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Classic Greek Islands Itineraries

As you might imagine, touring the Greek Islands involves some extent of water transportation, ranging from sailing, to small cruise ship touring, to large cruise line travel.

However, when browsing Greek Island tours you'll find there is an abundance of travel styles, itineraries, and activities to choose from. These range from active hiking and outdoor activity-packed excursions, to relaxing cruises filled with all there is to love about Greek culture, history, and food. Search through the 25 tour companies on Stride to find the perfect Greek Island trip for you!

Greek Islands in 1 Week

One week touring the Greek Islands gives you a taste of all the beauty the iconic region has to offer. Greek Islands tours lasting one week hit the main tourist attractions and historical landmarks the make up the Greek Islands.

Days 1-2, Athens: Explore the Panathenaic Stadium, where the first Olympic Games of modern times were held in 1896. Visit the famous ancient buildings of the mighty Acropolis.

Days 3-4, Santorini: Bask in the sun on the beaches of the famous island of Santorini, and explore the picturesque capital city of Fira. Don’t miss the iconic photo-op spot of the white and blue covered hills of Oia!

Days 5-6, Mykonos: Party it up in the lively Mykonos! Enjoy the sandy beaches and quaint town during the day, and dance the night away at a popular Mykonos party in the evening!

Day 7, Athens: Take a ferry to end your trip back in the historic Athens.

See all One Week Greek Island Tours & Trips »

Greek Island in 2 Weeks

Two weeks allows for a more thorough exploration of the magnificent Greek Islands. With two weeks’ time, you can explore all that the islands have to offer, while also including some historic tours and authentic Greek activities in your itinerary.

Days 1-2, Athens: Start your trip off in Greece’s capital city of Athens. Tour the ancient ruins of 5th-century BC landmarks such as the Acropolis and the Parthenon.

Day 3, Delphi: Explore the archeological sites of Delphi, including the 4th-century BC Temple of Apollo and Athenian Treasury.

Days 4-5, Kea/Delos/Mykonos: Explore the quaint island of Kea before sailing to the uninhabited archaeological site of Delos to tour the remarkable ancient ruins. Spend the night docked in Mykonos and enjoy the lively nightlife this island has to offer!

Day 6, Santorini: Venture to the most popular of the Cyclades Islands for a day to remember in picturesque Santorini! View the whitewashed buildings cascading over the cliffs overlooking the caldera.

Day 7, Rethymnon, Crete/­Knossos: The largest of the Greek Islands, Crete, is home to the ancient city of Knossos. Here you will explore the largest Bronze Age archaeological site, which is also considered Europe’s largest city.

Day 8, Kythira: Take a swim and enjoy the wonderful crystal-clear waters of Kythira. Soak up the sun on the beach for a relaxing Greek Island getaway day.

Day 9, Monemvasia/Nafplio: Located on a small island off the east coast of the Peloponnese, Monemvasia is a prominent medieval town with unique, well-preserved architecture. Explore the town of Monemvasia before sailing to the seaport town of Nafplio in The Peloponnese.

Day 10, Mycenae/Hydra: Tour the ­UNESCO World Heritage site, the striking ruins at ­Mycenae, before heading to the car-free, traditional town of Hydra.

Day 11, Piraeus/Athens: End your tour in the imposing, Athens, with a tour of the Benaki Museum and a farewell dinner to toast the end of a perfect trip.

See all Two Week Greek Island Tours & Trips »

Greek Islands Small Ship Cruises

Small ship Cruises are a great way to get an up close and personal Greek Islands experience. Many Greek Islands small ship cruises focus on adventure-packed island excursions and activities and exciting nightlife parties and dancing. These cruises usually explore the main sailing sights to see in the Greek Islands, lasting an average of 8-9 days.

Days 1-2, Santorini: Kick off your cruise in the wonderous, Santorini. Explore the caldera’s famous cliffs for a picture-perfect view.

Day 3, Ios: This island is most famously known for its nightlife and party scene. Enjoy a cocktail and dance the night away on the lively, Ios!

Day 4, Koufonisia: Explore this hidden gem and smallest island of the Cyclades. Experience the calmness and peace that the majestic beaches of Koufonisia provide.

Day 5, Naxos: Enjoy the rocky terrain and long stretch of beaches that the largest island in the Cyclades has to offer. Soak in the beautiful sunset in Naxos before embarking on your next destination.

Day 6, Paros: Famous for its water sports, have an active water day in Paros. If you’re more interested in a relaxing day, lay out on the beach before hitting the vibrant clubs at night.

Days 7-8, Mykonos: End your cruise in the most anticipated party destination in the Greek Islands. Experience all that the world-famous Mykonos nightlife has to offer!

