Episode #304: Essential Tips for Your 2026 Trip to Italy

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Planning a trip to Italy in 2026 but feeling overwhelmed by endless advice, changing travel rules, and not knowing where to start? Look no further for some clear, practical guidance – from when to book and how to choose the right destinations, to key events and major anniversaries shaping travel across Italy. You’ll learn how to cut through the noise, plan with confidence, and create an Italian journey that truly fits your travel style.

Contents

Summary

As we prepare to welcome in the New Year, host Katy Clarke breaks down exactly how to get started planning travel to Italy in 2026. From when to book flights and accommodation to navigating new travel rules and major events shaping the year ahead. Hear how events like the Winter Olympics and the 800th anniversary of St Francis could influence your plans, plus practical advice on pacing your itinerary and tailoring the experience to what matters most to you.

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What you'll learn in this episode

Why starting early is the smartest way to plan an Italy trip for 2026, including how early planning helps you focus on meaningful experiences instead of chasing a “perfect” moment, and why Italy rewards thoughtful, intentional travel
Learn how to cut through information overload and avoid planning traps, from conflicting online advice and social media noise to the risks of copying generic itineraries that don’t reflect your interests or travel style
How to design a trip around your personal travel goals, identifying your “why” for visiting Italy and choosing destinations, experiences, and pacing that align with what matters most to you – food, culture, art, relaxation, or connection
Practical guidance on timing, budgeting, and logistics, including the best seasons to visit, realistic budgeting tips, smart destination pairings, and how to choose between flights, trains, or driving without overcomplicating your plans.
What’s new and important for Italy travel in 2026, covering major events like the Winter Olympics and St. Francis anniversary, new transport developments, upcoming entry requirements, and how to stay informed using trusted planning tools and resources

Timeline Overview

06:22 Clear steps for planning an Italy trip, from choosing destinations to booking transport and accommodations at the right time
08:34 Slowing your pace leads to a better Italy experience and how to balance sightseeing with downtime
13:40 Budget-friendly alternatives to the Amalfi Coast that deliver scenery, charm, and fewer crowds
21:49 Important local events and festivals that can shape your itinerary and impact availability and prices
27:30 New seasonal flights, peak travel periods, and why planning ahead is essential for 2026 travel

LEARN MORE: About our Untold Italy Tours – destinations and itineraries >> here.

Italian places, foods and concepts mentioned

Places

Cortina d'Ampezzo – town in the Italian Alps, popular for skiing and host of the Winter Olympics 2026
Trevi Fountain – one of Rome's most famous and popular sites. The mayor of Rome has just announced that there will be a fee to access the very front tier of the Trevi Fountain. This is designed to protect this incredible monument, which gets exceptionally busy. Access will be charged between 9 am and 10 pm, but no further official information is yet available
Colosseum Metro C Line station – this new station and stop on Line C has finally opened (after two decades) in Rome. The station will also act as a museum for many artefacts found, as it was created
Bari – city in Puglia, home to one of the main airports in the region, with new flights from the US coming this year

Words / Concepts

Google Flights – set up alerts for your ideal travel dates and times to track flight prices
2026 Winter Olympics – held between 6th and 22nd February in Milan and Cortina d'Ampezzo, Italy. Officially named Milano Cortina 2026
2026 Winter Paralympics – held between the 6th and the 15th March – again in Milan and Cortina d'Ampezzo. The Games will mark the 50th anniversary of the first Paralympic Winter Games
Venice Carnivale – runs from January 31st to February 17th, with the main events happening from February 7th to 17th
Vespa's 80th anniversary – the famous scooter brand marks its anniversary in 2026 with a series of events across Rome between 25th and 28th June
Saint Francis of Assisi Celebrations – events throughout the year to mark the 800th anniversary of the death of St Francis – including the veneration of his remains between February 22nd – March 22nd, 2026
EES – the new European Entry/Exit System (EES) that started slowly rolling out from 12th October 2026 for all non-EU nationals, including Americans, Australians, Canadians and British, travelling in or out of the Schengen Area. This means registering at borders by having your fingerprint and photo taken. There may be longer border queues. More info >> here
ETIAS (European Travel Information and Authorization System) – starting what is looking likely to be late 2026, the European Union, including Italy, will introduce this new travel authorization process. This affects visitors from the United States, Australia, Canada, New Zealand, and about 60 other countries. Visit the official ETIAS website once it goes live, complete the online form, and pay a small fee of around €7 per person
Venice Tourist Tax – this was introduced in 2024, aimed at the large number of day trippers who put pressure on the city's delicate infrastructure. Dates have been extended to 60 days in 2026. Those staying are exempt but still must register or risk a large fine. Check dates and register >>> here
Neos Air – Italian airline soon to introduce flights from JFK to Bari, Puglia
United – US airline introducing flights from Newark to Bari
Air Canada – offering flights direct to Palermo in Sicily from Montreal in peak season
Alaska Air – will be flying direct from Seattle to Rome starting at the end of April 2026

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