*Our trip was six months ago, so this post is egregiously delinquent, but there always was another post that seemed more timely. Now that winter is around the corner, and the travel bug is starting to kick in, it feels right for a little spring dreaming.*
Our spring Italy trip was built around a deal and a hotel.
I saw a two-for-one flight sale from New York to Milan for $400 each. That put Milan on the map.
Then I read about an old palazzo-turned-B&B that shared the same renovation team as the Sistine Chapel. OK, so now we’re going to this sleepy town on the western coast of Italy.
It had never occurred to us to visit either places. But they were pinned on the Google map and now we had lots of blanks to fill.
With Italy, the choices for where to go are endless. Like most people, I had my sights on the glamorous Amalfi Coast, but I’m built like a lizard and sadly the May weather just wouldn’t cut it for relaxing by the water.
So we did a deep dive through Tuscany instead, spending 12 days on a road trip that took us through a little bit of everything around the region: chic cities, hidden gem emerald coastlines, poppy-dotted hills, and fortressed medieval towns.
And while we never set foot in a museum, somehow there was design inspiration for days.
Here’s what we did and how much we spent.
12-Day Tuscany Road Trip Itinerary
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Venice, Florence and Rome. Those are the big three hot spots everyone wants to know about. If that’s you, then this post might disappoint. My husband and I both happened to have visited the major cities before (but separately), so we only hit up Florence as a base for exploring small towns nearby. Our itinerary is better suited for a second-timer looking to explore, with no real agenda.
Our trip started in Milan, took us to the western coast in Orbetello, then east to the Tuscan countryside, and finally back up to Milan to fly back to NYC.
*Affiliate links below*
Here are the places we visited and where we stayed:
Day 1: Milan – Sheraton Diana Majestic
- A one-day sprint to see as much design and architecture as humanly possible
Day 2+3: Florence – La Maison Du Sage
- Crossing the Arno river to explore the Oltrarno area, and achieving our goal of not visiting a single museum(!)
Days 4-6: Orbetello – Casa Iris Orbetello (With day trips to medieval towns: Pitigliano / Capalbio / Magliano in Toscana)
- My husband’s Italian friend called Orbetello “The Hamptons for Romans.” A lesser-known coastal area for wild beaches and a little bit of glamour.
Day 7-10: Montepulciano – Limonaia Airbnb (With day trips to Montalcino and Pienza)
- Classic Tuscany straight out the postcards, with rolling hills, poppy fields and driveways lined with cypress trees
Day 11+12: Siena – Borgo San Luigi
- Indulging in stunning interiors at the famous Duomo
Note: If I don’t link a place, I probably don’t recommend it.
Thanks to the rental car, we were able to visit 10 places along the way!
How Much We Spent
Instead of trying to actively budget while we’re on a trip, we take a different approach: slashing costs by leveraging credit card points. I’ll share the exact strategies below.
The total cash value of the trip was $5,259.97, and we halved that by the magic of credit card rewards.
For a 12 days in Italy, we paid a total of $2,815.60 out of pocket, or $1,407.80 per person. This includes $300 for a cat sitter, which is an expense not everyone will have. Overall, I’d say we spent about 40% more than someone who’s actually trying to be frugal.
Looking at the chart, the numbers tell the story of how we prioritized our money:
Most important: Hotels and local transport. We spent more on getting around than food and flights!
Least important: Shopping and activities
If you’re curious to know what we spent per day without flights and pre-trip expenses, it was around $172.13 per day, per person. So, we won’t be winning any awards for frugality, but it also wasn’t flat-out luxurious.
For the TLDR version, here’s the full breakdown.
Which Credit Cards We Used
Since I knew we were going to Europe again in a few months for a wedding, I didn’t want to drain all our points on this trip. I’d rather spread the points around to save 30-40% of the retail cost, so we can take more trips.
