Road trip to Florida stops

Judi Travel CaricatureI’m back after a month away and am excited to share highlights from my first-ever road trip to Florida. Get ready, because I’m going to share details — from the planning of each stop driving south, to the 30 days my boyfriend L and I spent in our Airbnb beach cottage in Naples, including the restaurants where we dined outdoors , the beaches where I hunted for shells, and some of the area’s popular attractions we visited during our extended stay in the sunshine state.

Plus, I’ll give you a peek at what it’s like to take Amtrak Auto Train from Sanford, FL to Loudon, VA. It was our first time using this method of transportation. Needless to say there were laughs along the way as well as learnings to remember for the future.

Judy in Naples on the beach

I’m back from my road trip to Florida and can’t wait to share the details

Best of all — after a month of cohabitating, L and I are still together. What are those five C’s of a good relationship? Oh yes, commitment, compromise, caring, companionship, and communications. We practiced each one and smoothed over rough edges when our male and female personalities and daily habits clashed. In the end, all was and remains pretty good.

While I’ll be writing several blog posts about my Florida trip, for now let’s begin at the beginning…

Making a decision to go to Naples for a month

The past winters L and I have been exploring different parts of Florida’s Gulf Coast from St. Petersburg and  Sarasota to Sanibel Island and Bonita Springs. All are nice places and we thoroughly enjoyed each city and its beaches.

Last year, while in Bonita Springs, we visited Naples. There was a fabulous Whole Foods in the Mercato Shopping Center in the North end. At the time, we both chimed in unison: “This Whole Foods is so great we could live here.”

Mercato sign in Naples, FL

Whole Foods Market at Mercato in Naples is fabulous for takeout meals

As summer of pandemic 2020 came to a close at my condo on the corner at the New Jersey shore, we missed the warmth and walks on the beach. In September, with Covid-19 still raging, a vaccine far distant, and flying a non-option, we began to consider other alternatives for our annual Florida vacation. Since L can work from home and I’m retired, we decided to look for a place where we could stay a full month. It would be a good test to see what being a Florida snowbird would be like during life after 60.

Finding a place to stay

I contacted local realtors recommended by friends. Everything was booked. Most rentals require a three month stay. Finally, I went on AirBnb and looked at condos and small homes in different Florida cities to see what was available for February to March. I combed through all the listings along the Gulf Coast, reading reviews and looking at pictures.

Breezy Seashell Cottage in Naples Park

Our Breezy Seashell Cottage in Naples Park was decorated with beachy accessories

Then I saw it!  “Breezy Seashell Cottage with coastal decor. 2 bedrooms and 2 full baths. Clean linens and comfortable queen size beds. Bike or walk to the beaches of Vanderbilt or Delnor Wiggins State Park. Less than 1 mile to Mercato, an outdoor shopping/dining venue. Also nearby to Whole Foods, Trader Joes, and other grocery stores. Restaurants within a mile include fine dining as well as fast casual and ice cream, 2 bicycle beach cruisers.”

It fit all my criteria – 2 bedrooms, 2 bathrooms, near the beach, and drum-roll please…nearby Whole Foods. I knew this was the one. But would it be available? Another drum-roll please. Click, click, click. Early February dates were already taken. Click, click, click – mid-February to mid-March was available. It was expensive when you added in the 12% Florida tax on all rentals.

Beach cottage dining area

I knew I found the right place to slow down when the sign said RELAX

Should we, could we, would we? L and I looked at each other and we knew that this was the spot. “Let’s do it!” we both cried out as our smiles grew wider. Click, click, click.  No looking back, we were going to spend a month in Naples in winter 2021!

Planning my first-ever road trip to Florida

Now that we had found our home away from home for one of the coldest months of winter 2021, we were ready to plan our road trip to Florida. I researched routes from New Jersey to Florida (down I-95), determined hours to drive each day (some make the trip in two days, not me, no more than six hours in the car each day is my limit), and popular stops along the way. By November, I had booked hotels for each leg of our journey on

As the trip grew closer, I made a packing list. I found large duffel bags at which accommodated our clothes and accessories and fit perfectly in the truck of the car. Keeping the pandemic in mind, I brought healthy snacks and beverages in a cooler so we wouldn’t have to make as many stops. Of course, I brought plenty of masks and we used them whenever we went inside for a bathroom break.

Large Duffel Bag

Two large duffel bags fit perfectly in the truck

VIP Sale! Extra 30% off + 15% off Beauty with code VIP. Shop now at! Valid 3/26-4/4

First stop Rocky Mount, South Carolina

It was an easy six hour ride to Rocky Mount, South Carolina, where we had our first overnight. We were pleased with the cleanliness at Homewood Suites By Hilton Rocky Mount. It was just off the highway and we appreciated Hilton’s Clean Stay Program during the pandemic. Since we aimed to play it safe, we ordered takeout dinners from the Outback Steakhouse nearby and ate in our suite.

Rocky Mount sign

Our first stop was Rocky Mount, North Carolina

Next stop Savannah, Georgia

We left Rocky Mount early the next morning for another five hour drive to Savannah, Georgia. Unfortunately, the weather did not cooperate that day. It was chilly and stormy the entire way to Savannah. What was supposed to be a lovely first-time visit to Savannah ended up being a very soggy one. There would be no walking tour of the historic district or dining outdoors for Valentine’s Day.

Savannah River Walk

It was so rainy in Savannah that our River Walk View from the hotel was hazy

Exhausted and weary, we decided to cut our stay at Homewood Suites Savannah Historic/Riverfront short and use Uber Eats to deliver a takeout dinner.

“I’ll have to see Savannah next road trip,” I said to L. “Since it’s so wet outside, let’s head to St. Augustine tomorrow. That way we’ll have less of a drive to Naples on Monday.” Easy-peasy, came to the rescue and we were able to find a hotel in St. Augustine for the following evening.

Off to St. Augustine, Florida

St. Augustine had long been on my “places to visit in Florida” list, so I was glad to be stopping there. Unfortunately, we experienced more stormy weather and weren’t able to do much sightseeing. (Definitely hope to get back to St. Augustine.) After another exhausting five hour drive, we rolled into TRYP Wyndham Sebastian St. Augustine close by the historic downtown.

St. Augustine sign

Re-routing due to bad weather brought us to St Augustine

“Eat at Sunday,” said my son D who had visited St. Augustine the year before. We were lucky to find outdoor seating but by the time our lunch was ready the sky was ready to open up too. Takeout became our request of the hour and Uber Eats our call for in-room dining service that evening.

Final stretch to Naples, Florida

Naples Park home

We were so glad to reach our destination in Naples

By Monday, we were so glad to feel the sun on our back and be on the last leg of our road trip to Naples. In about four or so more hours we would arrive at Breezy Seashell Cottage. It had been a tiring few days to our destination. Now we were ready to slow down and settle in for the next month and find out why Naples was voted one of the happiest and healthiest cities to live in the U.S.A. and ranked #4 in this year’s U.S. News “Best Places to Retire in the U.S. in 2020-2021”

Can you guess the first place we went that night? Aww, I bet you know. “Let’s get takeout from Whole Foods,” we both declared with glee.


Note: This post contains affiliate links. If you purchase a product from the link a portion of the sale will be shared with me to help support my blog. Thank you.