How to Plan a Trip to Italy on Points (Rome, Florence, Amalfi)
A complete, step-by-step guide to planning the Italian dream trip — flights, hotels, trains, and experiences — using the credit card points you've already been earning.
Target Keywords: Italy trip on points, plan trip to Italy with credit card points, Italy travel for retirees, Rome Florence Amalfi on points, how to fly to Italy with points, Italy vacation using rewards points
Word Count: ~2,500
Category: Destination Guide (Aspirational + Educational)
Cluster: Cluster 7 — Destination Guides for 55+
Internal Links: Pillar 2 (Business Class on Points), Pillar 3 (Best Cards for 55+), Amex Membership Rewards Guide, Chase Ultimate Rewards Guide, Travel Score Quiz
Schema: Article, HowTo, FAQ
Meta Title: How to Plan a Trip to Italy on Points: Rome, Florence & Amalfi | WanderWise
Meta Description: Plan your dream Italy trip using credit card points. Step-by-step guide to booking flights, hotels, and trains to Rome, Florence, and the Amalfi Coast for travelers 55+.
Slug: /blog/how-to-plan-trip-to-italy-on-points-rome-florence-amalfi
Italy is the trip.
You know the one. The trip you've been talking about for years over dinner. The one you promised each other when the kids left. The one where you finally sit on a terrace in Positano with a glass of limoncello and think, "We actually did it."
Here's what most people don't realize: that trip doesn't need to cost $12,000. It doesn't even need to cost $5,000. With the right points strategy — and we're talking about points you may already have sitting in your credit card account right now — you can fly to Italy in a lie-flat business class seat, stay in beautiful hotels, and spend your actual money on the things that matter: the long lunch in Trastevere, the Chianti in the Tuscan hills, the boat ride along the Amalfi coast.
This is the guide that puts it all together. Not theory. Not "you could hypothetically." This is the step-by-step plan for a 12-day Italy trip — Rome, Florence, and the Amalfi Coast — with specific point costs, booking strategies, and a sample itinerary you can adapt to your own timeline.
Let's go.
The Trip at a Glance
Before we get into the how, here's the what:
| Component | Cash Price (2 people) | Points Price (2 people) | Savings |
|---|---|---|---|
| Business class flights (US → Rome, Naples → US) | $8,000–$12,000 | 120,000–140,000 points + ~$120 taxes | $7,880–$11,880 |
| Hotels (10 nights) | $2,800–$4,500 | 200,000–350,000 hotel points OR $1,400–$2,200 cash | $1,400–$2,300 |
| Trains (Rome → Florence → Naples) | $120–$200 | Pay cash (not worth using points) | — |
| Total | $11,000–$17,000 | 120,000–140,000 airline points + hotel points + ~$1,700 cash | $7,000–$12,000+ |
Read that bottom line again. A trip that costs eleven to seventeen thousand dollars in cash can be done for a fraction of that — business class included — with a smart points strategy.
Now let's build it.
Step 1: Book Your Flights on Points (The Biggest Win)
The flights are where points deliver the most dramatic value. A business class seat from the East Coast to Rome retails for $4,000–$6,000 per person. On points? You're looking at 60,000–70,000 points per person, plus a few dollars in taxes.
That's a value of 6–8 cents per point. If you've read our beginner's guide to credit card points, you know that anything above 2 cents per point is excellent. This is exceptional.
The best ways to book flights to Italy on points:
Option A: Chase Points → United MileagePlus (Best Overall)
Transfer Chase Ultimate Rewards points to United at a 1:1 ratio. Search United.com for "Saver" award flights to Rome (FCO). United partners with Lufthansa, Swiss, and other Star Alliance carriers, so you'll often fly on premium European airlines.
- Cost: 60,000 points per person in business class (one-way)
- Route examples: NYC → Rome via Frankfurt (Lufthansa), Chicago → Rome via Zürich (Swiss)
- Booking tip: Search 10–11 months out for best availability. Be flexible by a day or two.
Option B: Amex Points → Air Canada Aeroplan (Excellent Availability)
Transfer Amex Membership Rewards to Aeroplan at a 1:1 ratio. Aeroplan consistently has the widest business class availability to Europe, and their award chart is transparent.
- Cost: 55,000–70,000 points per person in business class (one-way)
- Route examples: East Coast → Rome via Montreal or Toronto on Air Canada or partner airlines
- Why it's great: If you carry an Amex Gold or Platinum, this is one of the strongest transfer partner options
Option C: Chase Portal (Simplest)
If transfer partners feel overwhelming, you can simply book through the Chase travel portal. You'll pay more points — roughly 300,000–400,000 for two round-trip business class tickets — but the process is as simple as booking on Expedia.
