Buongiorno! Welcome to your first morning in The Italian On Tour bubble. Everyday begins with breakfast in your charming boutique hotel (want the luxury of breakfast in bed? Room upgrades are available). 

You’ll always be met at your hotel before embarking on your adventure of the day.

Connect with a local history expert for your bespoke privately guided walking tour of Ascoli Piceno – exclusively arranged just for The Italian On Tour® guests. 

Energized from your morning espresso, you’ll explore epic millennial history, gorgeous renaissance architecture, dreamy travertine piazzas, Ernest Hemmingway’s favorite cafe, hidden churches, and the historic center of Ascoli that was the movie set of Dustin Hoffman’s Alfredo, Alfredo.

Worked up an appetite? Next up is a leisurely lunch at a Liberty style Villa followed by a picturesque drive to Italian truffle country.  Stop for a stroll and must-see views of central Italy’s largest mountain range: The Apennines.   

Post-passeggiata (stroll), and epic panoramic photo ops, you’ll return to Ascoli. Your evening is free to soak up the beauty of the piazza and have dinner on your own (for restaurant recos consult your exclusive The Italian On Tour® Dining Guide).

As in you’ll never have to worry about having a bad meal- with exclusive The Italian On Tour® restaurant recos found inside the Vacation Vault, you’ll have a variety of delicious options just walking distance from your hotel.

Meals: Breakfast, Multi-course lunch including wine & coffee

Activity: In the morning 2-3 hours urban walking on flat terrain. Easy afternoon stroll and light inclined walking (2-3 minutes of incline) 

Wake up and ease into your day with a creamy cappuccino and get ready to soak up the beauty of Italy’s most underrated coastline & One of Italy’s Most Beautiful Medieval Villages overlooking the Adriatic Sea.

You’ll travel along the Adriatic seaside to reach the Coast of Conero, a national park, dotted with white sand beaches, marked by the magnificent Monte Conero (Conero Mountain), and lined with endless turquoise waters. 

Post-passeggiata (walk) of the local seaside villages, it’s time for a 3-course seafood lunch inside an ancient military fortress with the most stratospheric views on this side of the Adriatic Coast.  This is postcard-picture-perfect pristine coastline at its best!

Next stop is Loreto, world-renowned pilgrimage site and home to a stunning renaissance basilica. Return to Ascoli in the late afternoon for some shopping at the local boutiques or chilling in the piazza. 

Your trip to Italy wouldn’t be complete without indulging in a gourmet pizza pie! Consult your exclusive The Italian On Tour® Dining Guide and wind up your evening with dinner at one of Ascoli’s multiple Gambero Rosso award-winning pizzerias located walking distance from your hotel.

Meals: Breakfast, 3-course Seafood Lunch paired with wine – designed just for The Italian On Tour® guests

Activity: 2 hours leisurely sightseeing by foot of Le Marche’s seaside villages on the Adriatic coast. Afternoon stroll to visit the town and Basilica of Loreto.

Enjoy a later start to your day with a leisurely breakfast or take in some solo-exploration.

Early risers can head to the local farmer’s market to discover seasonal ingredients and partake in a slice of everyday Italian life or check out the latest Italian fashion at the market stalls.

Mid-morning, be welcomed into the home of a locally renowned chef (featured in La Cucina Italiana) with a gorgeous spread of homemade organic pastries and savory bites, before readying yourself to discover the secrets to Italian cooking inside an authentic frescoed villa typical of Le Marche.

You’ll get the best taste of local cuisine with your exclusively curated cooking class where you’ll learn how to make one of Ascoli’s signature dishes, followed by a beautiful organic tasting menu of traditional Marchigiani fare.

After cooking up a storm, you can return to your hotel or optionally you can meet up with Chantelle or Giovanni to visit our favorite place for locally made leather goods, handmade ceramics & the best shop in town to get gourmet goodies to bring back home.

Your evening is free.

Now that you’re feeling full-on Italiana head out to the piazza for the local evening ritual of Apericena (Italian style tapas) and a post-gelato passeggiata (stroll).

