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Exploring South FL
Old 02-03-2019, 02:09 AM   #1
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Exploring South FL

We live in So CA but would like to consider spending winters somewhere with beautiful beaches and warm water. The only option in the continental US that is warm enough for us is South FL. We originally thought weíd rent a place and snowbird from one base, but then realized that weíd prefer to go from place to place. Weíre thinking of checking out the Keys, the East Coast up to Vero Beach, and the West Coast around Naples.

Is it practical to find places to stay on the fly during the winter? We are willing to be flexible on location, views and amenities, as long as we can get around to all the areas we want to experience. I thought everything might be booked in advance but I looked on Airbnb, VRBO, and Trip Advisor today and surprisingly it seemed that places in many locations were available immediately. Maybe itís easier to book for a few nights than a few months?

However, we donít want to get stuck with nowhere to stay. Iíd love to hear from others who have tried or done this how it has worked out for you. Thanks!
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Old 02-03-2019, 07:01 AM   #2
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DW and I have done this. It can be hard to find nice places close to beaches but you can always find something. We found short term units that would accept our dogs at Courtneys in Key West on short notice. We also found a one week rental that came available at at The Truman Annex in Key West on short notice.
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Old 02-03-2019, 08:10 AM   #3
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You may want to do more research on Naples. Beautiful area with lots of old and new money. Hurricane Irma 2 years ago made landfall as a Cat 4 hurricane. Naples and especially Marco Island got wrecked.
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Old 02-03-2019, 08:30 AM   #4
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I was in Naples last summer, most everything looked fixed. 5th avenue was totally normal for dinner/shops. Botanic gardens might have been whacked a bit. Beaches fine.

OP I'm sure you'll find places on short notice, but not necessarily the nicest ones. Depends if you are looking for resort-y stays in walking-distance to key spots, or ok with more 3* ish.
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Old 02-03-2019, 08:58 AM   #5
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We spent a month doing the east coast and the next year another month doing the west coast after we retired. I recommend you do the same.

After doing home swaps into SoCal, we ended up buying in PV MX.

(We have friends from Chicago who own in Vero Beach who are going to buy in PV if they can sell their condo. Cost of living is their primary driver.)
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Old 02-03-2019, 10:59 AM   #6
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DW and I have done this. It can be hard to find nice places close to beaches but you can always find something. We found short term units that would accept our dogs at Courtneys in Key West on short notice. We also found a one week rental that came available at at The Truman Annex in Key West on short notice.


Thatís good to hear. We had assumed we wouldnít be able to take our dog as the supply of dog-friendly places is much smaller. If you were going to do this again, would you take your dogs? We will have to cut our trip shorter if we leave ours at home ... wouldnít want to leave him for 2 months.
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Old 02-03-2019, 11:00 AM   #7
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I was in Naples last summer, most everything looked fixed. 5th avenue was totally normal for dinner/shops. Botanic gardens might have been whacked a bit. Beaches fine.

OP I'm sure you'll find places on short notice, but not necessarily the nicest ones. Depends if you are looking for resort-y stays in walking-distance to key spots, or ok with more 3* ish.


This is good to hear. Normally we prefer places in great locations but in this case we value flexibility more so we are willing to stay in less desirable locations.
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Old 02-03-2019, 11:02 AM   #8
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We spent a month doing the east coast and the next year another month doing the west coast after we retired. I recommend you do the same.



After doing home swaps into SoCal, we ended up buying in PV MX.



(We have friends from Chicago who own in Vero Beach who are going to buy in PV if they can sell their condo. Cost of living is their primary driver.)


Did you prearrange lodging or just move around spontaneously?
I think PV is beautiful but the beaches there are not like FL or the Caribbean.
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Old 02-03-2019, 11:33 AM   #9
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I just got back from Fort Myers Beach last night. Itís about an hour drive from Naples. Nice area, but I left 80 degree weather in So Cal and ended up spending most of the week in Florida dealing with rain and weather in the 50ís and 60ís. It did warm up the last day we were there.

But the thing I noticed most is how horrible the traffic is down there. Iím told the snowbirds descend on the area and stay until around the first week of April. Everything was super crowded and it could take fifteen minutes just to drive a mile down the road. So Iím not sure I would enjoy being a Florida snowbird that much. Especially if I was coming from So Cal, where the weather may be just as nice as Florida.
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Old 02-03-2019, 11:51 AM   #10
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I just got back from Fort Myers Beach last night. Itís about an hour drive from Naples. Nice area, but I left 80 degree weather in So Cal and ended up spending most of the week in Florida dealing with rain and weather in the 50ís and 60ís. It did warm up the last day we were there.