- Best for: People who want simplicity over optimization
- Card needed: Chase Sapphire Preferred (1.25¢/point) or Reserve (1.5¢/point)
Our recommendation: Option A or B for business class. The value difference is enormous. We walk through the entire transfer-and-book process in our guide to flying business class to Europe on points.
Pro tip for Italy specifically: Fly into Rome, fly out of Naples (or vice versa). "Open jaw" itineraries — where you arrive in one city and leave from another — eliminate backtracking and are usually the same point cost as round-trips. Most award programs allow this.
Step 2: Plan Your Itinerary (12 Days, 3 Regions)
Here's a sample itinerary that balances iconic highlights with the slower pace that makes Italy unforgettable:
Days 1–4: Rome (4 Nights)
Rome deserves time. Not the frantic "Colosseum by 8, Vatican by 11, Trevi Fountain by 2" approach, but the kind of visit where you wander through Trastevere at dusk, linger over cacio e pepe, and discover a piazza that isn't in any guidebook.
What to prioritize:
- The Colosseum and Roman Forum (book tickets in advance — skip-the-line matters)
- Vatican Museums and Sistine Chapel (go on a Wednesday morning when the Pope holds mass in St. Peter's Square and the museums are less crowded)
- Trastevere neighborhood for evening passeggiata and dinner
- A cooking class in someone's home (some of the best travel memories money can buy)
- A day trip to Tivoli (Villa d'Este and Hadrian's Villa) if you want to escape the city
Hotels on points:
- Marriott Bonvoy: Rome Marriott Grand Hotel Flora — 50,000–60,000 points/night, near the Spanish Steps
- Hilton Honors: Rome Cavalieri — 70,000–95,000 points/night, stunning hilltop views and pool
- Cash-friendly option: Boutique hotels in Trastevere or Monti — $150–$200/night, charming and walkable
Days 5–7: Florence (3 Nights)
Take the high-speed train from Rome to Florence — it's 90 minutes, costs about $30–$50 per person, and the views as you approach Florence are worth every euro. This is a case where cash is the right call; no points needed.
What to prioritize:
- The Uffizi Gallery (book timed tickets weeks in advance)
- A walk across Ponte Vecchio at golden hour
- The Accademia Gallery to see Michelangelo's David
- The Central Market (Mercato Centrale) for lunch
- A half-day trip to the Chianti wine region — rolling hills, medieval villages, extraordinary wine
Hotels on points:
- Marriott Bonvoy: The St. Regis Florence — 70,000–85,000 points/night, one of Italy's finest hotels
- Hilton Honors: Several options near the train station at 40,000–60,000 points/night
- Cash-friendly option: Small palazzo hotels near the Duomo — $180–$250/night
Days 8–11: Amalfi Coast (4 Nights)
From Florence, take the train to Naples (about 3 hours, $30–$40), then a private transfer or the SITA bus along the coastal road to your base on the Amalfi Coast. We recommend basing yourself in either Positano (glamorous, photogenic, hilly), Ravello (quieter, higher up, incredible gardens), or Amalfi town (central, more affordable, walkable).
What to prioritize:
- The Path of the Gods hiking trail (moderate difficulty, jaw-dropping coastal views)
- A boat tour from Amalfi to Capri
- Lemon groves and limoncello tasting
- An evening in Ravello — the Villa Rufolo gardens at sunset rival anything in Europe
- Simply sitting. On a terrace. With the sea below. This is why you came.
Hotels on points:
- Amalfi Coast hotel options on points are limited compared to Rome and Florence. This is where cash — or a hybrid strategy — often makes more sense.
- Marriott Bonvoy: The Le Meridien Positano is bookable on points (50,000–70,000/night when available)
- Cash-friendly option: Many gorgeous family-run hotels in the $200–$350/night range that are worth every cent
Day 12: Fly Home from Naples
Naples International Airport (NAP) is about 90 minutes from the Amalfi Coast. Fly home from here — preferably in business class, because you deserve the perfect ending.
Step 3: Book Your Hotels on Points (or Know When to Pay Cash)
Italy is one of those destinations where a hybrid approach works beautifully. Here's our rule of thumb:
Use hotel points in Rome and Florence — major chains have excellent properties, and 40,000–85,000 points per night beats $300–$500 in cash every time.
Consider paying cash on the Amalfi Coast — the best Amalfi Coast experiences are often at smaller, independent hotels and B&Bs that don't participate in points programs. A family-run hotel carved into the cliffside in Positano, with a terrace overlooking the sea? That's worth paying for.
