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7 Days Italy Undiscovered Culture and Culinary Tour in Ascoli Piceno, Italy

Ascoli Piceno, Italy 63100

Best Italy Tours Like a Local

Leave the umbrella waving tour guide (and crowded bus) behind, sip Sangiovese in the vineyard and indulge in 7 days of La Dolce Vita with Italy Undiscovered and explore Italy’s hidden regions like a local. This Italy itinerary is perfect for food and wine lovers that want a backstage pass to experiencing Italy like a local. For six nights, indulge in personalized service, authentic cuisine, and real Italian life. Plus, exclusively curated day trips (including some of Italy’s most beautiful medieval villages).

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  • A privately guided walking tour of Ascoli Piceno
  • Privately guided visit to the Largest Roman Cisterns in Europe
  • A visit to the Sanctuary of Loreto (one of Italy’s largest Basilicas)
  • Organic and biodynamic wine tasting at an award-winning family-run winery
  • Private cooking experience, farm and olive grove visit, and lunch with an Italian family
  • Private day trips and guides throughout Italy’s hidden regions of Le Marche and Abruzzo
  • 6 nights 4-star boutique hotel just steps away from one of Italy’s most beautiful squares
  • Airport and train station transfers and ground transportation in private vehicles
  • Optional sightseeing to Italy’s Narrowest alleyway and local Truffle Country
  • 6 breakfasts, 7 meals including coffee, dessert, and local wines
  • A visit to the Adriatic seaside villages on Conero Coast

Skill level

  • Beginner


6 days with instruction in English
The organizer also speaks: Italian
The maximum participants in the group is 12
Airport transfer included: Leonardo da Vinci–Fiumicino Airport
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  • Air-conditioned rooms
  • Café
  • Dining area
  • Environmentally friendly
  • Lobby
  • Lounge
  • Special menu request
  • Free Wi-Fi
  • Internet access
  • Laundry
  • Newspapers
  • Parking lot
  • Wireless internet

Smack dab in the middle of Ascoli Piceno’s historic center is your homebase. Locally owned and operated boutique 4-star hotel where famous guests slept (Sting stayed there!)

Home to one of Italy’s most beautiful squares, you’ll be walking distance to boutique shops, your perfect scoop of gelato, and streets lined with cafes that have something perfect everyone’s taste buds.


ay 1: Rome to hidden Italy

Benvenuti! You’ll be welcomed to Bella Italia by The Italian on Tour - Giovanni and Chantelle! Flick the switch to vacation relaxation mode.

Be whisked away from Rome’s airport to your boutique hotel, steps from fabulous shops, charming cafes and one of Italy’s most beautiful squares (and an artisan gelateria, perfect for that obligatory daily gelato fix).

Immediately you’ll sense the rhythm of La Dolce Vita. Unpack once, shake off the jet-lag with a post-flight espresso macchiato, and settle into your boutique digs.

Tonight, gather around the dinner table and get to know your fellow travelers and new Italian BFFs. Cin, Cin with a glass of vino rosso, great conversation, and delicious local eats. Round out your first evening with an passeggiata (stroll) in the piazza or hit the sack to catch some Zzz’s before day 2 begins. Buonanotte!

  • Meals: Lunch, Multi-course dinner
  • Pick-up point: Info Point in Terminal 3 located in Rome’s Fiumicino Airport at 11:30 a.m.

Day 2: The city of Travertine, 100 Towers and Truffle Country

Buongiorno! Welcome to your first morning in The Italian On Tour bubble. Every day begins with breakfast in the elegant courtyard of your boutique hotel. You’ll always be at met at your accommodations before embarking on your adventure of the day.

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

Energized from your morning espresso you’ll explore the epic millennial history, gorgeous Renaissance architecture, Ernst Hemmingway’s favorite cafe, and hidden churches that’ll make you go “Wow!”.

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

Post-passeggiata (stroll) return to Ascoli. Your evening is free to soak up the beauty of the piazza and have dinner on your own (for restaurant recommendations, consult your Vacation Vault for your exclusive Italian On Tour dining guide).

  • Meals: Breakfast, multi-course lunch
  • Activity: In the morning 2-3 hours urban walking on flat terrain. Easy afternoon stroll and light inclined walking (2-3 minutes of incline)

Day 3: Wine and Roman times

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!

Continue your journey through Roman history with a visit to a unique family-run organic and biodynamic winery that makes wine the Roman way. David, a sommelier and local winemaker, will welcome you to the cantina for a private tour of the Gambero-rosso award-winning wine production.

Settle into taste the goods with an exclusive wine tasting paired with local charcuterie and the perfect plate of ragu that’ll make you reach for another splash of vino rosso, or two!

After lunch, beat your pasta coma with a stroll in Moresco, a quaint hill-top town that is one of Italy’s “Borghi piu belli d’Italia” (most beautiful medieval villages in Italy) before returning to Ascoli.

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

  • Meals: Breakfast, multi-course lunch paired with local organic and biodynamic wines
  • Activity: A short walk in the morning to visit the city center of Fermo and its Roman cisterns. A visit to the cantina, relaxing on the vineyard’s terrace, and a short afternoon stroll.

Day 4: Learn the secrets to Cucina Italiana (Italian Cooking)

Wake up and ease into your day with a double cappuccino morning. Head to the local farmer’s market to discover seasonal ingredients and partake in a slice of everyday Italian life or simply enjoy some free time before your cooking class.

Ready yourself to discover the secrets to Italian cooking with a locally renowned chef. Be welcomed inside their kitchen for an “The Italian On Tour” exclusive cooking experience.

Post-cooking, sit down and enjoy a perfectly plated tasting menu that reflects the best of the season.

Late afternoon, join in on some afternoon sightseeing through the wine country and squeeze your way through Italy’s Narrowest Alleyway (this one’s in the Guinness world book of records).

The evening is yours to relax, dig into another plate of handmade pasta, (if you’ve managed to save some room after your cooking class).

  • Meals: Breakfast, Multi-course Seasonal Lunch (please note that the tasting 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!), optional afternoon sightseeing to visit Italy’s Narrowest Alleyway.

Day 5: Seaside sightseeing

Soak up the beauty of Italy’s most underrated coastline. You’ll travel along the Adriatic seaside to reach the Coast of Conero dotted with white sand beaches, marked by the magnificent Monte Conero (Conero Mountain), and lined with pristine turquoise waters,

Post-passeggiata (walk) of the local seaside villages, it’s time for a seafood lunch at a locally run restaurant with the best view on this side of the Adriatic.

The next stop is Loreto, a 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.

Or enjoy the art of Apericena (think Italian-style tapas) at one of Ascoli’s cafes just minutes from your hotel.

  • Meals: Breakfast, multi-course Seafood Lunch
  • Activity: 2 hours leisurely sightseeing on foot. An afternoon stroll to visit the town and Basilica of Loreto.

Day 6: The ultimate Italian family farm-to-table experience

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

Head south to one of Italy’s largest olive oil-producing regions. Stopover at a restored castle before a visit to a family-run farm that has been working the same land since 1824. 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 Alessio’s family home. 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. The rest of your evening is free.

  • Meals: Breakfast, multi-course authentic farm-to-table zero-km lunch paired at a family farm in Olive oil country
  • Activity: A short walk in the morning to visit the local village and its beautifully restored castle. A visit to the farm to learn about the local produce and how olive oil is made.

Day 7: Arriverderci!

It’s check out day…

You feel elated and invigorated after your trip with The Italian on Tour, you’re having this was the “best trip ever” moment. Be driven to Ascoli’s bus or train station to connect to the next leg of your trip. Should you wish to stay longer in Ascoli or explore Rome, Florence, Venice or connect with the ferry over to Croatia, they’ll be happy to offer their local insider advice on how to get to your next destination.

Bid farewell, with a hug and a kiss on each cheek (because after your trip with us you’ll be feeling like an Italian now).

Until next time “Arrivederci”! Buon viaggio!

  • Meals: Breakfast
  • Drop-off: Ascoli Piceno bus/train station. Drop-off available between 8:30 to 10:30 a.m.

Included excursions

  • Preparing a meal with a local chef
  • Walking tours
  • Farm visits
  • Olive oil tasting
  • Wine tasting


Giovanni Dagostino


This holiday will take place in Ascoli Piceno, Italy. Ascoli Piceno is a picturesque town located in the region of Le Marche in central Italy. Just a stone’s throw away from Umbria and Abruzzo, it is the perfect location to visit all three of these regions with ease. It is filled with architectural charm, boasting a history that dates back before the inception of Rome. Once known as the City of One Hundred Towers, it is covered in travertine and is home to one of the most beautiful squares in all of Italy, Piazza del Popolo.

In the evening the streets around the Piazza come alive, buzzing with energy, as friends meet-up to enjoy drinks, and the city emerges for the nightly passeggiata (stroll). In Ascoli, you can take the evening in like an Italian, enjoying an apertivo (cocktail) at Caffe Meletti (one of Italy’s 100 Historical Cafes) or follow the tempting aromas to one of the Centro Storico’s (Historic Centre) many restaurant tables.

