My husband and I rarely head to the same destination twice because there are so many places we’d like to visit! That said, when we decide to ‘repeat visit’, we follow a few rules when planning the trip.

We don’t replicate the entire itinerary from a prior visit, even if it was a good one.
We seek out new accommodations, even if the lodging during a previous visit was great.

Basically, we try to switch it up a bit, and here’s why:

We’re a bit adventurous and enjoy new experiences. It’s a big world out there. So why do the exact trip twice when there’s so much more to see and do? Every destination will have an additional neighborhood, tour, or other experience you didn’t have the chance to investigate the first time you visited.
We want to maintain the positive memories we have from exploring a new destination. With the tourism boom of late and many destinations embracing ‘progress’, the place you visit one year might be quite different five years later (and not necessarily in a good way). That can create disappointment.

Here are a few examples of what we have experienced and learned from:

Hawaii

We traveled to Hawaii twice within three years back in the early 90s. The second trip was due to a solar eclipse crossing over part of the Big Island. On this second trip, we decided to visit islands we hadn’t visited previously and stay in a different hotel on the Big Island (since we’d been to the island already) for the eclipse. The only thing we repeated was in Maui, where we stayed at the same hotel on Kaanapali Beach, a favorite during our last visit.

Even though it was cloudy during the eclipse (which made for a disappointing solar experience), everything on our trip was fantastic. Until we got to our hotel in Maui. Why? The hotel was noisier than we remembered (we were put right over the bar and could not move to another room), our room lacked the view that a free upgrade at check-in during the first trip had given us, and the pool area was packed. The atmosphere had changed from the oasis we remembered.

So now our memories of Kaanapali are mixed. If we had followed our ‘returning visit’ rule, we would have stayed in a different area than Kaanapali, or at least at a different hotel along that beach.

Be cautious about trying to relive a great memory.

Italy

Cinque Terre is a UNESCO World Heritage site on the Italian Riviera, and easily accessible via ferry or train. During a visit in June, 2004, we found it busy but very manageable. A visit to the area in June 2026, however, would bring wall-to-wall people, as it is now an over-touristed area (like Venice and Florence) of Italy. (Photo: Erik J Kramer)

Italy has been one of my favorite countries since my husband and I first visited back in 2004. We spent a whirlwind two weeks seeing Venice, Florence, Tuscany, Umbria, and the northwestern coast, including Cinque Terre. I was so excited for our kids to experience some of these areas when we returned with them in 2019.

Due to overtourism, the memories of Venice and Florence from 2004 no longer accurately reflect these cities today. The fairly empty piazzas we had walked through were now packed with hundreds of tourists, even during the shoulder season. Many of the quaint small businesses, such as meat, cheese, bread, and pastry shops, have been replaced with cheap souvenir shops selling identical items regardless of neighborhood or street. Many workers in the souvenir shops are immigrants who may speak some English but speak little to no Italian.

Even the hill towns in Tuscany and Umbria are more commercialized.

Don’t get me wrong. Italy is still magnificent. The history, art, architecture, and food are amazing. The crowds and added commercialism are not. So if it’s been a while since your last visit, beware of the changes that tourism, particularly in popular ‘Insta-worthy’ places, has brought.

If I return to Italy a third time, it will be to the less-traveled areas, such as the country’s southernmost regions or Sicily, that are still in their infancy in terms of tourism.

Make new memories. In countries you love, explore similar locales to those you enjoyed in the past. That way, you won’t be making an exact comparison of the past to the present.

Iceland

We visited Iceland as a family before it became a popular tourist destination. When people heard where we were heading, I was often asked two questions: where and why.

My husband’s parents had died within a month of each other, and he was in the middle of negotiating between several job offers after a period of unemployment. I remember one negotiation call on the road as we headed to a hospital six hours from our home. It was one of the toughest periods in our lives, particularly for him. I’ve no idea how he was able to make his job decision given everything he was dealing with.

I made last-minute travel reservations so that we could have some solid family time away from our home base before he started his new job. I remember him asking me about why I had chosen Iceland because we really hadn’t discussed it. I just said, ‘Don’t worry, you’ll love it. It’s like a big national park.’ (I said this with confidence, hoping I wasn’t too far off!)

We had a great trip. The waterfalls, glaciers, Icelandic horses, fields covered with wild lupine, and the midnight sun were amazing to all four of us. We even had a glacier flood that took out a bridge on the Ring Road, making it impossible to see a few highlights on our loose itinerary—but what a story! We watched them try to ferry people across the muddy, washed-out area, only to see big wheel buses and trucks get stuck in the deep, deep mud. We were shut out of the east side of the island that trip, but the memory of how the island handled glacial flooding that affected its main transportation route was interesting to see firsthand.

We are planning another visit to the island. Now that more infrastructure is in place, we plan to drive the entire Ring Road. However, I’ve seen pictures of the crowds in and around Reykjavik and the Grand Circle route—so different from what we experienced 15+ years ago. How will this affect our next trip there?

We’ll adjust expectations by spending most of our time outside the over-touristed areas (Reykjavik and the Grand Circle). By focusing on areas we didn’t see the first time, we won’t be comparing the past to the present of a specific Icelandic sight or location. This will help make our next trip to Iceland exciting and memorable in its own right. That said, we’ll check out Reynisfjörður Beach to see how it looks compared to our last visit, since the change is both natural and dramatic.

Bermuda

We honeymooned in Bermuda and revisited it on our 15th anniversary.

Our second visit was fabulous for the following reasons:

We knew what to expect from the island (it doesn’t change much from year to year).
We consciously booked a smaller hotel than the one we stayed at on our honeymoon because we wanted a more intimate setting than what we experienced on our first visit.
We wanted a low-key destination that we did not feel the need to explore.

We wanted to stay put in one place and enjoy each other’s company without interruption or responsibilities. As parents of a five- and a two-year-old at the time, we needed some basic R&R. We’ve learned that R&R vacations often don’t require much outside of the resort or hotel, but choosing the right one becomes the most important decision you make.

Sleep. Sunbathe. Swim. Service. Many Bermuda hotels have it all.

Know thyself and what you want and need from a trip.

When ‘Rinse and Repeat’ Works Just Fine

Some travel experiences are worth repeating. Some folks relax more easily when they are visiting a place they know like the back of their hand. Some need a few distractions or activities to relax, or they get fidgety.

One example I can think of is our family’s annual lake vacations, during which we stayed at the same camp on the same lake for many years. Fish counting and biggest catch contests. Nightly campfires. Boat trips to the ice cream shack at the end of the lake. In bathing suits all day, every day. Lots of daily traditions.

The only unknown when we booked the specific weeks? Will the local corn be ready for picking?

We found that our young family felt comfort in the familiar.

Choose Wisely

Travel is always good, but setting expectations is more important than ever when you are revisiting a destination. You may find it more crowded than before; a beach may have eroded significantly; locally owned shops may have been replaced by chain-like souvenir shops; a city may feel more cosmopolitan than insular. With time, many local customs seem to be adjusting to global trends. Good memories are sacred. Sometimes even better than reality. Protect them.

Creating new memories in a new place is exciting. If you love a country or culture, mix it up by seeing something new. Look beyond the top cities that are heavily visited (or that you’ve already visited) and, instead, head to a country’s secondary cities that haven’t been hit as hard (yet) with over-tourism. Or switch up your accommodations, tours, restaurants, etc., if you’re drawn to the same locale as on a previous visit.

Repeating a past vacation has its place. Sometimes, going to the same place repeatedly becomes a valued tradition. Plus, it’s simpler—you know what to expect and what to pack.

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