Meals: Breakfast, Mid-morning Snack at the Villa before you cooking class, Multi-course organic Lunch (please note that menu varies with the season to offer you the freshest and most flavorful local dishes)

Activity: 1–2 hours standing on your feet in the morning while you prepare a meal with a local chef (can’t stand the whole time, no worries, pull up a chair and relax, this is your vacation after all!)

Today’s adventure will take you underground, beneath the ancient Roman city of Fermo.  

Step inside an amazing architectural feat – the largest roman cisterns in all of Europe! 

Then onward to visit a 16th century palazzo which houses important paintings from Venetian & Le Marche school, including a Rubens, and the ancient Globe Room (considered by National Geographic One of the World’s Most Beautiful Libraries) which contains books from the days of Alchemy.

Pre-pranzo (before lunch) make your way deeper into Le Marche’s hinterlands to continue your journey through Roman history with a visit to a unique locally-owned and operated winery that has its history rooted in Roman military conquests. 

Your heart will be conquered by the award winning wines, top olive oil and 360 degree hills so stunning they’ve even named two of their wines after it!  

This 100 acres estate produces Pinot Nero, Syrah, Montepulciano, Lacrima, Pecorino, Sauvignon, Passerina and Chardonnay grapes, in addition to a variety of fruit trees including olives.

Kick off your 3-course farm-to-table menu and guided wine pairing curated just for The Italian On Tour® guests, with an olive oil taste.  

Post-pranzo you’ll get to enjoy a guided visit on wheels of the entire 50 hectare estate and snap up panoramic views of Le Marche’s hills that expand all the way to the Adriatic Sea. 

Next up is a private tour of the Wine Cellar and Gambero-Rosso award-winning wine production – exclusively for The Italian On Tour® guests. 

Optionally, before returning to Ascoli you’ll have time to grab a few bottles of wine and olive oil to bring back home and/or put in an order if you’re looking to purchase a few cases.

The evening is yours to relax, indulge in the rhythm of Italian life, and have dinner on your own. 

Meals: Breakfast, 3-course farm-to-table menu and guided wine pairing including coffee, water, bread and a tasting of award-winning olive oil

Activity: A short walk in the morning to visit the city centre of Fermo and its Roman cisterns and the ancient globe room. A visit to the cellar, relaxing on the vineyard’s terrace, and a guided tour of the estate (don’t worry you won’t’ have to walk the entire 100 acres, you’ll get a private visit via golf cart)

Put on your sturdy shoes and comfortable clothes, you’re headed into Le Marche’s truffle country to hunt with one of the best! 

Supplying famous chefs (Jamie Oliver, Gordon Ramsay & Gennaro Contaldo – just to name a few!) this local truffle hunter, and his pack of truffle hunting dogs, are just the team you need to find yourself a bounty of Gordon Ramsay approved summer truffles. 

Pre-pranzo (pre-lunch) ready your taste buds with a handmade pasta all’uovo making demonstration and enjoy an exclusive truffle menu crafted – just for The Italian On Tour® guests!

Pull up a chair, sit back and settle in for a gorgeous meal composed of organic ingredients, and freshly foraged summer truffles. After a satisfying lunch you’ll take in the beauty of Le Marche’s truffle country as you’re whisked away back to Ascoli Piceno.

Your evening is free to relax, dig into another plate of tagliatelle with tartufi, (if you’ve managed to save some room after your tasty truffle lunch).

Meals: Breakfast, Multi-course Farm-to-table Truffle lunch paired with local wine

Activity: A morning of foraging in the woods for truffles followed by a leisurely lunch composed of summer truffles and seasonal organic ingredients – arranged just for The Italian On Tour® guests. Sturdy shoes and comfortable clothing required. (Don’t feel like foraging? No problem!  Relax under the pergola and take in the scenery at the Agriturismo).

