Greek Islands Small Ship Cruise Tours & Trip Packages

Greek Islands Small Ship Cruise Tours & Trips

32 Greek Islands trips. Tours from 28 tour companies. 181 reviews. 4.1/5 avg rating.

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Small Ship Cruise
Yolo Yachting - Mykonos to Santorini
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3.9/5 Great
100+ reviews
Small Ship Cruise
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Flexible schedule

Visits

Mykonos, Santorini

Highlights

  • Drive to fascinating Mykonos Island
  • Explore Paros which is famous for its water sports with wind surfing
  • Enjoy the Aegean archipelago of Paros
  • Explore Santorini

Themes

Singles Travel, Small Ship Cruise, Sailing

What travelers are saying

"The Ionian Cruise was a ton of relaxation and very enjoyable. The only issue had with it is the lack of diversity at the events. But other than that it was an awesome time and I'll recommend the Ionian Cruise to all of my friend"

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YOLO CRUISE - Mykonos to Santorini
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3.2/5 Average
100+ reviews
Small Ship Cruise
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Flexible schedule

Visits

Mykonos, Santorini

Highlights

  • Drive to fascinating Mykonos Island
  • Explore Paros which is famous for its water sports with wind surfing.
  • Enjoy the Aegean archipelago of Paros
  • Explore Santorini

Themes

18 - 30's, 50 plus, Singles Travel, Small Ship Cruise, Sailing

What travelers are saying

"The Ionian Cruise was a ton of relaxation and very enjoyable. The only issue had with it is the lack of diversity at the events. But other than that it was an awesome time and I'll recommend the Ionian Cruise to all of my friend"

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Yolo Yachting - Santorini to Mykonos
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4.7/5 Excellent
100+ reviews
Small Ship Cruise
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Balanced schedule

Visits

Mykonos, Santorini

Highlights

  • World famous clubs and wild parties (Mykonos)
  • Memorable adventures
  • Traditional vintage cruise ships
  • Experienced local tour leader

Themes

Singles Travel, Small Ship Cruise, Sailing

What travelers are saying

"The Ionian Cruise was a ton of relaxation and very enjoyable. The only issue had with it is the lack of diversity at the events. But other than that it was an awesome time and I'll recommend the Ionian Cruise to all of my friend"

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YOLO CRUISE - Santorini to Mykonos
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3.8/5 Great
100+ reviews
Small Ship Cruise
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Flexible schedule

Visits

Delos

Highlights

  • World famous clubs and wild parties (Mykonos)
  • Memorable adventures
  • Traditional vintage cruise ships
  • Experienced local tour leader

Themes

18 - 30's, Singles Travel, Small Ship Cruise, Sailing

What travelers are saying

"The Ionian Cruise was a ton of relaxation and very enjoyable. The only issue had with it is the lack of diversity at the events. But other than that it was an awesome time and I'll recommend the Ionian Cruise to all of my friend"

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Harmony Cruises
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4.6/5 Excellent
100+ reviews
Small Ship Cruise
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Full schedule

Visits

Acropolis, Temple of Zeus, Venetian Lagoon

Highlights

  • Explore old cities of Athens over 3,400 years of history
  • Enjoy general city navigation and history, to philosophy, architecture
  • Enjoy all the meze and traditional Greek music to match your classic toga outfit.
  • Explore ancient town of Ermioni

Themes

Small Ship Cruise, Sailing

What travelers are saying

"The Ionian Cruise was a ton of relaxation and very enjoyable. The only issue had with it is the lack of diversity at the events. But other than that it was an awesome time and I'll recommend the Ionian Cruise to all of my friend"

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Sailing the Greek Isles
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4.9/5 Excellent
100+ reviews
Small Ship Cruise
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Flexible schedule

Visits

Athens

Highlights

  • Discovering the magnificent ruins of the ancient sanctuary of Delos
  • Birthplace of Apollo and Artemis
  • Explore the picturesque village of Pyrgos
  • Immerse yourself in the lively culture, mythology, and Venetian legacy of age-old villages
  • Explore the dazzling white monastery of Panagia Hozoviotissa
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Themes

Cultural, Family Friendly, National Parks, Nature & Wildlife, Small Ship Cruise, Sailing

What travelers are saying

"We particularly wanted to do this trip because of the abundance of wildlife we expected to encounter and selected this ship because they offered the kayaking experience. Overall, the weather was very good. Most people seemed like minded and were there for the adventurous experience. Accommodations Review They upgraded our cabin and we were very pleased with the amount of space and the amenities in the room. We appreciated the twin windows and being able to see humpbacks diving from our cabin. It was kept very clean and it was a treat to have our bed turned down with chocolates on the pillow each night. Meals Review We liked the variety and the quality of the food. There was always something new to try. The dining room staff was very professional and personable. Crew & Guides Review Solon was our Principal Trip Leader. He was incredibly professional and it seemed like he was constantly working to maximize the encounters with wildlife and scenery, taking advantage of all the weather opportunities and going to places that they don't often go. He worked very closely with the captain who was very accommodating and caring about us having a memorable voyage. Aymie and Andrew were our kayak guides. We went out to kayak 10 different times and were able to get to know both of them well. They worked hard to keep us safe and well informed. They made sure that we didn't miss out on any land excursions. We've had quite a few kayak guides over the years that we've paddled and we loved these two. Marla was the marine biologist aboard the ship. She was very enthusiastic and had a passion for marine mammals that was infectious. We loved listening to her presentations and looked forward to hearing her voice on the PA saying that there was another whale sighting. Colin, the geologist aboard the ship, was very knowledgeable and able to make difficult subjects understandable to the passengers. Itinerary Review The trip far, far, far, far, far, far exceeded our expectations. I had one "far" in the sentence when we left South Georgia Island after seeing 250,000 King Penguins at St. Andrews Point and added the second when we saw blue whales on two different days. The third "far" was added when we saw hundreds of whales for 6 hours along the iceberg, A68a. I added another "far" when we kayaked for over an hour with humpbacks all around and another "far" when minke whales were all around the kayaks the next day. The last "far" was added the day we didn't paddle since a leopard seal was all around the kayaks and then an orca came close. We had so many incredible experiences that we could never experience all of them in the same trip again. The guides told us that the close encounters that we had didn't happen very often and that we were very lucky that they all happened on our trip. The only thing that we didn't like was portions of the Drake Passage when it was a tad rough, but that experience gives us something to talk about. Transportation Review We made our transportation arrangements through another travel agency. Traveler Advice Make sure that you take sea sickness meds. Take advantage of every opportunity to see wildlife."

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Greek Islands Bike & Boat
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By UTracks
preferred
4.8/5 Excellent
62 reviews
Small Ship Cruise
Lodging level
Basic - 2 star
Physical level
Moderate
Trip pace
Flexible schedule

Visits

Aegina, Athens, Mykonos, Piraeus, Poros

Highlights

  • Cycling in the Cyclade and Saronic islands with dramatic scenery
  • Exploring the small towns and villages en route
  • Swimming and snorkeling in the azure waters of Kea and Poros islands
  • Soaking up the hospitality onboard the comfortable gulet

Themes

Cycling & Biking, Small Ship Cruise, Sailing

What travelers are saying

"A really difficult company to communicate with, slow to respond and not able to accept accountability for poor service. Used Tee Travel in Spain which was even worse. Not able to organize support or assistance and harassed me about luggage that wasn't mine. There were other walkers who appeared to have more support and assistance from their travel providers. Definitely avoid this company as overpriced and no actual service."

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Greek Isles & Turkish Delights
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3/5 Average
32 reviews
Small Ship Cruise
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Flexible schedule

Visits

Acropolis, Athens, Blue Mosque, Istanbul, Mykonos, Santorini

Highlights

  • The Parthenon and the Acropolis in Athens
  • Palace of the Grand Masters in Rhodes
  • White-washed buildings and blue domes of Santorini
  • Blue Mosque and Grand Bazaar in Istanbul
  • Chic boutiques and cafés of Mykonos
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Themes

