I Went On Vacation And You Didn’t!: Naples

Hello and welcome to the first installment of I Went On Vacation And You Didn’t!

Okay, maybe that won’t be the name of this series, but it made me laugh. Because, you know, that attitude is kind of implied whenever somebody writes about their vacation on a blog.  Showing your vacation photos in person is bad enough, but posting pictures and writing all about it online is like Brag City.

Do you have a good title for a series of travel posts with cost breakdowns? Let me know, because I’m at a loss.


Naples (17)

Starfish, possessor of the shells

Last winter was so terribly cold here in upstate New York, I made it my plan to get somewhere warm for just a few days this winter.  Luckily, with my hobby of churning credit cards, this is easy. Free domestic flights are pretty easy to come by using Southwest Rapid Rewards points, and most cities where Southwest flies are going to have hotels where you can use points to stay. That’s an easy, free weekend trip.

So here’s how we did it:


Retail Cost Discount Our Cost
Albany Airport Parking $30.00 $30.00
2 Southwest Flights $744.00 42,456 miles $77.67 Taxes and pro-rated annual fee
Uber from Airpot to Naples $43.25 $43.25
Uber from Naples to Fort Myers $52.14 $52.14
Total $869.39 42,456 miles $203.06


Clam Pass Beach (19)

Clam Pass Beach

Southwest Flight – We flew from Albany to Fort Myers, Florida early on Saturday and planned on coming back late Monday night. We used 42,456 Southwest Rapid Reward points for the two round-trip tickets. Most of these came from a credit card bonus of 50,000 miles. Some frequent flyer bloggers will claim that their flights and hotels are completely free. This is not true if you paid an annual fee to get the credit card. To calculate my actual cost, I include a pro-rated part of the annual fee on the card which was $69. Plus, they still charge you about $11 for each ticket in fees and taxes. All in, the two round-trip flights cost $77.67.

To be fair, we incurred some other fees for parking at the airport in Albany, $30. I looked into rental cars in Fort Myers, but they were well over $100 for the weekend, unless you looked off-site from the airport. Getting off-site and renting a car takes a lot of time out of an already short trip, so we used Uber instead. To get to our hotel in Naples and back, it cost about $95.

Ibis butts

Ibis butts

Two nights at the Hilton Naples – We are swimming in Hilton points since they have so many credit cards you can apply for, without any annual fees. We used 60,000 Hilton points for two nights here, and it didn’t cost a red cent. It was a nice hotel. Not five stars, but a really good Hilton. The reasons I decided to stay here was the location (near the beach) and the amenities. They have bicycles to borrow!

Naples Hilton (4)There is only so much beach reading you can do, so we took a great recommendation from Mrs. Pop at Planting Our Pennies and rode some bicycles down Crayton Road and Gulf Shore Blvd! I was surprised at how many people were riding bicycles on the roads. The bike lanes were actually respected by drivers, and though it was a pretty busy area, it was no problem riding alongside cars. We rode all the way down into one of the richest neighborhoods I’ve ever seen. I felt self-concious taking pictures of people’s houses, so you’l have to do with a picture of the street. Of course, you could just Google Streetview it and pretend you’re taking the same ride. It was a beautiful, sunny day, and stupid northerners that we are, our minds are not on sunscreen in January, and we were burned to a crisp.

Naples (3)

I see rich people

Bike riding around a quiet neighborhood makes for cheap entertainment, especially when the houses are that extravagant. (You should’ve seen the front lawn fountains!) And so is beach-reading. The Hilton is about a mile away from the beach, down a boardwalk through a county park. I’m not sure whether our hotel offered beach towels to borrow, so we participated in that time-honored tradition of taking your white hotel bathroom towels to the beach. If you see someone at the beach with a white towel, you know they took it from their room so they wouldn’t have to “rent” a beach towel.

