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

If you’ve ever dreamed of combining your love for motorcycles with an epic journey through Europe’s most stunning landscapes, this Harley Davidson tour might catch your eye. It’s a 13-day ride that takes you from Milan through five countries, with incredible scenery, legendary mountain passes, and cultural highlights along the way. We haven’t done it ourselves, but based on the detailed info, it sounds like a serious bucket-list adventure for motorcycle enthusiasts.

What really draws us in are the spectacular views of the Alps and charming villages and the chance to ride on iconic routes like the Stelvio Pass. Plus, the inclusion of cultural stops like Oktoberfest in Munich and a visit to Mont Blanc in Chamonix makes this more than just a scenic ride — it’s a well-rounded experience. However, the hefty price tag of over $14,000 for two isn’t for everyone. The tour is quite specialized, suited best for seasoned riders who can handle long days on the road and are comfortable with Harley touring bikes.

This trip is perfect for adventure-seeking motorcycle lovers who want a guided, hassle-free experience with supportive logistics. If you’re a confident rider with at least two years of Harley touring experience, this could be a dream come true. Just keep in mind that it’s a group limited to 12 people, so it’s an intimate vibe, but not a casual day trip.

Key Points

• Epic Route: Crosses 5 countries, including Italy, Switzerland, France, and Germany, with top scenic stops.
• Expert Guide: Led by a passionate, experienced tour guide who prioritizes good service.
• Motorcycles Included: Ride on high-quality Harley Davidson models like the Road Glide Ultra or Street Glide Ultra.
• Incredible Experiences: Boat ride on Lake Garda, cable car in the Dolomites, Oktoberfest tickets, and a visit to Mont Blanc.
• Hotels & Comfort: Stay in boutique 3-4 star hotels with breakfast, ensuring a good rest after long riding days.
• Pricing & Requirements: Cost is high but includes bikes, accommodations, some tickets, and support. Riders need two+ years of Harley experience and a valid international driver’s license.

You can check availability for your dates here:

Exploring the Itinerary in Detail

Starting Point: Milan and the Meet-up

The adventure begins near Milan, with a welcoming night at a hotel close to Linate Airport. This initial meet-up on Tuesday September 23rd, 2025, is designed for riders to get to know each other, break the ice, and prep for the journey. It’s a smart touch that the trip starts with some camaraderie before hitting the road. If you arrive early, the logistics are smooth — the transfer from the airport is every 20-30 minutes, which makes arrival simple.

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

The first riding days take you into the stunning Dolomites. The route includes a cable car ticket, so you get a taste of the mountain scenery from above, plus plenty of winding roads to satisfy motorcycle enthusiasts. We love that they plan a boat ride on Lake Garda — Italy’s largest lake — giving you a relaxing break amid spectacular water and mountain views.

Day 3-4: Climbing Stelvio Pass

This legendary mountain route is a highlight for many riders. Known for its famous curves and challenging ascent, the Stelvio Pass is a bucket-list climb that offers both a technical challenge and jaw-dropping vistas. The tour guide’s love for the route shines through, and we’re told the area’s scenery is truly unforgettable.

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Day 5-6: Crossing into France and the Mont Blanc Region

The journey continues into France, where you’ll visit Mont Blanc in Chamonix. Standing at Europe’s highest peak, this is a moment that many riders find awe-inspiring. It’s a chance for photos, rest, and enjoying the alpine atmosphere. The tour’s inclusion of a cable car ticket here adds extra fun and perspective.

Day 7-8: Germany and Munich for Oktoberfest

No European motorcycle tour would be complete without a stop at Oktoberfest in Munich. You’ll get tickets to party in the halls, soaking in Bavarian culture, music, and great beer. The timing during September allows for an authentic experience, and the tour ensures you have reserved access — a real plus given Oktoberfest’s popularity.

Day 9-10: Castles and Cultural Highlights

The visit to Neuschwanstein Castle is another standout. Known for inspiring Disney’s Sleeping Beauty Castle, it’s picturesque and a must-see. The tour balances riding and sightseeing, so you get a taste of fairy-tale Europe. Expect a full day exploring the castle grounds and surroundings.

Day 11-12: Return to Milan

As the adventure winds down, the route brings everyone back to Milan. The support van helps with luggage and any logistical needs, making the return comfortable. After 13 days of riding and exploring, this is where the shared stories and new friendships often come to a close — but hopefully, not the adventures.

