How we spent less than $300 and saved 85% on a week long vacation covering 4 states

budget, cut expenses, frugal, how we win, travel

The Winning Williams explored the beautiful mountains and Blue Ridge Parkway surrounding Asheville, North Carolina at the end of October. Following three beautiful days hiking through the mountains, immersed by fall foliage and its golden and rosy colors, we headed to the striking streets of Savannah. This was this the first of two days exploring and experiencing the charming and historic southern cities, with a day and evening sightseeing St. Augustine capping off the vacation. We then drove the 2017 Kia Optima rental car back to Tampa, ending the journey.

There were six hotel nights, a flight to Raleigh from Tampa, the aforementioned rental car that covered 1,200 miles on a one-way rental, delicious dining, wine imbibing, and even a distillery tour and tasting.

The cost for everything, including food, was $273. This easily would have cost $1,500 if we didn’t travel hack or plan the way Winning Williams does. This was our fourth travel hacking trip, following Iceland, New York City, and the Southwest U.S. journeys.

We optimize what is important to us and travel to where we are most interested. We know our priorities: hiking in stunning locations and simply enjoying nature (a nice change from our office jobs); also exploring areas that have historic charm / history / culture / something unique. Your priorities will differ, but until you define them, you can’t optimize. Our passion for hiking in new and unique places offers a direct challenge to optimizing and saving money: you need a rental car to get to the different locations and you often have limited hotel choices that can limit travel hacking opportunities. Winning Williams is okay with that trade-off, we’ll spend money where it matters most to us.

With that said, how were we able to save 85% on this trip?



We had two airfare options: fly to Charlotte or Raleigh. While Charlotte was an hour closer to our first destination of Asheville, Raleigh offered the distinct advantage of direct flights via Southwest. We could have used 25,000 of our American Airlines miles (for two passengers one-way) to fly direct to Charlotte; instead we used just 10,000 aggregate Southwest points to fly direct to Raleigh, saving future airline miles. Of course Southwest provided free checked bags adding an additional bonus so we can bring our hiking polls and food with us (see below for groceries) for free. But the flight consideration highlights a key to saving money and travel hacking: flexibility.

  • Cost: $11.20
  • Savings: $178 + a free checked bag

Rental Car:

While we didn’t book our car rental through Autoslash, a quick scan of a promotional e-mail they sent caught my eye. Hertz (and certain other brands) were (are?) trying to move some of their inventory to warm and sunny Florida to support all the snow birds. The promotion was a $5/day rental if you rent a car one-way from along the East Coast and drop it off in Florida. Given how expensive rental cars can be, this promotion was quite the incentive to take a trip and see Asheville, Savannah, and St. Augustine, three cities that were on our to-visit list. Then we could simply drop the car off right by the airport nearby our residence. The promotion was eligible for the most inexpensive economy car up through a few levels to arrive at a Group D rental. We of course moved up as far as we could, the cost was still $5/day, why not get a little more power and size!

  • Cost: $73 total with fees (the unavoidable fees increased the cost to about $12/day)
  • Savings: $180 on roughly $30/day over the estimated rate/fees excluding the promotion


Asheville, North Carolina: Four Points Sheraton: Three Nights – FREE

In Asheville we stayed at the Four Points Sheraton using SPG points. The hotel was within walking distance of downtown AND offered free parking. Several other properties were charging $20/night+ for parking. Total Points used: 21,000 SPG points.

Irmo, South Carolina at Hyatt Place: One Night – FREE

Splitting the drive between Asheville and Savannah, we stayed at a Hyatt Place in Irmo, South Carolina, just outside of Columbia. By staying outside the city, the Hyatt Place was a category 1 property, only requiring 5,000 Hyatt points. We’ve always had fantastic stays at Hyatt Place’s and would recommend them (pro tip: great breakfast buffets)!

Savannah, Georgia at Springhill Suites: One Night – FREE

Savannah was the most challenging location to find lodging. There are several chain hotels in the downtown area, but each required more points than we would like to use AND required expensive parking/resort fees. *Parking itself was a bit challenging there and that was even with mapping parking garages before coming into town!

