Planning for an 8 week long road trip to the American South: Yay, another road trip!


Coligny Beach Park, Hilton Head Island, SC

When my wife and I were thinking about where to spend our winter months during the winter of 2023, we had several options.  We could rent another month long (or longer) stay at an AirBnB or similar, stay at my brother-in-law’s place in North Carolina for about 6 weeks then travel for about 6 weeks, or travel for longer than 6 weeks.

In the end, we settled on traveling using hotels rather than AirBnB’s for the duration of 8 weeks.  We usually have to make our way to North Carolina to get stuff done (vehicle registration, vehicle inspection) as that is our official domicile.  As early retirees and nomadic travelers, we don’t rent or have a permanent residence of our own.

Instead, we rely on my brother-in-law to provide his place of residence as our official address for everything including driver’s license, vehicle registration, vehicle insurance, health insurance, etc.  On top of that, we stay with them from time to time at their place while we get our routine health checks, dentist appointments, and such done.  

For the year 2023, we stayed at his place for roughly 4 months as he needed our help while he was selling his house and to take care of his cat babies, one of which is a recently adopted stray kitten who needed frequent vet visits for things like checkups, vaccinations, and spaying.  We certainly didn’t mind, as he needed our help and we really love our cat niece and nephew.

As we made our way down to his place again in late November, we still hadn’t made up our minds on what we wanted to do for the winter.  As much as we enjoy our family’s company, we also realized we needed some time for ourselves after spending 4 months out of the year at their place.

What solidified our schedule was when we heard my brother-in-law’s kids would be coming home for Christmas around December 18th.  We wanted their family to spend quality time together without having unwanted distractions (us).

It worked out perfectly as my travel focused and euphoric mind at the news of upcoming travel, went to work once we knew we needed to leave on the 18th of December.  We thought about places we wanted to visit and revisit, then put those down on paper (well, on an iPad to be exact).

We came up with the following destinations after careful consideration:

  1. Myrtle Beach, SC - to see our friends who live there and to stay with them (possibly 2-3 nights)
  2. Hilton Head Island, SC - to revisit it again after about 20 years; we had only stayed over 1 night back then, we planned on seeing much more than the first time (2-3 nights)
  3. Savannah, GA - to revisit the city again; we did a downtown trolley tour our first trip but wanted to see more (2-3 nights)
  4. Jekyll Island, GA - we wanted to see Driftwood Beach and the island itself (stopover on our way to Jacksonville)
  5. Jacksonville, FL - we never actually spent time in Jacksonville and wanted to see the city (2-3 nights)
  6. Destin, FL - we heard of the incredibly beautiful turquoise waters of the Gulf Coast beach and wanted to spend couple of nights there (2 nights)
  7. Gulf Shores, AL - didn’t know much about the place except that it has a nice resort town feel and a nice beach (3-4 nights)
  8. Mobile, AL - wanted to see the city (2 nights)
  9. Biloxi, MS - to revisit Beau Rivage as we get 3 free nights at this upscale MGM Resorts destination (3 nights)
  10. Providence Canyon State Park, GA - I came upon this wonderful place while researching places to visit in Georgia (stopover on our way to Atlanta)
  11. Atlanta, GA - my wife had never been to the city and wanted to spend some time there (3 nights)
  12. Helen, GA - there’s a German influenced town there and wanted to see it (2 nights)
  13. Knoxville, TN - we stayed one night there 20+ years ago on our way to Memphis, and wanted to see the city (3 nights)
  14. Pigeon Forge, TN - it’s next to Gatlinburg and wanted to see the Smoky Mountains again (3 nights)
  15. Asheville, NC - never been to the city; wanted to see Biltmore Estate (3-4 nights)
  16. Outer Banks, NC - we never actually stayed overnight there and wanted to see the Wright Brothers Memorial (3 nights)
  17. Williamsburg, VA - it had been over 25 years since our last visit there and wanted to see attractions we hadn’t seen the first time (3 nights)
  18. Ocean City, MD - one of our favorite places on the East Coast so close to New York and Pennsylvania; wanted to relax there for the most part after all these travels (3-4 nights)
  19. Annapolis, MD - we visited there with Toby (our Pomeranian) about 7-8 years ago and wanted to spend time there again (3 nights)

After coming up with the places we wanted to visit/revisit, we thought about lodging options for the trip.  In the beginning, we wanted to use Choice Hotels which we have used the previous winter road trip to a great extent.

