From Milan: Harley Davidson motorcycle tour in 5 countries unique experience!

Planning a motorcycle adventure that combines breathtaking scenery, cultural highlights, and the thrill of riding a Harley Davidson sounds perfect, right? This 13-day tour from Milan promises just that—a trip through five countries, offering the kind of panoramic vistas and authentic experiences that motorcycle lovers dream of. We haven’t done the trip ourselves, but based on detailed reviews and the itinerary, it looks like a well-curated journey packed with memorable moments.

What we particularly like about this experience is the focus on spectacular landscapes, the chance to ride iconic Harley models like the Road Glide Ultra and Street Glide Ultra, and the opportunity to explore diverse environments—from the Swiss Alps to the historic castles of Bavaria. The tour’s small group size (limited to 12 riders) ensures a personalized experience, and the presence of an experienced guide makes a huge difference when navigating tricky mountain passes.

However, the tour price—around $14,178 for two riders—might seem steep at first glance. But when you consider the all-inclusive nature, including accommodations, most activities, and the rental of top-tier Harley bikes, it offers solid value for enthusiasts seeking an all-encompassing adventure. Keep in mind, this experience is best suited for experienced Harley riders comfortable with extended riding days and mountain terrains.

If you’re someone who loves motorcycling, scenic drives, and cultural festivals, this tour could be your ideal getaway. It’s perfect for those looking for a structured yet immersive adventure that combines riding, sightseeing, and socializing with fellow motorcycle fans.

Good To Know

• Comprehensive 13-day experience traveling through 5 countries with iconic Harley Davidson bikes
• Spectacular scenery, including the Alps, Dolomites, and Mont Blanc
• Cultural highlights like Oktoberfest in Munich and visits to Neuschwanstein Castle
• All-inclusive package with accommodations, activities, and support vans
• Limited group size for personalized attention and a more intimate experience
• Requires prior motorcycle experience with Harley Touring models, at least 2 years of riding

You can check if your dates are available here:

An Authentic Motorcycle Adventure from Milan

This Harley Davidson tour is designed for those who want more than just a simple road trip. It’s about feeling the wind in your face while cruising through some of Europe’s most stunning landscapes, and then soaking in local culture—whether that’s raising a stein at Oktoberfest or marveling at the grandeur of Mont Blanc. The route is thoughtfully planned to maximize scenic beauty and cultural richness, making every day a new adventure.

The Itinerary Breakdown

Start in Milan: You’ll meet your fellow riders at a host hotel near Milan’s Linate airport on September 23, 2025. After a quick orientation and some social time, you’ll spend the night there, preparing for the journey ahead.

Day 1-2: The Dolomites and Swiss Alps: The trip kicks off with a ride into the stunning Dolomites, where cable cars elevate you above the peaks, granting spectacular views. The highlight? Climbing the Stelvio Pass, famous for its tight curves and breathtaking vistas—an absolute must for motorcycle enthusiasts.

Day 3-4: Lake Garda and Northern Italy: You’ll enjoy a boat ride on Italy’s largest lake before heading north into Switzerland. Expect winding roads, mountain passes, and awe-inspiring scenery. The support van ensures your gear and any unforeseen issues are taken care of, keeping your focus on the ride.

Day 5-6: Germany and Munich: Crossing into Germany, you’ll arrive in Munich just in time to enjoy Oktoberfest tickets included in the package. The festival’s lively atmosphere, traditional music, and beer tents will likely be a highlight, especially considering the tour includes a dedicated evening for celebration.

Day 7-8: France and Chamonix: Heading south, you’ll visit the highest peak in Europe, Mont Blanc, in Chamonix. The ride here is both exhilarating and scenic, offering views that only the Alps can deliver.

Day 9-10: Bavaria and Neuschwanstein Castle: The fairy-tale castle is a strong visual anchor, and it’s a favorite among reviewers who mention that “getting to see Neuschwanstein on a Harley is an experience to remember.” The group often appreciates the mix of history and natural beauty.

Day 11-12: Return to Milan: The last stretch takes you back to Milan, where you’ll return the bikes and reflect on a journey that’s both physically demanding and emotionally rewarding.

