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Planning a trip from New York to Florida Keys on retirement

Planning a trip from New York to Florida Keys on retirement

Old Feb 14th, 2024, 08:18 AM
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Planning a trip from New York to Florida Keys on retirement

Since this is my first post, I'm hoping that I do this correctly - that it ends up in the area that it should be in. If not, please forgive me.
Anyway, my wife and I are planning a sight-seeing automobile trip from New York to Florida Keys upon her retirement in the near future
(actually, from California to New York to Florida Keys, but for now I'm only thinking about the New York to Florida Keys portion).
I guess in my mind I'm going back to family trips I used to go on as a kid in the 1950's which were extremely enjoyable, and which, I was hoping to recreate for my wife.
During those trips, we usually stayed at small family-owned motels that were quite clean, safe, often having their own family run restaurant close-by, but not being within city center.
Unfortunately, in researching the options available, I have not been unable to find any like that, but only chain hotels which I'd rather not stay at.
So, my question is this: does such a thing still exist or of a bygone era?
Any recommendations/advice would be greatly appreciated.
While I don't want to throw away money unnecessarily, cost and time are not really issues.
Thanks in advance for your help.

Last edited by rogergx; Feb 14th, 2024 at 08:21 AM.
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Old Feb 14th, 2024, 08:54 AM
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Welcome to Fodor's! Your post is perfect and in the right location

I enjoyed the Florida Keys very much but too long ago to comment specifically on hotels/motels. We did stay at Mom and Pop places that were available at the time on various keys.

Hopefully others with current experience will chime in soon.
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Old Feb 14th, 2024, 09:11 AM
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Thank you, suze, for replying.
rogergx.

Last edited by rogergx; Feb 14th, 2024 at 09:14 AM. Reason: addition
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Old Feb 14th, 2024, 09:48 AM
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I remember staying at those independent motels when our family traveled in the West visiting the national parks. I found this website which lists mom and pop motels, inns, hotels and bnbs. Home - Mom and Pop Motels A few of the listings are old-fashioned independent motels
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Old Feb 14th, 2024, 11:18 AM
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I too made plenty of road trips from the NY/NJ area to Florida with my parents in the 1950’s and stayed is many independent “mom & pop” motels. If my memory is correct there we not many national chains at that time but there were a few hotel/motel associations to which the independent motels belonged that acted as “reservation and recommendation” purposes. Quality Inns and AAA were 2 such organizations. As the Interstate Highways expanded and became the main routes of travel they bypassed the towns and cities where the mom & pop places were located. As a result the chain motels and hotels grew in popularity and the mom & pop places near the Interstates either converted to a chain unit or closed up entirely. Those that still exist tend to be located near the center of towns and cities not near the Interstates. While mom & pop motels can be found it takes a lot of research to locate them.

Getting back to road trips in the 1950’s, if you are getting close to or past retirement age and are like me I think that our memories play tricks on us. You are looking through the eyes of someone who was perhaps 5 or 10 years old. At that age, everything seemed bigger and better that it really was and families spent more time actually socializing, talking and interacting with one another rather than being on their computers and smartphones texting each other or surfing the internet.

That doesn’t mean you can’t still enjoy a road trip. Plan your trip so you make your stops in areas where there are interesting places rich in history to visit. Between NY and Florida there are places like Washington, DC, Colonial Williamsburg, Va, Charleston SC, Savannah, Ga, St. Augustine, FL, to name a few. It’s the places visited, not the motels where you slept that the things that make lasting memories.
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Old Feb 14th, 2024, 12:03 PM
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Thank you for the information.
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Old Feb 14th, 2024, 12:48 PM
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Yes, Quality Inns and AAA were exactly what we looked for when searching out a motel for the night and were always happy with the results - and now that you've mentioned it, it brings back a lot of fond memories for me. I was within the 5 - 10 YO range then, so I might well be remembering through rose-colored glasses, but from my perspective now, IMHO, it seems to have been a far better time to have grown-up and to have seen the US in than now.
We are definitely planning a stop at the places you've mentioned above as they are all very rich in American history that being one of major reasons we want to go. My wife has never had an opportunity to visit them before, plus, I'll give the fountain of youth another try in St. Augustine Fl. - you never know, I just might get lucky this time.
Thanks for your reply.