Cultural, Small Ship Cruise

What travelers are saying

""I do not recommend Windstar Cruises, at least not onboard 'Windstar'. The only reason I could see to sail with them is for the evening event in Ephesus, which was unforgettable. Reaching them via telephone, pre-cruise took 45mins+. Questions regarding one of Windstar's Private Driver & Guide tours I inquired about were not responded to, nor was a phone call made to me to report back. Instead, after 11pm, on the 3rd night onboard, I received an unacceptable, vague reply. Fortunately, in the week prior to cruise, my travel agent did a wonderful job of contacting a local tour/guide operator, and I had a wonderful experience. I sailed on The Windstar in August 2022 for a Greek Isles cruise. Unfortunately, I was underwhelmed in most aspects, except for the spa staff, who were wonderful, and cabin stewards, dining staff, and pool area bartenders/staff, who were excellent. While realizing it is a smaller 'sailing' ship, it needs a major upgrade/overhaul, or perhaps replacement with a new ship. Public areas, were substandard, pool had unsightly rusty colored sediment around the base of the waterline, whirlpool was neither heated, nor cooled, bed was uncomfortable, many times announcements by Captain could not be heard in cabin, nor were they repeated, in full, and slowly, a second time. Announcements meant for hallways or public areas only also were stated very quickly, and not repeated, slowly and with enunciation. I felt the destination briefings could have been interactive, with repeated times, and a fun, learning experience, with some ideas of what, and how, to experience the islands, other than the Windstar, or alternate booked excursions. Such as having information on car rentals, motorbike rentals, and perhaps a packet with information on all port calls, with maps, in the cabins, upon check-in, or a designated, sit-down office, wherein one could obtain information, comfortably, without interruptions. While I realize all lines are short-staffed the past couple of years, I felt it was grossly understaffed in the dissemination of information, reception, and destination briefing department, and that staff could have been available for a longer period of time for public Q & A's. I was actually distracted with number of times I heard 'Ladies & Gentlemen', during destination briefings, after almost every single sentence, that it interfered with information being given. While an understanding was reached after a couple days, and Reception improved, I was, one time, given an 'attitude' by reception staff, which won't easily be forgotten. My cabins portholes had exterior rust sediment build up which interfered with a nice view outside the portholes, and the smaller drain in the bathroom/head, outside the shower stall, had water coming up into/onto the toilet area and left the floorboards with that awful squeaky sound and also disallowed the use of fluffy area rug, instead needing 3 large towels to dry area after a shower. After this was reported to Manager, it was fixed, but by the night prior to end of cruise, it started happening again. I also feel the cruise rates, as compared to other lines, are overpriced. Perhaps Windstar's other, newer ships are different. One can only hope.""

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Walking on the Greek Islands
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4.2/5 Great
100+ reviews
Small Group Tour
Why we love them
With a huge range of trip styles and themes, they cater to basically every type of traveler out there- even those with super specific interests.
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

Athens, Santorini

Highlights

  • Discover the three islands of Naxos, Santorini and Paros
  • Gentle walks through idyllic scenery and remote villages
  • Enjoy delicious local Greek cuisine

Themes

Cultural, Hiking & Walking

What travelers are saying

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Mountains & Villages of Evia
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4.4/5 Great
100+ reviews
Small Group Tour
Why we love them
With a huge range of trip styles and themes, they cater to basically every type of traveler out there- even those with super specific interests.
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

Acropolis, Athens

Highlights

  • Discover an authentic Greek island
  • Walk along dramatic coastlines and visit remote villages
  • Savour delicious cuisine in traditional tavernas
  • Relax on deserted beaches and swim in the warm Aegean waters

Themes

Cultural, Hiking & Walking

What travelers are saying

"Discover Costa Rica is a great itinerary, covering varied habitats around the country and staying 2 nights each at 6 centres. Their birdwatching specials are led by local experts who really know their stuff."

Trip dates & details
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Health Safety +

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Yolo Yachting - Mykonos to Santorini
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3.9/5 Great
100+ reviews
Small Ship Cruise
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Flexible schedule

Visits

Mykonos, Santorini

Highlights

  • Drive to fascinating Mykonos Island
  • Explore Paros which is famous for its water sports with wind surfing
  • Enjoy the Aegean archipelago of Paros
  • Explore Santorini

Themes

Singles Travel, Small Ship Cruise, Sailing

What travelers are saying

"The Ionian Cruise was a ton of relaxation and very enjoyable. The only issue had with it is the lack of diversity at the events. But other than that it was an awesome time and I'll recommend the Ionian Cruise to all of my friend"

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Aegina And Agkistri Bike Tour
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5/5 Excellent
7 reviews
Group Tour
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

Acropolis, Athens, Piraeus

Highlights

  • Experience boat trip to Aegina
  • Visit Temple of Aphaia archaeological site from where you can even see the Acropolis
  • Explore Agia Marina small port and from there to the church of Saint Nektarios
  • Visit Dragonera beach where we relax and we enjoy the sun and the sea

Themes

Cultural, Cycling & Biking

What travelers are saying

"The best tour on a bike I had experienced in Greece! Very kind, and super service - in general, a great experience! Highly recommended to anyone who wants to see more of Greece and have fun exploring!"