Naples Hilton (1)

Another perk of staying at this Hilton: Tons of free food! I don’t keep track of my status at hotels, so I never know what to expect when we check-in. Water bottles and free wi-fi, at least. And yeah, they treat those water bottles like a special treat only for those with elite status. But when we checked in here, they gave us breakfast vouchers for both days. And this wasn’t some breakfast buffet either, but Shula’s, the Hilton restaurant. Anything you want on the menu, you could order. Nice!

Naples Hilton (6)And that’s not all! They upgraded us to the Executive Level, for some reason, on the fourth floor. And on the fourth floor, they’ve got a special room that they stock at breakfast and dinner with all kinds of more free food. If you wanted to make dinner out of it, you could, although it would be a weird dinner. They had what looked like miniature Philly cheesesteaks and taquitos, along with cheese and crackers, and veggies. You can see what we went for. Look at all those cookies!

Then Sunday night, it all fell apart…

We get an email from Southwest saying our planned Monday night flight home was cancelled due to impending winter storm Juno. I’ll leave aside the fact that we weren’t flying into any of the cities predicted to be hardest hit, and the fact that it didn’t snow on Monday, and the fact that our fair city got about 3 inches of snow. No, let’s just leave all those facts aside. Let’s forget those mistakes that Southwest made. Those flights were cancelled, and we had to re-schedule.

So how about Tuesday morning? I had no idea what the storm was predicted to do, so I re-booked for Tuesday, but needless to say, those flights were cancelled, too. Then panic set in as it looked like our Monday night flight was going to turn into a Wednesday or Thursday flight which means missing work, cancelling appointments, rabbits left alone at home because we weren’t supposed to be gone for more than a few days!

Fun fact: This is probably the last SkyMall to ever be published. I swiped it.

Fun fact: This is probably the last SkyMall to ever be published. I swiped it.

If we wanted to pay in the high three figures, we could try another airline. But that would be dumb, so we did our best re-booking for free with Southwest. Marge managed to get on a Wednesday flight, while I was stuck until Thursday morning. (She got the last Wednesday ticket!)

So suddenly, I had to find three more hotel nights somewhere. Our nice Hilton near the beach was already booked up, so we were going to have to move. In fact, a lot of hotels were booked. But my credit card hobby came to the rescue, and I managed to find two Hilton Garden Inns that met our needs (airport shuttle) for a reasonable number of points.

Monday afternoon we were delighted to meet up with NAME REDACTED, also known as Mrs. POP, the mind behind Planting Our Pennies for lunch at a deliciously vegan restaurant. Bloggers are real people! Wow! We heartily thank Mrs. POP for alerting us to her presence in the area when I fleetingly mentioned we were going to Naples on this blog. To my dismay, Mrs. POP insisted on paying at the restaurant. We’ll get you next time, Mrs. P, mark my words!

After the subsequent stranding, here’s how our hotel costs stacked up in the end:


Retail Cost Discount Our Cost
Hilton Naples – 2 nights 538.00 60,000 points
Hilton Garden Inn – 2 nights 580.00 40,000 points -
Hilton Garden Inn Airport 215.00 30,000 points -
Total 1,243.00 130,000 points
Per night cost 248.60


We still managed to spend no money on our stay! But I have to say, moving from the Hilton in Naples to the Hilton Garden Inns in Fort Myers was no picnic. With so few choices, we ended up at a hotel in the middle of office parks, condos and strip malls. And like I said, we had no car. So we were pretty much trapped in the most boring place on earth for a few days, waiting for our flights. Late Monday, we got pizza at the only remotely walkable takeout food place.

Fort Myers Publix HaulTuesday, Marge tried to work while a good part of my day was spent figuring out how to get food without eating in the overpriced hotel restaurant with weird hours. There weren’t even any restaurants nearby, this hotel was so in the middle of nowhere. I found a frugal traveler’s friend, the supermarket, within 20 minutes walking distance and made my way down there.

