Where to go

Firstly, don’t overdo it! On your trip to Greece in September, take the time to enjoy your surroundings, learn the history with a guided tour of ruins, or just relax on the beaches. Especially on your first trip, don’t try to squeeze too many islands in. That being said, when it comes to Greek islands, you've got some awesome choices!

Santorini is all about the striking village of Oia with white buildings with blue domes and those epic sunsets. Totally perfect for a romantic trip or a luxurious escape! There is even wine tasting on the island.

Mykonos, on the other hand, is the ultimate party island! Crazy nightlife, beautiful beaches and a super cool old town, perfect for all you party animals out there!

If you're into history and culture, Crete and Rhodes are the way to go! Crete has diverse landscapes and loads of history to explore, while Rhodes boasts amazing medieval architecture and ancient ruins. Both are larger islands that offer much more than beaches if you want an active trip to Greece in September.

For a more laid-back vibe, check out Corfu, Naxos or Paros. Corfu's got lush greenery and cool Venetian-style buildings, Naxos has beautiful beaches and ancient ruins, and Paros is all about chill vibes, water sports and yummy food.

Zakynthos, or Zante as some call it, has Navagio Beach or Shipwreck Beach, which is a total paradise with crystal-clear waters and jaw-dropping sea caves (although the beach closed this summer of 2023 due to falling rocks, you can still see it by boat).

Lastly, did you know you can go to Greece in September and not visit any islands? The Greek mainland can be quite an interesting trip all in itself. You can even stay in Athens and think about doing day trips from there. The mainland is rich in ancient history, historic sites and culture. Not to mention breathtaking landscapes and beaches!

How to Island Hop

While an island-hopping itinerary sounds exciting, let’s talk about the best ways to get around. You have options.

Greece is known for ferries, including its fast ferry or hydrofoil. If you like to spend time on the water, but don’t have the all day to cruise around on a ferry, talk to your travel advisor about travel times. I should mention, these Greek ferries are notorious for not staying on schedule. Islands by boat are much further than you would think by looking at a map. While riding on a fast ferry may save time, you are not allowed to go outside to enjoy the fresh air. Especially if you are thinking about upgraded tickets, you may want to just travel by air. Domestic flights between islands tend to be the best way to go. Yes, there is security at airports, but remember to weigh out your options.

Of course, if you love boats, but don’t love unpacking every time you go to a new island, consider a cruise. If you are thinking that a cruise isn’t for you, check out Virgin Voyages. Yes, Virgin has ships and they just started with Greek itineraries! An itinerary that includes Greece in September would show you the best Greece has to offer on your stops without the massive crowds of Summer. Virgin Voyages is an adult-only cruise line with plenty of entertainment, wellness including work-out areas, and a spa with sauna, delectable food options and no one to tell you when your mealtime is. This is how fun adults cruise.

For those restaurants that are more difficult to make a reservation, going to Greece in September may help you get a table a little easier! Here are a few options to get your taste buds watering.

Kastros in Mykonos: Revel in a contemporary take in Greek cuisine by the water in Little Venice, the most picturesque area of Old Town.

Balthazar in Athens: Renovated neoclassical building in the city center with a place known for its enchanting garden setting.

Ammoudi Fish Tavern in Santorini: Scenic restaurant framed by red volcanic rock, with a relaxed atmosphere, steps below the charming town of Oia.

M-eating in Mykonos: Located in town, in a traditional building for those who are looking for more sophisticated dining options.

OiaGefsis in Santorini: Go to the Sunset Bar for drinks with a romantic atmosphere and unobstructed sea views during golden hour.

Karma in Santorini: Located in Oia, this restaurant offers vegan-friendly options, and the food is always made of fresh, local ingredients.

The Clumsies in Athens: Making the Top 50 Best Bars list, this is an all day bar with multiple levels and indoor and outdoor space, that will turn from a chill vibe in the day to a party at night.

Black Rock Restaurant in Santorini: Yet another Oia restaurant, but this is you high-end choice, with of course, breathtaking views of the volcano.