Italy on Points and Miles: A 16-Day Itinerary of Savings and Splurges

My husband and I had wanted to visit Italy for years, and our 10th anniversary gave us the perfect excuse to finally make it happen. We planned a 16-day Italy trip using points and miles, traveling through seven cities from late August into early September 2024.

This post is intentionally diary-style. I’m breaking down exactly what we booked, what we paid in points vs miles vs cash, and where we chose to splurge because it genuinely added value. I’m sharing how this trip actually came together, not a perfect redemption fantasy with budget in mind.

This article is part of my Trip Planning & Redemptions series, where I break down real itineraries, costs, and decisions so you can plan smarter trips using points, miles, and cash.

Disclosure: Some links in this post may be affiliate links. If you book through them, I may earn a small commission at no extra cost to you. I only share experiences and tools I’ve personally used or would genuinely recommend.

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ITALY ON POINTS & MILES — TRIP SNAPSHOT
Duration: 16 days
Cities: Milan → Bologna → Parma → Lerici → Lucca → Florence → Rome
Total Points Used: ≈ 611,000
Total Cash Spent: $3,843.84
Estimated Retail Value: ≈ $22,000
Average Daily Cost (for two): $240 USD
Trip focus: a mix of luxury stays, local experiences, and strategic savings using Chase, Hilton, Delta, Virgin Atlantic, and Emirates points.

Below, I break down exactly how we used points versus cash, what was worth it, and what I would do the same way again.

How We Used Points and Miles to Save on Our Italy Trip

Before booking anything, I focused on earning transferable points instead of locking into one airline or hotel program. That flexibility let us cover the biggest expenses with points, mainly flights and a few higher-end hotels, while paying cash where it made more sense.

Our approach was simple:

• Spend extra only when it truly improved the trip
• Use points for long-haul flights and expensive hotel nights
• Pay cash for trains, local stays, and most experiences

Our 16-Day Italy Itinerary Using Points and Miles

I know it looks like there is some backtracking, but that was done due to train routes and actually saved us travel time.

We stayed in the following cities, in this order:

1. Milan (fly in)
2. Bologna
3. Parma
4. Lerici
5. Lucca
6. Florence
7. Rome (fly out)

Packing light made this trip so much easier. No lugging multiple heavy bags up and down train platforms and between cities. Here is how we traveled carry-on only for a long Italy trip.

Flights to Italy Using Points and Miles (Business Class and First Class – Per Person)

1. Raleigh to New York

Delta First Class positioning flight

Points used: 27,500 Delta SkyMiles
Cash paid: $5.50

2. New York to Milan

Emirates A380 Business Class

Points used: 87,000 transferred to Emirates
Cash paid: $105.50

This is the flight I was most excited about on their A380-800. It did not disappoint! Lie-flat seat, great service, and a smooth overnight flight.

Flights From Italy Using Points and Miles (Per Person)

Rome to Raleigh via New York

1. FCO to JFK flown on ITA Airways Business Class (lie flat)
2. JFK to RDU flown on Delta First Class

Points used: 92,500 transferred to Virgin Atlantic
Cash paid: $64.85

Flights Total Points per person: 207,000

Flights Total cash per person (taxes and fees): $175.85

Flexible points made these bookings possible. See How Smart Travelers Turn Everyday Spending Into Real Trips.

Was Business Class to Italy Worth the Points?

We knew going into this trip that using points would save us a significant amount of money on flights. What we chose to do differently was use those points to add comfort and ease, since this was a bucket list trip and a milestone we wanted to mark in a special way.

What surprised me was how much that choice changed the overall experience. Being able to rest, use lounges, and arrive without feeling worn down shifted the trip from the very first day.

Since then, I’ve found myself saving points specifically for long international flights. I’m fine flying economy closer to home, but for those long-haul trips, points make a level of comfort that’s genuinely hard to go back from.

I’ve learned some tricks for finding better flights when I’m booking with points (and I use these sometimes for cash flights too): How Points Travelers Book Flights: 9 Secrets That Unlock Better Trips.

Airport Lounges

Included with our flights:

• Emirates Lounge at JFK
• ITA Lounge in Rome

Total price for access, food, and drinks while in the lounges: FREE

Hotels in Italy Booked with Points and Miles (Where It Was Worth It)

Milan: IHG Crowne Plaza (1 night)

Points used: 22,000 transferred from Chase to IHG with a 60% transfer bonus (normally 35,000)

2. Rome Hilton Rome Cavalieri, a Waldorf Astoria Hotel (two nights)

Points used: 160,000 (earned and redeemed via Hilton)

3. New York: Hyatt Regency JFK (1 night)

Points used: 15,000 (points transferred from Chase to Hyatt)

This stay was unplanned due to a delayed flight home. Using points saved us from paying airport hotel prices in cash.

Total hotel points used: 197,000
Cash spent on points hotels: $0

Hotels in Italy Worth Paying Cash For

These were intentional splurges based on room quality and location, not just the hotel name.