We didn’t use points for the flights since they were such a good deal already, but we did travel hack some of the lodging, the food, and the ground transportation by mixing and matching the rewards from five credit cards:
Hotels:
- Chase Sapphire Reserve
- Marriott Bonvoy Business American Express Card
- Barclays Arrival Plus (No longer available)
Besides credit cards, it can pay to be loyal. Whenever I’m not staying at a big hotel chain I try to book through Hotels.com to take advantage of their rewards program. If you book 10 nights in one year, you earn a free night. After lots of hotel stays on the Asia trip, I finally got to redeem a night for Florence.
Cabs, gas and tolls:
Car rental and trains:
- Barclays Arrival Plus (No longer available)
Food:
The Barclays and Bank of America cards I signed up for in January, so about four-five months out. That gave me time to earn the signup bonuses.
Just like with your money, it pays to diversify your credit card points! Building up a cushion of points ahead of time gives you options, so you don’t have to scramble at the last minute.
Flights – $829.02
Through the free Scott’s Cheap Flights newsletter, I saw Emirates was having their annual sale from NYC to Milan. We paid $779.02 for two roundtrip, economy flights, and I also paid an extra $50 to choose our seats on the way over.
If you’re a longtime reader, then you know I waffled on whether I should spring for business-class seats. It was a two-for-one deal, you guys! But ultimately I decided the eight-hour flight wasn’t long enough to justify paying four times the price.
And man, if I had to do it all over again, it would have been a million times easier to fly out of Rome. But I guess that’s the price you pay for cheap flights.
Lodging – $1,149.92
With no major sights on the itinerary, our days were more relaxed. Which meant that the hotels mattered a little more than usual.
Italy is one of those places where picking the hotel is one of the funnest parts. Because you can stay in a castle! For $150 per night!
It sounds frivolous, but I like it when the hotel design matches the local vibe so I was going for “old-world charm with ornate decorations.” Think frescoed ceilings, velvet curtains, impossibly high ceilings and bed linens so over-the-top they might as well be for royalty.
My one indulgence was the Casa Iris B&B at $222 per night, because it was so thoughtfully designed and restored. The owner said they couldn’t find light switches that were accurate to the time (everything’s made of plastic nowadays), so he had them specially made. It was such a treat to wake up to a frescoed ceiling every day.
I normally don’t like the cookie cutter feel of chain hotels, so I was surprised that even The Sheraton in Milan had some old-world charm, with green carpets, high ceilings, and velvet curtains. And for a city room, it was big enough to do cartwheels in.
As for cost savings, for Milan I used my free annual night award from my Marriott Bonvoy card, saving $312. Then for our Florence hotel, I used one Hotels.com award to save $76.
The cheapest lodging for us was the Airbnb in Valiano at around $180 per night, and the most expensive was $312 per night at the Sheraton in Milan.
However, I noticed decent lodging was aplenty and could be had for around $100 per night. Plus, breakfast is included at most non-chain hotels, so that saves money, too.
When we got to the countryside, the question was: do we want to stay at a much-recommended agriturismo or an Airbnb?
My husband wanted to cook, so that sealed the deal for an Airbnb close to Montepulciano. Here’s our little hobbit-esque house.
And this is the owner’s house and the pool, which we totally took advantage of.
For Airbnbs in the springtime, a pool was definitely a must-have. Although the house we chose wasn’t our first choice at all. I started looking at Airbnbs over three months out, waffled too long, and the best ones got snapped up immediately.
And a lot of the cute B&Bs only have eight rooms, so if you have your heart set on a popular place, then book well in advance.
Ground Transportation – $43.73
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Trains would make our lives a lot easier, but who are we kidding? Complicating matters is completely on brand for me. Renting a car meant were were able to see so much more than we could by taking the trains.
But that came with a price. I found the cheapest car options through Auto Europe for a Siena pickup/drop-off for $425.55. That included full insurance, because if the car ended up damaged, I knew I wouldn’t be in the mood to deal with overseas customer service.
We drove over 8 hours each way, and gas and tolls ended up at $143.87.
