santorini and paros

By the time I hit the Big 50, I had already visited my top bucket-list destination, Italy, twice—but the runner-up was still out of reach: Greece, and more specifically, Santorini. I had always wanted to see the whitewashed buildings and the famous golden sunsets in person.  Jim and I had casually discussed Greece as a possible 50th birthday trip with our family, but never finalized plans. In 2022, one of my closest friends turned 50 (a year after I did), and our family was invited to join hers for a week in Porto Heli. Thanks to these wonderful friends, we were able to add a few days in Santorini and finally check it off my list.

The flight from Toronto to Athens is approximately 11½ hours. We chose to upgrade to premium economy, which we felt was worth the additional cost for added comfort and better rest before arrival.

We spent one night in Athens, staying in the Plaka neighbourhood at a boutique hotel called InnAthens. We booked a family room, which worked well for our short stay.  While walking through Plaka, I unexpectedly ran into a friend from home — proof that the world can feel very small.

We toured the Acropolis of Athens shortly after arriving, then stopped for an Aperol spritz before taking a short nap to adjust to the time change.  For dinner, I had reserved a table at Tudor Hall Restaurant, located on the rooftop of the King George Hotel in Syntagma Square. The restaurant offers fine dining, excellent service, and panoramic views of the Acropolis illuminated at night. Since our visit, it has been awarded a Michelin star. It was an exceptional meal and a highlight of our short time in Athens.  With only one night, we certainly missed many other sites, but our priority was Santorini.

The following morning, we arranged a transfer to the airport through Welcome Pickups and boarded an Aegean Airlines flight to Santorini.

Santorini was exactly as I had imagined — dramatic cliffs, whitewashed buildings, and sweeping sea views.

We travelled here just as the world was emerging from Covid. Tourism had not yet returned to full capacity, which allowed us to experience the island without overwhelming crowds. Pathways were manageable, viewpoints were accessible, and even the ferry was not overly busy. Having space to move and explore made the experience even more enjoyable.

For our family experience, I wanted to stay somewhere that felt like a traditional Santorini home. We booked a cave house via Airbnb in Imerovigli, which had a rooftop terrace and small plunge pool. Choosing the right location was a challenge: we wanted access to restaurants and sights but preferred a quieter, less crowded area. I decided on Imerovigli for a more private community and space for our family, with excellent access to Santorini’s highlights. Our villa provided amazing sunrise views from one side of the terrace and a beautiful caldera view on the other. We did not have direct sunset view from this property.  Even in June, evenings were cool and breezy. Bring a shawl or wrap.

We had three magical nights in Santorini, and from the moment we arrived, it felt like stepping into a dream. On our first full day, we took what turned out to be one of the most unforgettable tours of any trip we’ve ever done. Spiridakos Sailing Cruise offers a variety of options, but we chose the Sunset Sail—and we were thrilled we did. We were picked up right from our Airbnb and driven to the docks on the southern tip of the island. Boarding the catamaran, we set off slowly, hugging the coastline as the island’s whitewashed villages and turquoise waters unfolded around us.

Oia, as I’d imagined for years, is one of the most beautiful places in the world to watch the sun set. The golden light spilling across the horizon and reflecting on the water was breathtaking—a moment I will never forget. The cruise lasted about six hours, offering a traditional Greek BBQ buffet along with wine, beer, and non-alcoholic drinks. There were a couple of swimming and snorkelling stops to cool off and explore the vibrant marine life.

The private option was far more expensive, and while the standard tour was wonderful, a few fellow travellers occasionally made things a little tricky. It’s a one-time experience, so if your budget allows, a private tour might be worth considering. For us, despite these small hiccups, it was an absolutely perfect day.

The next day, we decided to make the trek from Imerovigli to Oia. This is a  10 km hike that winds through small villages and offers jaw-dropping views at every turn. I cannot overstate how stunning the scenery is—it literally takes your breath away. Very unintelligently, we started around 11 a.m., in the height of the midday sun. It took about three hours, and by the end, we were hot, sweaty, and exhausted. There are escape options if needed—you can hop on a bus or call a taxi—but we were determined to see it through. Bring plenty of water, wear sturdy shoes, athletic clothing, and a hat. There are a few stops along the way where you can buy water, cold fruit, or a quick refreshment, which is essential.

When we finally reached Oia, we collapsed with cold drinks and lunch, and our waiter couldn’t help but laugh at us. Apparently, few tourists attempt the hike in the middle of the day! We were happy to be among them, and I wouldn’t trade the experience for anything. The lesson: start early in the day if you want to tackle this hike.

I had made reservations for Ammoudi Fish Tavern for a late lunch. Unfortunately, we were too tuckered out to make it down the roughly 300 steep steps to the caldera-side restaurant. While you can take a donkey ride, it wasn’t something we felt comfortable with. We later learned that taxis can navigate the narrow winding road down the hill, which is a much easier option. Passing by after our catamaran cruise, it looked lively and inviting—definitely a place I’d love to visit next time.

Oia itself was busier than I expected, even in a low season post-COVID. I can only imagine how packed it must be during peak tourist months, especially with cruise ships docking in Fira and busing passengers over for shopping and sunset views. Originally, I had booked a hotel in Oia for the caldera views, but after seeing the crowds, I think I’d recommend staying right at the tip of town or just around the corner. Staying at the tip gives you the classic sunset view, but the corner offers quieter streets, better pricing, and a more peaceful stay.

Had we had more time, we would have done a wine tour. Santorini, in particular, produces some of the best white wines I’ve ever tasted—a delightful surprise.

Santorini met every expectation I had and more. It was magical, awe-inspiring, and utterly unforgettable. This island is a must for anyone planning a Greece itinerary.

From Santorini, we hopped on a ferry to Paros, booking our tickets through the FerryHopper app. When we first boarded, we felt a little uneasy leaving our luggage by the door, but it was perfectly fine. The ferries are comfortable and a really pleasant way to island-hop, letting you take in the sea and the islands as you glide between them.

We arrived in Parikia and checked into another Airbnb near the town square. That first evening, we wandered the streets and, I’ll be honest, were underwhelmed. The town seemed small, quiet, and with little to offer. It wasn’t until the following day that we discovered another side of Parikia that is situated directly on the waterfront, where a lively stretch of restaurants, bars, and nightlife completely changed our impression.

On our first full day, we rented two ATVs to explore the island, which was perfect for seeing a lot in just two nights. That said, if you’re like me and a little conservative about vehicles, I’d recommend opting for more powerful, larger ATVs than the entry-level models we had. I felt battered about on the highways, which made me nervous. We stopped for a few hours in Naoussa to explore, walk about, and enjoy lunch. Next time, I think I’d choose to stay here—it’s larger, livelier, and more vibrant than Parikia. We also made a stop at Kolymbithres Beach, cooling off in the crystal-clear water and marvelling at the granite rock formations the island is known for.

That evening, we had an unforgettable dinner at “Nice to Meat You” along the Parikia boardwalk. It was here that we tried Mastika for the first time—an herb-flavoured aperitif that’s seemingly more popular than ouzo, and in my opinion, much better! Since that night, it has become a regular feature in our home bar.

Notable Imerovigli Restaurants:

• La Maison – drinks after dinner 
• Aegean Restaurant – exceptional dinner experience