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Putting together all the pieces of a Greek vacation can be daunting to even the most seasoned of travelers, let alone those with children. Each of the more than 1,000 islands in the Greek archipelago has its own character and attracts wholly different sets of tourists. Choose the wrong island or the wrong hotel, and you could find yourself marooned among frat boys or throngs of German retirees.
Then, there are the logistics of timing and transportation — how long do you want to stay and how will you get there? The key to planning a Greek holiday with the family is to keep it simple. Resist the temptation to see all the islands at once. Selecting one or two islands, with an optional layover on the mainland, is the best way to keep costs low, maximize time and to stay sane.
That said, we've chosen our top five suggestions for their relative ease of access (each can be reached by plane or ferry from Athens or other European hubs); their family-friendly locations and amenities; and their reasonably-priced lodging options. While you may have to dispel romantic notions of yachting around à la Ari and Jackie O, you need not put a Greek isle hop on the backburner until your kids have finished paying their college loans. — Melanie Mize Renzulli
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Santorini
Although much of Santorini is overrun with tourists, it's a must for any first-timer to Greece. This Cyclades isle's postcard-perfect whitewashed homes and blue-domed churches cling to a caldera, the result of an ancient volcanic eruption. In fact, the still-active volcano (and its aftermath) now shapes many of the family-friendly activities available on the island. From volcano hikes to building sandcastles of black sand, Santorini is a beach holiday with a twist. You can even visit Akrotiri, a Greek version of Pompeii, where Minoan buildings and frescoes have been unearthed. 
Although much of Santorini is overrun with tourists, it's a must for any first-timer to Greece. This Cyclades isle's postcard-perfect whitewashed homes and blue-domed churches cling to a caldera, the result of an ancient volcanic eruption. In fact, the still-active volcano (and its aftermath) now shapes many of the family-friendly activities available on the island. From volcano hikes to building sandcastles of black sand, Santorini is a beach holiday with a twist. You can even visit Akrotiri, a Greek version of Pompeii, where Minoan buildings and frescoes have been unearthed.
Santorini has a reputation as a hotbed of hedonism, making areas such as Fira (the main town) undesirable for travelers with kids in tow. Furthermore, the cliff-side dwellings that have made the island so famous can be a bit scary for parents with little ones. Thus, a family's best bet for enjoying the island is a stay along the black sand shores of Perivolos Beach. Marillia Village, an attractive new boutique property within steps of the beach — and a kiddie pool — sports the typical Aegean architecture but without the rowdy crowd.
Marillia Village, from €145
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Rhodes
Situated at the crossroads of the Mediterranean and Aegean Seas and just eleven miles from the coast of Turkey, Rhodes has been of strategic importance to invaders for thousands of years. Just about every empire, from the Roman to the Ottoman, has left its mark here. The island is particularly notable for its Crusader-era fortifications — in fact, its medieval Old Town could easily stand in as a backdrop for a Harry Potter film.
Situated at the crossroads of the Mediterranean and Aegean Seas and just eleven miles from the coast of Turkey, Rhodes has been of strategic importance to invaders for thousands of years. Just about every empire, from the Roman to the Ottoman, has left its mark here. The island is particularly notable for its Crusader-era fortifications — in fact, its medieval Old Town could easily stand in as a backdrop for a Harry Potter film.
Travelers from all over the world invade the Dodecanese capital these days to take advantage of its spectacular climate. Blessed with approximately 300 sunny days per year, Rhodes boasts some of the best weather in Europe, thereby making it a year-round holiday destination.
As one of the largest and most popular Greek isles, Rhodes is rife with plenty of anonymous hotel complexes catering to package tourists. Hotel Dionysos, on the other hand, offers family-friendly amenities, such as connecting rooms and a kids' club, but in a sophisticated setting. If Dionysos' grand swimming pool, live music, and numerous sporting opportunities fail to entertain, however, then the heart of the Old Town is a short cab ride away.