1. Lerici: Doria Park Hotel (2 nights)

Deluxe Golfo Dei Poeti Room, breakfast included option (includes a huge private terrace with jacuzzi and lounge chairs. The hotel set up a table and arranged a moonlight dinner)

Cash paid: $716.15 (652 Euros)

2. Florence: Santa Croce B&B (3 nights)

1 King bed with Balcony-no breakfast option, 3 nights

Cash paid: $958 (850.50 Euros)

Total cash spent on hotels (5 nights): $1674.15

Here’s why this Santa Croce room ended up being one of our favorite stays in Florence.

Affordable Italy Vacation Rentals We Paid for in Cash

We booked Airbnbs in cities where points options were limited or unnecessary.

• Bologna for two nights: $317.86
• Parma for two nights: $312.40
• Lucca for two nights: $383.01

Total cash spent on Airbnbs: $1,013.27

Train Travel in Italy: Costs, Booking Tips, and When Italo Is Worth It

We booked all trains directly with Trenitalia and Italo.

Total train cost for two people: $223.46

Italian trains are affordable and easy to book, so paying cash made the most sense.

Quick tip on Italian trains:
Trenitalia is the state-run rail system, and national strikes usually affect its routes first, especially regional trains. Italo is privately owned and operates mostly high-speed routes between major cities. During our trip, we didn’t realize there were planned strikes on the day we were booked to ride from Florence to Rome and make our flight home. We lucked out that we booked with Italo as our train was uninterrupted, but 98% of the Trenitalia routes were cancelled that day.

Italy Experiences Worth Paying Cash For (And Which Ones We Skipped)

1. Bologna Three Hour Cooking class (with full lunch). We booked this cooking class directly through Cesarine, but the same experience is now available on GetYourGuide, which makes booking easier and includes flexible cancellation.

Cash used pp: $162.59

2. Bologna Clock Tower Visit (Torre dell’Orologio) self-guided panoramic views of Bologna (purchased at the door)

Cash used pp: 10 Euros (approx $11)

3. Parma Caseificio Ugolotti authentic Parmesano Reggiano factory tour, which we booked directly.

Cash used pp: $43.60

4. Tuscany Vineyard tour with full lunch and wine tasting at Tenuta Casanova, booked directly on their website here. We drove ourselves, which gave us flexibility to explore the countryside. If you don’t want to rent a car, guided Chianti wine tours from Florence are an easy option.

Cash used pp: $73.44 (plus much more on gifts to send home, but we won’t include that here)

See the actual recipe I brought home here: Tuscan Vineyard Lunch Experience: The Recipe I Took Home

We rented a car for the day to get here, but we used our Capital One Venture X travel credit and paid $0 out of pocket. Bonus: we took our time, driving back through the Tuscan countryside and stopped shortly in Volterra to get in some steps, espresso, and treats in the hilltop town. See our driving route below.

5. We had planned to get Rome Colosseum tickets, booking directly from the Colosseum site when they were released, but were so exhausted by the end of our trip, we skipped this.

Cash used pp: $0

Total Cash per person spent on booked experiences: $290.63

Final Cost Breakdown: What Our 16-Day Italy Trip Cost Using Points and Miles

So how did we fare after all was said and done? I’ll show you! For this 16-day trip for two people, the flights, accommodations, trains, and experiences could have cost us almost $22,000. Instead, we paid $3,843.84! I will take that as a win for balancing luxury and a reasonable budget. Of course, we still had food and shopping costs, but they didn’t feel like a burden when we had already saved so much!

This 16-day Italy trip on points and miles showed us exactly where rewards make the biggest difference, helping us save money while still making a bucket list trip feel special from start to finish.

Frequently Asked Questions

Is Italy expensive if you use points and miles?

Italy can be expensive, especially for flights and hotels in major cities, but points and miles significantly reduce those costs. Using points for long-haul flights and select hotels allowed us to keep overall trip costs reasonable while still enjoying a high-end experience.

How many points do you need to fly to Italy in business class?

Expect 70k–105k points (one way) depending on the airline and date. Emirates, ITA Airways, and Virgin Atlantic often have the best redemption rates from the U.S.

Which credit card points are best for Italy travel?

Transferable points from Chase, Amex, Capital One, and Citi are the most useful because they give you flexibility across multiple airlines.

Is it worth using points for hotels in Italy?

Yes, especially in major cities where hotel prices are high. In smaller towns, paying cash for local stays usually offers better value.

Should I book trains with points or cash?

Book Italian train tickets with cash. They’re affordable and usually not eligible for point redemptions. However, if you hold Amex Membership Rewards credit cards, it’s worth checking your Amex Offers. You can sometimes find cash-back or percentage-off deals for booking Italo tickets directly with your Amex card, making those already-low fares even better value.

For more Italy planning resources, see my complete Italy travel guide.

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