After thinking about it for MANY years, we enjoyed the Miami to Key West Poker Run, along with staying in Key West for 5 nights. My son and I came via the Skater, and my wife, daughter, and her little dog drove down from Miami. It was a ***** to find any kind of condo or hotel room that did not break the bank. We ended up renting a 2 bedroom, 2 bath sailboat docked right at Key West Bight, within walking distance of everything and within eyesight of the Skater. It was awesome to be in the thick of things and enjoying the sights and sounds while sitting attop the sailboat in the evenings (we were very close to the Cigarette Yacht). We also had access to private showers and restrooms about 100 steps away. If you love the water, it is a great way to do it! Best yet, it was $550 a night. Yes, expensive, but a hell of allot cheaper than 2 rooms anywhere close to the action and much, much more enjoyable than any room. We would do it again in a heartbeat. Another interesting tidbit. The sailboat docked right next to it (owned and rented out by the same guy) is the St Vida Dance which is no other than the exact same boat that Sonny Crocket and his pet alligator stayed on in Miami Vice! Anyway, a bit different, but an awesome experience!

Here is a link
https://www.vrbo.com/229193ha?Token=...m_source=adhoc

I checked it out, looks pretty cool! A little rich for my blood.... Is the slip for your boat additional fee? Or I'm assuming you were set with that since you did the poker run.
I'd also need to figure out parking my truck and trailer as well if we did that

Following

The biggest problem I've found, is finding a home for your trailer.

Not well known but in my little town

Beso Del Sol Resort FAQs

Plenty of islands to anchor up at, plenty of places to go and see and do. Dunedin is a blast when off the boat as well. Only thing is call about over night docking but I don't see it being an issue.

Sent you a PM.

Anything north of Tampa is going to much cooler in Temps this time of year, even Tampa\St Pete is 5 degrees cooler than Naples almost daily this time of year.I think Clearwater is the best bang for the buck as much a I love the Keys, though I could live the rest of my life with never seeing Key West again.

If any of you guys get in a bind for truck or trailer storage, I have secure room your welcome to
, but it’s 25mi inland from Bradenton.

You can park your boat at your condo here.

Hawks Cay Resort
61 Hawks Cay Blvd. Duck Key, FL 33050
Reservations: (888) 395-5539 I
nternational: +1 (888) 976-1038

We recently did a week on Marathon Key and stayed in a pretty nice townhouse with a slip right in front of our unit at this resort:
https://www.keyscaribbean.com/resort...lagoon-resort/

We rented a boat as it was a bit too much of a haul (around 3,500 miles) to bring one of our boats down.

Right next door is a really nice rack storage marina, and we did see trailers parked there darning our stay
https://www.theboathousemarina.com/

Instead of VRBO or AirBnB we rented from: https://rentalsfloridakeys.com/

Note, this was our first time in the Keys and all we absolutely loved it. I can't wait to go back