Trip Report: Two Weeks in Italy!

Hold onto your potatoes, friend, this post is a fat, juicy one! I encourage you to watch my more in-depth videos on my Instagram profile to get a better idea of our 2-week trip to Italy – there’s just so much more that can be conveyed through video. I’ve organized the Instagram video highlights by city.

Budget Breakdown

FLIGHTS:

• (2) Southwest economy class flights from Nashville (BNA) to New York City (LGA): 13,758 points + $11.20 taxes/fees.
• (2) Southwest Companion Passes: 0 points + $11.20 taxes/fees.
• (4) Emirates business class flights from New York City (JFK) to Milan (MXP): 290,000 points + $416.80 taxes/fees.
• (4) Air France business class flights from Rome (FCO) to Washington DC (IAD): 258,750 points + $1,217.60 taxes/fees.
• (2) Southwest economy class flights from Washington DC (DCA) to Nashville (BNA): 38,927 points + $11.20 taxes/fees.
• (2) Southwest Companion Passes: 0 points + $11.20 taxes/fees.

Total: 52,685 Southwest Rapid Rewards points + 548,750 American Express Membership Rewards® points (transferred to Emirates and Air France) + $1,679.20 taxes/fees.

LODGING:

• (2) rooms, 1 night at Holiday Inn in Milan: 60,000 points + $0.
• (2) rooms, 2 nights at Ca’ di Dio in Venice: 116,000 points + $0.
• (2) rooms, 4 nights at Hotel D’Inghilterra in Rome: 228,000 points + $0.
• (3) nights Airbnb rental – Casa Zi’Tonin in Praiano: $678.38 (we used two $300 travel credits from our Blue Bank premium travel credit cards).
• (2) nights, 2 rooms at The Tribune Hotel in Rome: 36,000 points + $622.45 family plan rate.
• (1) night, 1 room at Hyatt House in Washington DC: 6,500 points + $0.

Total: 60,000 IHG points + 386,500 World of Hyatt points + $1,300.83.

GRAND TOTAL: $2,980.03

This cost doesn’t include food, tours & excursions, train transportation within Italy, shopping, and other miscellaneous expenses. Complimentary breakfast was included in all of our Hyatt stays due to my Globalist status (Hyatt’s top tier loyalty status).

Milan / Milano

After a wonderful, comfortable flight across the Atlantic, we landed at the Milan airport around lunchtime. I usually don’t schedule anything major on a travel day so we’re not rushed or stressed about meeting a deadline. We leisurely made our way from the airport to our hotel via Uber with just two things on our agenda: 1) grab a quick bite near the main square so we can see the beautiful gothic Duomo and 2) eat some gelato! Happy to report, we did just that! We were all so tickled to be eating pizza and gelato IN ITALY!!!

Because occupancy limitations are generally stricter in Europe, we had to book 2 rooms in each city for our family of 4. I had some random points collecting dust in my IHG account so I redeemed 60,000 IHG points for 2 rooms for 1 night at the Holiday Inn in Milan. We weren’t looking for anything fancy – just something clean and comfortable near the train station, since we’d be taking the train from Milan to Venice.

The next day, we ate an Italian breakfast (cappuccino and a pastry) then embarked on our tour of Cenacolo Vinciano to see Leonardo Da Vinci’s famous painting, The Last Supper. Tickets can be a bit challenging to get – they typically sell out almost immediately after the booking calendar opens, which is 3 months in advance. You’re given only 15 minutes to view The Last Supper, but we found that it was more than enough time to admire such a massive and iconic painting. On the opposite wall is The Crucifixion by Giovanni Donato Montorfano (c. 1495). 

Book your tickets directly from the official website here.

The trains in Italy are incredibly efficient and can be quite affordable – it’s best to book as far in advance as possible because the price only goes up closer to your departure date. I booked all of our train travel several months in advance so our tickets were around $50-$100 per trip for 4 people. 

*Pro tip: I reserved the same train carriage every time to minimize any confusion. This way, the kids knew we were to board carriage #5 for every ride. The train rides were so nice and comfortable – I chose 4 seats that had a table in between so we had plenty of space to spread out. The train ride from Milan to Venice was about 2.5 hours.

Venice / Venezia

We arrived in Venice around late afternoon and once again, the only thing on our agenda was to check into our hotel, find dinner (and gelato!), and wander the nearby streets if time and energy allowed. Venice is small, charming, and absolutely magical (although there is the lingering smell of fish and dankness from the water). Cars aren’t allowed in Venice (this means no Uber!), so in this respect, Venice is really great for small children – no worries of car traffic! Our kids got a kick out of being able to walk in the middle of the street without Mom telling them to look both ways before crossing. However, not all the canals have railings or barriers, so there’s that.

I redeemed 116k Hyatt points for 2 rooms for 2 nights at the newly-renovated, luxurious Ca’ di Dio hotel. This beautiful hotel was in a prime location, right on the water, and the staff was friendly, welcoming, and excellent all around. I highly recommend staying overnight in Venice because the majority of the crowds are “day-trippers.” Once the day-trippers leave around late afternoon, it feels like you have the entire city to yourself and Venice is especially magical at night! Also, it’s worth noting that in an effort to mitigate mass tourism in Venice, the city will start charging visitors a daily tourism tax this spring. However, this tax won’t apply to guests who have overnight accommodations. 

We also booked an early morning photo shoot through Airbnb Experiences because it’s not everyday you get this stunning backdrop for family photos! 

*Pro tip: if you book Airbnb stays and experiences through the British Airways portal, you’ll earn 3 Avios points per dollar spent. Another way to maximize your Airbnb bookings would be to use this card to pay and receive the $300 statement credit for travel purchases.

The next day, the hotel concierge arranged a private water taxi for us, which we boarded straight from the hotel lobby. The water taxi took us to the train station in Venice, where we took the train to Bologna (1.5 hours). Bologna is known as a foodie city which is why we stopped there to grab lunch and it did not disappoint! We stored our luggage at the train station as we ventured out and explored the city for a few hours. Then, we caught the train from Bologna to Rome, which took about 2 hours and 20 minutes.

*Pro tip: pack light! We are totally on Team Carry-On only and this was especially helpful because we had to drag our suitcases from city to city, up and down stairwells, and over cobblestone streets throughout Italy. Our smaller, carry-on size luggage made our transfers so much easier and more efficient.

Rome / Roma

Rome was jam-packed with tours, sight-seeing, and once-in-a-lifetime experiences – what a vibrant and bustling city! I intentionally scheduled our time in Rome with back-to-back excursions because there is so much to do, see, eat, and enjoy! Also, I knew that we’d have a lot of downtime on the Amalfi coast, which would be our next stop, so there would be time for rest. 

I prefer “trips” and Adam prefers “vacations.” Make no mistake – there is a difference! On trips, you go, go, go and on vacations, you sit and do nothing (*yawn). So, as a compromise, I usually book a trip followed by a vacation to appease everyone’s preferences.

We arrived in Rome in the early evening, checked into our hotel, and grabbed dinner at a nearby recommended restaurant. It was a “pinch me” moment eating the most delicious cacio e pepe IN ROME! Side note: Italians seem to love al fresco dining – at nearly every restaurant, we ate outside which was a fun, cultural experience.

I redeemed 228k Hyatt points for 2 rooms for 4 nights at Hotel D’Inghilterra. Once again, this hotel was absolutely beautiful and delightfully bougie, in an excellent location, with a superb staff who went above and beyond to make our stay impeccable.

The next morning, we toured St. Peter’s Basilica and Vatican City. *Pro tip: head to St. Peter’s Basilica early (7am) so you can avoid the massive crowds of tourists. We were able to enjoy the Basilica and the Dome before the majority of the people arrived around 8:30-9am. Also, a creative souvenir idea is to send a postcard from the Vatican, the smallest country in the world! 

We also visited Mamertime Prison, where the apostles Peter and Paul were imprisoned before they were executed, as well as the Basilica of San Pietro in Vincoli, where Peter’s chains are on display.

