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The Ultimate Italy Insider’s Trip – Barolo, Bolgheri & Brunello 2020

$6,995 + Tax Per Person Double Occupancy
All Inclusive*

Are you ready to travel by luxury chauffeured mini-coach and discover all of the best that that Italy has to offer? Then join me for 10 days and 9 nights in “Il Bel Paese!” We’ll enjoy genuine insider VIP treatment at some of the world’s best wineries in Barolo and Brunello (Montalcino) and a special treat in Bolgheri. We’ll taste rare library selections, enjoy verticals of limited releases, and hang out with legendary, and up and coming winemakers. But that’s not all! We’ll dine at Michelin starred restaurants, and have the option to bike or e-bike the countryside, visit a beautiful castle, cook authentic Northern Italian Cuisine, visit a wine museum, go shopping in Alba and Siena, relax at an amazing spa and more.

Italy is one of my favorite countries in the world. It offers so much: centuries of culture, amazing wines, incredible food and that’s just the start! I’ve spent over a year visiting, studying and living in Italy. I lived in Milano, Bologna and Pescara, visited every major wine region several times, and I speak the language! Furthermore, I’ll be assisted by a native guide in each region! So, you’re guaranteed not to miss any highlights from the regions!

Montalcino, Italy

This Ultimate Insider’s Vacation is limited to 14 participants! Monsterville’s Wines members have priority to book until July 25th. After that date we’ll open the trip up to the general public. So, book now to reserve your seats!


Barolo, Bolgheri & Brunello
Travel Itinerary – May 1-10, 2020


Airport Pickup in Chauffeured Mini-Coach
Check in at Le Case dei Conti Mirafiore “Hotel Vigna Magica” (4-Star)
Sightseeing in Alba – Welcome Dinner

  • Private Mini-Coach pick up at Milan Malpensa Airport (MXP) and then to Serralunga D’Alba (One of the renowned communes of the Barolo region)! Lunch at Ristorante Bovio
  • Check in at Le Case dei Conti Mirafiore “Hotel Vigna Magica” (4-Star) Free Time to Relax at Hotel
  • Pre-Dinner Sightseeing Stroll thru Alba
  • Dinner near Alba at Michelin Starred Locando del Pilone


VIP Winery Tours – Winery Lunch – Educational Tastings – 3-Star Michelin Dining

  • VIP Winery Tour – Paolo Scavino Winery
  • Special Feature: Tasting the differences in the Barolo Crus
  • VIP Winery Tour & Winery Lunch – Conterno-Fantino Winery Tour & Light Lunch
  • VIP Winery Tour – Luciano Sandrone Winery
    Discussion of Barolo Single Cru vs Vineyard Blends
  • Rest & Relaxation at the Hotel
  • Dinner at Michelin 3-star Restaurant Piazza Duomo
    (Voted the 16th Best Restaurant in the World on Forbes Annual Top 50 List)


VIP Winery Tours “The Big & the Small” – Spa Option – Restaurant Dinner w/ Winemakers – Castle & Wine Museum Tour

  • Two VIP Winery Tours – A unique opportunity to visit a “mega big” quality Barolo producer (Marchesi di Barolo) and a tiny artisan producer (E. Pira’s Chiara Boschis) literally across the street from each other.
  • Lunch at the Marchesi di Barolo winery featuring a tasting of library vintages.

Afternoon options:

  • Afternoon at Il Boscareto Spa
  • VIP Winery Tour – Einaudi – Tasting of Dolcettos and Cru Barolos & Grinzane Cavour Castle & Wine Museum Tour
  • Free Time at Hotel
  • Dinner at the beautiful Michelin starred Ristorante “La Ciau del Tornavento”
    (My personal favorite in all of Piedmont)!


Active Day (E-Bike Tour) or Cooking Class – Afternoon VIP Winery Tours Michelin Starred Dining with Older Vintages

Morning Options

  • Guided E-bike Tour followed by a light Lunch
  • Cooking Class and Lunch
  • VIP Winery Tour – Elvio Cogno – Master of the Ravera Cru Tasting & Lunch
  • VIP Winery Tour – Fontanafredda Winery – Historic Winery w/ Tasting
  • Dinner at Michelin starred Ristorante Guido featuring Barolo vintages from the 1980’s & 1990’s!


