This itinerary is designed for families traveling with seniors, using Milan as a home base to explore Italy’s most iconic regions without the stress of constant hotel-hopping.
Milan, Florence, & The Coast | Nov 3 – Nov 12, 2026
Traveling with parents is about creating memories, not endurance tests. This itinerary uses Milan as a "hub" to see Italy’s icons while prioritizing senior mobility, flat walking paths, and built-in rest days.
🛡️ The Trip Essentials (Book These First!)
Safety First: Ekta Travel Insurance is my top pick for families because they cover travelers up to age 100.
The Big Bundle: Use Expedia to bundle your Milan stay and your flight to Las Vegas for the best rates.
Skip the Airport Stress: Pre-book a private car with Welcome Pickups. A driver meets you at the gate with a sign—total peace of mind for parents.
Tuesday, Nov 3: Arrival & "Soft Landing"
Arrive in Milan and head straight to your home base.
Stay: Find accessible, elevator-equipped hotels on Booking.com.
💡 Tip & Trick: For Day 1, order "Asporto" (takeout) or eat at a trattoria within 2 blocks of your stay. Keeping the "walking radius" small on the first night prevents arrival exhaustion.
Wednesday, Nov 4: Introduction to Milan
Ease into the local rhythm with a visit to the Galleria Vittorio Emanuele II and the Duomo square.
💡 Tip & Trick: Avoid the noon rush. Visit the main square around 9:30 AM for softer light and fewer crowds—it’s much easier for parents to navigate.
Thursday, Nov 5: The Florence Day Trip
The Journey: Milan Centrale to Firenze S.M. Novella (~1h 45m).
Logistics: Snag high-speed seats on TrainPal.
💡 Tip & Trick: Florence is the "City of Cobblestones." Use the Viator Collection to book a private golf-cart tour. You'll see the Duomo and Statue of David without the 10,000-step toll.
Friday, Nov 6: Milan Rooftops & Views
Take the elevator to the Duomo Terraces.
Tickets: Get skip-the-line elevator passes on Tiqets.
💡 Tip & Trick: The Rooftop is marble and can be slick. Ensure parents wear shoes with rubber grips. If it's a clear day, you can see the Italian Alps from the spires!
Saturday, Nov 7: The Coast (Genoa & Portofino)
The most scenic day of the trip! Pesto focaccia in Genoa, followed by a scenic ferry ride into Portofino.
Transport: For private coastal transfers, check EconomyBookings.com.
💡 Tip & Trick: Have Bus #782 as your backup. If the November sea is too choppy for the ferry, this bus is frequent, cheap, and drops you right in the harbor.
Sunday, Nov 8: Full Family Rest
A long, lazy Sunday lunch.
Storage: Stash bags at Radical Storage if you're in between check-ins.
💡 Tip & Trick: Sunday is "Pranzo della Domenica" (Sunday Lunch). Reservations are a must. Look for a place with "Cucina Tipica" for the most authentic experience.
Monday, Nov 9: Lake Garda (Peschiera del Garda)
Take the high-speed train to Peschiera.
💡 Tip & Trick: The station is slightly uphill. Grab a 2-minute taxi outside the station to the "Lungolago" (lakefront). It saves a 10-minute incline walk for the parents.
Tuesday, Nov 10: Lake Como (The "Drop-Off" Strategy)
Lake Como’s best views are often up steep hills. Here is how to see it all without the strain:
The Drop-Off: Take the ferry to Tremezzo and drop parents at Villa Carlotta. It is flat, has a stunning museum (with an elevator), lakeside gardens, and a beautiful café.
The Adventure: While they relax in the gardens, you hop on the 10-minute ferry to Bellagio or Varenna to explore the steep alleys. Pick them up 2 hours later!
💡 Tip & Trick: Use WeGoTrip for a self-guided audio tour of the lake villas while you're on the boat.
Wednesday, Nov 11: Bergamo’s Fairy-Tale Finale
Take the Funicular up to Città Alta.
💡 Tip & Trick: Once at the top, head straight for Piazza Vecchia. It’s the flattest part of the medieval town and perfect for a final celebratory Italian dinner under the evening lights.
Thursday, Nov 12: Las Vegas Bound!
Final cappuccino before heading to the airport.
Connectivity: Activate your Saily eSIM for the USA before you board.
Vegas Fun: Book your shows via Spotlight Vegas!
💡 Tip & Trick: If your flight is delayed, use AirHelp. You could get up to $650 back per person!
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The "Must-Have" Experiences (Tours & Tickets)
Since you are doing day trips to Florence and the Lakes, these are your best bets:
Viator Collection: This is your #1 resource for the Florence and Lake Como days. Look for "Skip-the-Line" Duomo tickets or a private boat tour on Lake Como to give your parents that "Grand Finale" feel without the crowds.
Tiqets: Perfect for your Milan Day (Nov 6). Use this specifically for Duomo Rooftop Elevator tickets. It’s the fastest way to get your parents to the top without them having to navigate the crowds at the ticket office.
WeGoTrip: Great for your Bergamo (Nov 11) or Genoa (Nov 7) days. You can download a self-guided audio tour so you can walk at your parents' exact pace rather than being rushed by a group guide.
🚆 Getting Around (Transport & Transfers)
Since you have 5 day-trips planned, logistics are everything:
TrainPal: This is the best tool for your Florence (Nov 5) and Garda (Nov 9) high-speed tickets. It often finds "split-ticket" deals that save money on the Frecciarossa while keeping you in the same seats.
Welcome Pickups: I highly recommend this for your arrival on Nov 3. After a long flight, don't make your parents navigate the train from the airport. A professional driver waiting with a sign is the ultimate "Welcome to Italy" for seniors.
Kiwitaxi: If the ferry in Portofino isn't running due to November weather, you can use this to pre-book a private van back to the station in Santa Margherita Ligure.