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

A 13-Day Harley Davidson Motorcycle Tour from Milan through 5 Countries: An Authentic Adventure

This comprehensive review explores a unique motorcycle journey that takes you from Milan into the heart of Europe’s most breathtaking scenery. Designed specifically for Harley Davidson enthusiasts, this 13-day tour covers over 3,250 kilometers through the Alps, the Dolomites, and several iconic towns and festivals. What makes this experience stand out is not just the miles covered, but the opportunity to ride top-tier Harley Davidson Road Glide or Street Glide touring bikes alongside fellow bikers while soaking in spectacular views.

Two aspects I particularly appreciate are the carefully curated itinerary and the personal attention from a passionate guide—Carlos Santillan, a seasoned motorcycle rider and tour leader. His enthusiasm and local insights promise to elevate the riding experience with tips on scenic routes and local culture. The second highlight is the inclusion of engaging activities like a boat ride on Lake Garda and a visit to Oktoberfest in Munich—adding cultural flavor to the scenic adventure.

One consideration worth noting is the requirement of at least two years of Harley touring experience. Riding through the mountains demands a certain skill level, so this tour is best suited for experienced motorcyclists comfortable with alpine terrain. Also, the cost might seem high at first glance, but considering the quality of bikes, hotels, and included activities, many will find the value justified for such a comprehensive, all-in-one European motorcycle journey.

Key Points / Takeaways

• Top-quality Harley Davidson bikes: The tour features Road Glide Ultra or Street Glide Ultra models, ensuring comfort and power on mountain roads.
• Cultural and scenic diversity: From the Dolomites and Swiss Alps to Munich’s Oktoberfest, every day offers a new backdrop.
• Expert local guide: Carlos Santillan’s passion and knowledge help navigate both the roads and the cultural highlights.
• All-inclusive for riders: Lodging, some activities like boat rides, and tickets to major events are included, making it a hassle-free experience.
• Limited group size: Small groups of up to 12 participants foster camaraderie and personalized attention.
• Extraordinary routes: Climbing the Stelvio Pass and visiting Mont Blanc provide some of Europe’s most thrilling riding and unforgettable views.

The Itinerary: A Symphony of Scenery and Culture

The tour kicks off in Milan, where you’ll gather at a hotel near the Linate Airport on Tuesday, September 23rd, 2025. After a casual meet-and-greet, you’ll get familiar with your Harley Davidson, which you’ll be riding for the next 12 days. The first day allows you to unwind and prepare for the adventures ahead.

Day 1-2: From Milan to the Dolomites and Swiss Alps

Riding from Milan, you’ll head northeast into the stunning Dolomites, recognized for their jagged peaks and picturesque villages. Expect spectacular views, crisp mountain air, and winding roads perfect for Harley touring. A cable car ticket is included, so you can take in the scenery from high above. The tour guide’s local tips will help you discover hidden gems in these alpine towns.

Day 3-4: Lake Garda and Alpine Crossings

A highlight is the boat ride on Lake Garda, Italy’s largest lake, offering a chance to relax and admire the surrounding mountains from a different perspective. The riding continues through the Swiss Alps, with the Stelvio Pass—famous for its 48 hairpin turns—providing a true test of riding skill and offering some of the most breathtaking vistas you can find in Europe.

Day 5-6: Crossing into France and Mont Blanc

Your route then takes you into France, culminating at Chamonix, home to Mont Blanc, Europe’s highest peak. Riding through this region, you’ll be treated to sweeping mountain vistas and the chance to stand at the highest point in Europe. These days combine thrilling rides with awe-inspiring landscapes.

Day 7-8: Bavarian Heartland and Munich’s Oktoberfest

After crossing back into Germany, you arrive in Munich to enjoy the world-famous Oktoberfest. Included in the tour fee, your tickets give you access to the legendary beer halls, lively music, and authentic Bavarian cuisine. This festive stop offers a cultural contrast to the serene mountain scenery.

Day 9-10: Castles and Cultural Landmarks

The journey continues to Neuschwanstein Castle, the fairy-tale fortress that inspired Disney’s Sleeping Beauty castle, and Hohenschwangau. You’ll appreciate this fairytale setting from your Harley, with plenty of photo opportunities. The guide shares insights on local legends and history, enriching the experience.

