When to book flights to Italy?

Some pretty good deals around that time if you have some credit card points to burn

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Some pretty good deals around that time if you have some credit card points to burn

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What are you seeing?

I am going the last two weeks in April.
Flying in to Athens and home from Venice on American Airlines.
Got what I considered a good deal.
$750 per persom was the base rate. It ended up being $900 per person after pre paid luggage and seat selection.

In terms of checking prices, look at other airports whether departing or leaving as well

For instance, you could fly to Florence, go to Florence main station Santa Maria N and get to Venice S Lucia in 2 hrs 15 min.

You need to allow a 6 to 8 hour travel time from Venice to Naples whether you’re flying or driving or taking a train.

What city could you fly from?

Someone tauggt me to use chat gpt and it works great. Give it the prompts you want and update accordingly.
It searches every site and helps you book. Saved me a ton.

Prompt --

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I'm planning a trip to Italy in April. Flying into Venice and flying out of Naples about 10 or 11 days later. Can you find the best options for travel. Including open leg fights? Trains? Best times of day to travel. Best locations to travel to. Maximizing price and also with upgrade options if economical.

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Perfect—open-jaw (multi-city) into Venice and out of Naples is exactly how to do Italy in ~10–11 days. Here’s a clean, price-savvy plan you can use right now; if you share your home airport + exact dates, I’ll pull live fares and specific trains.

Game plan (10–11 days)

Venice (2–3 nights) ? Florence/Tuscany (3 nights) ? Rome (3 nights) ? Naples or Sorrento/Amalfi base (2 nights) ? fly home from Naples (NAP).
(If airfare out of Rome FCO is dramatically cheaper, finish in Naples and take a 1h high-speed train back to Rome for your flight—details below.)


Trains you’ll take (fast, cheap, and upgrade-able)

Venice ? Florence (Frecciarossa or Italo): ~1h55–2h15; dozens daily.

Florence ? Rome: ~1h15–1h30; constant service.

Rome ? Naples: ~53–70 min on the fastest trains; 60+ per day.

Optionally Venice ? Naples direct (skip Florence/Rome): ~4h45–5h on the fastest direct trains.

Naples ? Pompeii/Herculaneum/Sorrento (Amalfi Coast gateway): Use the tourist Campania Express (AC, luggage space, reserved seats) rather than the crowded local Circumvesuviana.


Classes & smart upgrades

Trenitalia Frecciarossa: Standard / Premium / Business / Executive. Premium/Business often just €10–25 more for wider seats and a welcome drink—worth it on 1–2 hour legs.

Italo: Smart / Prima / Club Executive. Prima is the sweet spot (priority boarding + snacks) when it’s a small bump from Smart.


When to ride (to save money + sanity)

Mid-morning departures (˜ 09:30–11:00) hit the sweet spot: cheaper than early peak, arrive just before hotel check-in.

Avoid 07:00–09:00 commuter rush and Friday late afternoon price spikes.

For Venice departures, add 30–60 min for vaporetto/taxi to Santa Lucia station.


Flights (open-jaw/multi-city)

Book as one multi-city ticket: [Home] ? VCE (Venice), then NAP (Naples) ? [Home]. This prices better and protects connections.

If NAP ? [Home] is pricey, compare FCO (Rome)—Naples to Rome is ~1h by train, then fly from FCO; even with the train, total cost can drop.

Strong value carriers for April: Delta/Air France/KLM, United/LH/SWISS, American/British/Iberia (mix-and-match partners on multi-city).


A price-efficient route (with upgrade options)

Day 1–3 Venice

Arrive VCE. Stay in Cannaregio or Dorsoduro (good value).

Train Venezia S. Lucia ? Firenze S. M. Novella mid-morning; target Frecciarossa/Italo in Premium/Prima if +€10–20.


Day 3–6 Florence (Tuscany day trip optional)

Siena or Chianti by bus/tour; Pisa/Lucca by regional train.

Firenze ? Roma Termini around late morning; upgrade if small price jump.


Day 6–9 Rome

Colosseum/Vatican on separate days; Trastevere evenings.

Roma Termini ? Napoli Centrale ~1h; look for Super Economy/Low-Cost fares first, then consider Business/Prima upgrades if <€20 extra.


Day 9–11 Naples or Sorrento

If you want Amalfi vibes without the cliff-road drama, base in Sorrento and use Campania Express for Pompeii/Herculaneum and back to Naples for your flight.

Fly out of NAP (or train to FCO and fly if cheaper overall).


Booking moves (to maximize price)

Trains: Buy as soon as schedules drop (usually 2–4 months out). Look for “Super Economy/Low-Cost” tiers on Trenitalia/Italo—often €19–€39 on these legs. (Inventory is limited and rises over time; Italy’s HS trains can sell out or go up in price, and delays can happen—build a little buffer.)

Flights: Search multi-city in one ticket; try shifting your return by ±1 day and compare NAP vs FCO return. Saturday night stay is already baked into a 10-day trip.


Tiny but mighty tips

No baggage fees or checks on trains—just roll on. Sit near luggage racks and keep eyes open at major stations.

Seat maps: pick forward-facing when offered; on Italo, Coach 1 (Club) and Prima are quieter.

Easter 2025 is April 20. Week before/after is busy—lock trains and hotels early if your dates touch that window.



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If you give me:

1. your home airport,


2. exact April dates (flexible? max 1 stop?), and


3. upgrade preferences (e.g., “train Premium/Prima only if =€25 extra”),



…I’ll deliver specific multi-city flight options with prices, the exact trains to book (numbers, times, and seat class), plus a day-by-day with hotel areas that fit your style and budget.