The main medieval square of Arezzo, Piazza Grande, is lined with the remains of the aristocratic palace and the Vasari Loggia.

There are a handful of spots on Earth where ballooning is not a gimmick but a must (Cappadoccia, East Africa and Myanmar’s Bagan also figure on this list). Indagare members can contact our Bookings Team for help organizing an early morning flight.

The latest from the Ferragamo family, this hideaway close to Montalcino has a golf course, stables and impeccable amenities. During the harvest, guests can sign up for a day in the vineyards, helping pick the grapes and ending with an estate wine tasting and a hilltop picnic. In any season, food plays an important role in the CdB experience. The property has two restaurants, one more casual with incredible wood-oven pizzas, the other a more upscale affair. Vegetables and herbs come from the on-property garden, and guests are encouraged to stop by the kitchen, watch the chefs at work and make requests. Cooking classes are available, including ones specially created for children.

Situated between Florence and Siena, this wine-growing region is one of the world’s most famous. There are a number of attractive hilltop towns that can be visited in a day of touring, including Greve in Chianti, Castellina in Chianti, Gaiole in Chianti and Radda in Chianti. A great spot for a scenic, authentic lunch is Badia a Coltibuono, in Gaiole.

After lunch in Siena, explore the remarkable Crete Senesi, a 300-square-mile area south of Siena whose winding country roads afford breathtaking vistas of hills and woodland. It is best known for its ocher soil, made popular by Renaissance painters, as well as its Cinta Senese pigs, whose meat is a world-renowned delicacy. Don’t miss the stunning Abbey of Monte Oliveto Maggiore.

Much more so than compact Napa and Sonoma, Tuscany can overwhelm with its sheer number of wineries and vineyards. Some are large businesses with set-up tasting rooms and export service. But the ones to know are those normally closed to the public and producing just a small run of gorgeous vintages. Indagare members can contact our Bookings Team for help arranging a custom wine itinerary, where you tour with a local guide who can open the doors and make the introductions to some of the region’s most acclaimed wineries (boutique or big-time).

The one-starred Michelin chef of Il Falconiere, a lovely retreat near Cortona, hosts an excellent cooking school, with courses offered from one day, three days or six days.

Explore the best of Florence and the Uffizi with your own art historian including the Basilica di Santa Croce, known for its Florentine artwork and tombs of Michelangelo, Machiavelli and Galileo. Continue on to the artisan neighborhoods to see ironworkers, print and map makers before you end the day with a tour of the Uffizi with special access to visit the works of the masters.

Visit Michaelangelo's famed David in all of his splendor during a private visit without the hordes of tourists. Sculpture aficionados and artists may peek inside the restoration process and enjoy a private visit of the Opficio delle pietre Dure, founded by Medici in 1588 to complete the Chapel of the Princes, which remains one of Italy's most important centers for sculptural restoration. One of the restorers will take you on a private tour of the current-day workshops and the Opficio's most famous works of the past. Indagare members can contact our booking teams to arrange a visit with an expert guide, including ones specially trained to educate and engage children.

Explore the Tuscan coast from the water with a full day boat trip on a chartered boat with an English-speaking captain. Make a visit to the island of Giglio, where you can explore its charming village lanes, church, medieval castle and Roman villa. Visit the island’s pretty beaches by boat for swimming and relaxing. Indagare members can contact our Bookings Team for details.

Tuscan cuisine is not only fun to eat but it is a pleasure to cook. Classes in the area range from week-long courses in private villas with professional chefs to half-day classes in grand professional kitchens or casual outings where you accompany a local to the market for shopping and return to her apartment to learn family recipes. Cooking classes appropriate for children are also available. Indagare members can contact our bookings team for options.

Take a car and driver to explore two of the most scenic spots in the area. Your English-speaking guide will guide you through the streets and history of clifftop Orvieto with its wonderful historical center, duomo and archaeological museum. After lunch in a charming traditional restaurant, head to the stunning hilltown of Civita di Bagnoregio, which is reached via a narrow walking bridge. Indagare members can contact our Bookings Team for details.

During this in-depth tour, look closely into the complex history of the Medici family and their impact on the social, religious and political history of Florence over 400 years. You will accompany an art historian to trace the influence of the Medici family in Florence and the development of the Renaissance in Florence.

Wander along the Vasarian Corridor, the secret overground passageway built by Medici to directly connect the political center of the city (the Uffizi) with the new grand residence, the Palazzo Pitti to separate the family from the rest of the Florentines during their rule. Enjoy an exclusive bird's eye view of Florence, as well as admire the Medici's private collection of portraits spanning three centuries that line the walls. Indagare members can contact our booking teams to arrange a visit with an expert guide, including ones specially trained to educate and engage children.

Enjoy a full day tour of two of the region’s prettiest cities with an English-speaking guide. You can start with a visit to the famous leaning tower and stop at Gothic churches and scenic lookouts on the way to Lucca for a fabulous lunch in a neighborhood trattoria before exploring the duomo, amphitheater and other iconic sites. Indagare members can contact our Bookings Team for details.

Want to learn the secrets of Italian cooking? Whether you fantasize about preparing pizza, pasta, risotto or osso bucco, you can do so in a fabulous school environment where a class is tailored to you and then you get to sit down and feast on your creation. Or if you are renting a villa of your own, you can have the chef come to you and teach you in the kitchen. Either option comes with a booklet of recipes and can also be finished off with a visit to a top wine cellar for a tasting if you like. Indagare members can contact our Bookings Team for details.

Have an English-speaking driver pick you up and take you to the Chianti wine region for a tour of vineyards, charming towns and a lovely lunch before taking you to the designer outlet mall for an afternoon of shopping Gucci, Pucci, Valentino and Prada at majorly reduced prices. Contact Indagare Booking Team for details.