But the thing I noticed most is how horrible the traffic is down there. Iím told the snowbirds descend on the area and stay until around the first week of April. Everything was super crowded and it could take fifteen minutes just to drive a mile down the road. So Iím not sure I would enjoy being a Florida snowbird that much. Especially if I was coming from So Cal, where the weather may be just as nice as Florida.
Not sure of your age or driving abilities, but my ex boss, now retired, snowbirds to southern Florida. He says that if you want to beat traffic, go out after dark. Apparently, enough of the older drivers donít like driving at night or are in bed early.
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Old 02-03-2019, 11:55 AM   #11
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But the thing I noticed most is how horrible the traffic is down there. Iím told the snowbirds descend on the area and stay until around the first week of April. Everything was super crowded and it could take fifteen minutes just to drive a mile down the road. So Iím not sure I would enjoy being a Florida snowbird that much. Especially if I was coming from So Cal, where the weather may be just as nice as Florida.
When I lived in S FL, I liked the off season just for this reason.

Weather is tough in off season, though.

The suggestion for after dark is OK, but keep in mind other stuff like going to the grocery store or booking golf are crowded too during the season.
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Old 02-03-2019, 12:08 PM   #12
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Take a look at Sarasota area (Anna Maria Island, Longboat Key, Siesta Key). Lots to do. Quite beautiful. KG
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Old 02-03-2019, 12:16 PM   #13
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Take a look at Sarasota area (Anna Maria Island, Longboat Key, Siesta Key). Lots to do. Quite beautiful. KG

I would suggest Anna Marie Island or Bradenton Beach .I have lived in Florida for 22 years and January is our worst month weather wise .The traffic is terrible Jan, thru early April.If you are on Anna Marie Island or Bradenton Beach you can bike to everything plus they have a free trolley that covers the island .
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Old 02-03-2019, 12:26 PM   #14
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I thought everything might be booked in advance but I looked on Airbnb, VRBO, and Trip Advisor today and surprisingly it seemed that places in many locations were available immediately.

Many VRBO owners DO NOT update their calendars, and when you try to book their property, you will often get a 'Sorry it's already rented'. This happens especially in South Florida, where their units are booked for the entire winter and they leave their listing there for bookings in the spring and summer and are too lazy to update the calendar.


But, you should have no trouble booking a hotel 'on the fly'.....
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Old 02-03-2019, 12:29 PM   #15
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You may want to do more research on Naples. Beautiful area with lots of old and new money. Hurricane Irma 2 years ago made landfall as a Cat 4 hurricane. Naples and especially Marco Island got wrecked.

Hardly any damage from the hurricane.... Where did you get the information that Naples and especially Marco 'Got Wrecked'? --- There were warnings, but the hurricane pretty much dissipated when it got to shore.
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Old 02-03-2019, 12:34 PM   #16
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Hardly any damage from the hurricane.... Where did you get the information that Naples and especially Marco 'Got Wrecked'? --- There were warnings, but the hurricane pretty much dissipated when it got to shore.
Were you on Marco Island during Irma? Neighbor of mine condo was heavily damaged and flooding due to 130 mph winds.
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Old 02-03-2019, 12:38 PM   #17
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I just got back from Fort Myers Beach last night. Itís about an hour drive from Naples. Nice area, but I left 80 degree weather in So Cal and ended up spending most of the week in Florida dealing with rain and weather in the 50ís and 60ís. It did warm up the last day we were there.

But the thing I noticed most is how horrible the traffic is down there. Iím told the snowbirds descend on the area and stay until around the first week of April. Everything was super crowded and it could take fifteen minutes just to drive a mile down the road. So Iím not sure I would enjoy being a Florida snowbird that much. Especially if I was coming from So Cal, where the weather may be just as nice as Florida.
With many snowbirds that enjoy and support the local economy, they also bring their careful driving habits.
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Old 02-03-2019, 12:45 PM   #18
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I just got back from Fort Myers Beach last night. Itís about an hour drive from Naples. Nice area, but I left 80 degree weather in So Cal and ended up spending most of the week in Florida dealing with rain and weather in the 50ís and 60ís. It did warm up the last day we were there.

But the thing I noticed most is how horrible the traffic is down there. Iím told the snowbirds descend on the area and stay until around the first week of April. Everything was super crowded and it could take fifteen minutes just to drive a mile down the road. So Iím not sure I would enjoy being a Florida snowbird that much. Especially if I was coming from So Cal, where the weather may be just as nice as Florida.
Surprisingly, that was my takeaway after recently visiting the Miami area. The traffic in SoCal can be bad, but in the Miami area, it's broke. Never thought it would be such a negative, but it was.
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Old 02-03-2019, 12:48 PM   #19
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Were you on Marco Island during Irma? Neighbor of mine condo was heavily damaged and flooding due to 130 mph winds.

While there was certainly some damage to the area, to say that Naples and Marco island 'got Wrecked', and that it should change travel plans, it overstating the damage... I've got countless friends in the area that own homes and the hurricane did not affect them at all.


Naples and Marco island are 'Open' for Business.
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Old 02-03-2019, 02:53 PM   #20
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You may want to do more research on Naples. Beautiful area with lots of old and new money. Hurricane Irma 2 years ago made landfall as a Cat 4 hurricane. Naples and especially Marco Island got wrecked.
You'd be hard-pressed to know that this area (Naples/Marco) was hit by Irma. The only clue is a few blue tarps on roofs (usually due to a lack of tiles and/or labor.) Other than that, it's "all systems are go." C'mon down.

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