My last vacation was all the way back in November of 2019! Traveling during the pandemic seemed like a waste of money and an unnecessary risk. However, now that the calendar has turned to 2022, I’m ready to travel again. My main motivation is that I have a free night certificate, earned from my Hilton Aspire card, that expires in July. I also have two more Hilton free night certificates that expire later in the year. So my wife and I started researching potential vacation spots where we could use those certificates in late April.

Our initial research focused on Charleston, South Carolina and Park City, Utah, neither of which we have been to. We eliminated Charleston because the best available Hilton hotel was a Homewood Suites and we wanted to stay somewhere more upscale. Park City has a Waldorf Astoria, which looks incredible, but the weather seemed historically iffy in late April. After expanding our search to other locations, we found Coronado, California and the legendary Victorian Hotel del Coronado. Coronado is a resort city on a peninsula in the San Diego Bay, known specifically for this hotel, which opened in 1888.

The appeal of this destination and hotel is threefold:

Value: Rooms at the hotel go for $500+, so we’re getting a ton of value from the free night certificates
Weather: San Diego in late April should be beautiful with highs around 70 degrees
Relaxation: We decided we’d rather relax than do a ton of sightseeing

Airfare

I started my search with American Airlines because I have hundreds of dollars of gift cards that I’ve accumulated over the past few years. I sourced those gift cards from both credit card benefits and from a website called MyPoints.

Earning American Airlines Gift Cards

Credit Cards

Each calendar year, the Hilton Honors Aspire® Card offers $250 in annual airline credits. And prior to 2022, the American Express® Gold Card offered $100 in annual airline credits. These credits are intended to be used for incidental fees like baggage, seat assignment or change fees. However, up until last year, there was a loophole whereby the credit would trigger when buying gift cards. So I would buy $350 in American Airlines gift cards each year whether I had plans to travel or not, and American Express would reimburse those purchases making the gift cards completely free.

MyPoints

The other source of American Airlines gift cards is through MyPoints.com. MyPoints is similar to other shopping portals which give you points or miles if you start your purchase from their website. However, it’s unique in that they have even more ways to earn points, like doing surveys or watching videos. After earning enough points, you can redeem them for gift cards to lots of different merchants, including American Airlines.

Mypoints charges 15,880 points for a $100 American Airlines gift card. For this trip I earned points through online shopping, opening up a new bank account, making a charitable donation and completing surveys.

My biggest point earnings came from opening a bank account with Aspiration, in which I earned 13,000 points. I also earned 10,000 points after making a donation to the American Society for the Prevention of Cruelty to Animals. In addition, I earned 800 points signing up for a free trial to Starz+ streaming service and 840 points shopping at Amazon.

We saved ~$420 using gift cards and the Chase Sapphire Reserve annual travel credit.

I purchased the airfare from American Airlines because they had the cheapest tickets, but being able to pay with gift cards was a huge bonus! All told, I used $375 in American Airlines gift cards — $175 earned from my credit cards and $200 from MyPoints.

After applying $375 of gift cards, the final cash price was only $43.40.

After applying the gift cards to the purchase price, I was left with only $43.40 for the two round-trip tickets. To cover that cost, I paid with my Chase Sapphire Reserve® Card. I used this card because of the many travel-related perks, like trip cancellation insurance, trip delay reimbursement and lost baggage reimbursement. But the main reason is the annual travel credit. Sapphire Reserve cardholders get $300 in travel credits each cardmember year and I hadn’t used any up until this point. Chase will automatically credit me for this charge.

So in total, our flights cost $420 but they were paid entirely by gift cards and the Sapphire Reserve annual travel credit. That’s a savings of $420!

Hotel

For this trip, the Hotel del Coronado is definitely the draw. When it opened in 1888, it was the single largest resort hotel in the world. It’s hosted presidents, royalty, and celebrities and has been featured in numerous movies and books. The 1958 classic “Some Like It Hot” starring Marilyn Monroe, Tony Curtis, and Jack Lemmon, was shot at the hotel. There’s also a complimentary museum to discover the behind-the-scenes history of the hotel. Plus the hotel offers several historic tours of the grounds which can be booked for a small fee. Designated a National Historic Landmark in 1977, this beach resort is a San Diego icon.

Since the nightly rate was over $500 a night, I decided to use all three of my free night certificates for our stay. In addition, Hilton is one of a few hotels that waive resort fees when you pay with points or free night certificates. So at the end of the day, we’re paying absolutely nothing, for a total savings of almost $1,920!

But it gets even better! As a Hilton Honors Aspire cardholder, I receive up to $250 in annual statement credits for incidentals charged to my card at participating Hilton resorts. That money can be used on things like dining, activities and spa treatments. Of course I wouldn’t mention this unless the Hotel del Coronado is a participating hotel, so the first $250 spent on incidentals is going to be free!

Coronado Redemption Table

	Retail Cost	Our Cost	Miles and Points Used	Points Source
2 round trip tickets from Chicago (ORD) to San Diego (SAN)	$210 per person ($420 total)	$0	$375 American Airlines gift cards	- American Express credit cards - Mypoints.com - CSR annual travel credit
3 nights at the Hotel del Coronado, Curio Collection by Hilton	$525 per night + taxes ($1,920 total)	$0	3 free night certificates	- Hilton Honors Aspire Card
Total	$2,340	$0	- AA gift cards - 3 free night certificates	- $2,340 in total savings - 100% off retail cost

Bottom Line

The upcoming expiration of some of my Hilton free night certificates was the push my wife and I needed to start traveling again. We’re so excited for the long weekend and it’s even sweeter to know that our airlines and hotel cost us nothing out of pocket!