See all Greek Islands Small Ship Cruises »

Reviews of Greek Islands Tours
86% Recommend

4.1 out of 5
Excellent 81 Great 54 Average 11 Disappointing 4 Terrible 16
4.1 Guide
4.1 Activities
4.1 Lodging
4.1 Transportation
4.1 Meals


Does Not Recommend

Sail in Greece SUCKS June 2019


YOLO CRUISE - Mykonos to Santorini

Here is a May 2019 review. I would not recommend this tour to anyone. Our group of 10 emailed the company post-tour explaining our dissatisfaction with the whole week, and they are taking absolutely no ownership of any issues. We asked for reimbursement/compensation. It was declined. Please don’t make the mistake of thinking that because the reviews are conflicting, that they have pulled their socks up and improved recently. The more reviews I read, the more I notice many reviews are suspiciously vague and too positive. I suspect those reviews might be fake.

My main issues are with the safety and cleanliness of the boat. There are absolutely no safety briefings as you board the ship and a lot of my group did not know where the life jackets were. This became relevant when we had awful weather that was throwing the boat around as if it was nothing, breaking the anchor/chain. The crew were telling us that it was quite normal to have rough seas but if that is the case, it makes sense to prepare the group for the possibility. We had to sail for 8 hours in the night and we all had no idea what to expect or do. Things were smashing, broken glass everywhere, you could not stand or even sit without being thrown out of your seat. Communication from the crew was poor especially that night and would not have happened without our insistence.

The boat stinks. I absolutely refuse to believe that sailing boats normally smell like this. Vomit from seasickness and other human waste fermenting presumably in a septic tank is not something I had ever smelt before and hope never to smell again. This smell comes up through all the drains so it’s inescapable. The toilets were flushing with brown pooey water. Often you would find someone else’s poo in your toilet having made its way around all the pipes of the ship. It's horrifying. Oh, also I had a ‘functioning’ toilet. Half the ship did not so some of the group were literally holding in their poo until they got to land, so as not to make a big unflushable pile and make the smell worse. I didn’t know this until our final night on the boat. Many people bring the smell up when they review this tour and Sail In Greece state ‘no issues were reported by our staff’ every time. But based on what I saw, I doubt the crew are doing a daily updated check in with head office. For example: no toilet paper is allowed to go down the toilet, which is fair, but we were told the bins would be changed each day. My bin was changed once in 7 days. I doubt that if they give that few fucks about the cleanliness of the cabin bathrooms that they are doing daily quality assurance and reporting back on it. Oh and my ‘freshly made’ bed had a top blanket which had some crusty white stuff on it.

Things described on the itinerary are not likely to happen. Our itinerary described free ouzo, a night of unlimited cocktails, a private boat party with DJ. When we enquired about this, our tour guide had absolutely no idea. Because Niko was such a lovely guy I am reluctant to throw him under the bus but he is employed by the company and he should also be familiar with what has been quoted on the itinerary. Sail in Greece replied to our email saying "at no point did we say drinks are provided" but it absolutely read like that, otherwise we would not have expected it. For 10 separate people to interpret a statement the same way, you've used misleading words.

Sail In Greece have this disclaimer: ‘the itinerary is subject to change at the captains discretion or due to unforeseen circumstances’ but I think they use this to cover themselves to change things on a whim, things that are completely within their control. We are reasonable enough to understand that the weather can be unpredictable. But we lost two full days of activities and time on the islands due to a administration problems with them needing to get a new captain? It's frustrating beyond belief to be ready waiting to go and the crew can't tell you what is happening. And being stuck on the boat literally all day.

It was an absolute shitshow and if you read all that I am glad because it probably means you were quite seriously considering this trip. Don’t book with Sail In Greece.
Read more

Operator Sail in Greece


Does Not Recommend



Yolo Yachting - Mykonos to Santorini

"Itinerary" and "inclusions" are completely irrelevant. We were promised a DJ, unlimited cocktails, free shots of ouzo, beach parties, boat parties. They did not deliver on ANY of these promises. The biggest joke was the "unlimited cocktails" which they explained on the boat meant we could bring unlimited alcohol on the boat (that we purchase ourselves).

Our first captain who brought his feral dog on board (who pooped on the deck and bit the guests) was kicked off after 2 days and replaced with another captain. The two captains needed an entire day to figure out the transition and left us on the boat with ZERO communication about what was happening.

We all got off the boat a day early after the Captain snapped an anchor and we floated seemingly aimlessly in the water while everything came crashing down from the walls/shelves as the boat rocked violently from side to side. The crew were running around frantically, crockery and glass was smashed everywhere, we all thought the boat was going to sink and we hadn't been briefed on any safety procedures and had no clue where the life jackets were.