What Makes This Tour Special?

The Route and Scenery

We loved the way this trip combines spectacular mountain passes, lakes, and charming towns. The Stelvio Pass alone is often praised for its amazing curves and breathtaking views, making it an essential part of any serious motorcycle journey in Europe. Riding through five different countries adds variety, and the guide’s local knowledge can turn a good ride into a memorable experience.

Riding Quality and Equipment

The inclusion of Harley Davidson Road Glide Ultra or Street Glide Ultra bikes is a major draw. These models are comfortable for long days and have the power needed for mountain climbs. The fact that they use high-quality bikes indicates that the ride will be smooth, even on challenging roads. The bikes come with insurance, and the experience required — two years of Harley riding — helps ensure everyone can handle the terrain.

Support and Comfort

The tour isn’t just about riding; it’s about the whole experience. Lodging in boutique hotels with breakfast, a support van, helmets, and a surprise dinner make it feel like a well-organized adventure. The support van can be a relief during long riding days, especially when tackling mountain roads or sudden weather changes.

Cultural Experiences and Highlights

The inclusion of tickets to Oktoberfest and the Dolomites cable car makes this trip more than just a scenic ride. You’re getting culture and leisure activities woven into the itinerary. The boat ride on Lake Garda also offers a chance to relax and enjoy Italy’s beautiful water scenery.

The Cost and Who It’s For

A price of $14,178 for two people covers bikes, hotels, some tickets, and support. It’s certainly not cheap, but considering the inclusions — especially the high-end Harley bikes, accommodations, and guided experience — many would see it as a fair value for a premium adventure. Keep in mind, the price may seem steep if you’re not already experienced with long motorcycle tours, as the guide recommends at least two years of Harley riding experience.

This tour would suit confident riders who want a guided, all-inclusive trip, and don’t mind the high price tag for the convenience and quality. It’s ideal for those who love mountain scenery, cultural stops, and riding on iconic routes. If you’re traveling solo or as a couple, the group dynamic can be a fun way to meet like-minded adventurers.

Potential Downsides

The tour demands a good level of riding skill and physical endurance, especially considering mountain climbs and variable weather. It’s not suitable for children, pregnant women, or those with health issues like back problems or altitude sickness. Also, the cost excludes flights, meals (besides breakfast), gas, and other attractions, which can add up.

Final Thoughts

This Harley Davidson European tour offers a bold mix of spectacular scenery, cultural stops, and serious riding. For seasoned motorcyclists who want to explore Europe’s iconic mountain passes and villages without the hassle of planning each detail, it could be an unforgettable experience. The thoughtfully curated stops, quality bikes, and expert guidance mean you can focus on enjoying the ride.

If you’re craving a true adventure that combines adrenaline, scenery, and culture, and you’re comfortable with the cost, this trip might just be what you’re looking for. It’s best suited for experienced riders who appreciate details like scenic cable cars, historic castles, and legendary mountain roads. Just prepare yourself for some long days and the expenses involved, but be ready for memories that last a lifetime.

FAQ

Is this tour suitable for beginners? No, the tour requires at least two years of Harley Davidson touring experience because of the challenging mountain roads and long riding days.

Are the bikes included in the price? Yes, the Harley Davidson Road Glide Ultra or Street Glide Ultra models are included for the full 12 days, along with insurance.

What’s the group size? The group is limited to 12 participants, making it a more intimate experience, but also filling up quickly.

Are accommodations comfortable? Yes, you’ll stay in boutique 3- and 4-star hotels with breakfast included, providing a good level of comfort after days on the road.

What’s not included in the price? Flights, lunches, dinners (besides one surprise dinner), gasoline, and tickets to attractions not listed are extra.

Can I cancel if my plans change? Absolutely, you can cancel up to 24 hours in advance for a full refund.

Is this trip family-friendly? Not really. It’s designed for adult, experienced riders, and not suitable for children or pregnant women.

What should I bring? Passport, driver’s license, weather-appropriate gear, chargers, and a camera. Think layers, rain gear, gloves, and extra clothes.

What if I have questions before booking? You can contact the provider for more details about equipment, recommendations, and the trip schedule.

This Harley Davidson motorcycle tour promises a carefully curated mix of riding, culture, and scenery. It’s for those ready to tackle some of Europe’s most famous mountain roads with a supportive guide and fellow enthusiasts. If that sounds like your kind of adventure, it’s worth considering.

You can check availability for your dates here: