Anatomy of an Award: My First Trip To Florida's Gulf Coast

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I must admit, I’ve been to many countries throughout the world, but I’ve only been to Florida once in my life. So between the latest COVID-related travel restrictions that include testing before you can fly back to the U.S., and my need to escape the cold grey Midwest winter, I’ve decided that now is a good time to explore South Florida’s Gulf Coast. I was attracted by the wide, white sand beaches, mild February temperatures and opportunity to book some  very attractive properties with points.  

With hotel prices very high, but ticket prices very low, here’s how I booked the trip.

Getting There

I’ve decided to visit Marco Island and to fly into Fort Myers RSW, the closest airport to Marco island that has nonstop flights from my home airport. I had a choice of United, Spirit and Frontier. Ordinarily I’d choose United, but both the cash price and award price were very high. I definitely didn’t want to fly with a connection and Spirit, being the cheapest by far, got my business.

A lot of people scorn Spirit, and I understand why, but I am comfortable flying nonstop on Spirit. If there are delays leaving my home airport, I’ll just go home. And if Spirit significantly delays my return flight, there is no shortage of nice hotels in the Fort Myers area where I could spend the night.

I used my Chase Sapphire Reserve® to pay for the flights. Thanks to this card’s generous travel benefits, I am covered for flight delays and trip interruption up to $500 a day.    

My flight cost just $76 (it has since doubled in price in just a couple of days). Spirit’s ticket prices don’t include seat selection, carry on or checked bags, so that’s an additional expense. I have the American Express® Gold Card that I opened last year that comes with $100 airline incidentals credit, so after I booked the flights, I went back and paid for my bag and a seat selection on the outbound flight.

The total came to $102, a perfect amount to use up the airline credit on this card! I decided not to pay for my seat on the return flight since it’s not a super long flight, so I am going to take a chance and see what I am assigned on check in.

The American Express Gold Card replaced the $100 airline credit with a $100 Uber credit for new cardholders. But if you got this card before February 4th, you should have both credits.

Where I am Staying

I was looking for a resort type of property, somewhere on the water because I’ve heard great things about Marco Island’s beaches. Luckily, there are two very nice resorts on the island bookable with points. I’ll walk you through my decision process and why I decided to stay at the Hilton and not the Marriott.

JW Marriott Marco Island Beach Resort

JW Marriott Marco Island | Photo courtesy of Marriott.com

The cash rates for this beautiful property for my dates in February hovered around $600 and I certainly didn’t want to pay that much. This is a category 7 property and the standard rate is 60,000 points/night with peak rates at 70,00 points/night.

I have a good stash of Marriott Bonvoy points that accumulated over the last couple of years, and the property does look very beautiful, so in spite of the high nightly points rate it was in the running.

Marriott charges resort fees on award stays, so I was looking at a $35 daily resort fee and because I am going to rent a car, a $25 daily parking fee. So I was looking at paying $60 a night in fees!

I have Marriott Bonvoy Gold status thanks to The Platinum Card® from American Express, but the Gold status doesn’t actually come with any real benefits.

Hilton Marco Island Beach Resort and Spa

Hilton Marco Island Beach Resort and Spa | Photo courtesy of Hilton.com

I am also sitting on a good stash of Hilton points, as well as a free night award that came with my Hilton Honors American Express Surpass® Card after I spent $15,000 on it last year. The card also comes with the Gold status, but unlike Marriott, Hilton Honors Gold comes with some substantial benefits, such as free breakfast. Additionally, Hilton doesn’t charge resort fees on award stays.  

The standard rooms in February cost about $500 plus the $35 resort fee, so I’d consider 60,000 Hilton Honors points for a standard room a good deal!  

A few months ago Hilton upgraded me from Gold to Diamond status, so I called the hotel directly to inquire about the benefits extended to the Diamond members. I was told that Diamond benefits currently include $23 per person per room (up to two guests) breakfast credit, but there’s no executive lounge at this property. I will have to pay the $25 per day parking fee, though.

I wanted to book six nights, so that’s $210 in savings on resort fees alone, plus I’ll be getting a nice breakfast benefit. This was no brainer and an easy decision to make, so I booked Hilton Marco Island Resort instead of the JW Marriott Beach Resort.  

You can get fifth night free on award stays with both Hilton and Marriott, so I booked five nights on points for 240,000 Hilton Honors points and the sixth night with my free night award earned with the Amex Hilton Surpass card.

While JW Marriott looks a bit more luxurious and has a much more impressive pool, the savings heavily tilted the scale toward Hilton. I booked the cheapest room and, hopefully, thanks to my Diamond status, they’ll upgrade me to an ocean view room. I am aware that upgrades are never guaranteed and hotels could be very stingy with upgrades, but maybe I’ll get lucky.

Final Thoughts

I am really happy with the ticket price of $76 roundtrip and the 60,000 Hilton Honors points redemption I’ve found for my dates. The rental car is, of course, going to be an added expense and right now looks like Costco Travel has the best price for my rental. I’ll try my luck with Autoslash as well and see if I can save a little bit between now and the start of my trip.

Pro tip: Autoslash will look for the lowest price for your car rental reservation and email you when the price comes down. After you’ve made your reservation, enter the information on Autoslash and let them track your reservation.

Have you been to Marco Island? Please share your tips, things to do, places to eat and day trips ideas in the comments.