Towards the end, we had planned to take the train back up from Siena to Milan, but then we decided it would be easier to just drive up ourselves. That tacked on a one-way rental fee of $143.18. I think it was worth it, though, because we weren’t tied down to inconvenient train schedules.
Add everything up: the car rental, gas and tolls cost almost as much as the plane tickets!
As for trains, everyone says it’s cheap and easy, and that wasn’t the case for us.
Prices were less expensive the earlier you book, but the downside is you lose out on flexibility. Even well over a month ahead, the price for a Trenitalia train ride from Milan to Florence cost around $100 for two people. For a sub-two hour ride, that seemed really expensive, so I shopped around and saved $40 by booking on Italo. Same exact stations, same destinations, and everything.
And all the cab rides to and from each city/town added up at 10-15 euros a pop, plus the laughably expensive NYC airport rides, and we ended up spending $143.88 on cabs alone.
If you look at the sub-head for this post, and compare the amount to all these expenses, you might be wondering: how did we manage to spend only $43.73 out of pocket then?
That Barclays Arrival card did the trick! I knew this trip was coming, so I earned the 70,000 bonus points for spending $5,000 in three months. I then redeemed those points for over $700 in value. For the leftover amount, I used a little bit of our Chase Business Ink Preferred points.
Food – $325.95
It sounds lame, but food wasn’t a huge priority on this trip like it was in Asia, so we weren’t making an effort to eat at Michelin-starred restaurants.
I also found that there was plenty of room for mediocre, yet expensive meals, like $75 at Il Carpaccio in Milan. I don’t even remember what we ate.
But then you can also come across great values, like $35 at Bottega Conviviale in Florence. I’d say, if you try to keep dinner for two in the $35-$45 range, you probably won’t be mad.
I wasn’t eagle-eyed with food expenses, though, because I would be using the Bank of America Premium Rewards points to erase about $550 of it. So, $875 in food expenses went down to $325.95 out of pocket.
We also saved a little by cooking at home. My husband got inspired and made us a couple dinners in the Airbnb, like this store-bought ravioli, plus a cheap bottle of wine:
As for other meals, here were a few of my favorites:
Activities – $50.38
Per usual, we typically don’t spend much on organized activities. Not because we’re trying to be frugal, but because we value doing things on our own time. We spent most of our time walking and driving around, enjoying the scenery.
One of our main activities that cost $0 was walking through medieval fortressed towns that haven’t changed much in centuries.
Wandering through the crooked alleys, we discovered the most charming plant setups you’ve ever seen.
But there were a handful of actual sights and organized activities. One of the most memorable things we did was spend 14 euros each to tour Villa Necchi Campiglio in Milan.
The architecture and design of this house was from the 1930s, but still somehow completely contemporary. This garden room was my absolute favorite, because everyone needs a serpentine sofa.
The bathroom was the stuff of dreams, and I may or may not have been influenced to buy a round mirror for my own bathroom immediately upon returning home.
As a day trip from Orbetello, we stopped by Saturnia di Terme, an outdoor natural hot spring, and it’s completely free. It poured that day, but it would have been fun on a nicer day.
And on one of our last days, we spent 5 euros each to visit the inside of the Siena Duomo, which was incredibly inspirational with its black and white stripes and marble carvings.
Shopping – $116.60
Italians do dental care better, right? Judging from the souvenir shopping, that’s definitely a yes.
My husband also insisted on buying linen kitchen towels in Montalcino, and a Moleskine phone case in Florence.
Highlights
I sprinkled my favorite spots throughout the post, but here’s a list for easy reading:
MILAN
Milan in general – Everybody totally undersold Milan! I normally don’t like visiting cities much, but I felt like I could have spent at least three more days there. If you like design, there is so much more to do there than meets the eye. I didn’t have time to see the Fondazione Prada or Leonardo di Vinci’s vineyard, or even venture out from the main areas.