Take a tailored tour of Siena. Whether you want to focus on history and walking or special access, which can mean being treated to tales of intrigue about the aristocratic families of the region and then being invited into the home of an aristocratic family or coming during the famous Palio horse race and getting a view of the competition from a private home, we can arrange custom tours with excellent guides tailored to your interest. Tours of Siena can also include San Gimignano and area vineyards.

Combine the fun of hunting for truffles with a truffle expert with a cooking class in an Italian kitchen, in which you will learn how to prepare the bounty you have hunted. You will hunt the truffles with a local master and his team of dogs for a few hours and then be driven to a well-known cooking school for your truffle cooking class. Indagare members can contact our Bookings Team for details. Note: Only available in truffle season.

Have an English-speaking driver pick you up in a Mercedes for a tour of top vineyards in the region. You will visit Montalcino, the capital of the Brunello wine region, tour its medieval town, head to the Sant’Antimo abbey, then have a wine tasting at a family-owned vineyard followed by lunch at a fourth-generation Tuscan restaurant. After lunch, you will tour Pienza, a beautifully preserved Renaissance town. Indagare members can contact our Bookings Team for details.

Does your Italian fantasy include riding on a Vespa? One of the best ways to enjoy the Chianti region is by Italian motorbike. We can arrange a tour that has you wending your past vineyards and olive groves and includes lunch at a charming restaurant in the Florentine hills as well as olive oil and wine tastings. Indagare members can contact our Bookings Team for details.

A medieval city-on-a-hill, Montalcino affords astonishing scenery and a glimpse into a region relatively unchanged for the past 500 years. It also offers unparalleled varietals for wine enthusiasts. As home to the illustrious Brunello wine, Montalcino can safely be described as an oenophile’s dream. The town’s narrow, steep streets and medieval walls that encircle the center contribute to the authenticity and charm of the region.

See & Do In the mecca of wine country, Ciacci Piccolomini d’Aragona (Loc. Molinello; (39) 0577-835616) and Casanova di Neri (Podere Fiesole; (39) 0577-834455), both family-run wineries, have a more intimate feel and provide a good understanding of the region’s favorite libations.

Castiglion del Bosco offers cooking classes that allow guests to prepare and taste some of Italy’s most traditional and delicious recipes. Ingredients are selected from Castiglion’s organic kitchen garden and then chopped, sautéed and heated to perfection. Sant’Antimo Abbey, a 12^th-century monastery 35 minutes by car from Castiglion del Bosco, is home to monks clothed in traditional attire who sing Gregorian chants.

Read more about how to spend a day in Montalcino.

As the highest of Tuscany’s “hill towns,” Montepulciano, with its car-free, winding streets, encapsulates the long-standing history and culture of central Italy at its finest. Montepulciano offers the same abundance of wineries endemic to the region, and the surrounding Vino Nobile vineyards heighten the town’s pull for wine connoisseurs and oenology students alike.

See & Do Outside of the walled city sits the 14th-century Church of Sant’Agnese, a Gothic-style nave housing beautiful frescos. The town boasts beautiful palazzos and quaint streets that lead to its highest points and main square, Piazza Grande. The Palazzo Communale (town hall) has grand towers that provide a sweeping view of the city.

The Bottega del Rame (Via dell'Opio Nel Corso 64; (39) 0578 758753) is an artisan workshop that welcomes visitors to come and watch the centuries-old technique of copper beating, a family tradition passed down through generations. A range of their products, including pots, pans and baking trays, are sold on site.

Read more about how to spend a day in Montepulciano.

There’s not a ton to see and do here but Monticchiello is one of Tuscany’s most ridiculously picturesque walled villages, close to the Renaissance town of Pienza. It’s also become a foodie destination thanks to restaurant La Porta, which has an incredible local wine list and a gorgeous terrace overlooking the UNESCO-protected Val d’ Orcia.

Many coastal-bound visitors kick off their itineraries in this hilltop town, a little less than an hour’s drive northwest of Siena, whose medieval towers and walls have been beautifully preserved. Spend the morning marveling at the city’s fourteen remaining towers, among Tuscany’s main architectural attractions and a UNESCO World Heritage site. You’ll probably be coping with lots of tours, so plan your day for efficiency. Park the car outside the walls and go directly to the Piazza del Duomo for an up-close look at seven of the towers, including Torre Grossa—at 177 feet high, the tallest of the fourteen—which you can climb for an exceptional view.

Next visit the 11th-century Duomo (known as la collegiata) to see the wall-length 14th-century frescoes of Christ and the Chapel of Santa Fina, whose murals show San Gimignano as it was in the 1400s. If you have time, add in the Church of Sant’Agostino, well worth a visit for the seventeen-panel fresco The Life of Saint Augustine, surrounding its high altar and chapel. Shopping options are limited, but Leoncini (Via San Giovanni 60-64) carries hand-painted Italian pottery and tableware that can be easily shipped home. In June, the annual Ferie delle Messi turns the Piazza del Duomo into a jousting arena filled with knights, jugglers and locals in 14th-century costumes. San Gimignano’s market day is Thursday.

Indagare Tip: A San Gimignano combined-entry ticket includes access to Torre Grossa and the Chapel of Santa Fina, as well as to the Civic and Archeological Museums, the former of which contains artworks by Benozzo Gozzoli, Filippino Lippi, Pinturicchio and Lippo Memmi.

Art lovers should make a note to visit the hometown of Piero della Francesca, one of the early Renaissance most acclaimed artists. The Museu Civico features his Resurrection of Christ, once described as the “greatest painting in the world” by the English writer Aldous Huxley. There are three other della Francescas in the museum.