Milan • Cortina • Dolomites Winter Travel Planning 2026
Custom itineraries with private transfers, trusted hotels, and expert guidance for exploring Northern Italy during its peak winter season.
What We Handle for You
- Clear routes between Milan, Cortina, and the Dolomites
- Handpicked winter-friendly hotels and central town locations
- Private drivers and reliable transfers arranged in advance
- Optional add-on days in Venice, Florence, Rome, Sicily, Lake Como etc.
(Normally $99 — Free for a Limited Time)
Your Italy, Your Way - Select Your Winter Travel Package
Milan → Cortina → Venice
(9 Nights / 10 Days)
City to mountains, then a quiet coastal finish. Ideal for less movement after Cortina and a soft landing with food, cafés, and easy walking.
Starting at $7,892 per person
Milan → Florence → Rome
(10 Nights / 11 Days)
Begin in Milan, then head south for art, food, and warmer indoor winter experiences. Walkable centers and museum days without mountain travel.
Starting at $8,714 per person
Milan → Rome → Amalfi Coast
(12 Nights / 13 Days)
Begin in Milan and continue south for quieter historic streets and milder coastal weather. A relaxed route without mountain travel.
Starting at $11,384 per person
Upgrade to On-Site Support in Milan/Cortina
For travelers wanting extra support during their Milan stay, you can add private concierge services with owner Mark Murphy.
This includes help with transportation, navigation, reservations, translation, and moving around the city during peak winter dates.
You’ll have a fluent Italian speaker with firsthand local experience for cultural and communication support as needed.
Limited to 6 travelers in February 2026
What you can expect from us
Personalized journeys
Traveling with a private guide and driver you’ll do what you want, when you want with the freedom to change your plans on the fly.
Expert planning
With deep in-country knowledge, our Destination Experts tailor each experience to your preferences, ensuring you can make the most of your time away.
Local guides
Unlock details you may have overlooked with insider information only a local, private guide can offer.
Unbeatable support
Each booking includes 24/7 support, in case anything comes up and if changes to your itinerary occur, you’ll receive live updates via the Kensington app.