We had been planning a group trip with friends to Italy for a couple years but had to keep postponing for various reasons. This year, we finally were able to make it happen. To see as much of the country as possible in a two week span, we spent only 2-3 nights in each location and since we were in a large group, we stayed in a mix of hotels and group Airbnbs.
One of my strategies is to typically book a United Economy ticket using United miles as they can be canceled for free. This way, if a good flight in business opens up I can switch. On the way to Italy we snagged some business class tickets 2 days before departure on Austrian Airlines. Although I made the 50 minute connection in Vienna my bag did not. Fortunately, it was delivered to our hotel later that night.
Our first stop was Venice where we stayed 2 nights at the Ca' Sagredo Hotel using Hyatt points. After a train ride to Rome, our next hotel was the Rome Cavalieri using Hilton points and a free night certificate. Our longest stay was at an Airbnb on the island of Capri followed by a ferry and 2 night stay at the Amalfi Holiday Resort. Our final stop in Italy was a 2 night stay in Naples at the Renaissance Naples Hotel Mediterraneo using Marriott points and a free night certificate. Following Italy, we stopped in London to visit some friends and stayed 2 nights at the Andaz London Liverpool Street before a direct flight home on United Airlines business class.
Itinerary (Flights Per Person)
Austrian Airlines Business ORD-VIE-VCE: 63,000 Citi Points (transferred to Avianca Lifemiles) +$75 (one-way)
2 nights at Ca' Sagredo Hotel: 70,000 Hyatt Points
2 nights at Rome Cavalieri, A Waldorf Astoria Hotel: 80,000 Hilton Points + 1 Free Night Certificate
3 nights at Airbnb in Capri: $744
2 nights at Amalfi Holiday Resort: $705
2 nights at Renaissance Naples Hotel Mediterraneo: 40,000 Marriott Points + 1 Free Night Certificate
EasyJet Economy NAP-LUT: $323
2 nights at Andaz London Liverpool Street: 23,000 Hyatt Points + 1 Free Night Certificate
United Airlines Business LHR-ORD: 60,000 United Miles + $317 (one-way)
Capri 2023
Austrian Airlines Business ORD-VIE-VCE
Redemption: 63,000 Citi Thank You Points + $75 (one-way)
Cash Price: $2,014 (3.1 cents/point)
Austrian Airlines Business Class - 2023
Austrian Airlines is part of the Lufthansa Group and thus part of the Star Alliance. Overall, the business class product is pretty good although the one major drawback is not every seat has aisle access. The business product is best known for the food served and once we boarded, the chef (wearing a chef's hat) took everyone's order. For plane food I would agree, it was definitely one of the better meals I've had. You can read my full review here.
When booking trips where I can't find business award space, I usually book an economy award ticket on United so I can cancel it for free as the date nears and (hopefully) business award space opens up. In this case, these seats on Austrian opened up just 2 days before and booking through Avianca Lifemiles only cost 63,000 Points each.
Ca' Sagredo Hotel
Redemption: 70,000 Hyatt Points (2 nights)
Cash Price: $1,335 (1.9 cents/point)
Ca' Sagredo Hotel - Venice 2023
The only Hyatt hotels on the island of Venice are Small Luxury Hotels. Award availability is hard to come by and when it is available, it's quite expensive. While it was nice to stay in the heart of Venice, this hotel was a bit overpriced for what it was. You can read my full review here.
The World of Hyatt is my favorite hotel program because it's one of the few programs left that has a fixed award chart (peak and off-peak pricing was introduced in 2021) meaning you always know how many points this hotel will cost regardless of cash price. Additionally, you can transfer Chase Ultimate Rewards Points to Hyatt at a 1:1 ratio, which is probably my biggest use of Chase Points.