One of our favorite experiences in Rome was this private golf cart tour with LivTours. Riccardo, our knowledgeable, fun, and friendly tour guide picked us up at our hotel in the morning and drove us around Rome in his golf cart. We zipped around Rome’s tiny side streets and alleyways – it was the most perfect way to experience the city (and it certainly saved our feet)! The tour lasted 3 hours and we had so much fun, we wished it was longer. Riccardo took us to the typical sight-seeing spots, but he also shared some hidden gems along the way and tailored our tour to our specific interests.

If you want to book this tour or any other tour with LivTours, you can use my promo code and get a 10% discount: RICCARDO10.

Another fun and unique excursion we did was go truffle-hunting just outside the city! It was nice to escape the hustle and bustle of Rome for the day and take a hike in the Italian countryside with Matteo and his truffle-hunting dogs. After the hunt, Matteo cooked and served us an impressive 7-course meal at his lovely farmhouse. La dolce vita!

Speaking of food, we took this authentic pasta-making class in Rome, hosted by another Riccardo in his grandma’s kitchen. We learned how to hand-make spaghetti, linguine, tortellini, and ravioli, as well as whip up classic Roman sauces from scratch like carbonara and arrabbiata. It was so much fun, we bought a pasta machine as soon as we got home and hosted our own pasta-making party, inspired by our new Roman friend, Riccardo!

Other tours we took: a night tour of the catacombs (meh) and a night tour of the Colosseum (amazing). Booking the night tour of the Colosseum that included access to the Arena and Underground area is kind of a mess though. You can only book through the official website, Co-op Culture, and they release very limited tickets randomly – you just have to keep checking back or refreshing the page to find availability. If you do find available tickets, jump on them! They disappear in minutes. The process is frustrating, extremely limited, and there doesn’t seem to be any rhyme or reason as to when or how many tickets are released. However, if you’re not hell-bent on seeing the Colosseum by moonlight like I was, you can book various other tours for the Colosseum, Roman Forum, Imperial Forum, and Palatine Hill more easily.

The Amalfi Coast

After 5 fun-filled days in Rome, it was time to relax on the Amalfi coast. We took the train from Rome to Naples (1 hour, 15 minutes), then had to hire a private driver to take us from Naples to Praiano (2 hours). I didn’t find many chain hotels in the area where I could book with points, so I booked this 2 bedroom, 2 bathroom home in Praiano through Airbnb. I was able to utilize two $300 travel credits (because Adam and I each have this card) which brought the overall cost down from $1,278 to $678 for 3 nights. Not too shabby!

As promised, we had absolutely nothing on the schedule for the next two days. Good thing too, because the boys came down with a fever. God’s timing and provision couldn’t have been more perfect – not only did we have plenty of space and privacy to rest and recuperate in our Airbnb rental, we didn’t have the added stress of missing out on any pre-paid tours. Fortunately, it was just a 24-hour bug because after a full day of rest, the boys bounced back and were ready to explore the Amalfi coast! We took a water taxi to quickly and easily travel between towns. Don’t skip the lemon sorbetto while in Amalfi. It was – hands down – the most delicious thing we tasted in all of Italy!

We took a day trip to Pompeii, toured the Pompeii ruins with Giovanna, then had lunch before taking the train back to Rome. We spent 2 more nights in Rome, redeeming 36k Hyatt points to stay at a boutique hotel called The Tribune. Some Hyatt properties offer a discounted rate when booking a second room, called a “family plan rate.” Instead of paying for both rooms entirely with points, it was a better value for us to pay for the first room with points and the second room with cash at the family plan rate.

Finally, we took the intercity train from our hotel to the Rome airport (FCO) and flew back to the US with a short layover in Paris (CDG). Because we arrived in Washington DC (IAD) in the evening, we redeemed 6,500 Hyatt points and stayed at the nearest Hyatt hotel before flying back home to Nashville (BNA) the following morning. 

Whew, what an epic adventure! This trip wouldn’t have been possible without the power of points and miles and I am forever thankful to have discovered travel-hacking. If you have any questions, feel free to leave a comment!