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Planning Your Itinerary


Learn how to plan your best trip by taking into account your days available, your wish list of destinations (with an eye toward avoiding sightseeing redundancy), geographical proximity, festivals, weather, crowds, and your favored type of travel: spontaneous or planned out.

Complete Video Script

It's time to say ciao to Venice and head for Tuscany. Our next stop: Siena.

Siena is a stony wonderland…an architectural time-warp where pedestrians rule and the present feels like the past. Its main square, Il Campo, is enchanting. Five-hundred years ago, Italy was the center of humanism. Here, it's the city hall bell tower rather than the church spire that soars above the town. And today, the beloved square feels like a beach without sand.

At the edge of Siena’s medieval center, our hotel’s garden is a fine place for reviewing some ideas on itinerary planning.

Start your travel experience early by enjoying the planning stage. Talk to other travelers, choose books and movies with your trip in mind, nurture your travel dreams. Then develop a thoughtful itinerary in steps:

Brainstorm a wish list of destinations, put them in a logical geographical order, then write down how many days you'd like to spend in each place and then tally it up. 32 days. And now you've got to fit it with your vacation time. I've got 21 days off, that means I'm going to have to do some serious cutting here…minimize redundancy…can't do both the Italian Riviera and the French Riviera. Keep a balance between big cities and small towns. This is heavy on big cities. I think I'll have to cut Rome. Greece takes too much time to get to. It'll have to be on the next trip. Rather than spending an entire day on the train I can save a day in my itinerary by flying or taking the overnight train, from Bavaria to Venice. I still have to cut one day. I'll have to tighten up on Paris, three days rather than four and I've got it — 21 days. It fits.

Now fine-tune your itinerary. Anticipate any closed days. For instance, in Paris most museums are closed on Tuesday. Take your trip to the next level by researching events you’ll encounter along the way: concerts, sporting events, and festivals. Also, consider building in a few slack days… two days on the beach midway through the trip; that'll be very nice. One-night stops are hectic. Try for at least two nights per stop. And remember…open jaws — that's flying into one city and out of another city — that's very efficient.

Finally, be realistic about how much you can cover. You'll always find places you can't get to. I really wanted to get to Greece but squeezing it in would rush my entire trip. Assume you will return.

Travel is freedom. It’s rich with choices and exciting decisions. That’s part of the appeal.

Factor in your comfort level with doing things on the fly. Some people have a great trip with nothing planned at all. Others have a great trip by nailing down every detail before they leave home. I like to keep some flexibility in my itinerary — perhaps I’ll fall in love with Siena and stay an extra day.

Also, plan thoughtfully to get the best weather and the least crowds. The most grueling thing about travel over here is the heat and crowds of summer — especially in Italy. Check the weather charts. My rough rule of thumb: north of the Alps is like Seattle or Boston; south of the Alps is like Southern California or Florida. I prefer visiting the Mediterranean countries in spring or fall and I travel north of the Alps in summer.

We happen to be here in August. And it’s hot. Winter travel is a whole different scene. And it comes with pros and cons too: flights are cheaper, museums are empty, and the high culture — symphonies, opera and so on — is in full swing.

But in the winter, it rains more and gets dark early — especially in the north; and many activities and sights are closed or run on shorter hours. While small towns, outdoor sights, and resorts can be sleepy; big cities are vibrant and festive throughout the year.