Ashley Olano

Florence, Itatly

Italy is one of my most-requested destinations—and one I never tire of planning. I’ve traveled extensively across the country, most recently spending three weeks exploring a range of regions and visiting over 25 top luxury hotels. My travels have included Rome, Florence, Venice, Milan, Lake Como, Lake Garda, Tuscany, the Amalfi Coast, Capri, and Forte dei Marmi, to name a few.

Whether it’s your first time or your fifth, I design custom itineraries that help you experience Italy with depth, ease, and style. From luxury stays and private guides to food, wine, and pacing that fits your travel rhythm, I help you fall in love with Italy in your own way.

Popular Destinations Within Italy

Italy offers an incredible variety of landscapes and experiences. While each trip is fully customized, here are some of the most popular regions and styles of travel I help clients explore:

• Classic First-Timers: A well-balanced itinerary like Rome, Florence, and the Amalfi Coast with private tours, skip-the-line access, and memorable meals.
  
  
• Romantic Escapes: Think Lake Como villas, Tuscan wine tastings, and boat days off the Amalfi Coast—perfect for honeymoons and anniversaries.
  
  
• Food & Wine Lovers: A slower-paced itinerary through Piedmont, Tuscany, or Emilia-Romagna, including vineyard tours, cooking classes, and market visits.
  
  
• Southern Italy & Islands: Trips that explore Puglia, Sicily, or Sardinia—less touristy but equally spectacular, with a strong focus on culture, cuisine, and coastal beauty.
  
  
• Italian Riviera: The stretch of coastline from Portofino to Cinque Terre offers postcard views, cliffside towns, and elegant seaside charm.
  
  
• Dolomites & Wellness: For couples or active travelers, a few days in the Dolomites offers alpine hiking, modern design hotels, and destination-worthy spas.

Where You’ll Stay

Choosing the right accommodations is key to a seamless experience. I work with Italy’s top luxury hotels and boutique properties—including Virtuoso, Select, and other preferred partners—to ensure:

• Exclusive perks (upgrades, breakfast, spa or F&B credits)
• Personalized service and VIP recognition
• Prime locations that enhance your trip
• Unique properties that feel true to the region—whether modern, historic, or romantic

From grand lakefront hotels to vineyard villas, I’ll guide you to the stays that best fit your taste and trip goals.

What I Love to Include

Italy is about the details—and the experiences that go beyond a checklist. I often build in:

• Private market tours, cooking classes, or truffle hunts
• Wine tastings in Tuscany, Piedmont, or Mount Etna
• Aperitivo with a view, hands-on pasta making, or olive oil tastings at the source
• Private boat days along the Amalfi Coast or in Capri
• Behind-the-scenes access to museums, artisans, or historic landmarks
• Personal drivers to reduce stress and maximize comfort

Whether you're most excited about the food, the culture, or the views, I’ll tailor the trip to your priorities.

Italy has a way of capturing your heart—and no two trips should look the same. My job is to help you experience it in a way that feels personal, elevated, and effortless. If you're ready to start planning, I’d love to help you bring it to life.