SIENA, Italy -- Here was the moment I had dreaded ever since I convinced my friend from work that our families should travel together to the land of the Romans.

As we overlooked the ancient, red-tiled town from our B&B perch in the Tuscan hills and sampled homemade jams and pecorino cheeses, our traveling buddies -- a family of four -- enthusiastically planned a lunch tour of wine country with the lodge owners.

My husband, Dilip, and I exchanged looks. They assumed we'd love the idea. Not really. We liked wine, but not that much, and our 10-year-old, Rohan, would no doubt be offered a lot of cheese with his whines.

We had our eyes on the medieval town of San Gimignano, known as the "Manhattan of Tuscany" because of its skyline of "skyscraper" towers. We thought they'd think that was cool. So, I made the suggestion.

Several seconds of uncomfortable quiet later, we all decided that maybe, uh, this time we would go our separate ways.

What a relief! We didn't have to travel in lockstep.

That realization was the secret to the overall success of our first trip traveling with another family.

Keep in mind, that while the wives (Kathy Boccella was a colleague and friend) were well acquainted, the husbands hardly knew each other, and the children -- Jesse, 12, Julia, 14, and Rohan -- had only met a few times before. On top of that, we had different traveling styles. Our friends enjoyed early morning, high-energy regimens, while we preferred late starts and plenty of R&R, but not necessarily poolside.

It could have been a disaster. Instead, our joint exploration of central and northern Italy was delightful with only the rare moment of disagreement. In fact, it was far more enjoyable for all, but especially the children, than it might have been solo.

Driving in separate rental cars (a van was too expensive), we roamed from Rome to Siena, Florence, Cinque Terre and Venice. We walked until our feet ached, watched the kids play soccer in a church square overlooking the Gulf of Genoa, got a bird's-eye view from towers and churches in nearly every town we visited, sunbathed on a beach packed like sardines, found a great Indian restaurant overlooking a Venice canal, drove through ancient towns and quaint villages, and marveled at the bounty of spectacular views.

San Gimignano was one of the brightest gems. The walled, Middle Ages town of towers -- a lucky 14 remain out of the original 72 or so -- was a maze of winding paths, stone walls and long treks up narrow, tunnel-like stairwells, where the view was worthy reward.

In a cafe off the main square, the Piazza della Cisterna, we had exquisite gelato (mango, tiramisu and chocolate), the best we'd ever had. Since then, we've searched for that same divine flavor, but have, so far, tasted only disappointment.

That evening, the two families exchanged tales over snacks of cheese, olives and wine, all served in the gazebo on the front lawn of Frances' Lodge. Before us was the lush valley and in the distance Siena, punctuated by its fortress tower and zebra-striped dome. Each party had loved its day -- and it was a pleasure to share stories.

A couple of days earlier, we had connected with Kathy, her husband Will Bunch and their children, who had arrived a few days earlier to thoroughly tour Rome and its environs. Because my husband and I had visited the capital city before and the June sun beat down, Rohan got the nickel tour: Colosseum, Roman Forum, Pantheon and Vatican City (outside only).

The Boccella-Bunches, eager for some R&R after three days of intense tourism, left ahead of us for Siena, our hub to explore Tuscany.

By the time we caught up, they were lounging poolside at the Frances' Lodge B&B. This retreat was a wonderful find that Kathy discovered. We were thrilled she convinced us to splurge on the beautiful rustic farmhouse high in the hills with color-themed rooms and modern fixtures -- all surrounded by acres of olive trees and vineyards.

We didn't feel like swimming, so we headed into the town square, and everyone agreed to meet there for dinner at an upscale vegetarian spot (we preferred vegetarian mostly, and our friends accommodated us). There, we made plans for the next day's tour of Florence -- our first full day together.

Stateside, we had already sketched out an itinerary that the B&B owners had suggested. It included a visit to the Pitti Palace and Boboli Gardens and Michelangelo's David at the Galleria Dell'Accademia.

The next day, we went our separate ways -- they to wine country, us to San Gimignano -- before driving to our next stop: Cinque Terre, a coastal stretch of five communities clinging to the steep, rocky hills that are connected by hiking trails.

On the way, we opted for a side tour to Pisa, to see the famous tower that leans at a precarious angle. The icon of Italy is so famous, it was a must see for us. Our son humored us by taking our favorite cheesy photo: us holding up the tower.

Kathy's family went straight to the beach at Manarola, midway between the towns.

La Torrettas, a lovely B&B that was my find this time, overlooked the Gulf of Genoa and the rugged coastline with its pastel-hued palette of houses stacked along terraces. The rooms had many nice touches, including champagne, chocolates and fruits (kiwis, lemons) from the B&B's own garden. We all got a kick out of the royal-sized bathtub in the middle of our bedroom.

Stateside, we had agreed to walk the path that connected all five towns. It winds along the coast in many places. On one side is the brilliant blue sea, on the other the rocky hills, dotted with pink, yellow and blue-painted plaster walls of narrow houses that cling to the rugged terrain. But it was much more strenuous than expected, for us, anyway. Kathy & Co. had the energy. At one point, they were way ahead of us laggards. As we fell farther behind, we wanted to bail and take the train that connects the towns. Perhaps the Boccella-Bunches would like that idea, too, we thought.

They agreed, although they clearly would have preferred to continue the hike -- a compromise for which we were grateful. Our destination was the only sandy beach found in Monterosso. The adults relaxed while the kids splashed in the surf.

After a couple of hours, Will took the boys back to Manarola for a sea swim, while Kathy and Julia explored another of the five towns, Vernazza. Dilip and I walked around Monterosso, then caught the train to Vernazza, where a lookout point, once again, offered stunning views of the seaside town.

That evening, the parents chatted on the church square as the sun set over the gulf and the boys played soccer. This time, we were flexible about dinner, agreeing to a seafood spot, even though the vegetarian options were few.

Soon it was time to leave for the final leg, three days in Venice. It proved a favorite conclusion to our vacation. Rohan especially liked the city of canals because a favorite read, "Thief Lord," was set there. Jesse was a fan, too.

Another day, our family went to the Doges Palace, where the gallery of weapons and dungeons and the Bridge of Sighs were big hits. That evening, we all went in search of an Indian restaurant that ended up being an extensive hike (our friends begged off after 45 minutes) through a labyrinth of backways. For us, it was worth the journey. We got a delicious meal served canal side.

The final night, we all dined at a nice Italian restaurant along the main canal and recapped our trip that was nearly over. For Kathy's children, it was their first trip to Europe's mainland, and they loved it.

For us, one of the best parts of the adventure was traveling with another family. Sure it demanded compromise and flexibility on both sides. We didn't always get our way, and neither did our companions. But we each enjoyed sights and experiences we might not have alone. The give and take, we all agreed, was well worth the wonderful memories made with friends.

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