Santorini

From a Trial Run to Our First European Adventure

Two months before we landed in Santorini, we had taken our first international trip as parents: eight nights in Costa Rica with our 17-month-old son, Preston.

We had already booked some of the larger pieces of our European summer trip. My husband's work as a teacher and football coach shapes when our family can travel, and that year we knew spring break and summer would be our two major opportunities. Europe was on the calendar. Costa Rica became the trial run.

The flight was shorter. The destination was closer to home. But the trip allowed us to test the questions that had made us nervous: how Preston would handle an airplane, how we would manage naps and meals away from home, how much gear we actually needed and whether the difficult moments would outweigh everything we hoped to experience.

Costa Rica confirmed that traveling with a toddler could be hard and exhausting. It also confirmed that we could get through the hard parts.

Santorini asked us to carry that confidence much farther.

This was the first time any of us had traveled to Europe. It was also the longest flight any of us had ever taken, with or without a child. Our route began in Columbus, continued through Atlanta and Athens, then ended with one final flight to Santorini. Including the time we needed at the airport, we expected the journey to take roughly 17 hours.

Santorini was the first stop of a four-stop European trip that would continue to Crete, Positano and Rome. We chose it for the reason many travelers do: it looked extraordinary. The white architecture, blue water, sunsets and caldera views made it feel glamorous, beautiful and undeniably bucket-list worthy.

We were excited. We were also unsure whether a place so closely associated with honeymoons and couples would welcome a family carrying a 19-month-old through its narrow streets. We wondered whether the island would feel too crowded or too touristy. We knew the stairs would be difficult, although our hiking carrier gave us a plan. More than anything, we wondered how we would feel after bringing a toddler across the Atlantic and then boarding one more airplane.

Santorini did not surprise us by becoming something different from the photographs. It was breathtakingly beautiful, busy, polished and tourist-centered — exactly what we expected. What we could not know before going was how clearly it would help us understand our family's own travel preferences. We were glad to experience the celebrated destination. We were also beginning to realize that the quieter, slower places often stayed with us more deeply.

Our Route

Santorini was the opening stop of a two-week European summer trip that continued to Crete, Positano and Rome. We flew from Columbus through Atlanta and Athens, took one final short flight onto the island, and — after three nights — left the way we wish we had arrived: by ferry, gliding across to Crete in under two hours.

Before We Left

Why We Chose Santorini

Santorini felt like the Greece we already knew from photographs. Outside of Athens, it was the place that immediately came to mind: whitewashed buildings pressed into the caldera, blue water below and sunsets that appeared on nearly every list of places worth seeing.

We wanted a little beauty, a little luxury and the feeling of beginning our first European trip somewhere unmistakable. Santorini promised all three. It was also the kind of destination we felt we should experience for ourselves. We had seen it online. We had watched other people travel there. We wanted to know whether it would feel as extraordinary in person as it looked from home.

What Made Us Nervous

Our largest concern was not the island itself. It was reaching it. The itinerary required an overnight flight from Atlanta to Athens, then a smaller airplane from Athens to Santorini. Kyle does not enjoy flying, and the final aircraft was not particularly reassuring to him as it was a very small plane. With a lap child, limited space and no expectation that the adults would sleep, the journey felt intimidating before it began.

We also questioned how a toddler would fit into the image of Santorini. Would restaurants welcome him? Would the island feel designed only for couples? Would we spend the trip feeling as if our family disrupted the atmosphere other travelers had come to enjoy?

The stairs were the most visible practical concern. We planned to leave the stroller behind and use our hiking carrier, which had already become essential in Costa Rica. That decision gave us confidence, but it did not make the terrain disappear.

Arriving in Santorini

Our travel day began in Columbus, with a connection in Atlanta before the overnight flight to Athens. Preston was still under two, so he traveled as a lap child.

There were moments when the lack of an additional seat made the row feel very small. But Preston loved a contact nap, and we believed he would have slept on us even if we had purchased another seat. The real benefit would have been space rather than sleep. We sat in the window and middle seats beside a traveler we did not know. She was lovely — she enjoyed playing with Preston, gave us room to manage him and became one of the small kindnesses that made a very long flight feel more manageable.

