In Italy Vacation Part 1, I covered how I saved $2000 on our Groupon Getaway Italy vacation deal and the $1000 in freebies and travel credit we received at the airport.


I’m happy to report that our hotel upgrades were even more successful…and we didn’t even have to ask for a single hotel room upgrade!

In Italy Vacation Part 2, I’m going to cover the most valuable perks, upgrades and freebies we got during our trip: our luxury hotel stays and the free room upgrades!

Read on to find out what we got for hotel upgrades, and then read Italy Vacation Part 3 to get the details of how I maximized my hotel loyalty and travel rewards credit card accounts, which added up to over $1000 in travel points and hotel room upgrades!

The discount Italy vacation package hotel

Our Groupon Getaway deal included a 6 night stay at Grand Hotel Plaza in Montecatini, Italy. Montecatini is in northern Italy, near Pisa.

We stayed in this hotel on the first night of our trip, and the 2nd to last night.

This hotel is perfect if you plan to do a more local sightseeing tour daily, because you can sleep, wake up, eat your free breakfast, and go off and explore! In fact my husband booked us a dip in this thermal pool, steam bath (in a cave!) and mineral shower at this breathtaking spa, Grotta Giusti, which was about 20 minutes from this hotel.

Grand Hotel Plaza in Montecatini, the hotel that came with our package, wasn’t quite in the same caliber as the ones I’m going to get into, that were booked separately. Even so, it was cute, clean, came with breakfast, gave an authentic Italian bed and breakfast feel, and our room had windows that opened up to this lovely terrace.

After staying that first night and moved around the country with just a backpack, leaving the rest of our things in the hotel. It was handy to do it this way, and we lovingly referred to this hotel as “home”! It was really convenient to have a place to keep our things and go back to after some exciting (but exhausting!) sightseeing in Florence, Tuscany, and Rome.

Breathtaking hotel room upgrades…on a budget!

While the Grand Hotel Plaza was comfortable enough, for some of our trip, our hotel rooms are where we decided to splurge.

Travel rewards tip: If you’re going to spend a little to treat yourself on your trip, decide what is truly most important to you, maximize what you get for what you’ll pay, and do more budget spending elsewhere.

For my husband, splurging on flights was more important. His reasoning was that we weren’t going to spend much time in these fancy hotel rooms, and the comfort on an overnight flight could make or break our first few days of our trip.

For me, an upgraded hotel experience was important because it was an anniversary trip. I live with 5 males, including the dog, and I wanted a little pampering!

Not to mention, if we’re in Italy, and if we don’t have 3 cranky kids to drag around, we’re going to see as many sights as possible! How many times does one have the opportunity to be a stone’s throw away from the Colosseum or Michelangelo’s statue of David?

Moving around the way we wanted would require hotel stays outside of what came with our Groupon Getaway.

Of course, we ended up meeting in the middle with one first class flight segment and fancy hotels for just 3 nights of our trip.

Luckily, while we did spend extra on hotels, having the right travel rewards credit cards and hotel loyalty programs in place, working together, allowed us to get some incredible value from our stays and earn tons of points for a future trip in the process!

Travel Upgrade #4: Junior suite at La Bandita Townhouse, Pienza, Tuscany

This was my favorite stop in the entire trip. When I go to Italy again, I will probably stay in Tuscany the entire time!

La Bandita Townhouse is a Starwood hotel in the tiny town of Pienza, and is a refurbished medieval convent. It only had 12 guest rooms. It was so charming. I loved the small-town feel, the restaurant was absolutely to die for, and the service at La Bandita was probably the best I’ve had in my entire life!

The hotel sent a car for us and even made a pit stop for us on the way. When we arrived, the lovely woman working, Paola, showed us our guest room. I had booked a standard room for the night, so I was totally floored!

This was the junior suite and my poor video skills do not do it justice. It had 2 levels, a stocked, complimentary mini bar, a gorgeous bathroom (that’s saying a whole lot in Italy. The bathrooms there are atrocious, and they have the audacity to charge money to use them!), a huge bathtub in the bedroom, and a sitting area downstairs with a couch and TV.

