Itinerary #1: Experience the Best of Sicily
Fascinated by Greco-Roman wonders? Head to this Mediterranean paradise. With a week in Sicily, you have enough time to see many of the island's highlights, including Taormina and Mount Etna, the capital city of Palermo, and archaeological sites at Syracuse and Agrigento.
|Day 1||Explore Syracuse||Syracuse|
|Day 2||Ragusa - Modica||Ragusa|
|Day 3||Agrigento - Marsala||Marsala|
|Day 4||Erice - Palermo||Palermo|
|Day 5||Palermo - Monreale||Palermo|
|Day 6||Cefalù - Taormina||Taormina|
|Day 7||Mt. Etna - Depart|
Begin the adventure in Syracuse, once the largest city in the ancient world. You'll have a guided tour of Neapolis Archaeological Park and a boat tour around Ortigia Island before stopping in the town of Noto for a traditional Sicilian granita (a semi-frozen dessert made from sugar, water, and fruit juice). The following day, side-trip to Modica—a historic village known for its chocolates and cheeses, both of which you'll try while in town—and end up in Ragusa Ibla, where you'll have a leisurely dinner and stay overnight.
On day three, Agrigento and the Valley of the Temples await. On a guided tour, you'll see the ruins of the Temple of Zeus, known as the largest Doric temple ever built. In the afternoon, stop at a winery in Menfi for a cellar tour and wine tasting. A scenic drive on the following day takes you past ancient salt pans between Marsala and Trapani. Enjoy a boat tour around the Stagnone and Mothya island and take a break in the medieval town of Erice for lunch. By nightfall, you'll be in Palermo, the capital of Sicily.
The week rounds out with a private guided tour of Palermo, including an overview of architectural landmarks and stops for traditional street food, a visit to the extraordinary cathedral at Monreale, a drive along the coast to the fishing village of Cefalu, and an evening to explore the ancient ruins and stylish cafés of Taormina. On the last full day, go for a hike at nearby Mt. Etna and stop in another Sicilian wine to try a local varietal. Learn more
For more ideas on how to spend a week in Sicily, check out these three self-drive itineraries around the island.
Itinerary #2: Relax in Laidback Puglia
Compared to many Italian destinations, Puglia is quiet and sees a smaller number of tourists. Make the most of it with this seven-day itinerary that takes you to the ancient Matera caves, Baroque architecture at Lecce, and the medieval old town in Bari, not to mention several down-to-earth food experiences, like a cooking class in a local home.
|Day 1||Arrive in Puglia, Day in Alberobello||Alberobello|
|Day 2||Matera Morning Tour||Alberobello|
|Day 3||Alberobello to Lecce, Afternoon Cooking Class||Lecce|
|Day 4||Lecce City Tour||Lecce|
|Day 5||Lecce to Bari, Afternoon Food Tour||Bari|
|Day 6||Grotto di Castellana Afternoon Trip||Bari|
|Day 7||Goodbye Italy!|
On the first day of your week in Puglia, you'll tour the UNESCO-honored city of Alberobello, known for itsTrulli, circular 14th-century limestone buildings with cone-shaped roofs, and take a three-hour cooking class in the afternoon. Hosted by a local home cook, the course covers three traditional recipes. On day two, head to the ancient city of Matera to visit the legendary Sassi di Matera (cave dwellings cut into soft rock), considered to be some of Italy's first human settlements. In the afternoon, explore the historic center, including the Casa Grotta of Vico Solitario, one of Matera's oldest homes, Murgia National Park, and Central Market, where you can sample locally produced cheeses and snacks.
Day three combines sightseeing and cooking once again, with a morning tour of Lecce, an ancient city on the coast of the Ionian Sea. You'll see Piazza San Oronzo, the 17th-century Duomo, and the beautiful Paisiello Theatre before breaking for lunch. Save some room for the three-hour cooking class later in the day. Held at an elegant estate, the class is run by sommeliers, and the dishes you make will be carefully paired with Puglian wines.
