Four Tips for Planning Your Perfect Vacation

I get to talk to lots of travelers who are planning their Italian vacations. Whether you’re getting ready for a late summer trip or starting to dream about your vacation, my Top Tips for planning a perfect vacation might help.

Tip 1: Start With Any Must-Do’s

Greg's CivitaIf you or anyone else in your group absolutely must see Florence or Assisi or eat a fabulous dinner together at the villa on a particular night, plan those first.

I keep track of things to see or do near Rocca di Benano that might qualify for this  “must do” list. A visit to nearby Civita di Bangnoregio tops this list.

Rule #2: Mean to Meander

P1030073Hit the open road with only a rough idea of what you’ll do that day, know that you’ll probably get a little lost, and trust that you’ll come back with memories of a day you couldn’t have planned. Choose an opportunistic destination, grab a guidebook and a map (or, if you must, a GPS — but they’re not nearly as engrossing) and go see what your day holds for you. From Rocca di Benano, we like to wander:

  • In the direction of Siena. We could do this trip for days on end without seeing even a fraction of the storybook hill towns, thermal spas, wine meccas, historic churches, and gorgeous vistas on the road to Siena. We don’t often make it as far as Siena – that’s why I call this “in the direction of …”
  • In the direction of Perugia and Assisi. And those who don’t make it past Deruta can remember the day every time they use the gorgeous ceramic dinnerware they bought from one of the artisans in Deruta.
  • In the direction of Montefalco and Bevagna. This trip lends itself to a drive by Spoleto on one way and Todi on the way back.
  • In the direction of Montefiascone and Viterbo. These are big towns/small cities that many tourists miss, and there are several Renaissance gardens in the area that are also well with a visit.
  • In the direction of Tuscania, Tarquinia and Vulci. A great guide (see Rule #3) could help you learn a lot about the Etruscan civilization while you’re in the neighborhood.
  • A drive around Lake Bolsena. There are any number of inviting stops on a circumnavigation of Europe’s largest volcanic lake.

Rule #3: Engage Great Guides

t-blog3I feel strongly about this one. Great tour guides have enhanced our trips so much over the years that now it seems a little silly not to take that extra step to assure that we get the most out of whatever we go all that way to see. If a site is important, I would rather visit it with a knowledgeable and skilled guide and storyteller at my side.

Do your best to get a great guide. Italy is pretty careful about regulating guides in its tourist areas, but we’ve still managed to stumble over a few bombs. I keep track of great guides and will happily put you in touch with a great one or two. Here’s an example of some of the tours our favorite guide, Emanuela Visciola, has developed for our guests.

Hiring a great guide is a smart investment in the memories you’re creating.

Rule #4: Be Willing to Get Off the Beaten Path

ImageMany of our guests tell us that their most special memories of their visit to Central Italy is of “discovering” small, out-of-the way towns and their people. I love the way “Not Just another ‘Dolce Vita” expressed this in her “Things to Consider When Planning a Trip to Italy” post: “Don’t go somewhere just because you’ve heard the name.” Because there are valid reasons that tourists beat those well-trod paths to famous sites, you’ll miss a lot if you stay off the beaten path entirely.

So I encourage our guests to carve out some time for exploring out-of-the-way places. For example, I send people to the “tufa towns” of Southern Tuscany: Sorano, Sovana, and Pitigliano. There, they’ll find few crowds, little glitz and flash, an old town historically known as “the little Jerusalem,” inviting shops, and an unspoiled 12th Century church. More important, they’ll find a much more authentic Italian experience than what they will see in other, justifiably celebrated and very heavily touristed Tuscan towns.

Happy Planning!


  1. Mary Josephine Hall (Jo)

    Thank you, Karen, for some wonderful travel tips. My daughter and I are planning a trip later this year to Italy, and I wonder what you feel is the perfect time for a visit. We look forward to taking your advice and doing some sightseeing on our own (with a guide, of course) to the lesser known towns and places that are not so touristy. Both of us have traveled in Europe already but never to Italy. Your advice is just what we need!

    • I’m so glad this was helpful, Mary Jo! Personally, my favorite time to visit is in September or October — although you would miss the sunflowers. June is absolutely wonderful, too. We have an opening in June, so if you can get things together quickly, we would love to host you at Rocca di Benano — check in at and we can be in direct contact that way. Every season has something to recommend it. If you have lots of flexibility, you might find a festival or celebration to plan around. For example, Good Friday is something to see in these small towns. You can find other ideas on the “Special Events” boards on my Pinterest site:

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