Villa Necchi Campiglio – If you like interiors, this is a must. We did the first tour at 10am and I recommend going that early, since other tour groups won’t be around to cramp your style.
Pettinaroli – The store I regretted not buying anything from before I left Milan. I think buying leather goods in the hot spots cities is really tough, but this historic stationery shop clearly values craftsmanship.
FLORENCE
Pegna Drogheria in Florence – On the way to the Duomo, stop here and pick up some chic Italian supplies. It’s where I bought the vintage-y toothbrushes from, and I never found another pharmacy that sold the same ones.
Bottega Conviviale – I thought this restaurant was a good value. We got great pizza, gnocchi, and a shot of limoncello for two for 35 euros total.
ORBETELLO / THE MAREMMA AREA
Casa Iris Orbetello – There are only two rooms at this wonderfully restored B&B, so besides the unique and thoughtful design (and the frescoed ceilings), the warm hospitality is a treat.
THE TUSCAN COUNTRYSIDE
Buon Gusto Gelateria in Pienza – I ate a lot of gelato. They were all decent, because, is there such thing as bad gelato? But this one had a creaminess that was unbeatable.
Taverna del Grappolo Blu in Montalcino – I ordered the simplest dish here–shelled pasta that was then sautéed, topped with crispy pancetta and peas. But it was a surprisingly elevated twist on your basic heavy pasta. After eating here I immediately wanted to come again and try other dishes.
Practical Tips
When driving in Italy, do your research. Like way more than you ever thought possible. The people who seem to have a bad time driving here usually didn’t read up on all the rules ahead of time.
When deciding where to pick up a car rental in Tuscany, pick a place where the office is walkable from the train station. We had to cab it in Siena, but I’d recommend considering a rental in Pisa.
When visiting small towns, pick your home base in a centrally located area. Driving 20 minutes a day just to go to the grocery store gets kind of old.
Detailed Trip Costs for Two People
How much did a trip to Italy cost for two people? The total value was $5,259.97, but with credit card rewards, we were able to cut expenses by more than 40%! $1,407.80 per person for 12 days sounds reasonable to me, especially as we didn’t budget or sacrifice the experience.
Key savings factors:
- The flights could have easily cost us double. Capitalizing on the two-for-one deal saved us around $800.
- Getting creative with travel hacking. It’s not for just flights and hotels. Besides cards that earn you miles, it’s important to look for cash back cards to “erase” expenses in other categories. Cash back cards are lot more straightforward to redeem, too.
- Spend money on what you value…and almost nothing on what you don’t. We could have destroyed the activities category by signing up for cooking classes and things, but we get way more enjoyment by renting a car and driving around as we please.
The Barclays Arrival card below is no longer available, but a super similar card that’s still active is the Capital One Venture.
| Category | Raw Cost | With Rewards | Credit Card Rewards Used |
| Lodging | $2,139.54 | $1,149.92 | Chase Sapphire Reserve Marriott Bonvoy Business American Express Card Barclays Arrival Plus (No longer available) |
| Food | $875.95 | $325.95 | Bank of America Premium Rewards |
| Flights | $829.02 | $829.02 | |
| Car Rentals | $568.73 | $43.73 | Barclays Arrival Plus (No longer available) |
| Cat Sitter | $300.00 | $300.00 | |
| Cabs | $143.88 | $0.00 | Chase Business Ink Preferred |
| Gas and Tolls | $143.87 | $0.00 | Chase Business Ink Preferred |
| Shopping | $116.60 | $116.60 | |
| Trains | $92.00 | $0.00 | Barclays Arrival Plus (No longer available) |
| Activities | $50.38 | $50.38 | |
| TOTAL | $5,259.97 | $2,815.60 |
And there you have it, a 12-day Italian roadtrip where we travel hacked almost everything except for the flights.
Have you ever been to Italy? Which towns and spots were your favorite (because I’d love to return some day!)? Are you planning any trips next year?
Featured Image: The Luxe Strategist
