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Where to rent
Most underrated location
The Maremma in Tuscany is a gem for those who know the country well and are looking for an unspoiled region of Italy. The coastline is not particularly developed, and the landscape is fairly flat—friendly for families who want to get around on bikes. Once a malarial swamp, the Maremma became a weekend and summer destination for Italians in the 1950s and has since evolved into a vacation spot for modest numbers of Europeans; it is not overrun by Americans. The landscape includes a long stretch of sand beach from essentially Livorno to Ansedonia. The terrain is called macchia medditeranea—an area of low dunes covered in scrub pine, hearty shrubs, and pinewoods.
The Cilento Coast, south of Salerno, is what you see when you stand in Positano or Ravello and look out to sea and to the left. The Cilento is virtually unknown by North Americans and offers a great climate from April/May through October/November with a lot of outdoor activities, great food and wine (think bufala gelato, yogurt, and cheeses), and Paestum. If you enjoy ancient ruins or have an interest in Magna Grecia, Paestum is a must.
From a cost perspective, any villa near the sea is typically 35 percent more costly than countryside locations in Umbria and Tuscany because of supply and demand.
Most overrated location
Forte dei Marmi is overpriced, with most villas rented on a monthly or seasonal basis (such as July and August combined). Not many Americans can manage this much time abroad.
Best location for a beachfront villa
There is always the iconic Amalfi Coast, but Maremma and Cilento (see “Most underrated location,”) are better choices for experienced visitors to Italy. Remember to ask whether you will need water shoes. Many Italian beaches are made of pebbles, not sand.
Best Location for sporty travelers
Lake Como offers an amazing range of land- and water-based activities—golf, guided hiking, tennis, boating. Bicycling can be a challenge because of the hilly terrain, but kayak and hiking tours can be arranged for all ages and abilities, such as a kayak/lunch/hike excursion that circumnavigates the point of land occupied by Bellagio—a relatively quiet part of a touristy place.
Best location for a taste of village life
The holy grail is a house that is within walking distance of town, a stipulation that contradicts 500 years of land-use planning in Italy. The honest truth is that there are not that many truly “easy walking distance” houses out there, especially if you’re imagining a home within a sylvan stroll of a medieval hill town. If this is the quality you care most about, there are great options in Spoleto, Marina di Bibbona, Positano, Tremezzo, and a few other places.
Do’s and Dont’s
Worth the splurge
Hired help. The real villa experience emerges when you have someone else to shop, cook, clean, and do the laundry. What makes it a vacation is a break from everyday chores.
Not worth the splurge
Pools on the Amalfi Coast are on the small side, and besides, this is your chance to enjoy that truly great Italian invention, the stabilimente balneare. This version of the bathhouse explains why most of Italy goes to the beach wearing a fabulous outfit and carrying nothing but great sunglasses and a hat. No epic bundles of chairs, coolers, food enough for a week, umbrellas, toys, towels, etc. In Italy you pay a fee and get a sunbed, a changing area, showers for rinsing off the salty sea (if anyone besides the kids actually bothers to go in), bars, and restaurants that serve inexpensive, local, tasty dishes and great eye candy for both sexes.
Don’t forget to pack
Night lights, virtually unknown in Italian homes, are immensely useful in unfamiliar surroundings, especially for children who need to find their parents or the bathroom in the middle of the night. Combine with an adaptor for use with 220-volt current.
Leave your jeans at home (they’re heavy and slow to dry, even in the Tuscan sun) and opt for linen, so you can look fabulous and be cool. As for footwear, Italians will look first at your shoes, and sneakers scream “tourist.” Choose a proper, good-looking walking shoe instead.
Villa rentals are priced considerably lower in March and April. This is when the camellias, azaleas, and rhododendrons bloom on Lake Como, giving visitors an infusion of spring color; repair to the fabulous spa at the Mandarin Oriental on the occasional cool day. The Maremma in Tuscany is pleasantly warm in spring because of its microclimate—great for golfing, biking, and taking in Etruscan sites. The Amalfi Coast is better in fall—October and November—than spring, which is often rainy, but rates are usually high through the November 1 Ognissanti holiday.
Winter is really, really quiet on the Amalfi Coast and Lake Como; everything closes down after the November 1 Ognissanti holiday, and Bellagio is practically a ghost town. The only exception is the period from December 8 to January 6.
Holidays are not to be categorically avoided—villa travel helps you get local, and you could be treated to celebrations and festivals that are of real interest—but do take the potential travel and service disruptions into consideration. Italian holidays include Epiphany (January 6), Pasquetta (the day after Easter), Liberation Day (April 25), Labor Day (May 1), Republic Day (June 2), Ferragosto (August 15), and Immacolata (December 8).
* How far is the nearest town? Many travelers want to be within a comfortable stroll (or a short drive) of shops, restaurants, and other diversions, but people have different ideas about what that means. For example, Italians are generally comfortable—more so than Americans—with walking on the edge of a busy road. A good villa specialist will have tested the walk or drive and will understand how an American might experience it.
* How much is there to do onsite? More than location, an ideal villa vacation for a large multi-generational group is about the facilities and amenities at the house.
* Is the property designed for a group that wants to hang out together? Dine together? Play together?
* Does the layout permit early risers to make noise without disturbing those who want to sleep in?
* Is the heat included? If you’re planning a trip between late fall and early spring, you should know that heating costs can run into hundreds of euros per week.
* Is the house air-conditioned? Air-conditioning is not standard in private homes in Italy, and if it exists at all, it is likely to be confined to the bedrooms. Traditional Tuscan farmhouses are not light-flooded and do not need artificial cooling; their thick stone walls are designed to keep them cool in summer and warm in winter. But if air-conditioning is important to you, be sure to ask about it.
* What sort of child-care is available? The custom here is to take your kids along when you go out, no matter how late you plan to be, or to leave them with a family member. In other words, this is not a baby-sitting culture. If you are told that a sitter is available, be sure you understand what that means. The person who shows up might be (a) on their phone a lot, (b) smoking, and/or (c) not able to communicate in English. Give careful thought to how much child care you will want during your villa vacation and consider inviting a young niece or nephew or another family member or friend to come along with the express understanding that they get to travel at your cost in exchange for child-care when you want to go out.
* How many pool chairs and table settings? The more affordable homes tend to skimp on these items—as you may discover when you run out of cutlery or have to wash the lunch dishes before you can prepare dinner. (Note: Dryers are also uncommon and don’t have much oomph; the Italian sun dries clothes faster.)
Just about every square inch of Italy has a fascinating historical, geological, or ecological backstory, often best uncovered by exploring the outdoors. Walking paths crisscross the countryside—but they’re poorly marked, so arrange for a private guide to show you the way. There are even parts of the Amalfi Coast that look like Switzerland, and trails there that few travelers ever discover. If you prefer to explore on two wheels, bikes can be delivered to your villa, have a guide meet you for a ride to a local winery for lunch, or make sure you’re properly fitted for a serious road bike by the owner of the local cycling shop. (E-bikes are also available for those wanting a little assist on the hills.) If you’re near water, boating, kayaking, stand-up paddleboarding, and fishing can all be arranged.