least 3 days ...Stop in the Marquesas on the way down and boca Grande on the way back to break up the trip.
Moorings in Garrison Bight or stay at the marina, Dont anchor in Key West .

You will drag or someone will drag into you. Sand Key Light has 3 seperate snorkeling areas. The Keys are pretty beat up for snorkeling and diving but it depends on what your used to. We are used to the bay Islands.
Fly right into Key West Airport to save time or into Fort Lauderdale and enjoy the drive.

Good Luck. Look for Manta Cat Cecilia Marie and say Hi if you go.
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Old 14-06-2020, 14:19   #10
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Boat: 2023 Catalina 425 #95 (previously, 2016 Leopard 44 catamaran and 1997 Catalina 34 Mk II)
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Calypso Sailing in Key Largo (home of the African Queen) has very nice cats and rates that are hard to beat. 305-453-8006
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Old 14-06-2020, 16:07   #11
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We know the keys very well. We had our sail loft there in Islamorada for 31 years. I believe This is the best place to charter or sail in all of Florida.
Our charter season in the Bahamas dried up because of the virus so, we are sailing our Leopard 46 catamaran to the keys now to offer charters from late July to October. This can be a captain only or with Chef. Our prices, for the keys trips, are quite a bit less than what we are charging in the Bahamas. If interested, please check out our web site. I can be emailed through this. This shows the boat and what we offer.
I also know most of the other charter boats and captains in the keys. If we can't accommodate you, I can recommend another boat.
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Old 15-06-2020, 08:05   #12
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I live in Tampa and have been bareboat chartering with Sailing Florida out of St. Peterburg Vinoy Marina since 2006. Very clean and professional, most boats are 5 years or younger. Give Dave a call at either 727-894-7245 or 866-894-7245. They have 6 catamarans ranging from 40 to 47 feet.
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