What You Need to Know About Island-Hopping In Greece

With constellations of nearly 6,000 islands and islets scattered in the seas surrounding Greece, island-hopping here requires somewhat of a strategy. An easy way to visit some of the more infamous isles while discovering a few less-talked-about spots? By cruise. The downside, though, is limited time in port (and by limited, we mean you’ll be lucky if you have the day). 

Athens is the main entry point to the islands, so plan to start there for a night or two to sleep off jet lag and stroll through sites like the towering Acropolis, whose temples and theaters date back to the 4th century B.C.E. The nearby Acropolis Museum houses artifacts found on the Acropolis slopes and sculptures from the Parthenon. Get a taste of modern Greek fare on the terrace at Seychelles, a local favorite in the Keramikos neighborhood, before calling it a night in one of the city’s newer hotels nearby, like the minimalist-chic Moxy Athens City, housed in the old city courts, or The Foundry,  which boasts 12 industrial-style suites located inside a former 1930s-era font foundry. (Here, the rooftop garden and its Acropolis-facing view are also one of the city’s best secrets). 

From the main port in Athens, Piraeus, Saronic Gulf islands like Hydra and Poros are less than a two-hour ferry ride away. But, if you don’t mind settling in for a longer trip or hopping on a short flight, you’ll be in the Cyclades, known for their blue-domed churches and whitewashed villages that have become a honeymooner’s dream. Pair these charmers with the largest island in Greece, Crete, which sits at the crossroads of three continents (and arguably produces some of the best cheese and olive oil in the country), and you have the recipe for a perfect vacation spent island-hopping through Greece. 

Ahead, everything you need to know about island-hopping through Greece so that you can plan an amazing trip.

Santorini

Santorini’s capital city, Fira, hangs hundreds of feet over the Aegean on the edge of the crescent-shaped caldera. A four-hour walk along the “Caldera’s eyebrow,” or the balcony of Santorini, takes you past some of the island’s most scenic villages to the sunset hotspot of Oia. The town is home to cave homes and cliffside hotels like Mystique, a Luxury Collection Hotel, where maze-like cobbled paths connect 41 suites and villas with private pools and jacuzzis looking out to the active volcano that helped shape Santorini thousands of years ago. Dine at French chef Olivier Campanha’s modern Mediterranean eatery, Lure, whose al fresco tables dot the side of the caldera cliff, or make your way down to the water for sunset at Ammoudi Fish Tavern, which sits 300 steps below Oia in a tiny fishing harbor. Across the island, Istoria shows off a very different side of Santorini. The former mansion and its five stables now open up to 12 design-savvy suites looking out at the ink-black volcanic Perivolos Beach.

Mykonos

Mykonos is known for its bohemian beach clubs and swanky, Ibiza-esque parties on the sand. While Mykonos Town gets crowded — especially when cruise ships roll in — the capital’s marble streets are worth strolling around (If you’re looking to shop, Matoyánni Street is the place.). Scorpios, on the southern tip, is considered one of the island’s best beach clubs — and the restaurant is just as much of a scene — but one of the popular eateries to open in the center of town, Nōema, serves up new Cycladic cuisine in a hidden courtyard where international DJs and performers keep the party going post-dinner. For something on the quieter side, book one of the 40 rooms, suites, or villas at The Wild Hotel by Interni, which is designed amphitheater-style on a cliffside around a small cove with loungers and thatched umbrellas lining the golden shore.

Crete

On the northeastern side of Crete, the birthplace of Zeus, sisters Agapi and Costantza Sbokou are the design masterminds behind one of the island’s most lauded design hotels: Blue Palace Elounda, a Luxury Collection Resort. The 143-acre property cascades down the hillside and spills out along the sea in front of Spinalonga, the UNESCO World Heritage Site-nominated island with a 16th-century Venetian fortress that was home to Europe’s last leper colony. The resort’s traditional wooden caique leaves right from the hotel dock on day trips to the island and nearby coves, which are only reachable by boat. Recently, the property introduced its hotel-within-a-hotel concept of private villas inspired by Mediterranean homes with infinity pools overlooking the Aegean. While the locale is certainly a draw, so is the dining: At gastronomic restaurant Anthó, Cretan classics are reimagined with a more elevated approach enhanced by ingredients sourced in the on-site garden. Meanwhile, at the seaside Blue Door, an old fisherman’s stone house opens up as a Greek taverna serving family recipes and seafood dishes like salt-baked fish with homemade salsas. 