We brought familiar toys, loveys and more snacks than we thought we might need. We assumed he would not eat much of the airplane meal, so keeping him fed, entertained and comfortable became the plan. Preston slept. Kyle and I did not.

By the time we reached Athens, the airport felt unfamiliar and a little chaotic. Then came the smaller plane to Santorini. Kyle managed it because it was the only way to complete the route, although after experiencing the ferry later in the trip, he would probably choose to fly into Athens and travel to an island by sea instead.

Once we landed, the logistics became much easier. Our Airbnb host had arranged a transfer from the airport with a car seat, and a porter met us to help with the luggage. We did not have to search for transportation, explain where we were staying or determine how to carry our bags into Ammoudi Bay after the longest journey our family had ever taken.

The arrival was not cinematic. But the plan worked.

It was tired parents, an adjusting toddler and a series of unfamiliar airports. But we had crossed the Atlantic, reached the island and arrived at a place that immediately made the effort feel worthwhile.

Making Ammoudi Bay Our Home Base

We stayed at Nicoletta Ammoudi Suite A, a cave-like apartment built into the mountainside at the edge of Ammoudi Bay. The suite was one of the most beautiful Airbnbs we have ever booked. The palette was unmistakably Greek — white, blue and deep red. We walked directly into a small kitchenette and dining area, where dark reddish window trim framed the water outside. Natural light filled the room. When the windows were open, we could hear the waves and the movement of boats through the bay.

The main room held an enormous king bed with a seating area in front of it. The bathroom extended farther into the cave-like interior, with warm clay-colored walls that felt darker and more enclosed than the sunlit front of the suite. The contrast made the apartment feel distinctive rather than generic.

Outside the front door, a private patio faced the bay. There was a table, an umbrella and enough space to sit with breakfast, watch the boats come and go and allow the view to become part of the morning rather than something we needed to leave the property to find. A back door led to another set of stairs — one direction reached a private plunge pool overlooking the water, the other opened into a shared tiered pool area. The pools were small, but the views were exceptional. We could swim comfortably in the late-May weather, then return to the patio and remain connected to everything happening below.

The suite also made us pay attention. The pools, terraces, railings and stairs were not designed to allow a toddler to wander independently. We were on high alert whenever Preston was outside. For our family, that did not make the accommodation a mistake. It meant that enjoying the property required active supervision and clear adjustments from both parents. A crib or pack-and-play was provided, though Preston was still adjusting to the time difference and slept better near us. As in Costa Rica, he ended up in our bed. Everyone rested more when we accepted what worked during the trip rather than insisting that sleep look exactly as it did at home.

The 300 Steps — and the Longer Way Around

The beauty of Ammoudi Bay came with one unavoidable fact: Oia sat roughly 300 steps above us. We climbed the stairs once or twice before learning that a paved access road and sidewalk also wound around the hillside. The road took longer, but the gradual route was far easier than carrying a toddler up hundreds of steps in a hiking backpack.

Three hundred steps can sound manageable when reduced to a number. In practice, reaching the top was a workout. The view was beautiful when we arrived, but we also arrived exhausted. After discovering the access road, we chose it every time. It still required us to walk uphill, but the incline was distributed across a longer route.

Donkeys were available to carry visitors on the stairs. We never considered using them. The smell was unpleasant, and we were uncomfortable asking an animal to carry us simply because we did not want to walk. Candidly, I wish this mode of transport wasn't even an option. The access road gave us another way.

Oia and the Sunsets

Oia lived up to the hype.

The white architecture, blue water and caldera views looked exactly as they did in the photographs. Santorini is a place for travelers who want the picture-perfect vacation and still want the real destination to match the image they carried with them.

It was also crowded and more tourist-centered than we have come to prefer. We visited in late May, during the shoulder season, and locals told us the island was not yet close to its busiest period. Even then, narrow walkways and the most popular viewpoints could feel full.