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From Athens to Santorini – 8 days
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5/5 Excellent
5 reviews
Self-Guided / Independent Tour
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Flexible schedule

Visits

Akrotiri, Athens, Parthenon, Santorini

Highlights

  • See the highlights of the Acropolis and Parthenon at sunset
  • Stroll through the atmospheric streets of Plaka
  • Enjoy an amazing sailing day cruise around the volcanic islets of Santorini
  • Experience amazing Caldera sunsets and unforgettable wine tastings on Santorini

Themes

Cultural, Local Immersion & Homestays, National Parks, Nature & Wildlife

What travelers are saying

"Dimitris was everything we could have looked for in a travel agent. Following the parameters we laid out for him, he provided us with the absolute best options for our travels. He was both honest and patient with us, and made sure we took as much time as we needed to finalize a trip that felt right for our group. Dimitris informed us on everything that was going on throughout our booking and travel process, so there were no surprises along the way. He answered every question we had and made sure we were prepared when we arrived in Athens. Andreas went above and beyond in his role as our skipper for the week. He was patient and thoughtful with our group, and put so much effort into making sure we had the best trip possible. We felt very safe and protected throughout all of our travels, and were taken to some of the most incredible place – places that weren’t even on our initial itinerary. Andreas’ expertise in his craft and his companionate demeanor are the reasons our trip was as fantastic as it was. He exceeded all of our expectations and genuinely made this trip one of the best of our lives. Thank you, Dimitris and Andreas, for giving us a week we will never forget! We can honestly say we would not have had the same experience if it wasn't for all of your help and consideration."

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8 trips exactly matchall of the the filters you selected. We are displaying some similar trips.
My selections:
Small Ship Cruise

Greek Islands Reviews & Ratings

4.1/5  Great
181  Reviews
See all Greek Islands tour reviews
Excellent
23
Great
14
Average
6
Disappointing
2
Terrible
3
A

Anonymous

Oct 2018

Provided byExodus Travels

Waliking on the Greek Islands

Excellent Guide, Scenery and organisation. Some of hotels were not of a reasonable standard. The walk along the Caldera, Santorini. Excellent knowledge, very well...

A

Anonymous

Oct 2018

Provided byExodus Travels

Great trip!

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 mis...

A

Anonymous

Oct 2018

Provided byExodus Travels

Walking in the Greek Islands

This was a trip that stimulated all the senses, from the wonderful colours of the wildflowers on the walks and the blues and whites of the pristine villages we pas...

A

Anonymous

Oct 2018

Provided byExodus Travels

Vigorous.

I rarely give ten out of ten, but this came close. The sun shone every day, I slepped well and didn't put on weight. The walks were just right, leisurely as it sai...

A

Anonymous

Oct 2018

Provided byExodus Travels

Greek Islands Unplugged

A chance to see the parts of Naxos, Santorini and Paros that maybe most don't see. The trip ran smoothly, expertly organised by Cecile, and the weather was beauti...

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Greek Islands Tour Selection Trips

  • The Greek Islands are divided into six main groups, so you can choose a tour that either focuses on one group or on island-hopping among two or more
  • With more than 200 inhabited islands from which to choose, you could spend a lifetime trying to see them all – it’s more rewarding  to see them a few at a time
  • Small ship cruises are an ideal way to see the Greek islands, especially smaller, more off-the-beaten path isles where big ships can’t dock
  • Greek islands vary among desert  and lush, barren and forested, low-lying and mountainous, populated and sparsely occupied, undiscovered and trendy – choose your favorite(s)
  • Some of the best-known islands are overrun by tourists in the summer high season, so if your schedule allows, consider visiting in spring or fall
  • While Greece has suffered severe economic stress of late, don’t stay away – the locals are very grateful for visitors
  • If your focus is on touring mainland Greece, you can still find tours that add a nearby Greek island or two at the beginning or end

Additional details

Who will enjoy touring the Greek Islands?

