By Jeanne Muchnick
Portions of this trip that were hosted are noted. All opinions expressed are entirely my own.
It’s always hard, when planning a trip to Greece, to think about what islands to choose and how much time to spend on each. It can be even harder when you’re planning with your (adult) daughter. Inevitably, when travelling with someone else, you’ll have different ideas of how to spend your vacation time. For me, it’s beach all the way. For her, it’s history, adventure and lots of walking.
As we were both first-timers to Greece, we put Santorini on our list for its sheer beauty and uniqueness. We chose.Paros for its smaller pace and less touristy vibe. And Crete because we knew there would be a lot to do, so she could do one thing and I could do another.
Ultimately, where you go depends on your budget, your preferences and your timing.
Santorini

Santorini surprised me. I’d heard a lot about it – how beautiful it is, how the sunsets are to die for, how the food is fantastic – yet also how overrun with people it can be. I was prepared to feel overwhelmed by the crowds and feel like the place was too touristy. The reverse happened. I loved it and wish we could have stayed longer.
This magical spot — a prime destination for honeymooners – is like no other thanks to its postcard perfect scenery that’s so technicolor amazing your camera really can’t do it justice. There’s a lot to take in here starting with its multi-level craggy cliffs, whitewashed villages, blue-domes churches, rugged volcanoes and sun-kissed beaches.
The island also offers numerous travel routes for flying or ferrying to other cities and islands. We stayed in Fira, the capital of Santorini and the largest town, but staying in Oia would be just as good. Both are stunning; both have a host of restaurants and hotels and both have stunning sunset views. As an FYI: Fira may be a tad more convenient as it’s the main transportation hub of the island.
There’s a lot to do here; such as enjoying a catamaran cruise, touring a volcano, visiting one of their beaches including their famous red beach and black sand beach, taking a winery tour or sunset cruise and walking from Fira to Olia (which we did though you need to go early as the hotter it gets the harder it gets).
Santorini is also famous for its blue domes. To make sure you see everything you want (and snag photos!), you may want to book a private blue dome tour.
- Where to stay: Reverie Santorini Hotel, a cozy family-fun boutique property with a pool on the Caldera. They have a rooftop, too, to take in the view.
- Where to eat
- Galini Café with its perfect perch along the cliffs and its decadent breakfast and brunch. It’s also fun for cocktails and a light dinner.
- Roka in Olia, another winner for its food, ambiance and hidden backyard patio.
- Worth Visiting: Santo Wines for wine tasting and a sunset view and Atlantis Books for its warren of books in multiple languages and its antiquarian and collectors’ first editions
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Paros

Paros, folks say, is the new Santorini. In other words it’s gaining attention for its laid-back beach vibe, quiet villages, ancient Parian marble quarries, and charming port filled with weathered fishing boats. It’s still touristy but, provided you come in late August or early September or even more into fall, you won’t see as much of it making it a more authentic Greece experience.
And that’s glorious. For this is a town meant to be savored thanks to winding narrow walkways, lots of boutique shopping and beachside eateries where, though the food may be mediocre, have stunning views (so go for a cocktail!).
Paros is also great for day trips, namely to Lefkes, a stunning town with a mountain setting that’s been untouched by development. Here are the steep, mortared-stone paths of Greece that one dreams about, without the crowds.
Mainly, we spent time at the beach, took a bus to Lefkes and walked the town.
- Where to stay: The family-run Eleni Rooms (where I loved their restaurant for breakfast and lunch) or the Ayeri Hotel, also small, personalized and with a gorgeous outdoor courtyard.
- Where to eat:
- Dionysos with its luxe garden vibe
- Kastro Art Lounge, perched on a hill so you can see the sea (and the sunset)
- The Secret Garden Bistro at Eleni, a hidden low-key gem run by the same family behind the hotel.
Crete

Here’s where I wish I did more research before I went. Every article I read before we plotted our trip made Crete seem to be “the” happening island. It definitely has a lot – an amazing botanical garden (you’ll need to drive to), an Old Town full of maze-like streets worth exploring, gorgeous beaches and Knossos, the old center of the Minoan civilization which contains the ruins of the Palace of Minos (worth seeing if you like ruins but also a drive).
That said, Crete is big. And while I like exploring new places and particularly enjoyed the island’s Old Town – we stayed in Chania, the area I suggest for first-timers – the island, as a whole, didn’t give me the traditional Greek experience of Paros or Santorini would have. It just felt too large and city-like.
There are some highlights including, as I said, Old Town and the beaches. Because Crete is so large, you really need a car – -something I didn’t want to have to rely on – as public transportation is unreliable. And the Botanical Garden, beaches and Knossos are a drive away..
Another popular day trip is to Balos Beach, known for its crystal-clear turquoise waters, exotic pink sand, and rugged coastal cliffs. It’s a long day there and back which was fine, and it’s definitely remote and pretty. Just pack snacks and water; there are no real facilities on the beach.

- Where to stay:
- Cretan Dream Resort & Spa (my stay here was comped): best if you want something outside the city with a resort feel, a large pool and a beach across the street
- Monastery Estate Venetian Harbor: best if you want to stay in Old Town. This 16th century former mansion of a Venetian nobleman has an excellent restaurant.
- Where to eat:
- Worth Visiting: Head to the Botanical Garden where you can walk among lush plants and enjoy the lovely restaurant.

Mother/Daughter Travel Tips
The age of your child will determine the activities and meals you plan. Since I traveled with my adult daughter, these are my recommended tips.
- Communicate clearly what each of you wants out of the trip before you know from the get-go what each of you want.
- Plan for time apart. Five or seven or 14 days together all day/every day can be a lot which is why you both need to map out your own activities or plan for alone time at your hotel.
- Compromise. Maybe she wants an early dinner while you prefer shopping or one of you wants a beach day. Again, discuss each other’s expectations. I told my daughter a sunset dinner was important to me and that I cared more about the view than the food so we chose a place with mediocre food one night and the next found a spot with better food so we both were happy.
- Be flexible. Leave some of your plans open-ended. Also be aware that the sun is strong here meaning it’s best to do things early in the day or later and take the afternoon for lunch or to rest or swim/cool off.
- Enjoy each other – and each moment. Even though it may be a lot of togetherness, reflect on how lucky you are to be together and be on this vacation. Research from Harvard Medical School suggests mother/daughter trips can help relieve stress, boost your immune system, and decrease the risk of heart disease.

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