The hiking carrier helped us navigate. We saw other families using strollers, but stairs and crowds often required two adults to lift the stroller or maneuver it through spaces that were not designed for wheels. With Preston on our back, we could move more naturally and stop without immediately searching for an accessible route. We did not build a formal list of sights or tours. We explored Oia at our own pace, found places to eat, took in the views and allowed the island to lead the day without forcing ourselves to complete an itinerary.

One Sunset in Oia, Two in Ammoudi Bay

We watched the sunset from Oia one evening. The elevated view was beautiful, but the experience was shoulder to shoulder. Everyone was searching for a small opening where they could see the horizon or capture the photograph they had imagined.

The sunset was worth seeing. It was not our favorite way to experience it.

On the other two nights, we stayed in Ammoudi Bay. A path across from our suite led toward a rocky area where we could spread out, sit near the water and watch the light change without competing for a narrow slice of the view. The perspective was lower, but the evening was calmer. The quieter sunset became another example of what we were beginning to understand about ourselves: the most famous vantage point was not automatically the one that felt best to our family.

A Day Beyond Oia

Choosing a Car Instead of a Boat

We considered taking a boat from Ammoudi Bay or joining a tour, but the operators we spoke with could not confirm that they had a life jacket properly sized for Preston. We were not comfortable moving forward without one. Instead, we rented a car for our final full day. Golden One delivered the vehicle directly to Ammoudi Bay and provided a car seat that appeared suitable for Preston. The process was easy, and the car gave us a day without the stairs or the longer walk out of the bay.

Driving was relatively straightforward. Traffic increased near the entrances to Oia and Fira, but we did not find the island difficult to navigate. As we do whenever we rent a car, we photographed existing damage and recorded a full video immediately at handoff before placing anything inside. Before leaving the United States, we had also obtained international driving permits through AAA because we understood that they might be required in Greece. We were never asked to show them. Requirements can change, so travelers should verify the current rules for their own licenses and rental company rather than relying on our 2023 experience.

Kamari Beach

Kamari Beach gave us a different view of Santorini. We walked the promenade, ate an excellent meal and settled into beach chairs for a relaxed afternoon. It was the first beach we had visited where the shoreline contained more rocks than sand, but the difference did not prevent us from enjoying it. Preston even napped on a beach chair.

The area felt like somewhere we could use as a quieter home base. If we returned with someone who especially wanted to experience Santorini, we would consider staying in Kamari and visiting the more crowded tourist centers rather than living inside them for the entire trip. Santorini is not the Greek island we would choose for a traditional beach vacation — after seeing the beaches of Crete, that distinction became even clearer. Kamari was still a welcome place to slow down, enjoy the promenade and spend an afternoon near the water.

What We Ate

Food in Santorini was pricey, but it did not feel unusually expensive for a destination with the island's level of tourism and prestige. We compared it to eating in a major city: not inexpensive, but not shocking.

Elias Grill

A local parking attendant noticed that we were visiting and asked about our plans. He recommended two restaurants, beginning with Elias Grill in Kamari. We followed his advice and were glad we did. Kyle ordered his first Greek salad and became obsessed — from that meal forward, he ordered one at nearly every restaurant. He also chose the mixed souvlaki platter. I ordered a chicken gyro pita. Everything was incredibly good. Preston discovered his own favorite: hummus and pita. He ate them constantly throughout the trip, giving us an easy, reliable food we could order almost anywhere.

Metaxi Mas

The same parking attendant insisted that we also visit Metaxi Mas, a restaurant in the hills that felt removed from the busiest parts of the island. We arrived without a reservation and did not wait long. A high chair was available, and the staff spoke to Preston, made him laugh and helped our family feel completely welcome.

We ordered the broccoli soufflé because it had been recommended to us. It was not something we would have selected on our own, and it became one of the best dishes of the trip. Kyle ordered the roasted lamb shank, also based on the recommendation. I had chicken with hummus and vegetables. The meal remains one of our favorites from any destination. A small play area beside the restaurant made the experience even better — while we waited for the table and the food, Preston could use the swings, go down the slide and wander through the nearby lookout area.

Listen when someone who knows the place takes the time to tell you where to eat.

Traveling with a 19-Month-Old

Before Santorini, we worried that bringing a toddler to a destination associated with romance might make our family feel out of place. The opposite happened.

Restaurant staff welcomed Preston. High chairs were available. The airport transfer and rental-car company provided car seats. Other travelers expressed admiration that we were showing our son the world. One group of women spoke with us about the decision and applauded us for including him in the experience. People were sometimes surprised to see a toddler. They were never unkind about it.

Preston also adapted better than we expected — and, in some ways, better than the adults. The first night or two required everyone to adjust to the time difference, but he learned the new rhythm quickly. His naps happened wherever the day allowed: in the car, in the hiking carrier and even on a beach chair in Kamari. We stopped expecting his home schedule to control the trip. The goal was not to reproduce the same nap in the same environment at the same hour — it was to make sure he rested, remained fed and felt secure while we experienced the destination together.

What Helped Our Family

• The Hiking CarrierFor our family, the carrier was an absolute must. It let us navigate stairs and crowds without carrying a stroller from both ends. A front carrier could also work well for a younger or smaller child.
• Carry-On-Only PackingWe packed lightly for the full two-week journey. Carry-on luggage made transfers, stairs and the ferry journey much easier to manage.
• Familiar Items & Plenty of SnacksLoveys, favorite toys and familiar snacks helped Preston through the long flight. We assumed he would not want the airplane food and planned accordingly.
• Flexible SleepThe provided pack-and-play was useful to have, even though Preston slept better near us. On-the-go naps allowed the day to continue without ignoring his need for rest.
• A Light ItineraryWe did not fill the three nights with reservations and tours. Exploring independently gave us room to respond to jet lag, crowds and Preston's energy without feeling behind.

Leaving Santorini by Ferry

Our final transition changed the way we thought about traveling between Greek islands.

We booked SeaJets tickets approximately three months before the trip. Preston traveled without a fare in 2023, and the overall cost felt relatively affordable from our perspective. Our ferry left the Thira port in the early evening and reached Rethymno, Crete, in less than two hours.

Boarding was remarkably simple. We walked on, placed our luggage in the designated area and found seats that felt two or three times larger than airplane seats. The ferry was not crowded. We could spread out, get a drink and watch Santorini recede behind us. No one experienced seasickness. The vessel was large enough that we knew we were on the water without feeling significant movement. For our family, it was easier, calmer and more comfortable than flying.

The most stressful part happened before boarding. We had driven the rental car to the ferry port, where parking was chaotic and spaces felt improbably small. The rental company instructed us to leave the keys in the vehicle and they would find it. The arrangement worked, but it felt unsettling by American standards. The ferry itself erased most of that stress. If we return to Greece, our ideal route would be to fly into Athens, spend time in the city and travel by ferry to Naxos. The experience gave us a new favorite way to move through the country.

Crowds, Stairs & the Honest Part

Did We Feel Welcome with a Toddler?

Yes. We felt welcomed everywhere we went.

The concern that Santorini would reject the presence of a toddler belonged more to the destination's image than to our actual experience. People complimented us for traveling with Preston. Restaurant staff engaged him. Practical support — from high chairs to car seats — was available when we needed it. Santorini may market itself through romance, but families are not excluded from its beauty.

What the Photographs Do Not Show

The photographs rarely communicate the effort required to move between levels of the caldera. They do not show a parent carrying a toddler up hundreds of steps, the second parent helping maneuver a stroller or the constant supervision required around open terraces and pools. They also cannot fully capture the crowds at sunset. Oia's most famous views are genuinely beautiful. They are also shared with many other people who arrived hoping to experience the same moment. None of this made the trip unsuccessful. It simply meant that the real version of Santorini required more planning than the still image suggested.

