Summary: Explore the biggest travel events of 2026, including the FIFA World Cup, Winter Olympics, and Route 66 Centennial. Discover where to go and what to experience during this landmark year.
2026 is packed with once-in-a-generation travel events that promise unforgettable experiences for sports fans, history buffs, and adventure seekers alike. From the largest FIFA World Cup ever to the centennial of America’s most iconic highway, this year offers a rare chance to be part of global celebrations and cultural milestones.
Whether you're chasing totality during a solar eclipse or joining a coast-to-coast caravan, these events are worth planning your travels around.
The 2026 FIFA World Cup will be the biggest in history, featuring 48 teams and hosted across three countries—Canada, Mexico, and the United States. Sixteen cities will host matches, including Toronto, Vancouver, Mexico City, Guadalajara, Los Angeles, Miami, New York/New Jersey, and Seattle.
The final will be held at MetLife Stadium in New Jersey, while the opening match will take place at Mexico City's legendary Estadio Azteca.
This expanded format means more games, more fans, and more opportunities to experience the energy of the world’s most popular sporting event. Expect immersive fan zones, cultural showcases, and a global celebration of football.
Also Read: How to Follow Your Sports Team on the Road
The Milano Cortina 2026 Winter Olympics will be the most geographically widespread in history, spanning over 22,000 square kilometers across northern Italy.
Events will be held in Milan, Cortina d’Ampezzo, Bormio, Livigno, Verona, and other alpine towns. The opening ceremony will take place at Milan’s San Siro Stadium, while the closing ceremony will be held at the historic Verona Arena.
New sports such as ski mountaineering will make their Olympic debut, and visitors can enjoy Italy’s rich cultural heritage alongside thrilling competitions in alpine skiing, ice hockey, figure skating, and more.
Also read: Winter Olympics in Milan: What You Need to Know to Travel
Europe will experience its first total solar eclipse in 27 years, with the path of totality crossing parts of Greenland, Iceland, Spain, and Portugal.
Iceland’s west coast will be a prime viewing location, offering up to 2 minutes and 14 seconds of totality at Látrabjarg. Northern Spain, especially regions like Galicia and Castile and León, will also offer excellent viewing conditions.
This celestial event is expected to draw eclipse chasers from around the world, with cruise ships and guided tours planned to follow the path of totality across the Arctic and Mediterranean.
Learn More: Solar Eclipse in ’26: What to Know, Where to Go
America’s “Mother Road” turns 100 in 2026, and celebrations will span all eight states along the historic highway—from Illinois to California. The official kick-off will take place in Springfield, Missouri, on April 30, featuring concerts, car shows, and parades.
Satellite events will be held in Joliet, Amarillo, Albuquerque, St. Louis, and Santa Monica.
Highlights include the Route 66 Centennial Caravan (June 5–24), a 2,448-mile parade of vintage cars; the Great Race (June 20–28), a rally of classic vehicles; and dozens of local festivals, museum exhibits, and guided tours.
Also Read: The Best Road Trips Across the U.S. with Maps Included
The United States will commemorate its 250th anniversary of independence with events across all 50 states. In Washington, DC, expect major exhibitions at the National Archives, National Gallery of Art, and Kennedy Center.
Highlights will include the “National Scrollathon” art installation, the “51 Steps to Freedom Trail” augmented reality experience, and a series of concerts, reenactments, and civic engagement programs.
Also Read: The World’s Top Bucket-List Museums
From the roar of the World Cup stadiums to the quiet awe of a solar eclipse, 2026 offers travelers a rare mix of global celebration, cultural reflection, and natural wonder. Whether you're planning a road trip along Route 66, attending Olympic events in Italy, or exploring historic sites during America250, this is a year to be part of something extraordinary.
Before you book your trip, make sure you're prepared for the unexpected. Get a fast, free quote from Generali Global Assistance and travel with insurance and assistance services ready to help at a moment’s notice, so you can focus on the experience, not the disruptions.
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