On a mellow August evening, I found myself sailing down Venice’s Grand Canal. Not in a gondola, as one might expect, but aboard Wind Surf, Windstar Cruises’ elegant, yacht-classed sailing ship.

It was one of those moments when you have to remind yourself that this is really happening. A pinch-me moment, if you will.

For many cruise passengers, sailing into Venice itself has become a thing of the past. Restrictions on larger cruise ships mean that some now arrive at ports such as Trieste or Fusina, with a separate journey required to reach the historic city. Understandably, passengers who have dreamed of arriving in Venice by water can find that disappointing. There is something undeniably special about approaching this extraordinary city from its lagoon.

We were fortunate enough to experience it aboard a ship small enough to make that passage. Yet, as memorable as sailing down the Grand Canal proved to be, it wasn’t the only thing that made our first visit to La Serenissima so special.

Michael and I arrived with the usual expectations of first-time visitors: the famous sights, the restaurants we’d researched and the places we’d been told we simply had to see. What we hadn’t anticipated was how much we would enjoy the Venice beyond that familiar picture.

The quiet waterfront walks on Giudecca. The fishermen happy to stop for a chat. The little neighborhood supermarkets and narrow alleys where local life carried on without an audience.

We discovered that we didn’t need to avoid Venice’s famous sights to escape its crowds. We simply needed somewhere to return to when we’d had enough.

For us, that place was Giudecca. And it gave us a Venice we might never have discovered had we followed the usual script.

An arrival worth remembering

A delayed flight out of Palm Beach meant we missed a night in Venice. It was to be the first visit for both my husband, Michael, and me, so we were disappointed. A cheeky overnight stay at The Ritz-Carlton, Philadelphia, softened the blow, but nothing could quite make up for lost time in Venice.

Until, that is, we arrived.

Windstar Cruises’ representatives met us at Venice airport and whisked us away on our private transfer. If there is one piece of advice I would give anyone arriving in Venice, particularly after an overnight flight, it is this: don’t skimp on the transfer.

We were escorted from arrivals to a Mercedes Sprinter, driven to a dock and transferred to our private water taxi. I didn’t have to touch my luggage (I don’t travel light), and we were soon gliding across the water towards the Hilton Molino Stucky, Windstar’s partner hotel on Giudecca Island.

But what I remember most vividly is Michael’s face.

As we navigated the waterways, his expression said everything. The excitement, the wonder, the sheer pleasure of being there. My heart could have burst.

That was pinch-me moment number one.

Discovering the Venice we needed

I tend to stay at a cruise line’s recommended pre-cruise hotel. A little herd instinct, perhaps, but there is something reassuring about knowing you are in the right place, with the right arrangements, well ahead of embarkation.

Before visiting Venice, I had assumed we should stay on the main island. Isn’t that where everyone wants to be?

In fact, I was delighted to discover Giudecca.

Michael walks with a cane, and I have severe agoraphobia. Neither of us thrives in crowds, and the thought of negotiating Venice’s busiest streets and alleys was not especially appealing. Giudecca offered something rather different: a quieter waterfront, room to breathe, and the main island just a short ride away on the hotel’s water shuttle.

The Molino Stucky proved an excellent base. Giudecca also happens to be home to the fabled Hotel Cipriani and the recently arrived Airelles, giving the island an intriguing mix of understated calm and considerable glamour.

I had arranged to tour the Cipriani because I simply had to see it for myself. ILX Travel had clients due to stay there a couple of months later, so there was a professional reason, too.

Unfortunately, the Venice Film Festival was under way, and the hotel was full of movers and shakers. I couldn’t see as much as I had hoped.

Walking along the quay behind Heidi Klum afterwards went some way towards compensating for the disappointment. Better still, I managed to get a glimpse of the hotel’s world.

Then my shoe fell apart.

When you are visiting one of Venice’s most famous hotels and the heel falls off your shoe, what do you do? In my case, you call upon the hotel staff. The general manager’s assistant procured some tape and resolved the crisis with admirable efficiency.

If anyone ever tells you that the Cipriani isn’t full-service, I beg to differ.

A table at the water’s edge

With Michael’s mobility issues, we wanted to stay close to the hotel for dinner. I had researched restaurants all over Venice. Michael is a chef, and we had every intention of eating at some of the city’s best. We had even been inspired by our favourite food and travel program, including Anthony Bourdain: No Reservations and Somebody Feed Phil.

But travel plans have a habit of evolving.

We decided to explore the waterfront near the hotel and find somewhere to eat. It was an easy stroll, without the crowds we had expected, and we were happy to take our time.

Then came pinch-me moment number two.

We were walking slowly, Michael with his cane, when we approached a waterfront restaurant. There was one outside table left, a table for two, perhaps three rows back from the water.

Another couple was coming from the opposite direction. They saw the table. They saw us. And they sped up.

They got there first.

I turned to the server, hoping my Italian lessons had not been entirely wasted.

Vorrebbe una tavola vicino all’acqua?

Would you like a table near the water?

Si, per favore.

Yes, please.

He had seen what had happened. He disappeared inside and returned carrying a table, which he promptly placed right at the water’s edge, away from the other diners.

And there we were.

A wonderful waterside dinner, delicious food, a romantic setting and service that went well beyond what we had expected. We hadn’t secured the last available table, but somehow we ended up with the best one.

It was a small gesture, perhaps, but one that stayed with us. The server had understood what we needed without our having to explain it.

Before we left, we asked him where he would go for pizza. Michael had developed a yen for it, and we wanted a recommendation from someone who knew the neighborhood rather than another entry on a tourist list.

His suggestion turned out to be spot on.

The following evening, after visiting some of Venice’s major sights, we returned to Giudecca and its quieter pleasures. We wandered along the waterfront while Michael chatted with fishermen. I ordered a little prosciutto appetizer that would have fed an army. Michael’s anticipated pizza turned into calzone.

It was all good.

And that, I began to realize, was the beauty of staying on Giudecca. We could visit the places we had come to see, then return to somewhere that felt comfortable and unhurried. We didn’t have to choose between experiencing Venice and enjoying it on our own terms.

And then, the Grand Canal

Our third pinch-me moment came when we finally sailed down the Grand Canal aboard Wind Surf.

Venice glided past us, its palaces and historic façades reflected in the water. After the missed night, the unexpected detours and the little adventures that had filled our first days, there was something wonderfully fitting about seeing the city from the water.

It was the sort of moment you want to hold on to, even as you know it is already becoming a memory.

Ours wasn’t the typical first trip to Venice. We missed a night, discovered an island we hadn’t expected to love, lost a shoe, gained a table at the water’s edge and found ourselves enjoying the city in a way that suited us perfectly.

But it was ours.

And I wouldn’t have changed it.