On Stride you can find Greek Islands tours that will appeal to every traveler. There are tours offered that are geared towards family vacationing, solo or party-focused travel, group adventures, and relaxing senior cruising. There are 30+ trips offered on Stride that mix and match activity preference, physical level, and Greek cultural and historical exposure.

If you have only a brief period of time to explore the beauty of the Greek Islands there are several 7-day excursions that visit the most popular islands and attractions and offer relaxing beach days, exciting sailing adventures, and lively party nights out on the town.

Longer, more comprehensive tours exist that focus on the historical Greek highlights while also focusing on the unique and popular food and culture of Greece.

When is the best time to take a Greek Islands cruise?

The season for Greek Islands cruises lasts from May to October. The most popular months for cruises to the Greek Islands are the months of August and September, yet keep in mind that these are also the hottest months of the Greek summer, with temperatures rising above 100 degrees Fahrenheit (38 degrees Celsius). If you want to beat the crowds and experience cooler weather on your Greek Islands tour, opt for travel within the months of June, September, or October.

Common Greek Island Hopping Routes

With the countless Greek Islands and main landmarks to visit, there are various route options for touring the Greek Islands. Many itineraries hit the most popular islands, while others primarily focus on the surrounding geographical clusters.

A popular Greek Islands route looks like:

Athens - Mykonos - Rhodes - Crete - Santorini

Greek Islands hopping routes based on geographical region look like:

Cyclades:

Santorini - Mykonos - Paros - Naxos - Milos - Ios - Folegandros - Sifnos - Andros

Dodecanese:

Rhodes - Kos - Symi - Karpathos - Patmos

Ionian:

Corfu - Paxos - Zakynthos - Kefalonia

What to wear when cruising the Greek Islands

Considering that the common time for travel to the Greek Islands is in the summer months, most common attire will be lighter summer clothes and beachwear.

Bathing suits, sarongs, dresses, shorts, and party wear (if you are living it up in the Mykonos atmosphere) are popularly worn among tourists. Make sure to come prepared with sun protection, as it is very sunny and warm in Greece during the summer! Don’t forget your hat, sunglasses, and bathing suit coverups.

Light colors, flowy attire, linen, and strappy sandals are items frequently worn in the Greek Islands. While the weather is cooler during the spring and fall seasons, the temperatures in the Greek Islands remain moderate, so light jackets, long, flowy boat pants, and sweaters do the trick.

Greek Islands Cruise Packing List

You never want to be mid-vacation and realize you forgot essential travel items! When traveling to the Greek Islands, the must-pack list is pretty straightforward. You want to make sure you have all your beach gear, your photo-taking electronics, and Greek attire essentials. Follow this packing list, and you will be ready to go for your Greek Island summer adventure!

  • Bathing suit(s): With all the beautiful beaches to explore, this would be a bad item to miss! With multiple tour stops, make sure to pack more than just one! Make sure to bring a travel towel, beach bag, andsome coverups, too, so you are prepared after a day at the beach to shop and tour the local towns.
  • Sunscreen: Enjoy basking in the Greek summer sun, but stay safe while doing so!
  • Sunglasses & a hat: Stay stylish and shield your eyes from the vibrant rays.  
  • Mosquito repellent: You’ll want to be outdoors as much as possible when touring the Greek Islands, especially at sunrise and sunset, so be prepared! These also come in creams and bracelets.
  • Camera: Don’t miss the countless photo opportunities the Greek Islands have to offer!
  • Greece Travel Insurance: Have a carefree yet adequately prepared Greek Island adventure!
  • European Outlet Adapter: If you are from outside of the EU, you will definitely want an outlet adapter to stay connected and keep your devices charged.

 

Always Find the Best

On Travelstride you can find 32 trips to Greek Islands and more than 20,000 trips worldwide ranging from budget to luxury and private guided to group tours and everything in between. Only on Stride can you find and compare expert-planned trips from 1,000+ tour operators, cruise lines and local experts. Read traveler and professional reviews so you can confidently find your perfect trip.

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