However, after booking our first Choice Hotels branded hotel chain, Sleep Inn near Hilton Head Island/Savannah, I changed my mind soon thereafter, after learning about the questionable and at times bad reviews left by guests at that hotel.  I learned how bad the hotel condition was and how worse the hotel staff was.  Compared to Sleep Inns we used last winter, this was not what we expected.

The same day after reserving that hotel, I cancelled the reservation and started to look elsewhere.  I eventually found a newish hotel (5 years old) with sparkling reviews for Home2 Suites by Hilton at Hilton Head Island for only about $20 more per night.  I ended up booking that hotel for 5 nights instead of the 2-3 nights we had originally planned.  

I didn’t see hotels in our price range in Savannah downtown (under $100 or so), so we decided to stay 5 nights at Hilton Head Island to see both Hilton Head Island and Savannah.  After booking this hotel by Hilton, I thought about the Hilton hotels in earnest.

Sure, we used to be a member of Hilton way back and did use several of their hotels including the Hampton Inn and Hilton Hotel.  I had thought any Hilton hotels were out of our price range, so I hadn’t given serious consideration to using the Hilton hotels.

But after seeing the Home2 Suites for under $100 per night, my thoughts changed.  After researching their rewards program and their credit cards, we decided to open up a Hilton branded rewards credit card that automatically grants Gold member status and has many useful perks including getting 170,000 points after spending $3000 the first 6 months.

It was really a no brainer.  We knew Hilton hotels were class above (or two) from the Choice Hotels, and with all the points we’d be getting, it made sense to use Hilton hotels when situations allowed.  

In the end, we ended up using Hilton hotels for the most part, while still using a combination of Choice Hotels and other hotels using  When Hilton hotels were too expensive (usually over $100 per night or higher), we looked for cheaper options whenever possible.  If no other suitable options presented themselves, then we stayed with Hilton hotels to maximize points.

Packing clothes and other necessities 

We knew the trip would be 8 weeks long during the winter so we packed for just about every weather conditions including shorts, T-shirts, heavy winter jackets, and everything in between.  We took two bags per person for clothes, one bag for toiletries like toothpaste, floss, Listerine, and one other bag for kitchen stuff like knife, two cereal bowls, pair of spoons/forks, and emergency foods like granola bags, packaged mixed nuts, etc.

Because we wouldn’t be staying at AirBnB or similar, we left our usual assortment of kitchen tools like pots, pans, bowls, ladle, blender, as well as our go to items like Roomba, cleaning materials, etc.

Some of the many great things about staying at hotels is we don’t need to clean the place, nor cook our meals!  We can simply let the housecleaning staff do their work at check out and we can pick up takeout or eat at the hotel in many places.  

Our luggage was much lighter than even the prior year when we did a 10 week long road trip.  Last year, we packed way too much clothes, especially summer clothes which we thought we needed, but did not at all!

How we know whether or not we packed too much is when I can’t see through the rearview mirror from the driver’s seat.  This time around, I could see just fine and there was plenty of room left over in the back.

Budgeting for the trip 

We anticipated roughly $5000 for the 8 week long stay at hotels, $2000 for food, and $2000 for others like fuel, entertainment, tolls, entrance fees.  Like all good forward looking statements, we’ll probably be off somewhat once we tally up all our costs.

We’ll keep you posted!

In conclusion:

Traveling is just so contagious once you’ve experienced it.  I can’t wait to go on another as soon as one trip ends!  It has only been a year since our last long road trip, but that time felt like years…

There’s nothing quite like planning, thinking about, then wondering about all those places (both old and new).  Hotels, whether they’re a 5 Diamond rated ones or a 2 Diamond rated ones, still get me excited to experience something new.

Just staying at a motel or a hotel brings back good childhood memories of our family spending time together (although not often) at motel/hotel and making lifelong memories.  It’s still one of the best things about living these days, to experience a new place and enjoying new things and making new memories…

We were getting tired of staying at AirBnBs and frankly wanted a change from it.  We found hotels (last year’s Choice Hotels, and this year’s Hilton Hotels) so much better as we usually get free breakfast, sometimes evening receptions, and most importantly, safe environments to make new memories.  We look forward to using more of Hilton Hotels (and others at times) whenever situations allow.  

Please keep up with us as we travel through the great American South in the upcoming months, exploring such iconic places as Savannah, Hilton Head Island as well as great cities like Jacksonville, Mobile, and Atlanta.

Thank you for reading and happy trails!


Wandering Money Pig 

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