Day 11-12: Returning to Milan

The final days involve retracing your route back to Milan, giving you last rides through scenic passes and quiet villages. The tour concludes at the initial hotel near Milan airport, where you’ll return your bikes and reflect on the miles traveled and friendships made.

Ride Quality, Accommodation, and Logistics

The Harley Davidson bikes are a significant part of what makes this trip special. With models like the Road Glide Ultra or Street Glide Ultra, riders enjoy comfort over long distances and stability over mountain roads. Since the tour is designed for experienced riders (requiring at least two years of riding Harley Touring models), you’ll appreciate the bike’s performance and handling on challenging terrains.

Accommodations are in 3- and 4-star boutique hotels—not just practical places but charming spots that add to the overall experience. Most include breakfast, giving you a good start each day. The inclusion of activities like boat rides and cable cars adds value and variety, making the tour both scenic and culturally engaging.

The support van is a thoughtful addition, ready to assist with any bike issues or fatigue. Helmets are provided, and you’ll be riding in a group limited to 12, which encourages camaraderie without feeling crowded.

Logistics and Meeting Points

You’ll start in Milan, with the meeting at the hotel near the airport. If you arrive early or from elsewhere, accommodations are taken care of in your name, making check-in smooth. The tour ends back in Milan, simplifying travel plans for departure.

Who Is This Tour Best For?

This adventure is ideal for experienced Harley riders who enjoy scenic mountain roads and cultural stops. If you’re comfortable riding in alpine conditions and crave a blend of riding and sightseeing, this trip delivers. It’s not suitable for beginners, children under 10, or people with certain health limitations like back problems or altitude sickness.

Travelers who value small group sizes will appreciate the personalized attention, and those interested in mixing riding with festivals—like Oktoberfest—will find this experience especially rewarding. The inclusion of special tickets and activities makes it a good value for those seeking a complete touring package.

Price and Value Analysis

While the price might seem high at first glance, it covers top-tier Harley Davidson bikes, luxury accommodations, major activity tickets, and guided support, which would cost significantly more if booked separately. The opportunity to ride through five countries and visit iconic landmarks with a knowledgeable guide adds to the overall value.

Travelers should consider whether they’re ready for the physical demand of mountain riding and enjoy a well-organized, all-inclusive experience. For those passionate about Harley touring and scenic European landscapes, this adventure offers a comprehensive and memorable journey.

Practical Tips for Future Riders

• Riding experience: Make sure you meet the two-year Harley touring requirement and feel comfortable on mountain roads.
• Pack smart: Bring weather-appropriate clothing, rain gear, and gloves, since mountain weather can change quickly.
• Pre-trip prep: Consider a prep course to ensure you’re confident riding through challenging alpine passes.
• Documents: Have your passport, driver’s license, and international driver permit ready.
• Health considerations: Be mindful of altitude sickness and physical stamina, especially for longer riding days.

FAQs

Is this tour suitable for beginners?
No, it requires at least two years of riding Harley touring bikes and comfort with mountain roads.

What’s included in the tour price?
The fee covers Harley Davidson motorcycles, lodging with breakfast, a boat ride on Lake Garda, Oktoberfest tickets, cable car tickets, helmet, and support van.

Are flights included?
No, travelers need to arrange their own flights to Milan.

Can I join alone?
Yes, the tour is limited to 12 participants, making it suitable for solo travelers wanting a small group experience.

What should I bring?
Bring your passport, driver’s license, weather-appropriate gear, gloves, camera, and a charged smartphone. A change of clothes and rain gear are also recommended.

What happens if I can’t ride on a particular day?
The support van can assist, but the tour is designed as a riding adventure—so it’s best to be prepared and confident.

To sum it up, this Harley Davidson motorcycle tour from Milan into five countries offers a memorable combination of riding, sightseeing, and cultural experiences in a small-group setting. It’s best suited for seasoned riders who appreciate scenic mountain routes, iconic landmarks, and lively festivals. If you’re looking for a well-organized, immersive motorcycle adventure that balances thrill with comfort, this trip deserves serious consideration.