LATE APRIL – EARLY JUNE · SEPTEMBER – OCTOBER
Italy
the world’s most-booked trip right now
Ancient ruins, hand-rolled pasta, and a glass of something local in a piazza with no agenda. Italy is calling.
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THE DESTINATION:
Italy is having its biggest year on record. Here's how to make the most of it.
Italy was named the world's top travel destination for 2026 — and the numbers back it up. Tour operator bookings are at record levels. Airlines have added new direct routes from the US. And the cultural calendar is packed in a way that happens once a generation, from the aftermath of the Winter Olympics in Milan and the Dolomites to the Venice Biennale and a packed harvest season in Tuscany this autumn.
This week we're taking you to Italy in full — the practical stuff (when to go, where to stay, how to get around) alongside the things that make the trip genuinely great: which month to book, which Rome neighborhood to base yourself in, and the twenty things every first-timer wishes they'd known before they landed.
We've spent the past month building out a complete Italy guide on the site. Everything linked in this issue is part of that — and together they add up to the most thorough Italy planning resource we've ever put together. Let's go.
START HERE - COMPLETE PLANNING GUIDE:
The full picture — entry requirements (including the new EU biometric system now at Rome and Milan airports), budget benchmarks, which cities to visit, how to get there from the US, and everything that's new and different this year. If you're planning an Italy trip in 2026 or 2027, this is where to start. ETIAS authorization — the EU's new pre-travel system, similar to the US ESTA — is expected to launch in late 2026, so trip planning now means knowing what's coming.
ITALY AT A GLANCE:
PLAN YOUR ROUTE:
The Perfect 2 Weeks in Italy for First-Timers
Rome (4 nights) → Amalfi Coast (3 nights) → Florence and Tuscany (3 nights) → Venice (3 nights). The classic route, done properly — with every train connection, booking window, and day plan laid out so you don't have to work it out yourself. Includes train times and advance booking advice for every city. Fly into Rome, fly home from Venice to avoid backtracking and often save money.
PLANNING
Best Time to Visit Italy (Month-by-Month Breakdown)
The honest breakdown — weather, crowds, costs, and what's on for every month of the year.
ACCOMMODATIONS
Where to Stay in Rome: Best Neighborhoods
Centro Storico, Monti, Trastevere, Prati — who each neighborhood suits and what it actually costs.
TIPS
20 Things to Know Before You go
ZTL zones, train validation, cappuccino rules, tourist taxes. The things you learn on your first trip — before your first trip.
DESTINATIONS
Best Italy Cities to Visit in 2026
From Rome and Florence to Bologna, Puglia and Sicily — the full rundown of where to go and why.
INSIDER TIP:
The single most important thing to do right now
If you're planning an Italy trip for summer 2026, book the Vatican Museums, Colosseum, and Borghese Gallery this week — not next month, this week. The Vatican already has sold-out time slots through June. The Borghese Gallery limits entry to 360 visitors per 2-hour slot and sells out 4–6 weeks ahead. The travelers who arrive in Rome expecting to "just pop in" to these are the ones spending their morning in a queue instead of inside. Book at museivaticani.va, coopculture.it, and borghese.it directly — no third-party booking fees.
GETTING THERE:
Deal of the Week
NEW YORK → ROME (FCO): From ~$450 round-trip
Shoulder season window · May & September · Check Google Flights, Kayak & Momondo
How to find the best price: Book 3–4 months ahead for shoulder season. Fly mid-week — Thursday is consistently cheapest. Use the open-jaw trick (fly into Rome, home from Venice or Milan) — same price or cheaper, no backtracking. Set a price alert on Google Flights now and book when it drops below $500 RT from the East Coast.
BEST ROUTES FROM NYC
→ JFK or EWR to Rome FCO
→ JFK to Florence (via Rome or Milan)
→ Open-jaw: fly in Rome, out Venice
NEW ROUTES IN 2026
✦ Delta JFK → Olbia, Sardinia
✦ United EWR → Bari, Puglia
✦ Alaska SEA → Rome (new!)
Fare checked Google Flights and Kayak, week of April 7, 2026. Prices fluctuate — search now to lock your dates.
40 km of covered porticoes line its streets (a UNESCO World Heritage site in their own right). The university, founded in 1088, is the oldest in the Western world and keeps the city young and energetic in a way that Florence, for all its beauty, no longer is. Prices run roughly half what you'd pay in Florence for the same quality of hotel and meal. The film festival Il Cinema Ritrovato (June 20–28) celebrates its 40th anniversary this year and is worth building a trip around.
WHERE TO GO:
Hidden Gem: Bologna
For too long, Bologna has been treated as a pit stop between Florence and Venice. That's a mistake. Italy's food capital — the birthplace of ragù, tortellini, mortadella, and fresh pasta made with a rolling pin, not a machine — is also one of its most liveable, most beautiful, and most affordable cities.
Don’t miss:
The Two Towers (Le Due Torri)
Mercato di Mezzo & the Quadrilatero
Piazza Maggiore at Aperitivo Hour
The Porticoes — a UNESCO World Heritage Site
Il Cinema Ritrovato — June 20–28, 2026
THE MOST EXTRAORDINARY STAY IN TUSCANY:
Chiusdino, Siena · Tuscany
This is the one. A 5-star boutique estate on 300 acres of Sienese countryside, Borgo Santo Pietro was originally a healing stopover for medieval pilgrims on the Via Francigena — the ancient route to Rome. That spirit of restoration is still very much the point. The 300-acre organically farmed estate includes market gardens, herb gardens, vineyards, orchards, and a drove of pigs that supply the kitchen. Everything on your plate came from within a stone's throw of where you're sitting.
There are two Michelin-starred restaurants on the property. The spa runs on Seed to Skin, their own organic skincare line produced from the estate's botanicals. Monday evenings bring a Farmers' Market dinner where guests choose ingredients from the stalls and watch them cooked on the spot, outdoors, with live music. It is the antithesis of an anonymous luxury hotel — it's a place with a philosophy, and the philosophy is that genuine restoration requires slowing down entirely.
Why it's worth saving for: This is a once-in-a-trip stay — the kind of place you'll still be talking about two years later. Plan 2–3 nights minimum. Use it as a base to visit Siena (30 minutes), San Gimignano, and the Chianti wine country.
WHERE TO STAY:
Three Hotels. Every Budget.
One splurge, one mid-range, one smart pick.
AFFORDABLE: ROME
Condominio Monti
€100-130/night
The Time Out editors' pick for best affordable hotel in Rome — and one of the rare places that genuinely earns the description "feels luxurious while being actually affordable." Housed in a 20th-century building on the pretty Via dei Serpenti in Monti, Condominio Monti has 25 rooms with custom furnishings, built-in bookshelves that double as desks, retro-chic appliances, and handcrafted wallpaper. No two rooms are the same.
MID-RANGE: FLORENCE
SoprArno Suites
€150-200/night
Thirteen rooms on the upper floors of a 16th-century townhouse in Florence's Oltrarno neighborhood — the left bank of the Arno, quieter and more local than the tourist-dense centro storico across the river. The Michelin Guide describes it as a "vintage lover's hideaway," which is apt: the rooms overflow with art, antiques, original frescoes, and vintage typography, and no two spaces are the same. It feels more like staying in a very well-curated private apartment than a hotel.
SPLURGE: AMALFI COAST
Belmond Hotel Caruso
~€800/night
Perched 350 metres above the sea in Ravello — the hilltop village above the Amalfi Coast that Wagner, Virginia Woolf, and Gore Vidal all called their favourite place on earth — the Belmond Hotel Caruso is the most spectacular hotel on a coastline famous for spectacular hotels. An 11th-century palazzo with an infinity pool that appears to spill directly into the Tyrrhenian Sea, surrounded by terraced gardens tumbling down the cliff face. The views are genuinely among the most beautiful in Europe.
HOT TIPS:
3 Things To Know Before You Book
1. Book museums before you book flights. The Vatican Museums, Borghese Gallery, Uffizi, and Colosseum all require advance timed entry. The Borghese in particular sells out 4–6 weeks ahead. Book these at the official sites — no third-party fees.
2. Never drive a rental car into a city center. ZTL restricted zones are enforced by cameras with no warning. Fines of €80–160 per infraction arrive weeks later via the rental company. Park outside and take public transit. This catches experienced travelers every year.
3. The cappuccino is a morning drink. Order one after 11am and every Italian in the room will quietly notice. After meals: espresso. Always. A small thing that signals enormous respect for where you are.
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