We Planned a 20-Night Italy Honeymoon — Here’s Everything We Booked
When my husband and I started planning our honeymoon, we knew one thing for certain: we wanted Italy. Not a rushed 10-day highlights tour. The real thing — slow mornings, long dinners, and enough time to actually feel each city before moving on.
What we ended up with was 20 nights, 6 cities, 7 hotels, 12 restaurant reservations, and two trains booked across the most beautiful country in the world.
And here’s the part that might surprise you: a lot of it was funded by buying IHG points directly — at the right time.
My husband and I are pretty deliberate about watching for hotel points promotions. When IHG ran a 100% bonus points match sale directly on their website, we bought points at the discounted rate and instantly doubled them. No credit card tricks, no complicated transfers — just timing a direct purchase right. We stacked up enough IHG points to make luxury hotel stays genuinely accessible. If you look at our hotel list and notice it’s heavily IHG-oriented — Hotel Indigo Florence, Hotel Indigo Venice, Hotel Indigo Milan, InterContinental Rome — that’s exactly why. We built the itinerary around our points, not the other way around. The result is a 20-night luxury honeymoon that would have cost a dramatically different number if we’d paid cash for every night.
Here’s exactly what we planned — and why.
The Full Itinerary at a Glance
| City | Nights |
|---|---|
| Florence | 5 nights |
| Siena | 1 night |
| Rome | 4 nights |
| Venice | 3 nights |
| Lake Como | 4 nights |
| Milan | 2 nights |
The Hotels We Booked
We wanted a mix of boutique character and iconic luxury — and our IHG points strategy shaped almost every choice. Here’s the full breakdown of what we paid, what we redeemed, and what the cash value actually looks like.
A quick note on the points math: we purchased IHG points directly from IHG’s website during a 100% bonus points sale, which brought the cost down to just $0.005 per point (that’s $5 per 1,000 points). We then used those points for our IHG properties. Here’s how each stay breaks down:
Florence — Hotel Indigo Florence368,000 IHG points (purchased for ~$1,840) | Cash rate at time of booking: ~$381/night (~$1,905 for 5 nights) Our first stop and five full nights to ease into Italy. Hotel Indigo felt like the right balance of boutique charm and genuine comfort. Florence rewards slow exploration and we wanted a home base that felt personal, not corporate. The points redemption here was a modest saving over cash — but more importantly, it meant we didn’t have to pay a large lump sum upfront at booking time.
**Siena — NH Collection Palazzo Gaddi (GHA)**Paid cash | 1 night One night in Siena on the way south to Rome. We’re GHA members so the NH Collection was a natural choice — and honestly, Siena deserves more than one night. We’ll be back.
Rome — InterContinental Rome (2 nights)$1,100 USD cash — redeemed our annual IHG BOGO weekend coupon here The BOGO coupon only works on weekends, which is exactly why we routed through Siena first. Without this detour, we’d have arrived in Rome on a Monday and lost the deal entirely. Two nights at the InterContinental, effectively for the price of one.
**Rome — Rome Cavalieri Waldorf Astoria (2 nights)**210,000 Hilton Honors points (purchased for ~$1,050 during a 100% bonus sale) | Cash value: ~$2,000 for 2 nights (~$1,000/night for these dates) The Waldorf is a Hilton property, so this redemption used Hilton Honors points — not IHG. We bought these during one of Hilton’s regular 100% bonus sales, which brings the cost down to the same $0.005 per point as IHG. The Waldorf sits on a hill above the city with views that feel almost unfair. We moved here for the final two Rome nights to close out our Roman chapter in full glamour.
**Venice — Tapestry by Hilton Venice Mestre (1 night)**1 night transitional stay A practical overnight as we made our way from Rome to Venice proper. Sometimes logistics require a night that’s more functional than aspirational — and that’s okay.
**Venice — Hotel Indigo Venice Sant’Elena (2 nights)**189,000 IHG points (purchased for ~$945) | Cash value: ~$1,600 for 2 nights (~$800/night for these dates) Venice is a city that demands intimacy — and Hotel Indigo Sant’Elena delivers exactly that. A converted 1930s monastery in a quiet neighbourhood, away from the tourist chaos of San Marco.
Lake Como — Lake Como Edition (4 nights)$5,000 USD — 4th night free via Citi Prestige card benefit, breakfast included This was our most anticipated stop. The Lake Como Edition is the newest luxury property on the lake, and cash rates run ~$2,500/night for these peak season dates — meaning the 4 nights would have cost ~$10,000 at rack rate. The Citi Prestige 4th night free benefit alone saved us ~$2,500. Breakfast was also included through a Citi Prestige email offer.
