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How to Island Hop in Greece This Summer

Krista Nannery

The best vacation I ever had was island hopping by myself in Greece back in 2018. I started in Mykonos and then visited Paros, Antiparos, Naxos, and Koufonisia. (I have so much love for Koufonisia. I will never forget my stay here because Anthony Bourdain died while I was in Koufonisia.)

While some will say that it’s too late to island hop in Greece this summer, I will tell you that it’s not too late. If you do it right!! Talk to me. We’ll figure it out.

The key, IMHO, is finding a package. Don’t try to do it yourself!! With short-notice, sometimes a nice packaged product is what you need. (Greek ferries are a law unto themselves. It helps to have someone take care of all these details for you.)

Here are some great Greece itineraries for this summer. I’ve included four packaged itineraries and four private itineraries. The packaged itineraries come at a great price and give you plenty of downtime for exploring independently. The private itineraries can be tailored to your liking.

If any of these look good, please support a small business and reach out to me. I would love to help you with your trip. And if you don’t see something you like, contact me too! I can do all different types of Greek itineraries!

Greece Island Hopping Packages

Mykonos and Santorini can get eye-wateringly expensive in the summer months. So a package tour, where everything is pre-booked in advance, can be a really great way to experience the islands. These tours offer a good combination of group tours and downtime so you can do your own thing. Ready to book a Greek holiday? Book a complimentary vacation consultation here.

Greek Isles Yacht + Bike Tour: Sail to Kos, Symi, Bodrum + Beyond (8 Days)

I love this itinerary because it hits some lesser known islands and also includes Turkey. Cruise aboard a yacht to the neo-classical town of Symi, volcanic island of Nisiros, and lesser-known islands in between. Discover ancient sites with a lasting impact on modern society, from the Asclepion of Kos to the Mausoleum at Halicarnassus. Dine on Mediterranean fare prepared by your private chef, including vine-ripened vegetables, handmade cheese, local honey, and fresh-caught seafood. Experience a spectrum of natural beauty in a single day, biking to the lip of an active volcano before swimming in the Aegean Sea.

Sailing Greece - Mykonos to Santorini (8 Days)

Sightseeing while surrounded by vivid turquoise waters and some of the southern Cyclade’s lesser-known islands doesn’t sound too shabby, does it? Let’s add filling up on flavourful Greek food and wine in local villages, exploring historic ruins, and relaxing on picturesque beaches into the mix, and we’ve left shabby behind in our yacht’s wake. Straight ahead to sailing perfection captain (well, skipper). Explore the beautiful southern Cyclades by sailboat, stop at small off-the-beaten-path islands along the way, relax on white-sand beaches, try your hand at sailing (or just relax on the deck), stroll through local villages and sample traditional Greek food and wine

Greek Island Hopper, Classic Group (10 Days)

Set sail to Greece's most beautiful islands during this 10-day guided tour. Let a Local Expert show you Athens’ ancient Acropolis and Parthenon before setting sail for the crescent-shaped island of Santorini. Here, enjoy views of the caldera from your hotel’s pool, then toast with your fellow travelers to an unparalleled sunset over the Aegean Sea. Later, join a local geology expert to learn about how the volcanic island was formed. On Mykonos, a Local Expert will guide you in a walk of the island’s narrow alleys and iconic Cycladic houses followed by a private tasting of local delicacies. Plus, you’ll meet a Greek captain and board a vessel for a cruise along Mykonos’ stunning coast.

Greece Island Hopper (11 days)

In Greece, discover a place where age-old legends and monuments intertwine with warm sunshine and island-style living. Tour Athens with a local guide. Explore the Acropolis, home to the famous Parthenon and the city’s best lookout. Enjoy three days at leisure on the island of Mykonos, an Aegean paradise of sandy beaches and bustling energy. Uncover the past at the excavation site of Akrotiri. Make the most of a free day on the picture-perfect island of Santorini. From to the ruins of Athens to the bright rooftops of Mykonos and Santorini – embrace the country at its best.

Private Greek Island Hopping Packages

Sometimes you just want to do your own thing. Here are some great private Greek packages that can be customized to you. Ready to customize a Greek vacation? Book a complimentary vacation consultation here.

An Ultraluxe Private Yacht Journey to the Greek Islands

Charter a private yacht in Greece for a luxurious island hopping adventure in the Cyclades Islands. Begin in Athens, the birthplace of Western civilization where you will visit ancient highlights such as the Acropolis, the Museum of the Acropolis, and the ancient Agora. Then, board your luxury yacht in Athens’ port and cruise towards the Cyclades Islands. Spend the following days hopping from island to island where our expert team members will be awaiting you, disembarking for a variety of active adventures, sightseeing, and immersive experiences. While private yachting in Greece, visit popular islands such as Mykonos, known for its lively beaches and active nightlife, and Santorini, for a magnificent sunset hike around the caldera. You will also have the chance to explore islands that are less frequently visited. Stop at Polyaigos Island to swim at deserted beaches, enjoy a delicious dinner at a local tavern in Milos, and wander through the most impressive caves in the Little Cyclades. Along the way, there will be plenty of opportunities for swimming, snorkeling, and relaxing aboard your luxurious yacht. We’ll handpick the vessel based on the needs of your group, and all luxury yachts are fully staffed with an attentive captain and crew.

Off-the-Beaten-Path Cycladic Islands Greece (10 days)

Many of the Cycladic islands are popular holiday destinations known for their beaches, ancient sites, rugged landscapes, and traditional blue-and-white-stucco towns overlooking the sea, Santorini, and Mykonos being the most renowned. However, this island group is filled with off-the-beaten-path possibilities that perfectly combine exclusive accommodation choices, immersive tours and activities, and of course, plenty of unforgettable photo opportunities. Choose between a 10, 11, and 12-night stay with an option to add 1 additional island (Paros or Folegandros) for 12 night stays.

Athens & the Cyclades - Private Luxury Greece Tours (11 days)

An exclusive private tour of Greece for the most discerning luxury traveler, experience stunning landscapes and in-depth cultural touring on this private luxury tour of the top highlights of Athens and some of the most memorable destinations and dramatic landscapes of the Cyclades islands, including Santorini and Milos.

Athens, Paros, Santorini & Crete (13 days)

Guests can experience historical and modern Athens, Mykonos' famous beaches and nightlife, romantic Santorini including a private sunset yacht cruise, and the sheer diversity offered in Crete. Customizing a stay on a private yacht is an exhilarating way to explore the lesser known islands with complete flexibility and unparalleled relaxation. Greece's diverse mainland and islands are available to discover–let’s start planning today!

About Krista

I’m a Notre Dame grad and a Chicago Booth MBA. I spent over 11 years living and working in London, England, selling financial data. My career and personal travel have taken me all over the world. To date, I’ve been to 78 countries. Now I bring the joy of travel to others. Let me make your next vacation seamless for you.