Just try to have a bad time in Italy. Not possible. We found too much to cram into one article, so we’ll cover Italy in a few parts: town and country. Country first.

Lord of the Manor in Umbria
The best way to travel? Pretend the vacation is your life. The best way to do that? Rent a house in a small town, like Casa Magnolia in Spoleto, which is an artist’s house in an art city famous for its music festival. With an endless network of nooks and rooms (the best bed is on the second floor, overlooking the pool), you can bring a dozen friends and never see them — until you want to. (Book through Home Base Abroad, 781-545-5112).

Prefer hotels? Elegant Palazzo Leti (Via degli Eremiti, 10; +39 0743-224-930) just opened a few doors down. You’re on a hilltop, so get a room with a view.

As you road-trip through Umbria’s best-known cities (Todi, Assisi, Perugia, Gubbio), don’t miss the small charmers: Montefalco (for Sagrantino red wine), Norcia (for truffles), Bevagna (for Roman-bath mosaics), and the medieval town Spello.

Under the Tuscan Sun
Cliches are usually based in some truth. So it should come as no surprise that in Tuscany the rolling hills are picture-perfect, majestic cypress do line the horizon, and you will fall in love with someone totally inappropriate.

Back in the fourteenth century the Locanda dell’Amorosa (+39 0577-677-211) in Sinalunga was a small village. Today it’s an impossibly beautiful hotel with a dreamy saltwater pool. They may not have invented love here, but they know how to inspire it.

Driving north into Chianti, take the twisty State Road 484 (visit the Castello di Brolio) to the 408 and follow signs for Radda in Chianti (forgivably crowded), Badia a Coltibuono (classic foodie mecca), and Vertine (welcome back to the twelfth century). For an off-roading adventure, take the hilltop road from teeny Volpaia to slightly-less-teeny Panzano in Chianti. Stop for vino and fresh mozzarella at the enoteca by the fountain, then visit Italy’s famous Dante-quoting butcher, Dario Cecchini, at his Antica Macelleria Cecchini (Via XX Luglio, 11; +39 055-852-2020) for snacks and stories. Stay up the road at Villa Le Barone (+39 055-852-621). The views are stunning, the accommodations cozy, the food amazing, and the rates affordable.

On Your Marche
It’s generally acknowledged that people in the Marche would sell their mothers to make a deal. This is Italy’s outlet country and every small town has a specialty. In Pesaro it’s furniture. In Camerano, men’s shirts (Armani, Dolce & Gabbana). In Casette D’Ete, shoes. You’ll find company stores throughout the area (hint: spaccio means “outlet”), but the best is the Tod’s outpost (Corso Garibaldi, 134, Casette D’Ete; +39 0734-871-671). Feeling fancier? Get your kicks handmade by Silvano Lattanzi (Via Mostrapiedi, 167, Casette D’Ete; +39 0734-810-213; make an appointment), cobbler to countless presidents, Arnold Schwarzenegger, and the Emperor of Japan.

Where to sleep? The three towns on the Riviera del Conero, a seaside nature preserve. Portonovo is the exclusive beach town. There are only three hotels, a few great restaurants, and nothing touristy or tacky. Check into the Fortino Napoleonico (Via Poggio, 166; +39 071-801-450) and eat Adelaide’s fish stew at the Hotel Internationale restaurant (+39 071-801-001). Chic Sirolo is a bit more happening; Rocco Locanda (Via Torrione, 1; +39 071-933-0558) is the hotel here. Il Granaio di Valcastagno (Via Valcastagno, 12; +39 071-739-1580), near Numana, is a recently converted country house, run by the dashing and (you didn’t hear it from us) eligible Corrado Baldazzi. There’s easy access to sailing, hiking, and the new 27-hole Conero Golf Club.

O Sole Mio
Amalfi gets a bad rap. So, duh, go off-season. And rent a car: The roads are a thrill. Stop in Positano at Conwinum (Via Rampa Teglia, 12; +39 089-811-687), the newest beachside place for panini and Prosecco. Il San Pietro (Via Laurito, 2; +39 089-875-455) is the trendy restaurant; chef Alois Vanlangenaecker used to work up the hill at Don Alfonso 1890 (Corso S. Agata, 11; +39 081-878-0026), which remains one of Italy’s best restaurants. After dinner join the Iaccarino family for drinks and gossip in the library. Ask for a tour of the Etruscan wine cave and plan to stay overnight.

So is anything still undiscovered on the Amalfi coast? Yes: the Sorrentine Peninsula, which everyone misses on the dash from Sorrento to Positano. This is Ulysses country, in the shadow of Capri. Make the cliffside Hotel Delfino (Via Nastro d’Oro, 2, Massa Lubrense; +39 081-878-9261) your base for visits to Annunziata, Santa Maria, and Monticchio. Eat every meal at Lo Scoglio (Piazza delle Sirene, Marina del Cantone; +39 081-808-1026), an unassuming seafood joint (the only Amalfi restaurant literally on the water) that caters to locals and Hollywood celebs. Owner Beppe can taste the difference between fish caught in different parts of the bay and forages for wild arugula. In other words, he’s quite the character.

Which, come to think of it, could easily describe the country as a whole.