**Milan — Hotel Indigo Milan Corso Monforte (2 nights)**180,000 IHG points (purchased for ~$900) | Cash value: ~$800 for 2 nights (~$400/night for these dates) A two-night finale steps away from Via Montenapoleone and the Duomo. Milan often gets overlooked on Italy itineraries — we wanted to close the trip with great design, great food, and of course some proper shopping. One pro tip here: IHG uses dynamic points pricing, so the redemption rate can drop after you book. We originally booked at a higher rate, then cancelled and reboooked when the price dropped to 180,000 points. Always check back on your upcoming redemptions — it takes 2 minutes and can save you tens of thousands of points.
The full points and savings summary:
| Hotel | Program | Points Used | Points Cost | Est. Cash Rate |
|---|---|---|---|---|
| Hotel Indigo Florence | IHG | 368,000 pts | ~$1,840 | ~$1,905 |
| Rome Cavalieri Waldorf Astoria | Hilton Honors | 210,000 pts | ~$1,050 | ~$2,000 |
| Hotel Indigo Venice | IHG | 189,000 pts | ~$945 | ~$1,600 |
| Hotel Indigo Milan | IHG | 180,000 pts | ~$900 | ~$800 |
| Total IHG points | IHG | 737,000 pts | ~$3,685 | ~$5,305 |
| Total Hilton points | Hilton Honors | 210,000 pts | ~$1,050 | ~$2,000 |
Plus $1,100 cash for InterContinental Rome (BOGO applied) and $5,000 for Lake Como Edition — which runs ~$2,500/night in peak season, making the Citi Prestige 4th night free benefit alone worth ~$2,500.
The bottom line: we got 20 nights of luxury Italy hotels for a total that would have been dramatically higher if we’d paid cash rates — all by watching for points sales across two programs (IHG and Hilton) and knowing how to stack our credit card benefits.
Why We Planned It This Way
A few things shaped our itinerary — and I’m going to be completely honest about all of them.
The InterContinental detour that saved us $1,000 a night Here’s a tip nobody talks about: if you have an InterContinental annual BOGO coupon, it only works on weekends. Our award flight lands on a Monday, which meant we couldn’t use it at the InterContinental Rome right away. So instead of letting a $1,000/night saving go to waste, we built our itinerary around it. We start in Florence, take a one-night detour through Siena, and arrive in Rome on a weekend — just in time to redeem the BOGO. A one-hour train ride from Florence is a very small price to pay for a luxury hotel stay we would never have splurged on otherwise. Always let your hotel loyalty benefits shape your routing (at least for us
Florence first — for the jetlag and the soul Our flight lands on a Monday and we fully expect jetlag to hit hard. Florence is our soft landing. It’s walkable, manageable, and forgiving of a slow first few days. Rome can wait until we have our bearings.
Why we gave Florence five nights Honestly? Our friends and family told us to. Knowing that we like to take things slowly and dig into hidden gems rather than rush through highlights, everyone who’d been to Florence said the same thing: stay longer than you think you need to. Five nights to fully soak in the Renaissance vibes, revisit the same piazza twice, and eat at the places that don’t show up on the first page of Google. We listened. We’re glad we did.
We didn’t do the Amalfi Coast. Everyone asks. The honest answer: we wanted this trip to feel luxurious and unhurried, and Amalfi in peak season felt like the opposite of that. Lake Como was our nature and beauty fix — and it’s a very different, quieter kind of stunning.
The Restaurants
We have 12 restaurants booked across the 6 cities, with a focus on Michelin-starred experiences. Full reviews coming after the trip in May — but I want to share the single most valuable piece of advice I can give for dining in Italy:
If you’re celebrating something special, email the restaurant directly — before reservations even open.
We did this for Enoteca Pinchiorri in Florence, one of Italy’s most celebrated three-Michelin-star restaurants. Instead of waiting for their reservation system to open up, we emailed them months in advance explaining that we were celebrating our honeymoon. Not only did we secure a table for a date that wasn’t yet publicly available — they offered us a private wine cellar tour that isn’t normally offered to the public.
Read that again: a private wine cellar tour at a three-Michelin-star restaurant, simply because we reached out personally and told them what we were celebrating.
The best tables in Florence and Rome fill up months in advance. Don’t wait for the reservation portal to open. Email them. Be warm, be specific about your occasion, and ask if there’s anything special they can offer. The worst they can say is no. The best? You get an experience most people never even know exists.
What’s Coming Next
We’re heading to Italy soon. Every hotel, every meal, every moment — I’ll be documenting all of it here and on Pinterest at @CoutureAndCrumbs.
If you’re planning a luxury Italy honeymoon and want to follow along, save this post and check back after the trip for the full reviews.
Follow our journey on Pinterest → pinterest.com/CoutureAndCrumbs
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