7 Italy vacations that check every travel style (2024)

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With nearly 5,000 miles of coastline, Italy has an embarrassment of riches when it comes to beaches. If you’re hoping to get away from the pack, try the Maremma, Tuscany’s coastal area. “It’s not the Tuscany everybody knows,” says Simone Amorico, CEO of the private tour operator Access Italy. “This is where I go on vacation.”

Amber Guinness, author of “A House Party in Tuscany” and co-founder of the Arniano Painting School in Tuscany, vouches for the Maremma as “very, very Italian.” For a home base while you explore the region’s beaches, Guinness recommends staying in Capalbio, or booking a stay at dreamy hotels such as L’Andana or Locanda Rossa. Amorico’s pick for a Maremma hotel is Il Pellicano.

Farther south, Amorico also recommends the beach on Ponza, an island in the Tyrrhenian Sea that’s easy to get to from Rome. He say it not only has some of the country’s best beaches, but it also is laidback. “It’s more rustic, more like Italy in the ’90s,” Amorico says. Once you have spent some time sunbathing alongside the Romans and Neapolitans who frequent the island, take a short boat ride for a day of swimming and snorkeling around Palmarola, an uninhabited island that Amorico says was a favorite of explorer Jacques Cousteau.

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There’s a case to be made for the food from most regions in Italy, but if you only have time to explore one, both Guinness and Amorico choose Puglia.

“Puglia has had amazing food,” Guinness says. “I mean, really, really good food.”

Guinness recommends the Castello di Ugento in Salento for its cooking school, or booking accommodations at a traditional country guesthouse (a masseria) like Masseria Potenti to get a feel for the area, or stopping in Lecce or Ostuni if you’d like to stay in a bigger town.

Amorico would go with Trani, a fisherman’s village he describes as a little gem. “In my opinion it has the best fish and seafood restaurants out of all of Italy by far,” he says. Amorico says you won’t find five-star properties in Trani but lovely family-run hotels. One of his favorite activities to arrange for clients is to go out in the morning with a fisherman and take the day’s catch to a restaurant to be prepared for lunch or dinner.

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For those planning a getaway with a large traveling party, Amorico leans toward Sardinia. In the daytime, rent a boat to explore the Mediterranean’s second-largest island. There’s swimming and sunbathing, sandy beaches and clear water, visiting archaeological sites, wandering through the capital city of Cagliari or a smaller town like Bosa. Throughout the summer, Amorico recommends staying in Costa Smeralda for its nightlife scene.

“I’m not saying it’s like Ibiza or Mykonos, but it’s fun,” Amorico says. “It’s got a young vibe … but also [suits] adults.”

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When asked to supply a recommendation for history lovers, Amorico said one destination immediately comes to mind: Matera. The town in the southern region of Basilicata is famous for its Sassi district featuring millenniums-old cave dwellings.

“Matera is still popular, but not as much as the major cities,” he says.

Truth be told, you shouldn’t get too hung up while choosing a destination to appreciate Italy’s past. “Any place you go you’ll probably find ruins from an ancient civilization,” says Heather Dowd, co-founder of the active travel company Tourissimo. “I encourage people to get far off the beaten path and explore smaller cities and unknown hilltop towns.”

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While Sicily and its celebrated wines are becoming more popular with Americans, Guinness recommends the island specifically for oenophiles. For one, it’s a crowd pleaser, because wine overlaps with other travel attractions. “It’s great for people who like culture — you also have a lot of delicious food for foodies and amazing wine,” Guinness says. “And you also have incredible beach life for people who just want to chill out and sunbathe.”

After spending a day or two in Sicily’s capital, Palermo, Guinness suggests spending the rest of your visit staying at wineries in the countryside, such as Tenuta Regaleali or Baglio di Pianetto.

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Opportunities for adventure abound in the Dolomite mountains no matter what time of year you visit, Amorico says. In the warmer months, there’s trekking, mountain biking, road cycling, horseback riding and picnicking. In the winter, the region becomes a skier’s paradise that rivals nearby Switzerland and France. Amorico says you will also find fantastic food in the Dolomites, and not just in towns such as Cortina. “The restaurants up in the mountains are incredible as well,” he says.

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To get way off the beaten path, Guinness recommends visiting the tiny island of Giglio, off the coast of Tuscany. “It’s very beautiful and rugged and special and not that difficult to get to,” she says, adding that visitors will typically encounter Italian, Dutch and French travelers.

Giglio can only be accessed by boat; ferries from Porto Santo Stefano in Monte Argentario to the island run daily (the schedule varies by season), take about an hour and cost $15 per person (more if you’re taking a car). There aren’t many hotels on the island, so you will want to book your room well in advance. Guinness’s favorite is La Guardia.

Dowd’s hidden-gem pick is Molise, “a region that even many Italians don’t know about, and they joke that it doesn’t exist,” she says. (No, really. There’s even a hashtag about the conspiracy theory.) Later this year, Dowd is visiting for a trip centered on hiking through Molise’s mountainous terrain and exploring its regional cuisine.