The Harley Davidson Experience

You’ll ride Harley Davidson Road Glide Ultra or Street Glide Ultra models, which are comfortable for long days and capable of handling mountain roads. Riders need at least two years of Harley riding experience, ensuring everyone is comfortable with the type of terrain and extended hours on the bike.

Most reviews highlight the excellent support from the guide, Carlos Santillan, who is said to be “an experienced rider with a genuine passion for the route.” His advice and local knowledge are invaluable when tackling high-altitude roads and busy festivals. The support van is a comfort, especially if you’re prone to fatigue or technical issues.

What’s Included and What’s Not

The package covers most essentials—luxury accommodations, bike rental, breakfasts, and activities like the boat ride and cable car tickets. The Oktoberfest ticket is a significant bonus, providing access to one of Europe’s most iconic festivals.

However, flights are not included — so you’ll need to arrive in Milan independently. Also, meals beyond breakfast, gasoline, and extra tickets for other tourist attractions are on your own.

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The Experience’s Value

While the overall cost may seem hefty, it’s important to evaluate what you’re getting: a boutique hotel stay in each location, top-tier Harley bikes, guided routes through some of Europe’s most scenic spots, and cultural experiences like Oktoberfest. For motorcycle enthusiasts keen on combining riding with sightseeing, it’s a package that delivers both adventure and comfort.

Who Should Consider This Tour?

This trip is best suited for experienced Harley riders who enjoy mountain riding, as the roads include challenging curves and altitude changes. If you’re new to long-distance touring or mountain passes, you might find the demands a bit taxing.

It’s perfect for couples, friends, or solo riders who want a well-organized, immersive experience with a small group of like-minded enthusiasts. The small-group setting encourages camaraderie, and the bilingual guide helps make the experience more personal.

While not designed for children or those with mobility issues, it’s an adventure for anyone looking for a blend of scenic riding, cultural exploration, and lively festivals.

The Sum Up

This Harley Davidson motorcycle tour from Milan offers a thoughtfully curated journey through some of Europe’s most iconic landscapes and cultural sites. With its focus on scenic mountain passes, historic castles, and lively festivals, it’s tailored for seasoned riders who crave adventure with a touch of luxury. The inclusion of activities like Oktoberfest and boat rides, combined with comfortable boutique hotels, makes it a well-rounded experience.

The cost reflects the high-quality bikes, accommodations, and guided support, making it a worthwhile choice for dedicated motorcycle enthusiasts. It’s best for those who value authentic riding experiences, stunning scenery, and culture—all in a small, friendly group setting.

If you’re looking to combine your love of Harley riding with a European adventure, this tour seems like an unforgettable way to do it.

FAQ

Is prior motorcycle experience necessary? Yes, riders need at least two years of experience riding Harley Touring models.

Are meals included? Breakfasts are included, but lunches and dinners are not, so you’ll have the chance to explore local cuisine on your own.

What kind of motorcycles are provided? The tour uses Harley Davidson Road Glide Ultra or Street Glide Ultra models, perfect for long-distance touring.

Is the tour suitable for beginners? No, the tour requires experienced riders comfortable with mountain roads and extended riding hours.

What are the accommodations like? You’ll stay in boutique hotels rated 3-4 stars, offering comfort and local charm.

Are there support vehicles? Yes, a support van is included for gear transport and assistance.

What should I bring? Essentials include a valid driver’s license, passport, weather-appropriate clothing, riding gear, camera, and personal items.

Can I join if I don’t speak Spanish fluently? The tour guide speaks Spanish; some content is shown in its original language, but the experience is designed to be accessible.

What’s the maximum group size? Limited to 12 participants for a more personalized experience.

Are flights included? No, travelers are responsible for their flights to Milan.

This Harley Davidson adventure from Milan promises a rare blend of scenic riding, cultural celebration, and camaraderie among fellow motorcyclists. It’s a solid choice for those eager to explore Europe’s stunning landscapes on two wheels, with the added bonus of unique experiences like Oktoberfest.

You can check if your dates are available here: