Cool Destinations
Top Greece activities
Top Greece landmarks
Beyond Greece
Greece trip ideas
  • Tours by category
  • Tours by accessibility
  • Tours by feature
  • Tours by the numbers
  • Top Greece landmark tours
  • Tours in nearby places
  • Explore tours
  • Greece travel guides
  • Greece travel calendar
Language $Currency
Login / Sign up
Bookings
Bookings
Cool Rewards Rewards
$0.00
Cool Rewards Rewards
$0.00
Wishlists
Wishlists
Profile
Help Center
Language
Log out
Start your search
Change your search
Place or activity
Select Dates

Top Greece Multi-day Cruises

12 Results
Sort by:
Featured
Filter
Languages Clear
Time of Day Clear
7
5
2
Duration Clear
0
0
0
3
9
Price Clear
$0 $500+
Rating Clear
8
9
10
Specials Clear
5
1
0
10
2
Features Clear
4
0
7
1
11
6
Accessibility Clear
0
8
11
Families Clear
4
7
4

Greece Tours

Attractions

Guides

Calendar

Island Hopping: Santorini Catamaran Charter Cruise with a skipper

Design your own trip and explore the Aegean! Feel free to craft your own personalized sailing route. We are ready to make it happen. Set …More

Paros, Greece
4.9 (123)

Island Hopping: Santorini Catamaran Charter Cruise with a skipper

Design your own trip and explore the Aegean! Feel free to craft your own personalized sailing route. We are ready to make it happen. Set...

7 days
4.9 (123)
from
$8,547
8-day/7-night Zante Cruise

During our cruise, you will have the possibility to explore multiple different destinations that are not easily accessible by car, as we offer a unique …More

Zakynthos, Greece
4.6 (128)

8-day/7-night Zante Cruise

During our cruise, you will have the possibility to explore multiple different destinations that are not easily accessible by car, as we offer a unique...

8 days
4.6 (128)
from
$1,021
Sailing to Epidavros and Mycenae, Guided Tour and Wine Tasting

Embark on the Peloponnese Experience, a unique journey blending ancient history, breathtaking landscapes, and luxurious sailing. Begin your adventure aboard our premium yacht, cruising to …More

Likely to Sell Out
Likely to Sell Out
Athens, Greece
5.0 (1)

Sailing to Epidavros and Mycenae, Guided Tour and Wine Tasting

Embark on the Peloponnese Experience, a unique journey blending ancient history, breathtaking landscapes, and luxurious sailing. Begin your adventure aboard our premium yacht, cruising to...

2 days • Hotel pickup offered
5.0 (1)
from
$6,493
2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos

This cruise is unique and a must when visiting Milos. It gives visitors the opportunity to experience a night on-board a 13m sailing boat and …More

Milos, Greece
5.0 (10)

2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos

This cruise is unique and a must when visiting Milos. It gives visitors the opportunity to experience a night on-board a 13m sailing boat and...

2 days • Free Cancellation
5.0 (10)
from
$2,824
5-Day Ancient Greece & Zakynthos Turtle Island Tour

Experience the highlights of Greece and the stunning island of Zakynthos on this 5-day private tour. Explore the Ancient Theatre of Epidaurus, one of the …More

Athens, Greece
4.8 (12)

5-Day Ancient Greece & Zakynthos Turtle Island Tour

Experience the highlights of Greece and the stunning island of Zakynthos on this 5-day private tour. Explore the Ancient Theatre of Epidaurus, one of the...

5 days • Hotel pickup offered
4.8 (12)
from
$1,262
2-Day Santorini Bus Tour with Volcanic Cruise

See all of the best of Santorini in this 2-day tour, visiting all must-sees and experience the island's culture before you go back home. Explore …More

Santorini, Greece
5.0 (3)

2-Day Santorini Bus Tour with Volcanic Cruise

See all of the best of Santorini in this 2-day tour, visiting all must-sees and experience the island's culture before you go back home. Explore...

2 days • Free Cancellation
5.0 (3)
from
$116
Private sailing cruise Athens 1 week 1 to 6 people

Unique stay, tailor-made trip: private sailing cruise with French-speaking crew in the Greek Islands from Athens. All included. Experience a holiday differently. …More

Athens, Greece
5.0 (2)

Private sailing cruise Athens 1 week 1 to 6 people

Unique stay, tailor-made trip: private sailing cruise with French-speaking crew in the Greek Islands from Athens. All included. Experience a holiday differently....

7 days
5.0 (2)
from
$11,315
6-Day Private Tour Athens, Delphi, Meteora & Boat Trip to Aegina

Book on line a 6-day journey through Greece, exploring Athens, Delphi, Meteora, and indulging in a private boat trip to Aegina. Begin your adventure in …More

Athens, Greece
5.0 (1)

6-Day Private Tour Athens, Delphi, Meteora & Boat Trip to Aegina

Book on line a 6-day journey through Greece, exploring Athens, Delphi, Meteora, and indulging in a private boat trip to Aegina. Begin your adventure in...

6 days • Hotel pickup offered • Free Cancellation
5.0 (1)
from
$1,757
8-Day Cruise to Halkidiki, Mount Athos and Ammouliani Island

Golden sandy beaches, crystal clear waters, magical sunsets, local Greek food, Mount Athos, and sunbathing at Ammouliani island are not enough to express how unique …More

Thessaloniki, Greece
5.0 (1)

8-Day Cruise to Halkidiki, Mount Athos and Ammouliani Island

Golden sandy beaches, crystal clear waters, magical sunsets, local Greek food, Mount Athos, and sunbathing at Ammouliani island are not enough to express how unique...

8 days • Free Cancellation
5.0 (1)
from
$4,878
4 Nights in the Greek Islands from Athens: Santorini, Mykonos and Syros

Go island hopping in Greece on an unforgettable 5-day independent tour from Athens, taking in the islands of Syros, Mykonos and Santorini. In between ferry …More

Athens, Greece
3.4 (18)

4 Nights in the Greek Islands from Athens: Santorini, Mykonos and Syros

Go island hopping in Greece on an unforgettable 5-day independent tour from Athens, taking in the islands of Syros, Mykonos and Santorini. In between ferry...

5 days
3.4 (18)
from
$1,141
8-Day Private Experiential Cruise in North of Greece Islands

This is a unique cruise that combines nature, sailing, and SUP to secluded beaches and isolated bays. Throughout the trip, the whole process will become …More

Thessaloniki, Greece

8-Day Private Experiential Cruise in North of Greece Islands

This is a unique cruise that combines nature, sailing, and SUP to secluded beaches and isolated bays. Throughout the trip, the whole process will become...

8 days
from
$5,275
Sailing Vacation in the Aegean, Greece (8 days)

Island hopping in the Aegean together with Sailing School? What more to ask for your holidays in the Aegean? Experience the Greek island hopping while …More

Rhodes, Greece

Sailing Vacation in the Aegean, Greece (8 days)

Island hopping in the Aegean together with Sailing School? What more to ask for your holidays in the Aegean? Experience the Greek island hopping while...

7 days • Hotel pickup offered • Free Cancellation
from
$8,111

Frequently Asked Questions

These answers are based on answers previously given to Cool Destinations customers' questions.

Recent tour reviews
Wonderful experience
New York City
8-day/7-night Zante Cruise
suehJ7279UO, Sep 2026
Wonderful experience
Our expectations were very high for this holiday but it exceeded in every respect. The food was amazing and plentiful and certainly gave us the taste of Greece. Maria, our host, along with the amazing captain and wonderful crew worked hard to give us a fantastic experience. Thank you!
Read more
A beautiful cruise in Zante
New York City
8-day/7-night Zante Cruise
Scaltropoly, Sep 2026
A beautiful cruise in Zante
A big thanks to Cpt Nikos and his crew for taking care of us during our Corfu cruise. Great locations, our favourite was lakka and blue lagoon.
Read more
Unforgettable highlight of our family trip
New York City
2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos
N6201FHvictoriam, Apr 2026
Unforgettable highlight of our family trip
We travelled to Greece 🇬🇷 July 2024 for a family holiday. I was thrilled to find Oscar Private Sailing as an intro into a sailing holiday. Nikos made everything so enjoyable and perfect. From finding the best coves for swimming and relaxing, to creating amazingly delicious meals - everything was perfect. I would highly recommend Nikos for an authentic and fun sailing adventure. Thanks Nikos (sorry for the delayed review!).
Read more
Santorini sightseeing
New York City
2-Day Santorini Bus Tour with Volcanic Cruise
akb7105r, Aug 2025
Santorini sightseeing
Awesome service pickup and drop off recommended helpful and fantastic tour guide called Yaanis. It's worth using their service.
Read more
Dream trip
New York City
Private sailing cruise Athens 1 week 1 to 6 people
K2290ECjos_b, Jul 2025
Dream trip
A great experience. We went to Greece three weeks, one of which was on the sailboat. A very experienced dynamic couple. Everything was perfect nothing to say negative. 5 stars if you have the chance to make this trip do not hesitate me for a second. What wonderful memories!!!!
Read more
A trip out of time, supervised by exceptional hosts.
New York City
Private sailing cruise Athens 1 week 1 to 6 people
arthurz159, Jul 2025
A trip out of time, supervised by exceptional hosts.
We lived an absolutely unforgettable week on board the floating house of Flo and Alex. As soon as we arrived, they created a warm, simple and caring atmosphere, where you feel immediately at ease.What makes this experience so unique is their ability to adapt to everyone. My wife and I are quite introverted, and they have perfectly respected our need for calm and privacy, while offering us moments of sharing on board or during stopovers, always with great tact and kindness.They are excellent advice, whether for sailing choices, stopovers, walks or even meals. The stay took place at our own pace, like an "à la carte" trip, thought for us.Flo and Alex are a passionate, caring and deeply human duo. Thanks to them, this cruise was much more than just a trip: a precious, rejuvenating break full of beautiful discoveries.A huge thank you to both of us for this adventure that we will never forget. A&M
Read more
Best experience to date!
New York City
Sailing to Epidavros and Mycenae, Guided Tour and Wine Tasting
mar_az218, Jun 2025
Best experience to date!
We had the most amazing experience with SailBliss, largely thanks to our skipper and hostess, Alex and Veronica. SailBliss was very flexible in adapting the schedule to our needs and everything was organized very well. Alex and Veronica made the experience all the better by being extremely friendly, knowledgeable and helpful. We couldn’t recommend these two more and wish we could have them on all our sailing trips! Both were experienced sailors and made us feel safe on the boat, and Veronica’s cooking is to die for! We booked the Peleponese History, Wine & Sailing Escape, which we enjoyed very much, the perfect balance between visiting history and relaxing at the sea.
Read more
10 out of 10 private tour
New York City
5-Day Ancient Greece & Zakynthos Turtle Island Tour
laurahM2498IR, Oct 2024
10 out of 10 private tour
Spyros, our driver, was an absolute legend. He was fun, respectful and very knowledgeable. His driving made us feel very safe and comfortable. Spyros suggested delicious restaurants, stopped at fantastic places for photos and accommodated our requests. He always had water and never complained about our very heavy luggage. Spyros drove us around on his day of rest and acted as a tour guide when the third party operated boat cruise was cancelled due to low numbers. Before the tour even started our travel specialists Patty and Silia were so helpful over email. Always getting back to our questions in a really timely manner and accommodated our family of 4. The hotels we stayed at and the places we visited on the 5 day private tour with Zakynthos were so nice and the staff were all very friendly. Everything was organised for us which eliminated a lot of decision fatigue. We cannot recommend this tour enough and thank Spyros, Patty and Silia.