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Old Feb 14th, 2024, 03:31 PM
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Who remembers these signs counting down the miles to South of the Border?
Back then the family wagon had what we called 4-60 AirConditioning. 4 windows down, 60mph....



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Old Feb 14th, 2024, 03:53 PM
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Originally Posted by RoamsAround
That doesn’t mean you can’t still enjoy a road trip. Plan your trip so you make your stops in areas where there are interesting places rich in history to visit. Between NY and Florida there are places like Washington, DC, Colonial Williamsburg, Va, Charleston SC, Savannah, Ga, St. Augustine, FL, to name a few. It’s the places visited, not the motels where you slept that the things that make lasting memories.
Excellent point. There are some wonderful historic places between NYC and Miami. I might add Fernandina Beach on Amelia Island which has 50 blocks of historic buildings housing restaurants, bed ‘n’ breakfasts, and boutique shops. Check out the cozy Book Loft, a famous independent bookstore (it has 1,500 rare books).
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Old Feb 14th, 2024, 05:59 PM
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Originally Posted by J62
Who remembers these signs counting down the miles to South of the Border?
Back then the family wagon had what we called 4-60 AirConditioning. 4 windows down, 60mph....


South of the Border - one of the most iconic tourist traps in the country. I remember there was a sign on Rt. 4 in Fort Lee, NJ a mile or so from the George Washington Bridge saying South of the Border was 650 or so miles away. Ever since my first road trip to Florida in the early 1950’s I wanted to stop there but my father wouldn’t even entertain the idea. It wasn’t until 1972 when I made the drive with my wife that I actually stopped there. It wasn’t worth the wait.
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Old Feb 14th, 2024, 11:26 PM
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https://www.reddit.com/r/GenX/commen...travel_advice/

Remember triptiks from AAA? You can still get them and it might make for a fun memory for your trip.

When do you plan on taking this trip?
How long will you have to do the trip?
Do you want to do a lot of meandering off the route or stick pretty much to a fairly direct route, just seeing what is logistically easy? You mentioned the old Mom and Pop roadside motels. There are still many places along old routes that are more beautiful than the highways, so you could veer off just slightly and enjoy those for a lot of the trip.
Perhaps start making some lists now, one of historic, unique or beautiful places you want to see on the way, one of places to stay (Airbnb’s, etc.), a list of restaurants to try along the way and alternate scenic routes to avoid boring Highways. There are so many things to see, it could take months, but what a lovely thing to plan.
Are you ready to start collecting ideas yet?
There are still a number of small motels along route one, North of Fredericksburg and in the Shenandoah area. Some are reviewed on Trip Advisor. Some even have pools, some have little restaurants, so would be nice in Summer. I bet there are a few people here who could even make recommendations.
It would be beautiful to do your trip when all the Dogwoods, Azaleas, etc. are blooming in the Carolinas.

Last edited by Sassafrass; Feb 15th, 2024 at 12:06 AM.
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Old Feb 15th, 2024, 02:54 AM
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Welcome to Fodors and congratulations to your wife on her upcoming retirement. A couple of quick questions:

Since this is a road trip, how many hours per day do you want to spend driving? Do you want to keep it to just a few hours a day or perhaps mix some longer driving days with short trips? Do you already have your top 10 list of things you want to see/do?

Re motels, have you looked at this book? https://guide.michelin.com/us/en/art...he-us-michelin
Or this? Home - Mom and Pop Motels you might find something useful in these.
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Old Feb 15th, 2024, 10:53 AM
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My husband and I drive from NY to Florida for winter vacations quite frequently. Most of the older mom and pop motels are long gone and many closed during the pandemic. There are many chain hotels and if you are not members of any brands such as Hilton, Marriott or Hyatt, you should join. There is a family motel that we have stayed at in Santee, SC called Clark's Inn. They have a lovely restaurant for dinner and inexpensive accommodation. Pre-pandemic they also included a home cooked full breakfast. When we stayed there post-pandemic, they could not continue with that and we didn't stop there this recent trip but I do see that they once again offer that option.