Ascoli is easily walkable, allowing you to relax and go back in time while you cross its maze of tiny alleyways and cobblestone streets. Unlike many of the towns of Tuscany that have been surrendered to tourism, the heart of Ascoli still beats to the rhythm of its 50,000 residents. It is big enough to support a local shopping and dining scene, but small enough to have maintained its authenticity and culinary heritage, one which includes the second largest medieval reenactment in Italy, the Quintana, and the famous Olive all’Ascolana (stuffed olives) festival.

The hills around Ascoli are uncrowded and hide many gems of the region. There, you will find generational wineries, family-run agriturismi (farm-stays), and an award-winning olive oil production. Still relatively undiscovered, and located in a territory considered to be “all of Italy wrapped up into one region”, Ascoli is off-the-beaten-path offering all the charms of Italy’s well-known regions without the crowds. This up and coming status lends Ascoli to still being a city where you get to meet the locals and can truly experience the authenticity of genuine Italian hospitality.


During this culture and culinary holiday, you will be served six breakfasts and seven meals including wine, coffee, and dessert. Every day will begin with a delicious breakfast, composed of local products and seasonal pastries, served in the elegant courtyard of your hotel.

The Italian On Tour team makes it easy to enjoy fantastic cuisine and travel Italy gluten-free. Travel worry-free and inquire with them directly to make any one of ready-to-book itineraries gourmet gluten-free. Gluten-free supplement is available at 204 EUR per person.

The following meals are included:

  • Breakfast
  • Lunch
  • Drinks

The following drinks are included:

  • Water
  • Coffee
  • Alcoholic beverages

The following dietary requirement(s) are served and/or catered for:

  • Regular (typically includes meat and fish)
If you have special dietary requirements it's a good idea to communicate it to the organiser when making a reservation

What's included

  • 6 nights 4-star boutique accommodations in the historical center, just steps away from one of Italy’s most beautiful squares.
  • 6 breakfasts, 7 meals including coffee, dessert, and local wines.
  • All tips for drivers, restaurants, and guides included.
  • Privately guided visit to the Largest Roman Cisterns in Europe
  • All private day trips and guides to some of the Borghi piu belli d’Italia (most beautiful medieval villages) throughout Italy’s hidden region of Le Marche & Abruzzo.
  • Privately guided walking tour of Ascoli Piceno arranged exclusively just for our guests
  • All optional afternoon sightseeing including a visit to Italy’s Narrowest alleyway (as recorded in the Guinness World Book of Records) and local Truffle Country
  • A visit to the Sanctuary of Loreto (one of Italy’s largest Basilicas)
  • A visit to the Adriatic seaside villages on the Coast of Conero
  • All entrance fees to monuments included
  • Plus these exclusive experiences:
  • Private cooking experience using seasonal local and organic ingredients (designed exclusively for Italian On Tour guests!)
  • Organic and biodynamic wine tasting at a Gambero Rosso award-winning family-run winery (designed exclusively for Italian On Tour guests!)
  • Private farm and olive grove visit followed by a farm-to-table lunch with an Italian family (exclusively for Italian On Tour clients)
  • Pick-up and transfer from Rome’s Fiumicino Airport to Ascoli Piceno
  • Transfer to Ascoli Piceno’s bus/ train station from the hotel with a private driver
  • All ground transportation in private vehicles

What's not included

  • Any items not mentioned in the itinerary
  • Flights
  • Items of personal nature
  • Return transfer from Ascoli Piceno to Rome or elsewhere
  • Travel and trip cancellation insurance

How to get there

Recommended Airports

Arrival by airplane

Book your flight to arrive at Rome’s Fiumicino Airport (FCO). Meet your guide at Info Point in Terminal 3 located at the airport at 11:30 a.m. Pick up from this airport is included. On the departure day, you will be dropped off to Ascoli Piceno bus/train station. Drop-off is available between 8:30 to 10:30 a.m.

Airport: Leonardo da Vinci–Fiumicino Airport Airport transfer included: Leonardo da Vinci–Fiumicino Airport No additional charges. You can request this in the next step.

Cancellation Policy

  • A reservation requires a deposit of 20% of the total price.
  • The deposit is non-refundable, if the booking is cancelled.
  • The rest of the payment should be paid 60 days before arrival.
7 days / 6 nights
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Solo travelers

This tour can accommodate solo travelers. These set-date trips get you in touch with Italy, all while experiencing it with like-minded individuals. You will travel in groups of never more than 12 people, so you can travel to Italy authentically and make a few new friends along the way.


Custom dates

Custom dates for private tours are also available. These ready-to-book itineraries offer everything with the convenience of choosing your dates and going with your own travel companions. Please send an inquiry for private tour options.

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