Rome Cavalieri, A Waldorf Astoria Hotel
Redemption: 80,000 Hilton Points + 1 Free Night Certificate (2 nights)
Cash Price: $1,440 (0.9 cents/point)
Rome Cavalieri - Rome 2016
I first stayed at the Rome Cavalieri in the winter of 2016 and it's been on my list of top hotels since. We finally made it back in the summer of 2023 and although it didn't quite live up to my lofty expectations, it's still a great hotel and a perfect hotel to take advantage of the Hilton Aspire card benefits. You can read my full review here.
With the Hilton Honors Aspire card, you get a free night certificate that can be used for standard room redemptions. With rooms regularly over $500 per night at the Rome Cavalieri, this alone covered the annual fee of $450 for me. By booking far enough in advance we were able to get the second night for just 80,000 Hilton points.
Additionally, the Rome Cavalieri is considered a resort so the $250 annual resort credit can be used at this hotel as well. By charging our dinner at La Pergola (Rome's only three Michelin Star restaurant) to our room, we were able to take advantage of the full credit.
If you were to take advantage of the standard 150,000 sign-up bonus, this means you'd be able to get 3 free nights plus a $250 credit to La Pergola for just the $450 annual fee.
Capri Airbnb
Redemption: $744 Cash (3 nights)
Capri 2023
With a large group of 8 people, we rented a large house that could fit everyone on the island of Capri. We were located near Marina Piccola and it was a bit of an uphill hike to get to the Capri city center.
Holiday Resort Amalfi
Redemption: $705 Cash (2 nights)
Holiday Resort Amalfi 2023
With fewer hotel options and limited time, we chose the Holiday Resort Amalfi for our 2 nights in the town of Amalfi as it was centrally located.
Renaissance Naples Hotel Mediterraneo
Redemption: 40,000 Marriott Points + 1 Free Night Certificate (2 nights)
Cash Price: $1,071 (1.3 cents/point)
There aren't many American Hotel chain options in Naples except for the Renaisance Naples Hotel Mediterraneo. While the hotel is quite expensive in cash, it turned out to be a great redemption for the 35,000 point free night certificate from the Marriott Bonvoy Boundless credit card. Then, I was able to add a second night for 40,000 Marriott points.
EasyJet Economy
Redemption: $323 Cash (one-way)
There were very few options to fly direct from Naples to London and a connecting flight would have taken up most of the day. To avoid spending too much time in airports, we opted for an EasyJet flight from Naples to London Luton airport. This was my first time taking EasyJet or flying to Luton, but all was smooth.
Andaz London Liverpool Street
Redemption: 23,000 Hyatt Points + 1 Free Night Certificate (2 nights)
Cash Price: $1,649 (3.6 cents/point)
Andaz London Liverpool Street - London 2023
After staying 60 nights in a year with Hyatt, you get a free night certificate for category 1-7 hotels. Unfortunately, they only give you 6 months to use this certificate so if I didn't use it on this trip it would have gone to waste. The Andaz London Liverpool Street was the only Hyatt hotel on this whole trip that I could find with availability. As a category 6, I left some value on the table but it was better that I use the certificate than let it expire.
United Airlines Business LHR-ORD
Redemption: 60,000 United Miles + $317 (one-way)
With 3 daily flights between Chicago and London, United often has business saver award availability during the middle of the week. We were able to get a couple seats in business with United Miles as we were returning on a Wednesday.
Trip Booking Summary
63,000 Citi Points
93,000 Hyatt Points
1 Hyatt Free Night Cert (cat 1-7)
80,000 Hilton Points
1 Hilton Free Night Cert
40,000 Marriott Points
1 Marriott Free Night Cert (35k)
60,000 United Miles
$2,164
After a couple years of planning, our summer trip to Italy with friends was everything we could have hoped for. We visited 5 different locations over the course of two weeks and I was able to take advantage of several free night certificates. While my preference is to usually stay at least 3-4 days in each place, we had a good mix of activities from the history of Rome, to wandering the canals in Venice, taking in the Sun on Capri, and celebrating the final match of the season for SSC Napoli.
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