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

Planning a motorcycle trip that combines breathtaking scenery, cultural highlights, and the thrill of riding a Harley Davidson through multiple countries sounds like a dream. This 13-day tour promises just that, weaving through Italy, Switzerland, France, and Germany, culminating in an experience tailored for seasoned motorcycle enthusiasts. Whether you’re a Harley owner looking for a guided adventure or a lover of scenic rides, this tour offers an exhilarating way to see Europe differently.

What we really like about this experience is how it balances adventure and comfort, with well-chosen boutique hotels, organized logistics, and opportunities to enjoy local festivities like Oktoberfest. The second highlight? The chance to ride some of the most iconic routes in Europe—think Stelvio Pass with its famous curves or cruising on Lake Garda.

A possible consideration? The tour is quite intensive, covering over 3,200 km and demanding a certain level of riding experience—two years on Harley touring models are required, and a good preparation is advised. It’s best suited for riders who are comfortable with long distances and mountain passes, and who enjoy group riding with fellow enthusiasts. If you’re looking for a leisurely holiday, this might feel more like a motorcycle adventure than a laid-back sightseeing trip.

If you’re passionate about motorcycling, love exploring varied landscapes, and enjoy meeting like-minded travelers, this tour is a strong contender. It’s perfect for those who want to combine their love of bikes with authentic European experiences.

Key Points

• Epic route spanning 5 countries with stunning mountain passes and lakeside views.
• Authentic experiences like the Lake Garda boat ride and Oktoberfest celebrations.
• Comfortable accommodations in boutique hotels with breakfast included.
• Guided by an experienced motorcyclist who loves the route and offers personalized service.
• Harley Davidson models provided for the entire trip—Road Glide Ultra or Street Glide Ultra.
• Designed for experienced riders with two years of riding Harley touring bikes required.

You can check availability for your dates here:

An in-depth look at the Harley Davidson motorcycle tour from Milan

This adventure kicks off in Milan, a city full of style and energy, and sets the scene for a trip that mixes scenic riding with culture. The tour’s starting point is a host hotel near Milan’s Linate airport, where you’ll meet your fellow riders on a Tuesday evening, breaking the ice over a relaxed evening before hitting the road the next day. This initial gathering is an excellent chance to connect, share expectations, and prepare for the days ahead.

Day 1: Setting out for the Italian Alps and Lake Garda

The journey begins with a ride towards the Dolomites and Swiss Alps, with your first stop at Lake Garda. Known as Italy’s largest lake, Garda is a stunning backdrop for a boat ride, offering a chance to relax and admire the scenery from the water. The inclusion of this boat ride is a thoughtful touch, providing a peaceful interlude amidst the riding adventures.

Day 2-3: Climbing Stelvio Pass and exploring the Alps

One highlight of the itinerary is tackling the Stelvio Pass, renowned for its 48 hairpin bends and breathtaking mountain vistas. This mountain pass is a magnet for motorcyclists worldwide, and riding it on a Harley Davidson adds an extra thrill. The tour guide, a dedicated lover of the route, will ensure you experience the best lines through the curves and share interesting tidbits about the area’s history and landscape.

Expect long, exhilarating climbs, with plenty of photo stops and opportunities to soak in the scenery. The route through the Swiss Alps offers views that stay with you long after the trip ends. The tour includes cable car tickets to the Dolomites, giving you time to enjoy the vistas from above — a valuable addition that enhances the experience without adding hassle.

Day 4-5: Crossing borders and visiting cultural hotspots

The route takes you across the border into France, where you’ll visit Chamonix and witness the Mont Blanc massif — Europe’s highest peak. From here, the roads wind into Germany, with a stop at the Neuschwanstein Castle, a fairy-tale castle that looks as if it belongs to another century. Riding through these iconic locations provides a mix of natural beauty and fairy-tale architecture, appealing to both scenery lovers and history buffs.

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Day 6-8: Munich and Oktoberfest

Arriving in Munich, you’ll experience Oktoberfest, the world’s largest beer festival. Your ticket to the festival is included, which means you can enjoy the lively halls, traditional music, and authentic Bavarian cuisine without extra planning. The tour guide emphasizes that this is a real highlight for many, with authentic beer tents and a festive atmosphere that’s hard to match elsewhere.

Day 9-11: High peaks and scenic rides

The last part of the trip takes you back into France and Switzerland, riding through spectacular alpine landscapes. The return journey offers views of Mont Blanc once more, along with relaxed rides along lakes and mountain roads. The tour concludes back in Milan, where you’ll return your Harley Davidson motorcycles, ending a 13-day adventure filled with unforgettable sights and shared camaraderie.