Once we settled into our room and went back downstairs, Paola informed is that she had made us dinner reservations (I had mentioned I was hungry!) and personally walked us into the restaurant and introduced us by name to the waiter and chef.

The food at La Bandita Townhouse was some of the best I had during the entire trip. (Sorry vegans. It was delicious.)

After dinner Paola invited us to use the “Library Bar”, which was a beautiful, open room that felt like home. The Library Bar was full of books, old records to play, and a self-service wine bar that operated on the honor system. Really! When you pour yourself a glass of wine you write it down in a book so it can be charged to your room. Is that not adorable?!

I was so blown away by the service at La Bandita Townhouse that I told my husband that they must have somehow known I’m a big-mouthed blogger, but I watched Paola usher another set of guests in with the same care and attention that she gave us.

I do know that the upgraded room and free breakfast we got with our stay, however, came from our Starwood Preferred Guest Gold status, which is a perk of having the Platinum Card from American Express.

The cost for the junior suite including breakfast today at La Bandita is €450, which is about $535 USD. I’m here to tell you, it’s worth that, even though I didn’t pay that much!

It really was just a fabulous little place in a gorgeous little town in the rolling hills of Tuscany. If you ever find yourself in that part of the world, please do yourself a favor and book yourself a stay there! The hotel is on the pricier end, but I will never forget my experience at La Bandita Townhouse.

Since we’re SPG Gold members and we also used our Starwood Preferred Guest Card from American Express to pay for the room and the charges we made to the room, we earned tons of points here on top of the extras we got.

To put those points in perspective, since Starpoints are worth around 2.7 cents each, we earned nearly $100 worth of travel rewards in points during this stay. By maximizing the points earned, we got about a 28% return on the room rate in hotel points alone…on top of the free upgrades we got!

Travel rewards tip: If you spend money on food or drink at your hotel, charge the bill to your room if possible, because you’ll likely earn bonus hotel points on the entire amount.

Travel Upgrade #5: Imperial room, The St. Regis Rome

This Starwood hotel is one of those iconic 5-star hotels that kind of gives you bragging rights if you actually get to sleep in it. I’ll take my bow now. Thank you, thank you. So fancy.

But in reality, I did not pay full price for this hotel room.

Are you crazy? After I spent all that money at La Bandita the night before? No way could I justify a $600 hotel room, even though I really wanted to stay at The St. Regis (and La Bandita was worth every penny—no regrets!)

Nope, I used a program that Starwood Preferred Guest offers called Cash + Points. It’s just what it sounds like.  Basically instead of paying for a room in all cash or all points (either would have hurt my heart), I did a little of both.

For 10,000 Starpoints and $180, this gorgeous, very Romanesque room in the heart of the Eternal City was ours for 24 hours.

Actually, I did not even pay for this room, with points or cash. I paid for a deluxe room, which is smaller and not quite as plush as the one shown above. This is an imperial room, another free upgrade with our SPG Gold status!

The room did not disappoint. It was luxurious. We had sitting area, plush rugs with slippers set on either side our bed, big spa robes, a waterfall shower, a good sized bathtub, chandelier with a dimmer, the whole 9.

The service was not as attentive as La Bandita, but was friendly and accommodating. The food was okay, but again, the St. Regis had big shoes to fill after our stay the night before, so I won’t hold it against them.

The atmosphere though, in the room and the hotel itself, was absolutely breathtaking. I’d stay again just to sit in this lobby.

The cost of the room we got with our free upgrade and free breakfast for our Starwood Preferred Guest Gold status today is €500, or about $595 USD.

While you normally won’t earn points on hotel rooms that you pay for with points, I was still able to get 2 Starpoints par dollar I spent because I used my Starwood Preferred Guest Card from American Express to pay for our room, dinner and drinks (not included in total expenses). Maximize, baby.

In the totals below, I’m not going to assign a dollar value to the Starpoints spent, because they didn’t cost me anything to collect.

Travel Upgrade #6: Superior room, Boscolo Exedra Roma

The Boscolo Exedra Roma is a Marriott hotel. Since Starwood hotels are now owned by Marriott, the Gold status we received because of our Platinum Card from American Express gives us a status match with Marriott.

In other words, by linking our SPG and Marriott Rewards accounts, we have Gold status for both programs, which makes us eligible for all kinds of perks at both Starwood and Marriott hotels, including room upgrades when they’re available. Yassss!

We were upgraded from a standard room to a superior room, with breakfast included. The cost of this room today is €294 or $350.

We happily took our leveled up hotel room, which was beautiful, as was the hotel itself. More amazing food and service, and free breakfast thrown in as well.

Stays at Marriott hotels earn Marriott points, which are less valuable and flexible than Starpoints, but can easily be transferred to Starwood Preferred Guest.

Since the two hotel companies have merged, I also used my Starwood Preferred Guest Card from American Express to pay for this room, because doing so earns 2x Starpoints per dollar in addition to Marriott Rewards!

The cherry on top of all these upgrades/freebies/points that were included with this stay, is that I registered for a promotion that gave me a full free night after completing this stay, good for a future stay at a Marriott hotel—no points needed! (That’s why I chose a Marriott hotel over a Starwood hotel for this last stay.)

How to maximize hotel loyalty programs

There are several moving parts to maximizing hotel rewards and perks in order to get the most value for the cost. When you combine loyalty program points, hotel upgrades, and freebies, you can make out like a bandit!

First, you do have to join the hotel loyalty programs where you want to collect points, but that alone would have only provided a fraction of the value I got, and upgraded rooms would not have come into the equation.

Using my Starwood Preferred Guest Card from American Express for regular purchases before the trip is what allowed me to collect the points necessary to stay at The St. Regis Rome for just $180. Those 10,000 Starpoints I used to pay for the hotel room cost me exactly $0, because I earned them just by paying for things I was buying anyway.

Also, I mentioned in Part 1 that Starpoints are worth about 2.7 cents, according to The Points Guy. However, the way I used them gave me a value of 4.1 cents each, since I spent $180, used 10,000 Starpoints, and got $595 in value!

Using my Starwood Preferred Guest Card from American Express at Starwood and Marriott hotels also allowed me to earn double the normal rate of points I would have earned by simply being a member of these hotel loyalty programs.

The heavy hitter for the value we got from these hotel stays though is actually the Platinum Card from American Express. This is because when you hold this card, you get upgraded to Gold status with both your Starwood Preferred Guest and Marriott Rewards memberships, which is very valuable during your travels.

Travel rewards tip: Hotels don’t hand out their best rooms and suites to just anyone, usually. They reserve them for their customers with high loyalty status!

Not only do you get perks like upgrades and gifts when you have a higher hotel loyalty status, but you also earn hotel points at a higher rate than everyone else, which is how I earned 7,219 hotel points just from these 3 nights to redeem later, worth about $164. That’s a 21% return on the cost of the rooms!

Travel rewards results

Since this was a special anniversary trip, I was willing to spend some, but I’m still a frugal person. I wanted a few frills, but the hotels I chose far exceeded my expectations for what I paid, and some strategic planning really allowed me to stretch what I spent.

In all, I spent a little over $2340 on this trip for 2 that gave us $6,355 in value. I spent more than that on Costa Rica for 2, and all I got back was $29 from Ebates! (No shade on Ebates, but as you can see, the return can be far more valuable in the travel rewards game.)

If only I knew then that I know now.

We received $3300 in discounts and freebies and $716 in airline and hotel credits and rewards that we can use towards a free trip in a few months! (Helloooo, spring break!)

Next up, Part 3: How to maximize Starwood Preferred Guest and Marriott Rewards. Full details on how to get started earning maximum rewards not just for Starwood and Marriott hotels, but for flights too, just by making the most of these travel rewards programs!

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