Where to get hotel points:
- If you carry a Marriott Bonvoy credit card, you're earning hotel points on every purchase
- You can transfer Amex Membership Rewards to Marriott Bonvoy (but the transfer ratio isn't ideal — better to earn Marriott points directly)
- For a full walkthrough of hotel bookings on points, see our guide to booking hotels with points for first-timers
Step 4: The Points Budget — What You Actually Need
Let's put the full picture together for a couple:
| Component | Points/Cash Needed |
|---|---|
| Business class flights (2 people, round trip) | 120,000–140,000 airline points + ~$120 taxes |
| Rome hotels (4 nights) | 200,000–240,000 Marriott points OR ~$800–$1,200 cash |
| Florence hotels (3 nights) | 120,000–180,000 Marriott points OR ~$550–$750 cash |
| Amalfi Coast hotels (4 nights) | ~$800–$1,400 cash |
| Trains (Rome → Florence → Naples) | ~$120–$180 cash |
| Food, experiences, miscellaneous | ~$1,500–$2,500 cash |
| Total | 120K–140K airline points + 320K–420K hotel points + ~$2,500–$3,900 cash |
Compare that to $11,000–$17,000 all-cash. The savings are real. The trip is identical — actually better, because you're flying business class.
Don't have enough points yet? If you're starting from zero, one sign-up bonus from the Chase Sapphire Preferred (80,000 points) plus 6–9 months of regular spending can get you to 120,000+ airline points. A Marriott Bonvoy card adds hotel points on top. Most couples can accumulate enough for this trip within a year of intentional earning. Our guide to earning 100,000 points in six months maps out the exact strategy.
Timing Tips: When to Go and When to Book
Best months for Italy:
- May and early June: Warm but not scorching. Flowers everywhere. Fewer crowds than peak summer.
- September and October: The sweet spot. Warm weather, thinner crowds, harvest season in Tuscany.
- Avoid: August (everything is hot, crowded, and many family-run restaurants close for vacation) and late December–February (cool and rainy, many Amalfi Coast hotels shutter).
When to book award flights:
- 10–11 months before departure for the widest business class availability
- Mid-week departures (Tuesday/Wednesday) typically have better award space
- Be flexible by 1–2 days in each direction — it can make the difference between finding a seat and not
When to book hotels:
- Award hotel availability tends to be better 3–6 months out
- For the Amalfi Coast (especially Positano), book 4–6 months ahead regardless — popular properties sell out
Frequently Asked Questions
Can I really fly business class to Italy on points?
Yes. This is arguably the single best use of credit card points — international business class flights deliver the highest per-point value anywhere in the rewards ecosystem. Read our complete business class booking guide for the full walkthrough.
What if I only have 50,000 points?
You can still make a meaningful dent. Use 50,000 points for one-way economy flights for two people, or save them for 3–4 hotel nights in Rome. Every point used is cash you don't spend. Take our Travel Score Quiz to see what your current balance can do.
Should I book flights or hotels with points first?
Flights. Always flights. The per-point value on international flights — especially in premium cabins — is dramatically higher than hotels. Lock in your flights first, then figure out hotels with whatever points remain.
Is Italy safe for older travelers?
Italy is one of the most popular destinations for travelers 55+ worldwide, and for good reason. The culture is welcoming, healthcare infrastructure is excellent, and Italians have deep respect for older adults. A few practical notes: cobblestones are everywhere (comfortable walking shoes are non-negotiable), summer heat in Rome can be intense (carry water, take midday breaks), and learning a few Italian phrases goes a long way.
What about travel insurance?
We strongly recommend it for any international trip. Many premium travel credit cards include built-in trip cancellation and interruption insurance — check your card benefits before buying a separate policy. Our travel insurance guide for seniors covers exactly what to look for.
Your Italy Action Plan
- Check your points balance across all programs. Log into Chase, Amex, and any airline/hotel accounts you have.
- Pick your dates. May–June or September–October. Build in flexibility.
- Book flights first. Transfer points to United (Chase) or Aeroplan (Amex) and search for business class availability.
- Lock in Rome and Florence hotels on points through Marriott or Hilton.
- Book Amalfi Coast accommodations in cash — choose character over chain.
- Start earning if you need more points. The Chase Sapphire Preferred and Amex Gold together can accumulate 150,000+ points in year one from normal spending.
The terrace is waiting. The limoncello is chilled. And the points — your points — are ready to take you there.
Andiamo.
Planning an Italy trip on points? Join the WanderWise Community and share your itinerary — our members love helping each other find availability and hidden gems.