A Bucket List 16-Day Italy Itinerary: Saving with Points and Miles, Splurging Where It Mattered

My husband and I had wanted to visit Italy for years and our 10th anniversary gave us the perfect reason to finally make it happen. We settled on a 16-day adventure in seven Italian cities around late August to early September 2024. While we wanted to celebrate with an unforgettable trip, we also needed to stick to a realistic budget—balancing smart savings with well-placed splurges to enhance our experience.

How did we do it?

By strategically combining points, miles, and money (cash or credit). Months before the trip, I focused on earning as many transferable points as possible to offset major expenses like flights and accommodations. This approach allowed us to splurge on what mattered most—upgrading our travel experiences and enjoying activities or destinations we might have otherwise skipped.

We made intentional decisions about when to use points and when to pay out of pocket. For flights and luxury hotels, redeeming points helped minimize out-of-pocket costs. On the other hand, we chose to pay for unique experiences, local stays, and dining, knowing these moments would make our trip unforgettable.

Here’s How We Balanced Saving and Splurging on Our Italy Trip: Flights, Luxury Hotels, Cash Vacation Rentals, and the Full Cost Breakdown in Points, Miles, and Cash

Our Itinerary

(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)

Flights 

(Values Per Person)

1. Raleigh (RDU) to NYC (JFK) positioning flight First Class on Delta, booked through Delta

Points used: 27,500 Delta Points (earned via Delta)

Cash (taxes and fees): $5.50

2. NYC (JFK) to Milan (MXP) on Emirates business class (lie flat)

This is THE flight I was most excited about on their A380-800. It did not disappoint! 

Points used: 87,000 points transferred into Emirates and booked via Emirates

Cash (taxes and fees): $105.50

3. Rome (FCO) to Raleigh (RDU) with a layover in NYC (JFK). Booked through Virgin Atlantic.

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 points transferred to and booked via Virgin Atlantic.

Cash (taxes and fees): $64.85

Flights Total Points per person: 207,000

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

Lounges

With our tickets, we visited the following lounges for free:

1. Emirates Lounge in JFK
2. ITA lounge in FCO

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

Hotels booked with Points

1. Milan IHG Crowne Plaza (one night)

Points used for one night: 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 for two nights: 160,000 (earned and redeemed via Hilton)

3. NYC Hyatt Regency JFK Airport at Resorts World New York (one night

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

Note: we only had to book this room as our returning flight from JFK to RDU was delayed until the next day and there were no other flights we could reasonably make. 

Total Points used on Hotels: 197,000

Total cash spent on points hotels: $0

Hotels booked with Cash

Both of these hotels were absolutely worth the expense for us for a trip like this, but SPECIFICALLY because of the rooms we chose. The rooms we chose were the best rooms in the hotel and both offered incredible views.

1. Lerici Doria Park Hotel: Deluxe Golfo Dei Poeti Room, breakfast included option, two nights (includes a huge private terrace with jacuzzi and lounge chairs. The hotel set up a table and arranged a moonlight dinner)

Cash used for 2 nights: $716.15 (652 Euros)

2. Florence Santa Croce B&B: 1 King bed with Balcony-no breakfast option, 3 nights

Cash used for 3 nights: $958 (850.50 Euros)

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

Vacation Rentals booked with cash

These vacation rentals booked via AirBNB allowed us to stay in places where there may not have been as many or no points options. 

1. Bologna AirBNB two nights

Cash used for two nights: $317.86

2. Parma AirBNB for two nights

Cash used for two nights: $312.40

3. Lucca AirBNB for two nights

Cash used for two nights: $383.01

Total cash used for AirBNBs (6 nights): $1,013. 27

Train Tickets between cities

TrenItalia and Italo Economy/Ordinary and First Class tickets

Cash used per person: $111.73 ($223.46 total)

Experiences Booked with Cash

1. Bologna Three Hour Cooking class (with full lunch) booked through Cesarine here.

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: !0 Euros (approx $11)

3. Parma Caseificio Ugolotti authentic Parmesano Reggiano factory tour, booked via their website here.

Cash used pp: $43.60

4. Tuscany Vineyard tour and full lunch and wine tasting at Tenuta Casanova, booked via their website here.

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

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

Total Points and Miles plus Cash Amounts for the Trip

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!

Have you booked a perfectly balanced trip mixing money savings and extraordinary experiences? Tell me about it!