You'll have more time for culture and history on day four: visit Lecce's 2nd-century Roman Amphitheater and Palazzo Celestini, a former monastery with lovely gardens. Relax on one of the city's public beaches, characterized by unusual rock formations and aquamarine waters. If you have time to head out of town Spiaggia di Alimini, a half-hour drive southeast of the city, is considered the best beach in the area.
Expect more great food and beautiful architecture as the week heads to a close. You'll tour the medieval city of Bari with its 12th-century Basilica of Saint Nicholas and 13th-century Bari Cathedral, then take a break in the Orto Botanico di Bari (botanical gardens) before a street food tour in the afternoon. On the last full day, you'll take an afternoon trip to the Grotte di Castellana, an interesting network of caves in the countryside outside Bari, to learn about 90 million years of geographic history. Return to the city at sunset to enjoy a Puglian feast of seafood, pasta, and wine. Learn more
Have another week to spare? Check out this 15-day itinerary around Puglia.
Itinerary #3: Eat and Drink Your Way Through Italy
It's not hard to find a great bowl of bucatini or a good glass of wine in Italy. But this week-long itinerary takes you around the country for the best of the best, from local cheeses in Bologna and full-bodied Chianti in Tuscany to thin-crust pizza in Rome. There's time for sightseeing, too: enjoy the works of Leonardo da Vinci with a side of creamy gelato and a visit to the Vatican followed with an Aperol spritz.
|Day 1||Arrive in Rome, Travel to Bologna||Bologna|
|Day 2||Day Trip to Parma: Ham and Parmesan Tasting||Bologna|
|Day 3||Bologna to Florence||Florence|
|Day 4||Tour of Tuscany & Wine Tasting||Florence|
|Day 5||Florence to Rome, Full-Day Rome Excursion||Rome|
|Day 6||Pizza Making Class in Rome||Rome|
|Day 7||Goodbye Italy!|
Kick off your trip in Bologna, one of Italy's foodie capitals. Work up an appetite on a walking tour of town, with highlights including Piazza Maggiore, the central plaza surrounded by the city's oldest buildings, the 14th-century Basilica di San Petronio, the 11th-century University of Bologna, the former Jewish Ghetto, and the Pinacoteca Nazionale di Bologna (National Art Gallery). After a leisurely lunch, go on a walking food tour of the city with a local guide, stopping to sample artisanal tortellini, mortadella, and a variety of cheeses. You'll taste even more on day two when you side-trip to Parma, located in the Emilia-Romagna region of northern Italy. The day's schedule includes visits to local production facilities of Parma ham and Parmigiano Reggiano cheese.
Catch the train to Florence for world-class art and more gourmet food and drink. See Michelangelo's 'David' sculpture at the Galleria dell'Accademia and tour the world-famous Uffizi Gallery before indulging in another walking food tour. This time, the emphasis is on gelato, coffee, truffles, and, of course, wine from the Chianti region just outside of the city. You'll head directly to the wineries the following day, sampling wines where they're made, and enjoy a few hours of sightseeing in Siena before returning to Florence for the night. On day five, day-trip to Rome for classic sightseeing—the Colosseum, Piazza Navona, Trevi Fountain, the Pantheon—and a few unforgettable meals, not to mention coffee and gelato. You'll spend the night in the Eternal City before spending the last full day of the trip on a food-focused schedule: namely, learning how to make a Roman-style pizza with an Italian chef. Learn more
Read more about Italy's best culinary experiences here.
