Shuttle bus to The Keys (Key West)
 

Is there any kind of shuttle from/to The Villages and The Keys

I'm sure you have already checked, but if not, I looked on the Greyhound Bus web site and saw that there is bus service from either Ocala or Orlando to Key West. I suspect that would be your best option, unless there are some travel group going. You might check with either AAA or some of the local travel agents to see if there are any travel groups going to Key West that would fit into your desired schedule. I was surprised that the Greyhound rate from Orlando wasn't as much as I thought it might be. And if you really wanted to make an adventure out of your trip, take Amtrak from Wildwood down to Miami and then the bus to Key West.

Fly to Miami for 50 bucks and catch the bus

You will find that the amtrak station in wildwood is actually a bus station now.

High speed ferry to Key West
 

I think there is a high speed ferry to the Keys from Tampa or Fort Myers. I also think one of the tour companies (Villages or AAA) has a bus from here to the ferry.

Do not know of a "shuttle bus to the Keys. Upper Keys are 300+/- miles and Key West is another 125 miles. Suggest looking into high speed ferry from Fort Myers to Key West, or fly to Miami and rent car.

It’s not a difficult drive. We go every year for a week. 1st day we leave about 11 or 12 drive to Naples or Marco island, have a nice dinner, next day we have breakfast and leave via the Tamiami Trail through the Everglades, we do this because we like to eat lunch at Sparky’s Landing in Marathon and stop for a Bloody Mary at Sunset Point Bar that overlooks the 7 mile bridge also if it’s stone crab season Keys fisheries in Marathon is great for claws. Spend our week in KW and when we leave we drive straight home via the turnpike, 7-8 hours depending on traffic and stops. You can fly Silver Air from Orlando or Tampa direct to KW but you miss so much of the other keys.

Allegiant has round trip flights from Sanford to Key West for less than $70.

The flight time is just over one hour.

Flights

YES- this is on my bucket list!

Key West
 

Workman Travel sponsors trips there

Good to know.

Mine too...
:a040::clap2:

Flight to Key West
 

Allegiant only flies to Key West certain days and is known to cancel flights. It is only $80 r/t,but be careful…could cost hundreds to stay an extra week

This catamarans goes from Ft. Myers or Marco Island to Key West. Nice ride, round trip around $125 per person. Go down and come back on different day. I have taken this catamaran twice, nice ride 3-4 hours depending on where you leave from.

It’s only a 7 hour drive.....430 miles

I/we just took the ferry a few months ago. It was nice, but I won't do it again. It leaves early in the am, so you either have to get up VERY EARLY in TV, or drive down and spend the night(which we did). The return ride doesn't leave until LATE afternoon, which is not convenient, when you have to check out at 11:00am?! Then, you don't get back to Ft Myers until almost 11:00pm, then drive home?!

If it’s possible for you try driving , the ride along the keys on a good day is fun , take your time stop different places

I want to go with you, lol!! Sounds like fun.

I’m always up for fun , soon entering my twenty third year of retirement and still having fun

To EviesGP: Where do you stay in Naples or Marco Island? Do you stay another night when you stop at Sunset Point Bar, if so where? Sounds like a nice trip. Do you have a favorite place to stay in KW?

We usually stay at Hampton Inns, in Ft Myers and Naples. Marco is mostly condos. We were down over Labor Day week this year and we stayed at a old refurbished hotel in Everglades City, it was a adventure LOL, not bad but not a Hampton.
Key West has been really pricey since the pandemic, hard to find a hotel room under $500 a night. This September we stayed at a Hyatt Time share 2 bedroom condo. Very nice. Have stayed at a lot of B&B in KW but they have gone up too $300-$400 a night.
When you get to Sunset Point bar you are only about 2 hours or less from KW. We make at least one more stop at Babies Coffee for our coffee for the condo and still get into KW around 4-5. Check in at most of the places is 4.
Lots of great restaurants in and around KY, wonderful seafood. Almost every day you can find wahoo, hog fish,Dolphin, whole fried snapper and of course Key West pink shrimp and royal red shrimp.