Week long vacation?
-Beach
-some warmth
-cigar friendly
-two 50 year olds traveling, no kids
-decent food and drink
-walk friendly
-safe

Thoughts?

My first choice would be Tampa/Ybor City...…..then a hop skip and jump on down to Sanibel Island for those gorgeous sunsets

Wife and I very much enjoyed St. Augustine. Plenty of nice pubs, plenty of souvenir shopping, good restaurants... beaches... alligator farm...and an old military fort.

Destin

Destin

St. Augustine rocks. The UDT/SEAL museum in Fort Pierce is a must hit also. For the squid types anyway. 🍺

When? The time of year matters.

To keep with a big city, it's hard to beat South Beach. Close to Little Havana and a couple hundred other cool things. Plus, there are these trams that are pretty neat that can take you to a few locations. Great food at tons of places. I would NOT go out at night, however. Got lost a couple times in some neighborhoods that seriously worried me. Ft. Lauderdale a bit up the coast is also nice. For maximum fun, my wife and I love Key West. If I had the money and health, I'd move there. Spent our first anniversary there and have been back twice since. Couple of very nice beaches on the Atlantic side, great snorkeling offshore and if you buy a ride on a dive boat, it's even more amazing. You can spend a ton or go cheap(ish). Even the graveyard is interesting and fun (seek out a Park Ranger for a map, even better). Tons of historic stuff, great places to walk (even the main streets in the heart of town). The island is the polar opposite of uptight, and plenty of good food (especially seafood). You can fly or boat from Miami, but if you have the time, drive it. Amazing drive (day time...night driving there sucks...idiot drivers and tiny deer, plus you'll miss the view). IIRC, it's about a half day drive from Miami if traffic is OK and you take a couple breaks. Google says 165 miles. Motels on the north end are usually cheaper, and it's really not far to the south end (although you'll want to ride/drive, not walk that entire way). For return, my wife and I came back the night before flight to stay at the airport hotel in Miami. Expensive, but how many times do you get to jet out the door and take an elevator down to TSA lines? Pay the extra, sleep more.

End of February. Good call out. Imagining Destin would be a little nippy.

Yeah prolly will. Didn’t know it would be in Feb.

If tou make it to St Petersburg stop by the Undertow for a couple beers... very nice scenery when I was there.. there's a cool fort there too... 🍺

I thought tampa also but the keys are pretty nice

Yep... Key West is pretty damn nice. Took my wife there for her birthday in 2015. We went to a fancy restaurant on Sunset Key; we had to take a boat to get to it.

Or maybe it was so I could go charter fishing for Mahi? Whatever. We had fun. I caught a bunch of Mahi and we cooked Mahi burgers in our hotel room. The Navy Lodge has full kitchens, pots, pans, dishes, utensils, etc. Commissary/exchange right across the street.

Loved Key West and the Duval Crawl.

Lots of chikens running around Key West... 😟

Yes, Destin is a vacation destination for the Japanese in February, but there's nothing wrong with that.
No need to get vulgar...

34 craft breweries in Tampa Bay Area........just sayin'.

For the recluse looking for remote quiet beaches - search south of Bay along Gulf. Google Earth gives you a good idea of concrete to nature ratio.

I heard Drafter is thinking about moving to Key West.

Destin is more Lower Alabama than Florida

The Keys are nice. I was there for a week back in 2016 and had a blast.