Itinerary #4: Have an Italian-Style Family Adventure
Thanks to the abundance of pizza, gelato, and sunny parks and plazas, Italy is fun for children. This week-long itinerary is particularly focused on kid-friendly activities, including a scavenger hunt in Venice and "gladiator school" in Rome.
|Day 1||Arrive in Rome, Travel to Venice||Venice|
|Day 2||Family-Friendly Venice Walking Tour||Venice|
|Day 3||Venice to Florence, Family-Friendly Food Tour||Florence|
|Day 4||Treasure Hunt & Kid-Friendly Museums in Florence||Florence|
|Day 5||Florence to Rome, Kid-Friendly Colosseum & Forum Tour||Rome|
|Day 6||Family-Friendly Vatican & Gladiator School||Rome|
|Day 7||Goodbye Italy!|
This family-friendly trip plan begins in Venice. "The Floating City," by its very nature, is of interest to children and adults alike. Cruise down the city's canals in a water taxi or gondola, wander through pigeon-packed Piazza San Marco and take photos at the ornate Doge's Palace. The following day, you'll enjoy a kid-friendly walking tour with a private guide, ending at the famous Bridge of Sighs. Have pizza or pasta at one of the city's many outdoor cafés, the perfect spot for people-watching.
The following day, catch a train to Florence, the so-called "Jewel of the Renaissance." Walk or bike around the medieval city center before embarking on a walking food tour of the city led by a local guide. Kids, in particular, will enjoy the variety of creamy gelatos and chocolate focaccia you'll sample along the way. On day three, join a small group of families for a half-day treasure hunt of the city's highlights, featuring games and quizzes as you explore the city center. Afterward, go for a spin on the antique carousel in the Piazza della Repubblica and take a picnic to the Boboli Gardens.
Take the high-speed train to Rome for more kid-friendly sightseeing, including a three-hour walking tour of the Colosseum and a treasure hunt-style tour of ancient Rome. A major highlight is the Gladiator School of Rome Museum, located on Appian Way near the Colosseum, where kids receive a two-hour gladiator training, ending with a full tournament and prizes. Learn more
Itinerary #5: Cycle and Eat Your Way through Tuscany
Trace the path of the country's top cyclists—going at a slower pace, of course—on a seven-day itinerary through Tuscany. The Eroica is a world-famous bike race that weaves through the vineyards of the Chianti region. This traveler-friendly version of the route features several stops along the way, including hilltop towns, wineries, and the UNESCO-honored historic center of Siena.
|Day 2||Siena to Buonconvento||Buonconvento|
|Day 3||Montalcino and the local Brunello||Buonconvento|
|Day 4||Buonconvento to Castelnuovo||Castelnuovo|
|Day 5||Castelnuovo to Radda||Radda|
|Day 6||Radda to Siena||Siena|
The trip begins in medieval Siena. Take some time to wander through the narrow streets, stopping for a cappuccino and a relaxed trattoria lunch. On day two, you'll have an early start on your bicycle, pedaling through Chianti's rolling vineyards. You'll sleep in an agriturismo—a country hotel—with a swimming pool and a dinner made with fresh local produce and olive oil grown on the premises.
The next day, the road leads to the charming village of Buonconvento and onto Montalcino, where the Eroica race traditionally culminates in an altitude of nearly 2,000 feet. Order a bottle the famous Brunello di Montalcino wine and enjoy the view of the surrounding scenery before cycling back to the agriturismo for a homemade Italian meal.
The following day, you'll cycle to Asciano on the Strade Bianche. Take a break at Santa Maria Abbey of Monte Oliveto Maggiore and the Church of Saint Agathe before the ride gets a bit more challenging, continuing up a series of small climbs and descents to the village of Castelnuovo Berardenga. You'll overnight here and have a chance to try more locally produced wines and olive oils at dinner. It'll be an uphill climb the next morning to the hilltop town of Radda (1,640 feet). Lock your bike and walk around the fortified village, inhabited since the 9th century, with views of vineyards and olive groves spread out around the town.
You'll loop back to Siena on the last full day of the itinerary. Make sure to step inside Siena's Gothic cathedral and the crypt under the Duomo—and to sit down for another bowl of hand-rolled pasta and a glass of wine. And a gelato. This is a food-themed trip, after all. Learn more
Work up an appetite with this guide to eating in Tuscany.
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