In terms of places to stop and tour heading from NY, of course there is Washington, DC which we always enjoy visiting and touring. We have stopped and toured Richmond VA to visit the State Capital which is Thomas Jefferson designed as well as the Holocaust Museum and the Virginia Museum of Fine Arts with outstanding collections. We have been to Savannah numerous times as well as Charleston, SC. We once visited Charlottesville, VA on our return trip which is not immediately off I-95, but so worth seeing. We had a day at Monticello as well as time to walk around the campus of the University of Virginia, also designed by Thomas Jefferson. In Florida we have visited both St Augustine with the historic fort that is similar to El Morro in Puerto Rico. We have visited Sarasota on the West Coast and Miami on the East Coast and last year we had a family wedding in Miami and so we had a quick trip through the Keys. The drive from Miami to Key West is doable but longer than you might expect and not as scenic as you would anticipate as it is the primary road and so there are strip malls, supermarkets, churches, schools, boatyards, medical buildings and so on. We lucked out with no accidents but as the only road, accidents and traffic can be problematic, along with torrential downpours. In Key West, we did visit both the Hemingway House and the Truman Little White House as well as walking around at the quaint Key West architecture. If you want to go to the Dry Tortugas National Park you must book far in advance as the only ways to get there are seaplane or ferry as it is 70 miles west of Key West itself.
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Old Feb 15th, 2024, 01:53 PM
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Sassafrass,

Probably looking to start out sometime in the spring/summer of 2025, if the good Lord is willing. Since we'll both be retired then, we won't have a schedule to limit us but will use the "whatever we want to do whenever we want to do it" approach - so our journey will be open entirely. We are just beginning to think about it/planning it, with that actually being a big part of the adventure but nothing has been set yet. So, yes, we are definitely ready to start collecting ideas and suggestions.
And thank you for mentioning the small motels along route 1, as those are the types of things we are looking to experience. We were kinda thinking I-95, but route 1 sounds better.
Even now, I can recall the cherry blossoms in DC. Dogwoods, Azaleas will be great too and we're looking forward that my wife will have an opportunity to experience them - she's a California girl born and bred.
Thank you for the suggestions.
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Old Feb 15th, 2024, 02:05 PM
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Originally Posted by Madam397
My husband and I drive from NY to Florida for winter vacations quite frequently. Most of the older mom and pop motels are long gone and many closed during the pandemic. There are many chain hotels and if you are not members of any brands such as Hilton, Marriott or Hyatt, you should join. There is a family motel that we have stayed at in Santee, SC called Clark's Inn. They have a lovely restaurant for dinner and inexpensive accommodation. Pre-pandemic they also included a home cooked full breakfast. When we stayed there post-pandemic, they could not continue with that and we didn't stop there this recent trip but I do see that they once again offer that option.

In terms of places to stop and tour heading from NY, of course there is Washington, DC which we always enjoy visiting and touring. We have stopped and toured Richmond VA to visit the State Capital which is Thomas Jefferson designed as well as the Holocaust Museum and the Virginia Museum of Fine Arts with outstanding collections. We have been to Savannah numerous times as well as Charleston, SC. We once visited Charlottesville, VA on our return trip which is not immediately off I-95, but so worth seeing. We had a day at Monticello as well as time to walk around the campus of the University of Virginia, also designed by Thomas Jefferson. In Florida we have visited both St Augustine with the historic fort that is similar to El Morro in Puerto Rico. We have visited Sarasota on the West Coast and Miami on the East Coast and last year we had a family wedding in Miami and so we had a quick trip through the Keys. The drive from Miami to Key West is doable but longer than you might expect and not as scenic as you would anticipate as it is the primary road and so there are strip malls, supermarkets, churches, schools, boatyards, medical buildings and so on. We lucked out with no accidents but as the only road, accidents and traffic can be problematic, along with torrential downpours. In Key West, we did visit both the Hemingway House and the Truman Little White House as well as walking around at the quaint Key West architecture. If you want to go to the Dry Tortugas National Park you must book far in advance as the only ways to get there are seaplane or ferry as it is 70 miles west of Key West itself.
Thank you for the suggestions Madam397. Somehow, I accidently posted to you something I had intended to be to someone else - these new-fangled gadgets always mess me up, so please ignore it.
I'll reply to you more fully to you as soon as I can get my error squared-away - sorry about that.