Hotel Dionysos, from €115
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Poros
Few cities are as revered and reviled as Athens. With the lure of the islands beckoning, the home of the Acropolis is little more than a necessary blip on the itinerary for most tourists to Greece. It is for this reason that Poros, a small island in the Saronic Gulf, is so appealing. Less than one hour from Athens by ferry, Poros is close enough to the capital to take in the sights yet far from the urban commotion that can make traveling with small kids unbearable.
Few cities are as revered and reviled as Athens. With the lure of the islands beckoning, the home of the Acropolis is little more than a necessary blip on the itinerary for most tourists to Greece. It is for this reason that Poros, a small island in the Saronic Gulf, is so appealing. Less than one hour from Athens by ferry, Poros is close enough to the capital to take in the sights yet far from the urban commotion that can make traveling with small kids unbearable.
Its calm waters and sheltered bay have also made Poros a place where beginners can learn all sorts of water sports. So, after dragging the kids around to architectural ruins, you can appease them with several afternoons of snorkeling or sailing lessons. Saga Hotel and Studios, located on Askeli Beach and a short walk from Poros town and the port, offers apartments equipped with kitchenettes. But, if you don't feel like cooking while on vacation, you can dine in the hotel restaurant, which features organic products from the owners' farm, or at one of Askeli's many lively tavernas.
Saga Hotel and Studios, from €150
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Corfu
If you can't quite commit to a Hellenistic holiday, the easiest way to get a taste of Greece is to head to Corfu. Accessible from several Italian cities via ferry, Corfu has a cultural, culinary and architectural heritage that is largely influenced by past rulers from Venice, France and Britain. Nevertheless, this Ionian island is thoroughly Greek. Gods and heroes of Greek myth, including Poseidon, Hercules and Jason, figure into Corfiot lore. Parts of Homer's Odyssey are even set on Corfu's shores.
If you can't quite commit to a Hellenistic holiday, the easiest way to get a taste of Greece is to head to Corfu. Accessible from several Italian cities via ferry, Corfu has a cultural, culinary and architectural heritage that is largely influenced by past rulers from Venice, France and Britain. Nevertheless, this Ionian island is thoroughly Greek. Gods and heroes of Greek myth, including Poseidon, Hercules and Jason, figure into Corfiot lore. Parts of Homer's Odyssey are even set on Corfu's shores.
History lessons aside, Greece's westernmost outpost is also its greenest and most temperate. Abundant with olive groves, vineyards and citrus orchards and fringed with pebbly beaches and coastal lagoons, Corfu lays claim to some of the most stunning natural scenery in the Mediterranean.
Of course, with such a pedigree, Corfu has seen an overdevelopment of many of its beaches. But a stay at Fundana Villas, a converted Venetian mansion near hiking trails and horse stables, will put your family within reach of Paleokastritsa, the gorgeous beach where Odysseus touched down, and in touch with Corfu's illustrious past.
Fundana Villas, from €100
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Chios
A Greek island unspoiled by mass tourism is a rarity. But pick almost any island in the Northeast Aegean and you will find near-empty beaches and downtowns populated with more natives than tourists. Chios, with its dusty villages, mastic tree farms, and Byzantine structures, especially those in Pyrgi and Nea Moni, has an air of crusty authenticity that's increasingly hard to find in the rest of the archipelago. This small town feel is what drives many families to vacation here year after year.
A Greek island unspoiled by mass tourism is a rarity. But pick almost any island in the Northeast Aegean and you will find near-empty beaches and downtowns populated with more natives than tourists. Chios, with its dusty villages, mastic tree farms, and Byzantine structures, especially those in Pyrgi and Nea Moni, has an air of crusty authenticity that's increasingly hard to find in the rest of the archipelago. This small town feel is what drives many families to vacation here year after year.
Parts of Chios are, indeed, bucolic. But, with its position across the strait from Çesme, one of Turkey's most fashionable resort towns, Chios is not without its comforts. The unassuming but chicly outfitted Erytha Hotel & Resort in Karfas overlooks its own private beach and also has a pool and games to keep kids busy. Should you want to take the family on a sightseeing excursion around the island, you can rent a car at the desk or leave the kids in the care of the on-site babysitter.
Erytha Hotel & Resort, from €136
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