The islands surrounding Greece offer the kinds of experiences that holidaymakers crave. Whether you’d like to sample the local cuisine, hike through the countryside, lounge on the deck of a yacht while taking in the sparkling azure sea, or perhaps all of the above, the chances are that there’s a Greek island that’s right for you.

To select the right destination, you’ll need to pick out an island that aligns with your preferences. But exactly what might this mean?

Greek Island Hopping or Single Island Stay

Your holiday plans might start with a simple decision. Are you going to stay in one place, or are you going to move between them? The former approach means less travel time and less disruption. You’ll spend more of your holiday actually relaxing. The latter approach, on the other hand, means you’ll get a more varied experience – and the sense of adventure that comes with knowing there’s a new destination just around the corner.

There are countless villas spread across these islands, so wherever you stay, there’s sure to be somewhere to accommodate you. However, the more destinations your itinerary includes, the more planning and advance booking you’ll need to do.

Ambience and Activities

Your choice of island adventure should be informed by your preferences. If you’re looking for a bouncing nightlife, then a larger island like Corfu or Rhodes might be worth considering. On the other hand, if you’d like more seclusion and relaxation, then a tour of the smallest islands might be preferable. There are more than six thousand to choose from – and so it’s worth looking past the major ones.

If you have a particular activity in mind, it’s worth picking out an island that suits it. For watersports, you might consider Paros, Naxos, and Mykonos. All three are famed for their windsurfing. The region enjoys favourable wind throughout the year, making it perfect for this particular activity. If you are looking for more must do activities in the Greek islands you can find more inspiration in my earlier article.

Budget and Travel Style

You’ll also need to think about how much you’re going to be spending and how much luxury you’re going to be splashing out on. Hotels, villas, and apartments are available for travellers on just about every kind of budget – but generally speaking, the more travel you’re doing between the islands, the more you’re going to end up spending.

Time of Year and Weather

One excellent way of reducing the overall cost of your trip is to prefer the so-called ‘shoulder’ seasons. These are the times of year when summer hasn’t quite arrived. Consequently, the weather might not be quite as balmy, and the sea breeze might have a distinct chill to it – but you’ll avoid the crowds, and your costs will be lower.

Crete has among the warmest winter weather in Europe, at around 15-16°C. The same goes for Rhodes, which is almost deserted at this time of year. This makes winter an ideal time to explore historic parts of these islands, like the famous Old Town in Rhodes.

Accessibility and Transportation

One thing you’ll need to consider is the possibility that your travel plans will be disrupted by cancellations. You might get around this by being as flexible as possible. Think about car rentals, taxis, and buses. You might even think about chartering your own yacht if your budget allows for it. This has the advantage of allowing you to tour multiple islands without the hassle of unpacking. For the same reason, a cruise ship is also a great option.