What Santorini Confirmed

Santorini did not surprise us by defying its reputation. It delivered exactly what it promised: beauty, glamour, white architecture, extraordinary views, tourism and crowds. What surprised us was how useful that clarity became. We learned that our family could navigate a major, celebrated destination. We also learned that we did not need to chase every place simply because it looked extraordinary online. The calmness we had loved in Costa Rica — and would soon find again in Crete — fit us more naturally than the constant energy of a world-famous tourist center. Hindsight makes the preference seem obvious. It was not obvious before we went. We needed to experience Santorini to understand it.

The Honest Part

Santorini is likely a one-time destination for our family. That statement is not criticism. Three nights felt exactly right. We saw the view, stayed somewhere extraordinary, explored Oia, found a quieter rhythm in Kamari, ate exceptional food and left satisfied rather than wishing for more time.

We would recommend that anyone drawn to Santorini experience it. The first view is remarkable, and the island deserves its place among the destinations people dream about. But we would not return simply to recreate the same trip. Greece is not one and done for us. Santorini probably is.

What We Would Repeat & Change

What We Would Do Again

• Visit in late May, when the weather was warm enough for the pools and the island had not yet reached its peak-season crowds.
• Stay three nights — enough time to adjust, experience Oia and explore another part of the island.
• Book Nicoletta Ammoudi Suite A again for the cave-like interior, bay views, patio and pools — while remaining realistic about the stairs and supervision.
• Arrange the airport transfer, car seat and porter through the host before arrival.
• Use a hiking carrier instead of a stroller.
• Keep the itinerary light and allow naps to happen on the go.
• Rent a car for the final full day and use it to reach Kamari and the ferry port.
• Follow local restaurant recommendations, especially Elias Grill and Metaxi Mas.
• Leave Santorini by ferry rather than adding another flight.

What We Would Change

Very little. The trip worked because we did not ask Santorini to become something it was not.

• If returning with someone who especially wanted to visit, we might stay in Kamari and make day trips to Oia rather than staying in the busiest area — though you go to Santorini for those Oia views, so it is hard to imagine staying anywhere else.
• We would consider a sunset boat tour only after confirming that properly sized child-safety equipment was available.

Who Is This Trip For?

Santorini may be a good fit for travelers who:

• Want to experience one of Greece's most iconic landscapes for themselves.
• Value architecture, caldera views, sunsets and memorable accommodations.
• Are comfortable building a short stay around walking, stairs and changing elevations.
• Can remain flexible with a toddler's naps and meals.
• Want a polished, celebrated destination and understand that tourism is part of the experience.
• Would enjoy pairing Santorini with a quieter Greek island.

It may be a more difficult fit for travelers with significant mobility limitations, families seeking a traditional sandy-beach vacation, people hoping to avoid crowds entirely or travelers who want their home base to feel primarily local rather than tourism-centered. Families with young children can absolutely visit. The question is not whether toddlers belong. It is whether the adults are prepared to plan for the terrain, supervise actively and let the day remain flexible.

Would We Return?

Probably not to Santorini on our own — but absolutely to Greece.

Santorini gave us a complete experience in three nights. We would return if we were traveling with someone who deeply wanted to see it, and in that case we might use Kamari as a quieter base. Otherwise, our next Greek journey would move in a different direction.

Crete became the island we fell in love with and would revisit without hesitation. Naxos is now high on our list. We can imagine flying into Athens, spending time in the city and boarding a ferry for a longer, slower island stay. Santorini opened the door to Greece. The rest of the country gave us reasons to keep walking through it.

What Santorini Left With Us

Santorini proved that our family could complete the intimidating travel day. We could board the overnight flight with a lap child. We could arrive in an unfamiliar airport, take one more small airplane, carry a toddler through the caldera and begin a two-week European trip far from home.

It also showed us that traveling with a child did not make us unwelcome in the places we had once imagined only for couples. Preston was not an interruption to the trip. He was part of it — from contact naps on the airplane to hummus at the table and a beach-chair nap in Kamari. But the most lasting lesson was quieter. Santorini helped us separate what photographs beautifully from what feels most natural to our family. We were capable of the splashy destination. We simply did not need every trip to be built around one.

Costa Rica had given us confidence. Santorini gave that confidence direction.

We left grateful that we had seen the island and ready for the next place. That was not disappointment. It was clarity.