Your 2026 Italy Vacation Planner: Beyond the Olympics

Here’s what you’ll learn after reading this article:

The 2026 Winter Olympics in Milan and Cortina d'Ampezzo are driving excitement for travel to Northern Italy.
Beyond the Olympic venues, travelers can easily extend their trip using Italy's extensive railway network to visit popular destinations such as Lake Como, Venice, Florence and the Amalfi Coast.
It's essential to start planning early to secure preferred hotels and experiences due to rising demand around the major events. Your Italy Vacation Planner – your Dream Vacations Travel Advisor – can assist with creating a personalized itinerary.

Travelers around the world are already dreaming about Italy in 2026. With the Winter Olympics taking place in Milan and Cortina d'Ampezzo, excitement around Northern Italy is rising fast. This Italy Vacation Planner explores the top regions, landscapes and cities you can easily pair with your Olympic-season adventures as you discover your ideal itinerary.

Explore the Regions Around Milan and Cortina d'Ampezzo

Milan is one of the best places to visit in Italy, whether or not you’re attending the games. Its fashion district, Gothic architecture and iconic art – including Da Vinci’s treasured The Last Supper – make it an excellent starting point for your vacation. After exploring the city, many travelers branch out to nearby destinations like Lake Como, Verona or Bergamo for a mix of culture and natural scenery.

Cortina d'Ampezzo, also known as the “Queen of the Dolomites,” is surrounded by dramatic peaks and charming villages. Travelers can pair their Olympic visit with winter hiking routes, scenic gondola rides or day trips to South Tyrol for a blend of both Italian and Austrian culture.

Adding More Iconic Destinations to Your Itinerary

Beyond the Olympic venues, Northern Italy offers alpine towns, lakeside communities and vineyard-covered hills that give travelers even more of a reason to visit. From the Dolomites to the Italian Riviera, this unforgettable region blends panoramic views, historic charm and (of course) world-famous cuisine.

If you’re planning a longer adventure, Italy’s railway network makes it easier to expand your trip into other regions. Lake Como, Venice, Florence and the Amalfi Coast continue to top lists of the best travel destinations in Europe, with each destination offering its own version of Italy’s signature art, food and scenery.

Italy’s size and accessible transportation make it easy to visit multiple regions on one trip without feeling rushed. A Dream Vacations Travel Advisor can help you organize the perfect combination of cities and seaside escapes.

Traveling With Friends or Family

Italy works beautifully for group vacation packages, thanks to its mix of culinary traditions and postcard scenery. Travelers can explore lively piazzas, wander through centuries-old neighborhoods or gather for long, relaxed dinners that bring everyone together.

Italy offers countless ways for groups to connect and enjoy the journey, and a Dream Vacations Travel Advisor can help plan a trip that’s ideal for the needs of you and your travel party.

When Is the Best Time to Start Planning?

With excitement building around Milan and Cortina d'Ampezzo, many travelers are wondering about the best time to visit Europe for a 2026 Olympic-season trip. Since demand around major events rises quickly, securing your preferred hotels and regional experiences early is essential.

Whether you plan to attend the games or extend your stay into another season, a Dream Vacations Travel Advisor can help you plan early so you get the tours, experiences and pacing that fit your travel style best.

Explore More Italian Destinations

Curious about the best Rome shore excursions for your adventure? Your Travel Advisor can help!
Dreaming of a relaxing Capri vacation with sparkling blue waters and cliffside views? It’s easier than you think.
Looking for the most idyllic vacation in Venice, Italy? You’ll find endless canals, cafés and charming neighborhoods to explore.

Plan Your Dream Escape With an Expert Travel Advisor

The 2026 Winter Olympics spotlight gives travelers a fun reason to explore Northern Italy, but this Italy Vacation Planner goes far beyond the games. From alpine towns to iconic coastlines, Italy’s regions offer endless opportunities for once-in-a-lifetime memories.

Start your 2026 Italian getaway with the expertise of a Travel Advisor. They can help craft a personalized itinerary that matches your travel style, interests and budget.

Ready to make Italy yours? Find a Dream Vacations Travel Advisor near you or call 800‑278‑4736 to begin planning your dream escape.