Greece boasts hundreds of islands, which can make choosing the best to visit a daunting task. However, with the right planning, you'll know whether a day trip to the historic isles of the Saronic Gulf or a couple days lazing on the sands of Santorini and Crete is the perfect vacation for you. Or combine locales to get the most out of this region's beaches, food, nightlife, and ancient ruins.

Planning Your Trip to the Greek Islands

Beyond the famous islands mentioned above, there are others you might have heard of, including Milos, Paros, Corfu, Cephalonia, Zakynthos, Skopelos, and the list goes on and on. Each is a desirable destination in its own right, and each offers attractions that appeal to certain types of travelers. Many are renowned for gorgeous beaches while others make a great stop for food and wine tours. Some are home to ancient villages while others draw crowds for their nightlife scene.

The answer to the titular question regarding how long to spend in these islands wholly depends on you: your personality, interests, and timeframe. These criteria will determine whether you’ll get the most out of a brisk two-day trip or an island hop that takes a week or more. Not to worry, because below you’ll find expert travel advice to cover any Greek-isles itinerary, no matter how long or short.

And if you’re curious as to the best times to visit Greece to maximize the sunshine, then take a look at this mini-guide.

1-2 Days in the Greek Islands

There are no cars on historic Hydra

Yes, it’s possible to enjoy an unforgettable slice of Greek island life in just one or two days. However, to get the most out of this limited time you should focus on the logistics of transport, arrival, and departure, as well as laser in on the one island above all else you simply must visit. The easiest access from Athens, and thus the best bet for a quick 24-48-hour trip, would be one of the islands of the Saronic Gulf.

There are some amazing historic sites on Aegina, which is accessible via a 40-minute ferry ride from the port at Piraeus, just outside Athens. Come here to visit the lovely beaches and tour the historic landmarks like the Temple of Aphaia and the Monastery of St. Nektarios. Foodies will love that Aegina grows some of the most delicious pistachios anywhere.

If you have an eye toward a romantic getaway or even a brief honeymoon, consider the island of Hydra. Its stone port town makes quite the first impression as it's positively castle-like. There’s also a peacefulness here due to the fact that no cars are allowed on the island. That tranquility makes walking the waterfront at sunset the perfect way to end a romantic day in Hydra. 

Then there's Spetses. Located on the west end of the Saronic Gulf off the coast of the Peloponnese Peninsula, this island also boasts a romantic, well-preserved old town situated at its port. Take a romantic walk along the glimmering waters or go all out with an unforgettable horse-drawn carriage ride from town.

If you don’t mind rushing, you could spend one night each in two of these locales or combine them with a jaunt to the Peloponnese. It's a great opportunity to enjoy a food tour plus visit incredible locales like the historic port town of Nafplio. Perhaps see Olympia, where the first Olympic Games were held in the 8th century. Also incredible are the archeological remains of the ancient Greek military stronghold, Mycenae.

3-4 Days in the Greek Islands

 Elafonissi Beach, Crete

3-4 days is a timeframe where you can really stretch those legs and relax. And you won’t have to rush in order to get the most out of the experience. It's also the perfect length of time to discover one of Greece’s most famous islands.

A great option is a three-day tour of Santorini. Located in the Cyclades archipelago and known for its volcanic landscapes, there are great sunset/sunrise views from the lip of its caldera in whitewashed villages like Oia. The gorgeous scenery is in addition to the inviting beaches near the capital of Fira, like the black sands at Perissa. There’s all that great wine, too—particularly the island's flagship Assyrtiko, a full-bodied white wine with a mineral and citrus flavor profile.

Then there’s Crete. This “island for all seasons” is a dream any time of year and has it all: turquoise waters, white-sand beaches (head straight to Balos Beach, on the north of the island), ancient archeological sites (think the Palace of Knossos, which dates to 1450 BCE), and great hiking in the White Mountains. If you do come here, head to the bright pink sands at Elafonissi Beach. There’s nothing quite like it anywhere in the world.

Last but not least, you could choose Mykonos, another Cyclades isle. Smaller than Crete (you can get from one end to the other in less than half an hour), it's a good place to go for history and culture—ok, and its world-class nightlife, upscale restaurants, and glitzy beach clubs. Definitely try the fresh seafood in Mykonos town and tour the ancient temple ruins at the adjacent isle of Delos. For the utmost in sandy fun, visit the bars and clear waters fronting Paradise Beach.

5-7 Days in the Greek Islands

Consider an escape to Naxos

With around a week to spare you can treat yourself to a famous highlight like the big three islands mentioned above plus discover the Cyclades highlights like Santorini and Mykonos. That said, thee other great islands in this archipelago that make great additions to any vacation itinerary. 

Possibly start with Syros. With its amazing views, beautiful port town of Ermoupoli, and medieval village of Ano Syros, it's like a mini Mykonos—minus the crowds. There's also Tinos, known for the whitewashed homes of its historic seaside villages. Interestingly, for the last 300 years Tinos has been a hotbed of marble craft, which you can see on the famous "marble trail" that links various towns. 

You certainly won't want to miss Naxos, the largest of the Cyclades group. Justifiably famous for its food (try the Naxos roosters braised in red sauce) and beautiful beaches (re: Agios Prokopios Beach and Plaka Beach), here you can get the best of the Greek isles without so many tourists. Naxos town, the main port village, features romantic white-washed homes fronting the water. A great activity here is to pull up a seat at a patio café and while away the hours admiring the Venetian architecture. 

With up to seven days you’ll also have the option to stay longer on one island. One idea is to really get to the heart of Crete. Sure, you can see the highlight beaches in a couple days, but with more time you can venture deeper, touring the charming coastal villages and historic Venetian towns. Perhaps take a food tour and sample artisanal olive oils while imbibing in the local vino. Then cap the trip with a hike through Samaria Gorge, a World Biosphere Reserve and the longest gorge in Europe. 

8+ Days in the Greek Islands

Instagram and Syros go hand in hand

With eight days you can really start playing with combination trips to different islands. Maybe go for two popular options like Mykonos and Santorini but also combine them with Naxos, where you can unwind away from the tourist crowds and enjoy some authentic Greek hospitality in the form of great food and drink.

If you’re the type who keeps your Instagram account close while on holiday, consider not just the beautiful caldera sunsets of Santorini and the beaches of Crete, but the throwback villages of Syros as well. Pics of these locales are guaranteed to send your social media followers into the throes of daydream wanderlust.