This YOLO cruise was absolute chaos, Sail in Greece refused to acknowledge our complaints and have really shown themselves to be total scam artists.
Read more

Operator Sail in Greece


Does Not Recommend



The Greek Islands

DO NOT TRAVEL WITH EF ULTIMATE BREAK. They do not value returning customers, they will not help you if your trip goes awry. I am really disappointed in this agency and how they handled my request for a partial refund for my trip due to things I missed because of their negligence. I just went on the Greek island getaway tour with them and spent $3000 to not get to visit the Parthenon and the acropolis when that was one of the most important things I was looking forward to. I tried to plan it on my own around the itinerary but was reassured we would visit it and we didn’t. Their customer service is awful and they don’t care whether you’ve been a customer for years. The whole trip was a disaster and they do not show any empathy for you. If you want to visit Greece you are better off planning it yourself. Don’t book with them. Read more

Operator EF College Break (EF Ultimate Break)



Such a Wonderful Company November 2018


Greek Island Hopping

This is such a professional and caring company. They are a great example why it's best to deal with real people instead of internet searches. I booked a condo on Tripadvisor for a month in Greece and found out about a week later that they had double booked and I was out of luck. But not really out of luck--a friend turned me to Wingbuddy and, considering the various curves our party of four threw at them (leaving from and returning to different cities, changing our minds, etc.), they proved to be patient, organized and reliable! They have an equally amazing partner in Greece called Courmouzis Travel. I had my passport stolen on the plane from Montreal and so was detained at the airport for a day. They did not miss a beat in providing logistics for me separate from the rest of the larger group to get me a new shuttle and ferry ticket. And when we did not like one of our accommodations, they immediately changed us the same day to a very acceptable alternative. I needed to extend my stay in Athens and they were kind enough to arrange their special pricing for me at the very nice Jason Hotel. I cannot say enough great things about them, but I do thank both Wingbuddy and Courmouzis in my most sincere way, Read more

Operator Wingbuddy



Great trip! October 2018


Walking on the Greek Islands

Very good in spite of unseasonable weather for September. High winds
cancelled ferries for several days. As a consequence we stayed only one night
on Paros and missed Santorini entirely. But we got to know Naxos very well,
and it is an island with plenty to do. it might have been frustrating, but
leader Cecile Deltreil made superhuman efforts to keep us well occupied.
Although we saw her frequently glued to her cell phone, she never seemed
stressed out and explained changing arrangements in a way that kept us calm
and happy. She was also an excellent guide on walks and in the towns we
visited. If Cecile is typical of Exodus quality of service, it is an
excellent company.

In general accommodation was good and food excellent. Cecile has friendly
relations with lots of good restaurants.

I would certainly recommend this trip, and will be investigating other Exodus
trips in future.
It was all good. I especially enjoyed exploring the small viliages, and the
museum in Naxos was a surprise - really good.

I praise Cecile Deltreil to the skies. She deserves a bonus for this trip and
a raise!

A word of caution about "leisurely," a word subject to interpretation. The
walks were not long, and there were stops for points of interest. But Greek
islands are up and down, and in some cases footing was rocky. So the walking
was easy for hikers of any level, but more challenging if you have any
walking difficulties. ( I had broken my leg 4 months prior, and found the
walks a bit hard. Again leader Cecile was wonderful in figuring alternative
activities for me as needed.)

Did I mention how wonderful Cecile was?

Read more

Operator Exodus Travels



Greek Islands Unplugged October 2018


Walking on the Greek Islands

A chance to see the parts of Naxos, Santorini and Paros that maybe most don't

The trip ran smoothly, expertly organised by Cecile, and the weather was
beautiful, late 20's. I travelled on my own and joined a lovely and friendly
group of 15 (3 couples, and the rest of us single, aged between 40 and 70).
We chose to have most meals together. All hotels had a swimming pool, all 3
star and air conditioned.

My favourite hotel was on Naxos and it definitely had the best breakfast. A
lovely traditional island with lots going on, a good beach, excellent
restaurants and beautiful countryside. I would definitely go back to Naxos.

Santorini was beautiful with fantastic views, but very steep, noisy,
expensive and busy, especially when a cruise ship arrived! My knees
struggled a bit on the uphill parts of this, the longest, walk. I cheated
and left early for a bus back to the hotel. Definitely glad I went by cable
car both ways to the boat trip too! Most walked down and got the cable car
back up, which wasn't scary by the way, and avoided using the few little
donkeys still having to walk up and down the hundreds of steps.

Paros was delightful and relaxing, a sleepy traditional island with beautiful
beaches and countryside, lovely shops and restaurants. If you want to shop
wait until you get to Paros, especially for clothes, in the lovely and cool
sheltered streets.

I arrived home from this holiday pleasantly tired and very happy, definitely
one of my favourite trips.
Walking through the countryside in Naxos and Paros.

Cecile was lovely, friendly and attentive, she listened to what everyone
wanted and fitted in with us and what we wanted, always available and giving
advice when needed. Her knowledge and love of the Greek Islands and the
Greek people clearly showed.

Take a small, light and comfortable rucksack, good walking boots/shoes and
stick/s as you will need them, some of the hills are steep and can be slippy.
Get out walking before you go as slightly harder than I had expected of a
Level 1 Leasurely, although, to be fair, I have never been on a walking
holiday before (hats off to anyone going on a Level 10!).

Travel between the islands and mainland was by ferry. A time to relax, maybe
sleep, or chat. Your suitcase is stored down below. Don't forget to take
something warm upstairs to wear as the air conditioning can be extremely

Read more

Operator Exodus Travels

See all reviews for Greek Islands Top Operators & Trips
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