Head south to Abruzzo for a visit to Civitella del Tronto, the  largest and most formidable medieval fortress in all of Italy! Climb to the top to score the best view in the house. Ready your camera, it’s time for an epic one-of-a-kind 360-degree view of Le Marche and Abruzzo. 

After enjoying panoramic views, so good you won’t need to buy a postcard, you can try squeezing through Abruzzo’s Narrowest Alleyway (Don’t like small spaces? No problem! It’s not obligatory to walk through this tiny pathway)

Journey across the beautiful valley of Val Vibrata to a family-run farm-to-table restaurant that is passionate about Slow Food and holds the title of Italy’s Top Slow Food Restaurant for Traditional Cooking. 

Surrounded by rows of Montepulciano d’Abruzzo vines, dig into hand-made pasta and local meat dishes that have made some of our guests’ lists of “the best meal of my life”. 

Post-wining and dining, before returning to Ascoli, feel free to explore the vineyards and snap up some stunning photos to share with your friends & family back home.

Your evening is free.

Meals: Breakfast, Multi-course Family Style Lunch (multiple seasonal appetizers, main course, dessert, wine and coffee) immersed in Montepulciano d’Abruzzo wine country at Italy’s Top Slow-Food Restaurant for Traditional Cuisine

Activity: In the morning 2-3 hours walking on varied terrain with some short steep inclines, sturdy shoes recommended. If you find walking uphill difficult, you’re always welcome to relax at a local cafe and we’ll come get you after.

Get ready for another beautiful day in the Italian countryside — and another exclusive The Italian On Tour® experience.

Head south to one of Italy’s largest olive oil producing regions. Upon arrival you’ll be welcomed by a family of local farmers that has been working the same land since 1824.  

Before lunch, you’ll visit the working farm to see where all the seasonal produce, from the olive oil to the zesty sugo al pomodoro (tomato sauce), is grown and made by La Famiglia (the family). 

Get a taste for true Italian southern hospitality as you’re invited into their family home to gather around the table for lunch. Cooking and eating among four generations you’ll get a taste of what it is like to have your own Famiglia Italiana (Italian Family). 

Grateful for this once-in-a-lifetime experience, with your heart and belly full, say your goodbyes and jet back to your homebase in Ascoli.  Rest of your evening is free.

Meals: Breakfast, Multi-course authentic farm-to-table zero-km lunch paired with wine at a multi-generational family-run farm in Abruzzo’s Olive oil country

Activity: A visit to the farm to learn about the local seasonal produce and how olive oil is made. This is a relaxing day, as if you were spending a Sunday with your very own Italian family.

Take a bite out of the sweet life by saying Buongiorno (Good day) to wine country and Offida, one of Italy’s Borghi più belli (Most Beautiful Medieval Villages)!  

Be transported back in time as you stroll through this quaint town, working up an appetite for an afternoon full of wine tasting and zero-km dining. 

You’ll be welcomed by the owner & local wine maker to a Gambero Rosso award-winning, SlowWine, family-run estate that produces: Pecorino, Passerina, Montepulciano and Sangiovese.

Take spectacular views as you settle in to dine al fresco with a 5-course tasting menu cooked by a private chef– designed just for The Italian On Tour guests.

Enjoy lunch with a guided pairing of 5 wines overlooking endless rows of vineyards and olive groves before you’re taken to the cellar to learn about the wine production.  Here you’ll have the opportunity to ask the winemaker himself about his wine and optionally you’ll also have the time to purchase some vino to take back home or put in a request to have it shipped (please note shipping availability will vary on state and country)

Afterwards, float in the relaxation zone as you enjoy the scenic route through the Piceno wine country on the way back to your hotel. Your evening is free. Now that you’re feeling full-on Italiana head out to the piazza for the local weekend ritual of the Apericena (Italian style tapas) and a post-gelato passeggiata (stroll).

Meals: Breakfast, 5- course lunch paired with local wines

Activity: 2-3 hours walking/standing on cobblestone streets, a visit to the cantina, wine production, and lunch al fresco paired with wine (if the weather is not in your favor you’ll enjoy dining inside the agriturismo).