Last June, Teddy and I applied for the Citi Hilton Reserve credit card. The signup bonus came with 2 free nights at a Hilton property as long as you use the certificate on a Friday, Saturday or Sunday night. I figured we’d use our 4 free nights while in Italy this April. This trip has been planned since summer of 2014, but I never got around to booking the free nights since I wasn’t sure if our dates would change. I also didn’t think that the hotels we wanted to use the certificates on would be completely booked 3 months in advance. I was completely wrong. 

I finally got around to searching for Hilton properties in Italy that we’d want to use our 4 free nights on. To get the most out of the certificates, I wanted to choose expensive Hilton properties that we normally wouldn’t stay at if we were paying out of pocket.

The 2 certificates you receive as a welcome offer from Citi can only be used on weekends and they can only be redeemed towards standard rooms. What does this mean? If your hotel is completely booked and has no standard rooms available, Hilton will NOT allow you to use your free night certificate. Guess what? BOTH hotels I wanted to stay at in Italy were completely booked the weekends I wanted to use my certificates. I’ve never seen a hotel booked a full 3 months in advance! I guess I don’t travel that much? I’m still new to travel hacking, so I’ve never traveled this much in a year! I’m learning lots along the way and I’m passing my travel tips on to you!

Citi Hilton Reserve credit card

The Citi Hilton Reserve comes with 2 free nights at most Hilton properties as long as you stay on a Friday, Saturday or Sunday.

I missed out on getting the most out of our Citi Hilton certificates

We’re going to Italy in April, so just under 3 months away. After doing a bit of research, I found there aren’t a lot of Hilton properties. However, the 2 hotels I really wanted to use my certificates on were the Waldorf Astoria in Rome and the Hilton Molino Stucky in Venice. Both hotels cost roughly €300 a night, so that would be an excellent use of our free weekend certificates! The only problem is that the Waldorf Astoria was only available on Sunday, April 12 and the Hilton Milino Stucky wasn’t available at all on April 18 or 19 🙁

Waldord Astoria Rome

We won’t be able to use our free Citi Hilton weekend certificates at the Waldorf Asotria in Rome because the weekend is completely booked for standard rooms.

I tried our luck for booking 2 free nights at the Hilton Molino Stucky in Venice for April 18 and 19, but they were completely sold out! After looking for alternate dates, I found they were completely sold out on standard rooms through most of the Spring and Summer! We should have booked our free nights LAST YEAR! Oops! Huge mistake on my part! I didn’t realize how popular these hotels were ;-(

Hilton Stucky in Venice

Since we procrastinated, we will not be staying at the Hilton Stucky in Venice ;-( we should have booked our free nights last year if we wanted to guarantee our reservations.

Since Hilton only allows you to use your Citi certificates on standard rooms, we were out of luck for both hotels. I could continue to monitor Hilton’s website for cancellations, but I decided to settle for the Hilton Garden Inn Rome Claridge. The room is only valued at €165 per night for the weekend, but it’s better to get the room for free versus letting our certificates expire in July.

Where we’ll stay in Venice

We’re only staying in Venice, Italy for 2 nights. April 18 and 19. Since we weren’t able to book the Hilton Stucky hotel, I decided to book 2 nights at the Marriott Boscolo Venezia, Autograph Collection. Teddy was approved for the Chase Ritz Carlton credit card this month and we have to spend at least $3,000 within the first 3 months in order to receive our 140,000 bonus points. Normally I just manufacture spend to receive the points, but I figured if we’re going to pay for a hotel stay we might as well receive 5x points for the hotel booking and have it count towards the minimum spending requirement.

Boscola Venezia Autograph Collection

We’ll be staying at the Marriott, Boscola Venezia Autograph Collection in Venice, Italy!

Final thoughts

If you signed up for the Citi Hilton Reserve card, do NOT procrastinate to use your free weekend certificates! I thought I could wait 3 months before our trip, and I completely failed! I should have made reservations last year in order to secure our free nights at the hotels I wanted. Instead we had to settle for Hilton hotels that are worth much less per night. We’ll still get 2 free nights, but the certificates will only be valued at roughly €165 per night versus €300. Not a great redemption on our part. I guess it’s a lesson learned for next time!