We selected the Springhill Suites midtown, a Marriott property. This was located several miles out of the central downtown, but provided exactly what we needed, a quiet restful sleep, after another long day of exploring and walking. And free parking. And free breakfast. The Springhill Suites was 15K Marriott points, which is on the lower end for Marriott properties and at least half of what downtown Savannah would have required.

St. Augustine, Florida at the Holiday Inn: One Night – FREE

The Holiday Inn is located at the North end of the primary walking downtown district and again, I’m getting a bit repetitive here, offered free parking. We recently signed up for the IHG credit card (80K initial bonus rewards offering) for the sole purpose of booking this hotel. It required a little more points, 30K, but was the final piece of the puzzle of a week of free lodging.

  • Cost: $0 total with fees
  • Savings: $1,136 on six nights at the locations above, this would have worked out to $189/night.



Breakfast: complimentary breakfast was provided for five of the six mornings in the hotels. We’re not sure if our special SPG status resulted in free breakfast those three mornings in Asheville or if we somehow lucked out and got grouped with a larger traveling group that was staying at the hotel. In any situation, we took advantage of said breakfasts like any Mustachian would, and ate rather well to start each day J The Holiday Inn was the only location that we would have had to pay for breakfast. We had some gourmet Pop-Tarts from Aldi instead.

Snacks/Other: With our free checked bag, we loaded up on snacks from Aldi before the trip. Our first stop upon arrival was also at a Wal-Mart to get the fresh items (and wine) we wouldn’t want to check. These items gave us the needed nourishment to hit the trails, during the long drives, and supplemented our meals (well the wine was separate). We’re talking almonds, trail mix, crackers, apples, cheese, bananas, chips, cookies (night-time desert), etc.

Lunches: Most days we were out and about and possibly without any food options. That’s perfect. That’s exactly what you want (well at least we do) when getting away, and especially for hiking. Our go to lunch: tuna packet in a tortilla with cheese, perhaps with some avocado or simply BBQ sauce for additional flavoring. Add in trail mix, an apple, and other side items and you’re good to keep going. Cost per lunch was very minimal.

Dinners/Eating Out: Our second night in Asheville, we went to Papa’s & Beer. Absolutely delicious Tex-Mex and the usual huge portions. Does anyone actually eat the full meal?! Don’t answer that please.  After loading up on free chips at the restaurant, we ended up getting TWO nights of leftovers from this meal (and we supplemented with some of the other snacks). That’s half of the dinners! Then we feasted at Zunzi’s in Savannah. We somehow scored an extra sandwich with some R&D efforts they were conducting. Zunzi’s helped cover a couple dinners with the bonus food.

  • Cost: $53 (Zunzi’s & Papa’s & Beer) & $36 for groceries = $89 (less than some will pay on a single meal out)

Let’s summarize where we are at and the total cost:

asheville costs

So we talked about flights, car rental, hotels, and food above. Outside of those items, we spent $100 on an Uber to the airport, parking in Savannah, and gas. That totals $273 total trip costs!

How else did we save:

  • Asheville is EXCELLENT for hiking. Simply research beforehand where you want to hike, get your directions, and hit the road. Nearly all hiking in the area is FREE. Check out Romantic Asheville. It was a fantastic website for exploring different hiking options. Also, check road conditions if you are going in the wintertime (late October and onward). We had to utilize some alternative hikes as part of the Blue Ridge Parkway was closed for the first day we were in Asheville.
  • Savannah and St. Augustine are very walkable cities. You can peruse their visitor information centers for maps, etc. But, we researched everything prior to arriving, had maps, self-guided walking tours, etc. Therefore we got most of the same information you would get from a paid tour, with our pre-trip preparation.
  • Take advantage of free activities!
    • Check the tourist information centers / local websites calendar for events that might be happening when you’re there! We were in St. Augustine on the First Friday of the month. That happens to be a day when many art galleries open with special features like free wine and snacks! We also experienced a couple artists painting live and interacting with guests as part of the event. It made for a very special and romantic evening with Mrs. Winning Williams.
    • Augustine also has wine tours (with a free tasting) at San Sebastian Winery and distillery tours (with a free tasting) at St. Augustine Distillery. Check the websites for available times and its of course great to patronage these locations as you deem fit.

12.8 St Aug


And here is the video of our hikes:

3 thoughts on “How we spent less than $300 and saved 85% on a week long vacation covering 4 states

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