Dreaming of getting away in May and longing for the food, culture, style, and gorgeous landscapes of Italy but not sure where you should go? It’s a perfect time of year to visit and we have lots of lovely villas in Italy with availability for May 2025 located all throughout the country but there are some particularly appealing destinations that we think warrant a special mention…
Sicily
As the Mediterranean begins to really warm up for the summer, Sicily becomes an increasingly attractive option for those who would like to enjoy a getaway full of sun and fun in May. With a vacation rental in Sicily at this time of the year, you can expect a sun holiday and long, lazy days at the beach, without the larger tourist crowds that can be found during the busier months of June, July, and August. For those who don’t enjoy sizzling temperatures but still want pleasantly hot and sunny conditions, this is also a preferable time to enjoy a holiday in Sicily. Furthermore, if you enjoy a festival then May is a great time to visit as there are some major events and interesting celebrations that take place at this time of the year across the island. The Festival of St. George boasts a massive fireworks display, parade, music, and parties in Ragusa. Beloved local iced treat granita is celebrated in Acireale. As part of the Cantine Aperte festival, wine producers across Sicily open their cellars for special tastings and events and Palermo hosts a beer festival for those who prefer craft beers to wine. For culture-lovers, meanwhile, there is the Greek Theatre Festival in Syracuse, where you can enjoy performances of three traditional Greek comedies and tragedies.
Florence
Florence is another wonderful destination in May as it is much easier to make the most of lazy meals sitting out in piazze framed by wonderful works of art and architectural gems as well as darting around the place to see as much as you can when the weather is sunny and hot but not too sunny and hot. Again, you’ll beat many other tourists to the punch and find queues shorter, as a result, but it’s the milder, pleasant weather that will really allow travellers to get out and take in as much as they can. You’ll also be able to enjoy Florence as it blooms, adding a dash of floral beauty to this grand city. The famous iris garden is open in May (and free to visit), at the very beginning of the month you might just get the tail end of the blooming of the gorgeous wisteria tunnel in the Bardini Gardens, the city’s gorgeous rose garden starts to come to life, and the Lemon House at the Boboli Gardens begins to grow heavy with the scent of citrus. Parks, meanwhile, will grow fully green and everything will be lush and alive and lovely. It is, therefore, a truly dreamy time to book a stay in one of our villas in Florence.
Rome
Speaking of a dreamy time for travel, a vacation in Rome in May affords many of the same charms – the milder but still sunny conditions that make exploring ideal at this time of the year, the slightly smaller crowds, the lush parks and gardens. However, in particular, those who find a holiday rental in Rome for May will discover that this month is when there are many free days at some of the most famous attractions in the city including the Civic Museums on Sunday the 4th of May 2025 (including the Capitoline Museums, Ara Pacis, Villa Torlonia, and Trajan's Market – advance booking required), the Colosseum on the 4th of May, and the Vatican Museums on the 25th of May 2025. These days, unlike some in May, will absolutely be packed with visitors so this might not appeal to some but for the bargain-hunters out there, it is a chance to see these famous sights for free.
Apulia
A villa in Apulia in May also means perfect weather for a sun holiday, without generally reaching scorching temperatures. Of course, serious sun-worshippers may want to wait until later in the summer but the traveller who likes the sun but wants to be able to get out and about and see and do things comfortably might prefer this time of the year for a vacation in Apulia. The calm of this time of the year also means that you can enjoy exploring the towns and attractions of the region like a local. Take your time discovering the great Baroque city of Lecce, admire the gleaming White City of Ostuni, stumble upon dreamy beaches and charming seaside resorts, sample the delicious local cuisine, and, if you’re around during the last weekend, check out the local branch of the Cantine Aperte festival to visit wine-makers producing some of the most incredible wines in Italy. May spent in a holiday rental in Apulia is a time to slow down, enjoy the best things in life, soak up the sun and the wonders of the region, and to really escape all of your worries and daily concerns.
So, whether you are after an early sun holiday or you want to enjoy one of Italy’s most famous cities and cultural hubs – or, perhaps, move about and combine the two – these are the destinations that we recommend for a dreamy vacation in Italy this May.