Trip to Italy: Planning

Introduction

In November of 2018, I undertook my very first international trip to Italy. While I have traveled outside of the US, those trips were always to South Korea, and always to visit my parents and extended family.

While initially I planned to go on this trip with a friend, some things came up and it turned into a solo trip. Fortunately, my sister decided to join me, which made planning for the trip easier.

Visiting the Colosseum has been a dream for me and my sister since we watched The Gladiator as kids!

Visiting the Colosseum has been a dream for me and my sister since we watched The Gladiator as kids!

Here are some things I planned prior to the trip:

Note: Some of the links below for credit cards are my personal referral links, for which I would earn referral bonuses should you choose to apply for the cards using them. To the best of my knowledge, the sign-up bonuses you can earn using my links are equivalent to the best public bonuses.

Flight

This was the first thing I arranged, and what really initiated the trip. I saw a fare alert on https://www.theflightdeal.com for a roundtrip fare from Los Angelex (LAX) to Rome (FCO). The fare was for Norwegian Air, a low cost carrier that has been aggressively expanding its intercontinental routes between the US and Europe. The total fare was $439.80.

Note: Norwegian Air, like its contemporary Wow Air, has been in the news for having trouble with its finances. I would advise caution booking airfare with them, as the airline’s insolvency will result in cancellation of your flights without a refund.

I booked the flight using the American Express Platinum Card, which earns 5 Membership Rewards (MR) points per dollar spent on airfare (when purchased directly from the airline’s website). In this case, I earned 2,199 MR points, which can be transferred to partner airline loyalty programs, such as Virgin Atlantic.

My sister Autumn booked her non-stop, round-trip flight from Chicago (ORD) to Rome (FCO) on Lufthansa for $531.70 using my American Express Platinum Card, earning 2,658.5 MR points.

Accommodation (Hotel)

I had initially planned to book and stay at Airbnb listings, since that would have been the easiest way to stay at the same place with my friend. However, as the trip changed into one with my sister, I decided to use Marriott points (which I had in abundance thanks to the Starwood acquisition).

I booked five nights at the St. Regis Florence, and 3 nights at the St. Regis Rome. My sister and I booked an additional four nights at an Airbnb property in Rome (while the original trip with the friend was planned for 8 nights, my sister and I decided to extend the trip to make better use of Thanksgiving).

While I can’t remember exactly what the going rate of the rooms were, a 5-night reservation at the St. Regis Florence for similar dates in 2019 shows a total price of 2,577.80 Euros, which comes out to a redemption value of 1.2 cents per point (at a conversion rate of 1.12 USD to 1 Euro). Seeing as Marriott points are generally valued at around 0.7 cents per point, I considered this a pretty good deal.

Had I paid using cash, I would have had to fork over close to $3,000!

Had I paid using cash, I would have had to fork over close to $3,000!

The 3-night stay at The St. Regis Roms came out to a redemption value of around 1.36 cents per point

The 3-night stay at The St. Regis Roms came out to a redemption value of around 1.36 cents per point

Marriott has a great promotion for award stays, where a five-night stay only costs the amount of points for four-night stays. As the St. Regis Florence and the St. Regis Rome are both Category 7 hotels at the time of booking (60,000 points per night), this amounted to a total of 240,000 Marriott points for the five nights at the St. Regis Florence, and 180,000 Marriott points for the three nights at the St. Regis Rome*.

* If I regret anything, it’s that I made these reservations before extending the trip. Because of the dates I had booked to stay at the St. Regis Florence (right in the middle of the trip), I couldn’t make use of the five-night award stay benefit at the St. Regis Rome. I had enough Marriott points at the time to cover for two five-night stays, and even if I hadn’t, Marriott has a nifty Points Advance feature on award reservations:

Points Advance – Members can book stays when they do not have enough points if they earn or purchase the needed points at least 14 days prior to check-in. Members who wish to book a points advance redemption under the current Marriott Rewards and SPG award chart are encouraged to order redemption certificates before March 5 to lock in the rate. On March 5, redemption bookings are subject to the new unified program award chart.

The Airbnb reservation cost $255.52 for four nights, which Autumn (my sister) paid using the American Express SPG Luxury Card (now re-branded as the American Express Marriott Bonvoy Brilliant Card), earning 511 Marriott points **.

** While this wasn’t the best choice for maximizing earning potential, Autumn had recently applied for the card and needed to complete the minimum spending requirement for the sign-up bonus of 100,000 Marriott points. Had that not been the case, I would have used the Chase Sapphire Reserve Card, which would have earned 766.56 Ultimate Rewards (UR) points.

Transportation (Train)

When the trip was initially for 8 nights, I planned visit three cities: Rome, Florence, and Venice. However, I quickly realized how packed and relentlessly on-the-move the whole trip would have been (even with the additional four nights), and cut out Venice from this particular trip. This meant I still needed to figure out a cost and time-efficient way to get to Florence and back from Rome.

I found ItaliaRail.com upon research, and booked a round-trip fare in business class from Rome (Roma Tiburtina) to Florence (Firenze Santa Maria Novella) for $127. The train ride would take 1.5 hours one-way, and booking business class guaranteed a seat. I booked this using the Chase Sapphire Reserve Card, which earns 3 Ultimate Rewards (UR) points per dollar spent on travel. In all, I earned 381 UR points, which can be transferred to partner travel loyalty programs, such as Virgin Atlantic (Korean Air was my favorite transfer partner, but dropped out of the partnership with Chase in August 2018).

Summary

All in all, we had taken care of the major transportation needs (flight + inter-city transit) and accommodation for a total of 12 nights with the following amount:

Total Dollars Spent: $1,098.50

Total Points Spent: 420,000 Marriott points

Total Points Earned: 4,857.5 MR points + 381 UR points + 511 Marriott points

Now all that was left was for us to loosely plan our itinerary and mark Points-of-Interest (POI) for our 12-night stay in Italy. Be on the lookout for an update on this story!