Bolgheri – Home of the Iconic Super Tuscans:
Ornellaia, Sassicaia & Biserno – Ornellaia Lunch – Biserno Dinner – Biserno Relais Hotel

  • We depart for Bolgheri (Tuscany): the home of the original Super Tuscans!
    Here Cabernet is King! Here starts the second half of our incredible journey.
  • Lunch
  • VIP Winery Tour & Tasting – Ornellaia
  • Check in at Biserno Relais
  • VIP Winery Tour, Tasting & Dinner at Biserno Winery


Chauffeured Mini-Coach Drive to Montalcino – VIP Winey Visit at Sassicaia

  • VIP Winery Tour & Tasting – Sassicaia
  • Lunch
  • We depart for Montalcino (2-hour drive)
  • Check in at Casanova Di Neri Relais
  • Sightseeing stroll of Montalcino or
    Free time at Hotel
  • Dinner at Vineria Le Potazzine Restaurant


3 Amazing VIP Winery Tours w/ Special Tastings

  • VIP Winery Tour – Fuligni – Vertical Tasting of Older Vintages & New Releases
  • Lunch at Il Leccio Restaurant
  • VIP Winery Tour – Ciacci Picolomini – Tasting of Current Releases and Barrel Samples
  • VIP Winery Tour – Casanova dei Neri – Tasting of New Releases and Library Selection
  • Dinner at Casanova Di Neri


Morning of Options – E-Bike, Hike or Spa – Winery Lunch – 2 VIP Winery Visit & Tastings

Morning Options:

  • E-Bike Tour
  • Wine Country Hike
  • Spa
  • VIP Winery Tour, Tasting & Light Lunch – Val di Suga Winery
  • VIP Winery Tour & Tasting – Il Marroneto Winery
  • Free Time at the Resort
  • Dinner at 2-Star Michelin Restaurant “Adolfo” in Siena


Saturday, May 9th – Discover Siena – Shopping – Guided City Tour – Free Time VIP Winery Visit and Farewell Winery Dinner

  • Guided Tour of Siena
  • Free Time & Shopping in Siena Lunch in Siena
  • Relax at Resort
  • VIP Visit, Tasting & Farewell Dinner at Costanti Winery in Montalcino


Depart for Florence Airport or Wherever the Wind Takes You!

  • Our Mini-Coach will transport us to the Airport in Florence (FLR) for the trip home.

This Ultimate Insider Trip includes: Amazing 10-Day/9-Night VIP Insider Trip includes all “on the ground expenses” except optional Spa Services. It Does Not Include Airfare.


  • Airport Transfers for Recommended Flights
  • 9 Nights’ Accommodations
  • 9 Breakfasts
  • 9 Lunches w/ wine
  • 9 Dinners w/ wine
  • Bike and/or E-Bike Rental
  • Fees for all museum, attractions and activities (except spa services)
  • Fees for all winery visits and tastings
  • Chauffeured transportation by mini-coach

Monsterville will be your full-time tour leader with assistance from local Italian guides.

Wineries, restaurants and hotels are subject to change. However, any and all necessary replacements or substitutions will be comparable.


United Airlines Recommended Flights

Outbound Flights
UA 748 – Departs Houston (IAH) 12:00 pm – Arrive Newark (EWR) 4:38 pm
UA 19 – Departs Newark (EWR) 6:35 pm – Arrive Milan (MXP) 8:40 am

Return Flights
UA 8797 – Departs Florence (FLR) 10:00 am – Arrive Frankfurt (FRA) 11:35 am
UA 47 – Departs Frankfurt (FRA) 1:35 – Arrive Houston (IAH) – 5:35 pm

The coach will pick up from Milan and drop off in Florence based on the above flight times.

A 50% non-refundable deposit is required to book this trip. The remaining 50% is due by February 1, 2020. Members or participants may sell or find replacements for their tickets, however, due to the guarantees involved there can be no refunds.