Keys versus Fajardo

Good fishing in the keys and easy access especially nowadays with the all the Testing and travel hassles. That said the keys are not great cruising grounds for larger boats (anything over 55/60 with 5’ draft).

Have you considered the Bahamas? Great fishing and amazing cruising grounds.

I would base the choice on your flight connections. Where can you get quickest and easiest? If flying commercially, then neither Bahamas, Keys or Puerto Rico are likely quick and easy from Wisconsin. Have you considered choosing somewhere near a major airport, with direct flights?

Fort Lauderdale, Miami, Tampa, West Palm Beach.

There's a reason so many keep their boats in Fort Lauderdale. Boating services. 50 miles to the Bahamas.

I'm just encouraging you to look at all aspects of each of the areas you're thinking about. Can be many factors.

For instance, we kept a boat after looping on Lake Pickwick a while. Ever tried to get there from Fort Lauderdale? Great boating. Full day to get there or get home unless you charter a small plane. Fly commercial to Memphis. Well, let's see. Leave for airport at least 2 1/2 hours before flight since flying from Miami. 2.5 hours flight. 30 minutes renting car. 2 hours to the lake. Then 30 minutes or more returning the rental car. Over 8 hours and dictated by flight schedule. We could drive it in 13 hours.

The more difficult it is to get to your boat, the less often you'll use it.

Nassau has a ton of flights to all the major hubs. Yes it means a connection but we had guests flying to Nassau from pretty much everywhere.

From Milwaukee, 6 hours or so by air to Nassau including one stop which is about the same as to Fort Lauderdale. From Chicago, non stop available to both. 3 - 3.5 hours.

Actually are some non stop from Chicago to Key West as well.

Now the unfortunate part is he's about 3 hours from Chicago. So, the drive is about the length of the flight. Anyway you look at it, a day of travel to and from.

Yeah but the best cruising grounds one can wish for and great fishing. FTL or Mia don’t have much to offer for cruising especially FTL.

FTL has coastal cruising plus the Bahamas plus the Keys, plus good access to the Gulf Coast. Nassau has the Bahamas plus access to the FL coast. Much depends on speed of boat and desired cruising. I'm assuming by all this that current situations change.

7 hours from Chicago, but occasional non stop at 5, 8 hours from Milwaukee to San Juan. I love Puerto Rico and the Virgin Islands. Plus it's a gateway to the Eastern Caribbean. Or why not directly to the Virgin Islands?

For fishing, cruising destinations, amazing water, and a feeling that you're "someplace else" in the world I'd say Fajardo or just south of there in Palmas. Short trips to fish are easy and going somewhere for a few nights or weeks will be amazing in that area.
But also weigh the costs of getting the boat there, travel time, logistics if you have other guests arriving and departing on different schedules. Is the boat going to be new? What's the dealer service like in that area? Or is it used and you need to shake it down for a season in Lauderdale where you can get parts and projects taken care of easily?

As a fellow midwesterner, when I bought my 54’ Flybridge in 2018 I chose to buy and base our boat in FLL. Reasons

1. Largest market of boats to select from.
2. Nonstop flights to FLL. I don’t want to connect, rent a car & drive or need a passport every time I go.
3. FLL has Access to any service, supply, parts
4. Easy training wheel cruises; ICW, Biscayne Bay, Keys, Okeechobee Waterway. You and your midwestern guests will love these cruises before you tackle big water. You won’t get bored.
5. Then easy access to more challenging cruises crossing Gulf Steam to West End or Bimini, Abacos, Chub, Nassau, Exumas…. Or head up to St Augustine, Savannah, Charleston, Chesapeake or Nantucket.

OlderBoater nails it- you have to make it easy to access for you AND your guests. Learn how you like to Cruise, THEN you can decide the ultimate spot, you’ll then know if that place is worth the hassle of getting there…

Good luck