I’m going to do another entry on saving money on food while traveling. But the food in the picture covered us for a good day and a half.  Yeah, I bought plastic forks for 95 cents. What are you gonna do, sue me? You try to find a fork in a place like that. Am I supposed to eat my lentil salad with my hands like an animal?

All in, here’s the total cost of our trip:

Retail Cost Discount Our Cost
Total $2,202.39 42,456 miles, 130,000 Hilton points $203.06


And if you’re interested, our total food bill:

Taco Ardiente 13.09
Hotel hors d'oeuvres
Hotel Breakfast
Publix 26.09
Hotel Breakfast
Hotel hors d'oeuvres
Taco Ardiente 14.35
Vegan restaurant Thanks, Mrs. POP!
Blue Moon Pizza 19.33
Publix 25.22
Chik-fil-A 8.00
Dunkin Donuts 3.00
Total Food 109.08
Nights 5
Per Day Food cost 21.82
Per Day Per Person 10.91


The view from my not very exciting final hotel in Fort Myers

The view from my not very exciting final hotel in Fort Myers

One thing I can say about staying in the office park wasteland, followed by the hotel in the weird location above (that is a mall in the background that purports to be the “town center”) is that the lack of pedestrians allows for a lot of silent walking-around-and-thinking time. After Marge’s flight left on Wednesday, I had all the time in the world to just walk around listening to music (Ariel Pink’s excellent new album Pom Pom, if you must know).  There were no responsibilities. Other people were racing around, but I didn’t have to be anywhere. I used to do a lot of this in high school and college. Not so much anymore. Seems like there is always an office that needs to be occupied, work that needs to be done, food that needs to be cooked.  So I got to thinking if this whole early retirement plan might be like walking around an empty nighttime office park. I could walk around all day with my headphones on, enjoying the scenery and having deep thoughts about the way Ariel Pink says the word “elevators.”  There’s nothing better than no responsibilities, if you ask me. Maybe early retirement will more like high school in that way. Sounds good to me.

Stay tuned for more braggy photos and cost comparisons on the next edition of I Went On Vacation And You Didn’t!


  1. Great job on the churning over there. Got to love Southwest and their generous program. My husband and I both have the SW companion pass and our kids named as our companions. So basically we can fly anywhere and only pay for the first two tickets with points. It’s weird to get BOGO when you didn’t really pay for the first ticket to begin with.

    • Norm

      February 2, 2015 at 9:04 am

      I’m jealous! Somehow we’ve managed to accrue hundreds of thousands of Southwest miles without ever earning the companion pass. Marge finished one business card this month, so maybe if she gets another one in a few months, it will finally happen.

  2. Those are some great photos – especially the one of the starfish! So glad you guys made it home safe and sound. I’m sure the bunnies were overjoyed at your return.
    Hopefully next time there won’t be major travel hassles to leave you with a less than relaxing trip. =)

    • Norm

      February 2, 2015 at 11:11 am

      Thanks, Mrs. Pop! The rabbits were very excited indeed. Today we are dealing with another 12 inches of snow. If our trip had stretched into a second week, I wouldn’t mind!

  3. Nicely done! Though bummer on the delays. We love grocery shopping for our food while on vacation too. Your forks crack me up–we’ve had that same problem! Hotel rooms DO NOT contain forks or spoons ;).

    • Norm

      February 3, 2015 at 9:13 am

      Our nice Hilton in Naples had silverware for the taking! Not the business hotel, though. I maybe could’ve stole some out of the restaurant… or just asked the front desk. I wonder why all supermarkets don’t have some plasticware next to the takeaway food. That’s madness.

  4. This sounds like a great getaway! Even better with that price tag.

    BTW, I nominated you for the Liebster Award. Check out the post here: http://settleyourfinances.com/liebster-award/

  5. Loved your blog! We are a DIN (dropped the K seven years ago 🙂 family and passionate travelers and your blog is perfect for us. Bookmarked it and looking forward to do our future trip plannings with the help of your reports.

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