What makes this tour valuable for riders?

The tour’s value lies in the combination of professional organization, high-quality bikes, and authentic experiences. The Harley Davidson Road Glide Ultra or Street Glide Ultra models are well-suited for long-distance touring, with comfortable seating, ample storage, and smooth handling, ensuring you won’t just be riding but truly enjoying every mile.

The accommodations are in boutique hotels rated 3 or 4 stars, which strike a good balance between comfort and character. Breakfast is included, so you start each day with a hearty meal before heading off on your adventures. The inclusion of the boat ride, Oktoberfest ticket, and cable car passes enhances the experience without hidden costs—what you see is what you get.

The organized logistics, including a support van, helmets, and insurance, make this tour accessible for those who want to focus on the riding. However, the requirement of two years of Harley touring experience ensures the group stays safe and cohesive on challenging mountain passes.

Price analysis

At around $13,642 per group for two, the cost might seem steep at first glance. But when you consider the all-inclusive nature—bike rental, hotels, tickets, support—the price reflects the quality and exclusivity of the experience. For dedicated motorcycle travelers who love multi-country rides and culture, the value can be justified, particularly given the guided nature of the trip and the unique routes.

Practical considerations and what to bring

Preparation is key. Riders should bring driver’s licenses (including international if needed), comfortable and weather-appropriate clothing, and gloves for riding. Since the trip covers mountain passes, packing warm clothing and rain gear is advised. The tour also emphasizes the importance of two years’ Harley riding experience to ensure everyone’s safety and enjoyment.

Participants should also be prepared for some physical activity, especially when climbing passes or taking cable cars. Gasoline isn’t included, so you’ll need to fill up at designated stops. The tour’s small size—limited to 12 participants—permits a more personalized experience and closer group cohesion.

Who should consider this Harley Davidson adventure?

This tour is ideal for experienced riders who feel confident handling touring Harley models and navigating mountain roads. It suits those who want to explore Europe’s most iconic sights on two wheels, with the support of a knowledgeable guide. The inclusion of cultural highlights like Oktoberfest and scenic stops makes it a well-rounded trip for travelers who enjoy a mix of thrill and culture.

While not suitable for children or those with certain health issues, the trip offers a memorable adventure for motorcycling enthusiasts seeking a comprehensive European tour with a focus on scenic riding and authentic experiences.

The Sum Up

This 13-day Harley Davidson tour from Milan offers a rare opportunity to combine spectacular landscapes, cultural festivities, and the pure joy of riding through some of Europe’s most celebrated regions. The route, meticulously organized, delivers a perfect blend of mountain passes, lakes, castles, and festivals, making it a genuine journey for motorcycle lovers.

The high-quality bikes, cozy boutique hotels, and inclusive tickets for key sights make it a solid proposition for those who value well-planned, immersive travel. The experience is most rewarding for experienced riders who crave a challenge and authentic camaraderie among fellow Harley enthusiasts.

If you’re seeking a trip that mixes adventure with cultural richness and don’t mind a demanding schedule, this tour could be the highlight of your motorcycle riding career. Just remember, it’s a full-on adventure—so come prepared for long days on two wheels, spectacular views, and unforgettable memories.

FAQ

Do I need previous experience riding Harley Davidson touring models?
Yes, the tour requires at least two years of riding experience on Harley touring bikes to ensure safety and enjoyment.

Are accommodations included in the tour price?
Yes, you’ll stay in comfortable 3- and 4-star boutique hotels with breakfast included for all 13 days.

What are the main highlights of this trip?
Expect to ride through the Alps, visit Mont Blanc and Neuschwanstein Castle, enjoy Lake Garda, and celebrate Oktoberfest in Munich.

What should I bring for the trip?
Bring your driver’s license, weather-appropriate clothing (including warm and rain gear), gloves, camera, and a charged smartphone. Also, carry your travel insurance and international driver’s license.

Is this tour suitable for beginners?
No, it’s designed for experienced riders comfortable with mountain passes and long-distance riding on touring Harley models.

What is the group size?
The group is limited to 12 participants, fostering a more personalized and inclusive experience.

Are food and gasoline included?
No, meals (lunches and dinners) and gasoline are not included. The first tank of fuel is provided, but you’ll need to fill up during the trip.

When does the tour start and end?
It begins in Milan on a Tuesday evening and concludes back in Milan after 13 days. Check the availability for specific starting dates.

Embarking on this Harley Davidson journey offers a mix of adrenaline, scenic beauty, and cultural discovery—sure to be a highlight for any seasoned rider seeking authentic European adventures.

You can check availability for your dates here: