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Experience all of Italy wrapped-up into one region with a journey that will take you from savoring slow-food on sun-kissed rolling hills to soaking up the sunshine by the seaside. Enjoy a relaxing vacation by unpacking once and unwinding with nine days located just steps away from one of Italy’s most beautiful piazzas (town square). You will be joined by a fully-bilingual, 100% Italian, 100% local guide with an International culinary resume that will ensure your vacation is nothing but spectacular. Travel the road-less-taken and enjoy the in-depth experience of authentic Italy that you have been craving.
Nestled in the heart of Ascoli Piceno’s Centro Storico (historic center), the selected accommodation is a stunning property that is locally-owned and operated. Once having its life as a noble palace and convent, the two were combined to create a perfectly curated luxury boutique 4-star stay that is a unique expression of this territory.
Tucked away down a cobble-stone paved alley its position offers tranquility, yet it is conveniently located just steps away from the city center and one of Italy’s most beautiful squares: Piazza del Popolo (The People’s Square). It is the perfect location to immerse yourself in the rhythm of the city, allowing you to easily enjoy an evening passeggiata (stroll), and ease into what the Italians call “La Dolce Vita”.
This itinerary will focus on introducing you to the most iconic Italian experiences. You will meet the vintners of the territory that have etched their story inland through award-winning wines, and experience first-hand their passion that continues to be passed on from generation-to-generation. While you explore the territory, you will be introduced to the Italian trifecta: food, wine, and people, allowing you to get in touch with the culture of the territory and learn some culinary secrets along the way. Your hands-on cooking class will be set in the backdrop of a 17th-century abbey, not only exposing you to local cuisine and recipes handed down from Nonna (grandma), but also to the old-world charm and pure rhythm of “La Dolce Vita”.
Welcome to Italy! Meet your guide and enjoy a comfortable ride in a private vehicle from Rome’s Fiumicino Airport directly to Ascoli Piceno. No need to wait for buses or taxis, just hop on with your guide and arrive directly at your hotel. Enjoy the scenery of the National Park on the way or simply nap to recover from your jet lag. You will stop for a quick lunch on your way from Ascoli to Rome.
In the late afternoon, you will arrive at Ascoli and settle into your home for the duration of your stay. Your hotel is located just a stone’s throw away from one of Italy’s most beautiful Piazzas making it the perfect location to relax and explore the city by foot. Before dinner, meet up with your guide and trip designer for an optional mini-orientation tour of Ascoli Piceno. After, take in a relaxing evening with a glass of Rosso Piceno (a variety of local red wine) and enjoy your first dinner with your fellow travelers and new-found friends.
Every day will begin with a delicious breakfast, composed of local products and seasonal pastries, served in the elegant courtyard of your hotel. Your guide will always meet-up with you at your hotel before embarking on the adventure of the day.
This morning, let’s take a bite out of the sweet life by saying Buongiorno (Good day) to wine country and one of Italy’s most beautiful hill-top villages! The group will drive east down countryside roads to make your first stop of the day: Offida, one of Italy’s Borghi piu belli (most beautiful villages). Step back in time as you stroll through this quaint town working up an appetite for an afternoon full of wine tasting and true zero-km dining. Bid Arriverderci (goodbye) to Offida’s old-world charm and hello to wine and dining Italian style.
Today, you will meet one of the owners, whose father is the Original Purveyor of the Pecorino vine. She will take you on an exquisite journey of the taste buds, pairing local charcuterie, and rustic dishes with award-winning wines. After a leisurely lunch, you will make your way from the Cantina to the beautiful Vigneto Storico (historic vineyard), where you will have the opportunity to savor your last sip completely immersed in wine country. In the late afternoon, you will return to Ascoli. Your evening is free. Relax, take an evening walk, and enjoy dinner on your own at one of Ascoli’s many local hot spots.
Today, you will meet your local guide and resident Ascolana (Person from Ascoli Piceno) for a privately guided walking tour of Ascoli Piceno, which is heralded for one of the most beautiful squares in all of Italy! By foot, you will explore Ascoli’s magnificent piazzas, and visit the beautiful Duomo, all while learning about the art, culture, and history of the powerful people called the Piceni.
After working up an appetite, you will travel to the land of Tartufo Nero (black truffle) for lunch at a family-run establishment where Nonna is known for making the best Olive Ascolane (stuffed olives) in this neck of the woods. After a leisurely lunch with your fellow travelers, you will make your way to deeper into truffle territory with a visit to a typical mountain village of the region. After enjoying a stroll through this ancient Roman outpost, and experiencing stunning views of the Apennines Mountains, you will make your way back to Ascoli. The rest of your evening is free to enjoy a little solo exploration and have dinner on your own.
Wake up and ease into your day with a relaxing breakfast. Your guide will meet you at your hotel and whisk you away into the Italian countryside for a cooking class at a 17th-century villa that once had its life as an abbey. Admire its beautiful frescoes while you get a hands-on cooking lesson from a locally renowned chef that was featured on Italy’s Cuochi d’Italia and learned her secrets from the best, Nonna (Grandma).
After cooking up a storm take some time to enjoy the fruits of your labor and breathe in the tranquility of this peaceful property with a lunch in the gardens and relaxation by the villa’s pool. In the late afternoon, your guide will meet you at the villa and you will return to Ascoli. Optionally, you can join your guide for some afternoon sightseeing through the heart of truffle country to the foothills of the Apennines. The evening is yours to relax, take a stroll, and eat some delicious Italian fare.