In the northeast coastal town of Malia, the Sbokou sisters also worked with Greek architect Vana Pernari to transform the former campsite of Cretan Malia Park into a boho-chic beach hideaway just a few minutes from major ruins like the Minoan Palace. Rooms here are outfitted with oversized macramé chandeliers and LRNCE ceramics and are surrounded by gardens that extend to the beach. If you’re traveling with children, consider the family-friendly bungalows, which feature a separate kids’ room with a bunk bed. Also, there's even a Little Explorers Kids’ Club and an exclusive area for teenagers, ensuring everyone is entertained throughout the stay. Lastly, the island’s UNESCO-protected food heritage is put on prime display at on-site eateries like Mouries, where chef Lefteris Iliadis incorporates vegetables picked from the hotel garden and roasts meat and fish over an open fire in an outdoor kitchen.

Paros & Antiparos

Paros and its smaller sister island, Antiparos, draw the jet-set crowd minus the flash. Celebrities stay in private villas on laid-back Antiparos, which sits less than one nautical mile from Paros (ten minutes away via ferry). Greek luxury villa rental company The Thinking Traveller (formerly White Key Villas) is an excellent option for those who want white-glove service (plus custom-tailored excursions, private chefs, and spa services); however, for something that feels nearly as exclusive — but at a more wallet-friendly price point — book one of the 16 private homes at The Rooster, which sprawls across 30 acres of rocks, ruins, and dunes above untouched Livadia Beach. The recently opened Cosme, a Luxury Collection Resort, which features 40 seafront rooms along Agioi Anargyroi Beach, is just a seven-minute walk from the whitewashed fishermen’s village of Naoussa, the heart of the island’s bar and restaurant scene. Don’t miss farm-to-table Mario, which spills out into Naoussa’s main square, and be sure to stop for a nightcap upstairs at the lively cocktail bar, Somaripa Consolato.

Getting Around 

While major European cities like Paris and London offer direct flights to islands like Santorini, Mykonos, and Crete (often on budget airlines like Wizz Air or easyJet), Athens is the main entry point to the islands. A high-speed catamaran ride from Athens (Piraeus) to Santorini takes between four and five hours; from Santorini to Crete or Mykonos, the ride is about two hours. It's worth noting that the ferries can book up fast in the summer months, so it’s better to reserve your tickets in advance. Flying is also an option between some of the islands, but not all flights are direct; between Crete and Mykonos, for example, you’ll have to transfer in Athens.

Cruising the Greek Isles

Cruise ships of all sizes and styles visit ports throughout the Greek islands, so you can opt for a variety of tours through the Aegean that hit the main spots like Santorini, Milos, and Mykonos. A few top picks include the budget-friendly, Greece-based Celestyal Cruises, plus luxury lines like Regent Seven Seas Cruises and Windstar Cruises.

Also, the family-owned Variety Cruises offers a seven-night Jewels of the Cyclades aboard a 24-cabin, wood-paneled ship that visits some of the islands' smaller ports, including the uninhabited Delos (the birthplace of Apollo), the more off-the-beaten-path Folegandros, and sister islands Paros and Antiparos. Unlike larger cruise ships, the yacht-style Galileo is more affected by the Cyclades’ characteristically strong winds, so the itinerary changes with the weather. The experience is more of an expedition that may combine some islands with a portion of the Peloponnese, and the boat can access tiny coves and beaches that larger ships can’t.

Want to take that trip for free — and score some valuable miles for your next excursion? Check out our top pick travel credit cards for the best welcome bonuses, perks, and plenty of cash back.