Italy Tour – 11 Days- Daily Itinerary

 

La Dolce Vita: The Grand Italian Northern-to-Southern Tour

Tour Dates: May 28 – June 7, 2027 | Group Size: Strictly Limited to 8 Guests

  

🗺️ 📋 The Complete 11-Day Itinerary: La Dolce Vita


Part 1: Lakes & Alpine Glamour


Day 1 (Friday): The Journey Begins

  • Depart the USA  on an evening transatlantic flight.
  • Work Impact: 0 Days Off. Travel begins after the standard work week ends.


Day 2 (Saturday): Arrival at Milan & Drive to Lake Como

  • Land at Milan Malpensa Airport (MXP). Step straight into our private luxury 9-passenger automated van.
  • Enjoy a scenic 1-hour drive north to the deep blue waters of Lake Como.
  • Check into our lakeside hotel and unwind.
  • 6:00 PM: Join your host, Jen, for a 2-hour Welcome Reception featuring regional Italian wines, local beers, cured meats, and cheeses. (Welcome Reception Included)

Day 3 (Sunday): Choose Your Adventure on Lake Como

  • Leave the van parked safely at the hotel.
  • Board the scenic passenger ferry to explore the historic cobblestone streets of Bellagio and Varenna
  • INCLUDED EXPERIENCE- Injected Adrenaline: Customize your morning with your choice of one thrill:

1. eFoil Flying Lesson: Learn to "fly" silently over the water on an electric surfboard with the Alps as your backdrop.

2. Jet Skiing: Zip across the water past legendary alpine villas.

3. Canyoning Excursion: Rappel down mountain waterfalls and jump into hidden gorges.

 

Part 2: The Venetian Lagoon


Day 4 (Monday): Lake Como to Venice

  • Work Impact: 0 Days Off (Memorial Day Holiday).
  • Enjoy a  beautiful 3.5-hour drive east across northern Italy.
  • Park our luxury van securely in a garage for our two-night stay.
  • Board a private water taxi straight to our Venetian hotel.
  • Spend a relaxed evening watching St. Mark’s Square illuminate under the stars.

     

Day 5 (Tuesday): The Lagoon Islands & Sunset Gondola

  • Work Impact: Day Off 1
  • Beat the morning crowds by taking a water taxi to the vibrant, colorful island of Burano.
  • Stop at Murano for an exclusive master glass-blowing demonstration.
  • Cap off the day with an iconic Sunset Gondola Ride winding through Venice's historic back-canals. (Gondola Ride Included)

Part 3: The Heart of Tuscany

Day 6 (Wednesday): Venice to Montecatini Terme & Pasta Masterclass

  • Work Impact: Day Off 2
  • Retrieve our luxury van and drive 3 hours southwest into the cinematic hills of Tuscany.
  • Check into our historic hotel base in the elegant spa town of Montecatini Terme.
  • Ride the historic vintage funicular railway up to medieval Montecatini Alto Montecatini Alto for sweeping sunset views over the valley.
  • INCLUDED EXPERIENCE- Tuscan Pasta Masterclass: Gather in the evening for a private, hands-on cooking lesson. Under the guidance of a local master chef, you will learn the secrets to crafting perfect, authentic fresh pasta from scratch. Celebrate your new skills by dining on your culinary creations, paired perfectly with regional estate wines. (Funicular entry, pasta class, dinner, and wine are fully included).

     
  • Day 7 (Thursday): Volcanic Vineyard Lunch to Sorrento
    • Work Impact: Day Off 3
    • Drive south to the striking cliffside town of Orvieto (2 hours 15 mins).
    • INCLUDED  EXPERIENCE- Volcanic Vineyard Tour:  Head 10 minutes outside the city walls to the historic Azienda Agricola Palazzone vineyard, nestled in rich, volcanic ash soil. Enjoy the "Pilgrims Tour" wine tasting paired with local Umbrian charcuterie directly in the vines.
    • Drive the final 3.5 hours south to check into our beautiful, cliffside hotel base in Sorrento.
       

Part 4: Capri & The Amalfi Coast

 

Day 8 (Friday): Sorrento Exploration

  • Work Impact: Day Off 4
  • Spend a relaxed day exploring Sorrento’s historic center at your own pace.
  • Wander through lemon groves, shop for local leather or hand-painted ceramics, and enjoy sunset drinks overlooking the Bay of Naples.

     

Day 9 (Saturday): The Isle of Capri & Blue Grotto Side Trip

  • Leave the van safely parked at the Sorrento port garage and take the morning passenger ferry to the Isle of Capri.
  • INCLUDED EXPERIENCE- Private Gozzo Charter: Step onto a private wooden gozzo boat charter to explore the towering Faraglioni sea  stacks and witness the glowing electric-blue waters of the world-famous  Blue Grotto.
  • Ride the  open-air chairlift up to the summit of Mt. Solaro in Anacapri for  360-degree views of the Mediterranean before ferrying back to Sorrento. (Ferry, Boat Tour, Blue Grotto, & Chairlift Included).

     

Day 10 (Sunday): Vintage Vespa Tour & Pizza Masterclass

  • INCLUDED EXPERIENCE- Vintage Vespa Excursion: Hop on the back of a vintage Vespa driven by a professional local guide. Zip past the traffic along the hairpin turns of the spectacular SS163 coastal road with free time to wander the vertical towns of Positano and Amalfi.
  • INCLUDED EXPERIENCE- Farm Pizza Masterclass: Celebrate our final evening at a family-run farm in the Sorrento hills. Learn to proof dough, toss it in the air, cook it in a roaring wood-fired oven, and eat your creation alongside local wine and homemade limoncello.       (Vespa Tour & Pizza Masterclass Dinner Included)

     

Part 5: Departures

 Day 11 (Monday): Departure via Naples

  • Work Impact: Day Off 5
  • Take a quick 1-hour drive north to Naples International Airport (NAP).
  • Drop off the rental van directly at the terminal and catch your flights home, landing you home on Monday afternoon.
  

🔒 Booking Terms, Conditions & Financial Policies-

To maintain the premium, intimate nature of our boutique tours, the following policies apply to all registrations. Please review them carefully before placing your deposit.


💰 Investment Details

  • Prepaid Tour Price: $5,150 per person (Double Occupancy)
  • Single Supplement: A $1,200 charge applies if a solo traveler requests a guaranteed private room throughout the trip.


📅 Payment Schedule

  • Initial Booking: A $1,500 non-refundable deposit per person is required to lock in your space.
  • 90 Days Prior (February 26, 2026): 50% of the remaining balance is due.
  • 60 Days Prior (March 28, 2026): The final remaining balance (plus Single Supplement if applicable) is due.
     

❌ Client Cancellation Schedule

Because accommodations, vehicle contracts, and private boat charters are locked in and paid for months in advance, client cancellations/refunds are not possible.

  • All Payments: The initial $1,500 deposit is retained; all other payments made are retained.

 
 

🧳 Luggage Covenant

To ensure physical comfort and adequate safety space inside our luxury 9-passenger van, this tour is strictly carry-on only. Each guest is limited to one standard carry-on suitcase and one personal item.

 

🛡️ Travel Insurance Suggested

Because your tour is strictly non-refundable, we strongly recommend that every guest purchase a comprehensive travel insurance policy (covering trip cancellation, flight delays, medical emergencies, and medical evacuation) within 14 days of placing their deposit. This protects your financial investment.

  

🎟️ Ready to Secure Your Seat? Click Here to Contact Jen & Place Your Deposit!