This article was originally published in The Detour in August 2024

A First-timer's Guide to Italy at Christmas

Q:&nbsp;&ldquo;So, I am planning a trip to Italy over Christmas holidays, specifically December 25 - January 1. I am not a world traveler. To be fair, I have only been to Mexico, the Virgin Islands and the Bahamas out of state. I know&hellip;boring! But I so desperately want to see other places.&nbsp;
That being said, I need advice on where to go during the winter months. This is a Christmas gift to my 23 and 27-year-old kids and my husband and me. We do not want to ski and we are budget minded. My knowledge of traveling in other countries is limited so I have some anxiety about planning and maneuvering through different parts of Italy. I definitely want to experience the food and wine scene, but also want to visit Rome and the historical landmarks. There&rsquo;s so much information available that I am overwhelmed right now. Please help.&rdquo;

Hey, reader, I absolutely feel you &mdash; organising your first trip to Italy is definitely overwhelming&hellip; there&rsquo;s just so much to see!
For a 7-day trip, I&rsquo;d suggest two types of itinerary:

The Classic&nbsp;&mdash; Rome &amp; Tuscany
Why? Start with a bang with a deep-immersion into Rome&rsquo;s magic, and then get lost in Tuscany&rsquo;s hills for the rest of the trip.
How? Book a round trip ticket to Rome (unless you find some budget-friendly&nbsp;<a href="https://jacksflightclub.com/travel-hub/how-to-find-and-book-cheap-multi-city-flights?lid=rxr5x03eqyyj">multi-city trips</a>&nbsp;landing/taking off from Florence) and plan your first three days in the capital. This allows you plenty of time to walk through the main parts of the city, and to overindulge in&nbsp;<a href="https://italysegreta.com/20-foods-you-must-eat-in-rome/?lid=xnhi8gedygd3">carbonara and Roman artichokes.</a>

On your fourth day (or, the third evening) hop on a high-speed train up to Florence and spend a day ticking off the main sights in the birthplace of the Renaissance &mdash; Uffizi, David and Duomo Cathedral non-negotiable! Also, don&rsquo;t forget to stop for a&nbsp;<a href="https://italysegreta.com/11-best-panino-shops-in-florence/?lid=7cwhhbst6kht">lampredotto</a>&nbsp;for lunch.
Spend a night in Florence and kick off your last two days by renting a car and driving around the Tuscan countryside. The&nbsp;<a href="https://italysegreta.com/wild-boars-stolen-peaches-and-the-long-road-from-florence-to-siena/?lid=ko0mb0yppo55">picturesque hills and borghi</a>&nbsp;around Siena, San Gimignano, Montepulciano, and Orvieto will make you forget about the crowded spots you&rsquo;ve just been through. Plus, it&rsquo;s the kingdom of&nbsp;<a href="https://italysegreta.com/tuscan-farmhouses/?lid=99v4f1rgsobm">agriturismi </a>and vineyards, so good&nbsp;<a href="https://italysegreta.com/natural-wine-in-tuscany/?lid=miv1jjny4wnv">(natural!)</a>&nbsp;wine and food is guaranteed!
Hot Tip:&nbsp;You don&rsquo;t need to return the car in Florence, drive all the way down to Rome and leave the car at the airport before your flight :-)

The Hardcore&nbsp;&mdash; Venice, Florence &amp; Rome
Why?&nbsp;Personally, I believe these are the essentials for a first (short) trip to Italy. They&rsquo;re rich in history and culture, and all very different from each other.
Plus, they&rsquo;re conveniently connected by non-stop, high-speed trains (Trenitalia&rsquo;s&nbsp;Frecce), which will make the transport process easy and comfortable. Just remember to book your train in advance &mdash; the earlier, the better!
How?&nbsp;It&rsquo;s a more upbeat itinerary, which would be ideally planned with a&nbsp;<a href="https://www.google.com/travel/flights/search?tfs=CBwQAhopEgoyMDI0LTEyLTI0ag0IAxIJL20vMDJfMjg2cgwIAxIIL20vMDdfcGYaKRIKMjAyNC0xMi0zMWoMCAMSCC9tLzA2YzYycg0IAxIJL20vMDJfMjg2QAFIAXABggELCP___________wGYAQM&amp;hl=en&amp;curr=USD&amp;lid=j2sj7u8nyu9h">multi-city trip like this one&nbsp;</a>(assuming you&rsquo;ll be flying from New York City).&nbsp;
You can start by landing in Venice (or Milan and then hop on a train to Venice, if that&rsquo;s more budget-friendly) and spend two days in Venice. This will give you enough time to check out the touristy attractions on the first day (like San Marco square, Rialto bridge, the Biennale, etc) and stroll around more local neighbourhoods (like&nbsp;<a href="https://lionsinthepiazza.com/cannaregio-venice-guide/?lid=2zvf153sjkfg">Cannaregio</a>&nbsp;&amp; Giudecca), or hop over to Murano, Burano, and Torcello during your second day.

Then, onto an evening (or early morning train ride) to Florence. The same 2-day plan applies here, to visit both the upper and lower Arno neighbourhoods, and fill your belly with Chianti classico and fiorentina. I shared some restaurant recommendations in&nbsp;<a href="https://jacksflightclub.com/detour-144-cruise-debate-continues?lid=p8kw18fvewte">this past Detour edition</a>.
Finally, onto the capital. Rome is immense, and two days are definitely not enough to discover all the city&rsquo;s wonders, but you&rsquo;ll be able to tick off the Coliseum, the Pantheon, and the prettiest piazzas in the city.
It is worth looking for a (free) walking tour in each of the three cities on the first day. That way, you&rsquo;ll be sure to visit all the essential sights ASAP!
Whichever itinerary you end up choosing, I strongly recommend booking your trains, accommodation, and museum tickets in advance &mdash; these cities tend to get a significant amount of (especially local) tourists over the Christmas holidays.

Christmas in Italy for First Timers

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