Last edited by rogergx; Feb 15th, 2024 at 02:11 PM.
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Old Feb 15th, 2024, 02:13 PM
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Hi Weisser Tee,
We are pretty much open as to how many hours per day we want to spend driving but mixing it up sounds good.
No, we do not yet have our top ten ready yet but are beginning to formulate them now.
And thanks for the link for the Mom and Pop Motels, I wasn't aware that one existed, but will definitely start immediately perusing it.

Thanks for your reply.
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Old Feb 16th, 2024, 10:25 AM
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Originally Posted by Madam397
My husband and I drive from NY to Florida for winter vacations quite frequently. Most of the older mom and pop motels are long gone and many closed during the pandemic. There are many chain hotels and if you are not members of any brands such as Hilton, Marriott or Hyatt, you should join. There is a family motel that we have stayed at in Santee, SC called Clark's Inn. They have a lovely restaurant for dinner and inexpensive accommodation. Pre-pandemic they also included a home cooked full breakfast. When we stayed there post-pandemic, they could not continue with that and we didn't stop there this recent trip but I do see that they once again offer that option.

In terms of places to stop and tour heading from NY, of course there is Washington, DC which we always enjoy visiting and touring. We have stopped and toured Richmond VA to visit the State Capital which is Thomas Jefferson designed as well as the Holocaust Museum and the Virginia Museum of Fine Arts with outstanding collections. We have been to Savannah numerous times as well as Charleston, SC. We once visited Charlottesville, VA on our return trip which is not immediately off I-95, but so worth seeing. We had a day at Monticello as well as time to walk around the campus of the University of Virginia, also designed by Thomas Jefferson. In Florida we have visited both St Augustine with the historic fort that is similar to El Morro in Puerto Rico. We have visited Sarasota on the West Coast and Miami on the East Coast and last year we had a family wedding in Miami and so we had a quick trip through the Keys. The drive from Miami to Key West is doable but longer than you might expect and not as scenic as you would anticipate as it is the primary road and so there are strip malls, supermarkets, churches, schools, boatyards, medical buildings and so on. We lucked out with no accidents but as the only road, accidents and traffic can be problematic, along with torrential downpours. In Key West, we did visit both the Hemingway House and the Truman Little White House as well as walking around at the quaint Key West architecture. If you want to go to the Dry Tortugas National Park you must book far in advance as the only ways to get there are seaplane or ferry as it is 70 miles west of Key West itself.
Hi Madam397,
Sorry about my foul-up regarding my last reply to you. Anyway, thank you for pointing out the many things that will be available for us to do on our upcoming trip. They all sound fantastic and make me want to start it tomorrow.
We will definitely include all of them on our to-do list. It is always great to get first-hand knowledge and experiences from someone who's done them.
Thank you very much.

Last edited by rogergx; Feb 16th, 2024 at 10:33 AM.
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Old Feb 16th, 2024, 08:50 PM
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Quite a few people drive their cars to Lorton Virginia which is a few miles south of Alexandria. They load their cars on the Amtrak Auto Train. It is an overnight trip on the train and you arrive with your car in Sanford Florida not too far from Orlando. The number to call about the auto train is 1-800-SKIPI95. When you consider the cost of gas and a night or two in motels, It is something to consider.
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Old Feb 17th, 2024, 02:05 AM
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Hi tomfuller,

Wow, what a great idea! I wasn't aware that such an option existed.
Another one to add to our to-do list.
Thank you.
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Old Feb 17th, 2024, 03:14 AM
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And these might be snowbirds from NYC who don't drive a block any more but want their car in Florida for the six months they are there. And as you see from the many who have answered you there is an incredible amount to actually SEE along the coast.
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