Today’s adventure will take you into another wine valley of the region, exposing you to a different landscape and continuing your journey of the senses. First stop of the day will be Moresco, a quaint hill-top town that is one of Italy’s “Borghi piu belli d’Italia” (most beautiful hamlets in Italy). After a quick stroll through this medieval beauty, you delve deeper into wine country to enjoy award-winning wines made the Roman way.
Take a journey back in time as you learn about how this unique winery still produces wine the way the Romans intended. The owners will welcome you to their cantina giving you a private tour of the production before settling in for the wine taste. Make yourself comfortable on the terrace overlooking rows of vines and sit down to taste organic wines paired with local charcuterie. Each pairing will perfectly transcend the characteristics of every bottle you taste, allowing you to slow down, completely relax and breathe in the beautiful panoramas of Fermo’s wine region.
After this in-depth tasting experience, you will say goodbyes to this unique winery and drive down country roads for lunch at a local Agriturismo (farm-to-table restaurant). In the late afternoon, you will enjoy some sightseeing in Le Marche’s idyllic countryside before making your way back to Ascoli. The evening is yours to relax, take a stroll, and eat some delicious Italian fare. Dinner is on your own.
This morning, you will head to Civitella del Tronto, the largest and most formidable medieval fortress in Italy, which remained unconquered for over 350 years! There, you will experience a view like no other. A unique 360-degree view of the territory.
After your visit, you will continue your journey across the beautiful valley of Val Vibrata and make your way to a family-run restaurant that is passionate about slow food and holds the title of Italy’s top slow food restaurant for traditional cooking. There is your chance to taste some delicious Abruzzese cuisine, the Arrosticini (skewered meat) is not to be missed.
Following this leisurely lunch, you will return to Ascoli in the late afternoon. Optionally you can meet up with your guide for some early evening shopping of genuine Italian leather purses and shoes. Your guide will be there to assist with translation to ensure you will find the perfect fit! Or you can simply have your evening free to enjoy dinner on your own and try one of Ascoli’s many local establishments.
Wake-up, get your caffeine fix and say Buongiorno to farm fresh ingredients with a visit to the local farmers market. There, you will meet the real farmers of the territory and get inspiration for your next cooking class. After a relaxing stroll through Ascoli’s beautiful squares and market stalls, you will join your guide to enjoy your second cooking class.
Today, you will learn from Mirko, a master pizzaiolo (master pizza chef), the secrets to making the perfect pie. This gourmet pizza class will introduce you to new flavors and show you the methods behind a great slice of pizza. From selecting right ingredients to leavening the dough, and choosing the right oven temperature, Mirko will take you on a journey for the senses. Following a morning of kneading and rolling out the dough, you will heat up the oven in preparation to indulge in a little slice of gourmet pizza heaven.
In the afternoon, you can simply relax or enjoy some optional afternoon sightseeing and visit to Ascoli’s favorite gelateria. The rest of your evening is free to relax and enjoy Italy’s aperitivo (cocktail) hour at one of the lovely café’s that line the beautiful square of Piazza del Popolo.
Today, you will travel to the Adriatic coastline to reach the famous Conero Coast lined with blue flag beaches and pristine turquoise waters. Don’t forget your camera as today’s panoramas are sure to please! After some relaxing sightseeing by foot of the local seaside villages, you will make your way to lunch enjoy the catch of the day and the best view in town.
In the later afternoon, you will visit Loreto’s world-famous Sanctuary. Legend has it that the house of Nazareth is located within its walls. This is a place of pilgrimage, considered second only to Lourdes, with a Basilica ripe with history and adorn in renaissance art. Return to Ascoli in the late afternoon where you will have the evening free.
Now is the perfect time to head out for a Passeggiata (stroll) or grab an evening Aperitivo (cocktail with small plates). Still, have room for another plate of handmade pasta or wanting a romantic evening out? Ask your guide for tips of where to go to get your fork-on!
After a final breakfast, it is time to say goodbye to your Italian on Tour guides and your new-found friends. You will be driven to Ascoli’s bus or train station connecting you to the next leg of your trip. Should you wish to stay longer in Ascoli or explore Rome, Florence, or elsewhere, your guides will be happy to help you book your own alternate travel arrangements. Until next time “Arrivederci”!
While it is Italian On Tour's intention to adhere to the route described above, the order and inclusions of specific activities are subject to change. They always leave some room for spontaneity, building a certain amount of flexibility into the itinerary and on occasion, it may be necessary, or desirable to make alterations to ensure they can offer you the best of what is available in season.
It is important to note that some activities are dependent on the weather and may vary due to the time of year and/or forces beyond their control. The trip details and itinerary are a general guide to the tour and regions you will be visiting. Any mention of specific destinations is by no means a guarantee that they will be visited. Additionally, any travel times listed are approximations only and may vary due to local circumstances.
This trip is appropriate for people who enjoy a good stroll and feel comfortable while on the move. Daily walking times vary from one to four hours, from urban strolls to uphill walks in medieval fortresses and standing on your feet for an up to three hours while cooking up a storm.
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 eight breakfasts and nine 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 304 EUR per person.
Leonardo da Vinci–Fiumicino Airport
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.
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