Read more
Catamaran in Santorini.
New York City
Island Hopping: Santorini Catamaran Charter Cruise with a skipper
robertE5153SL, Oct 2024
Catamaran in Santorini.
From end-to-end, the service was perfect. Arrangements were easy and convenient. All staff on the boat were fun and accommodating.
Read more
Excellent holiday in Greece
New York City
5-Day Ancient Greece & Zakynthos Turtle Island Tour
OnAir689759, Aug 2024
Excellent holiday in Greece
We spent 9 days touring Greece with Private Tours Greece, combining Athens with other destinations. The agency was extremely professional, polite and helpful booking our holiday, and best of all, they provided us with a driver called Spyros. Spyros was a gentleman and an excellent driver who made sure we were in all the right places at the right time, whether it was catching a ferry or pre-empting coach tours to avoid the crowds. Spyros was always cheerful, informative and helpful, with plenty of advice on the local stuff, and he went out of his way to make sure we enjoyed our holiday, for which we are very grateful! He knows the roads of Greece backwards and knows exactly where to stop for the best photo opportunities. We saw lots, had fantastic local guides (also booked by PTG), stayed in excellent hotels and had a wonderful time! As far as Greece goes, it is an amazing country of welcoming and generous people, excellent food, breath-taking views and mind-blowing history. Unless you are an expert on Ancient Greece, we highly recommend booking the tour guides. They are all local and professional guides who bring each site to life and make sure you leave with a greater understanding of the life and times of long ago. We are very happy to name the best of them here: Maria (Souninon), Elena (Olympia), Mirsini (Delphi). Patricia (Meteora).
Read more
Thanks Nikos from our heart
New York City
2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos
Culture767261, Jul 2024
Thanks Nikos from our heart
Where to start...? We both love the water, swimming, snorkelling and diving. it was simply perfect. Nikos is a very professional and relaxed person it it was simply beautiful to have spend these days on his boat with him. Nikos is a real pro and knows how to read the sea, the wind and we had some proper sailing - there was one big problem: it was too short. .-)) we felt so sorry that we have to leave as it felt to stay longer as we had such a good time. Thanks Nikos for this beautiful experience from my heart- as we said we hope to be back very very soon and if possible this year. Take care. Aleksandra & Stephen
Read more
Perfect from start to end thanks to Peter
New York City
Island Hopping: Santorini Catamaran Charter Cruise with a skipper
dylanbC7544TR, Jun 2024
Perfect from start to end thanks to Peter
I cannot recommend this company enough, but mainly because of one person: Peter. My wife, friends and I had the good fortune of meeting Peter in Oia, and writing this review I do so knowing I cannot do justice to how wonderful he is. Never in my life have I met someone so dedicated to making sure the people he meets have a good experience on holiday. He did a fantastic job listening to what we wanted to do, recommending an experience based on what we told him and explaining the ins and outs so there were no unpleasant surprises. He is an absolute credit to his company in this regard. He also went above and beyond assisting with tour options; any time we stopped by for a friendly chat he would ask about our plans for the day, make recommendations and help wherever possible to make sure we had the best day possible. Peter is so genuine, knowledgeable and straight shooting that we new we could take him at his word, always. His passion for Santorini is matched only by his honesty and friendliness.As for the tour itself, we went on a morning catamaran cruise. It was perfect, and such good value for money. The boats were new and well cared for, the crew was professional but also incredibly fun and personable (Konstantinos in particular was an amazing and hilarious host on our tour), the locations picturesque and the food/drink delicious. Couldn't ask for more.All in all I don't think I've ever been more impressed by a tour company in my life. Peter started the experience on a positive note, the tour delivered, and the care Peter showed outside of organising the tour had a massively positive impact on our holiday. Thankyou Peter and thankyou Spiridakos.
Read more
Exceptional 6-day tour!
New York City
6-Day Private Tour Athens, Delphi, Meteora & Boat Trip to Aegina
187ioannist, Jan 2024
Exceptional 6-day tour!
We booked a trip to Athens, Delphi, and Meteora, and the experience exceeded our expectations. The highlight was the private yacht trip to Aegina, where we enjoyed swimming and indulged in delicious food. Communication was prompt and clear, and the accommodations were top-notch. Highly recommended
Read more
Unforgettable holidays
New York City
8-Day Cruise to Halkidiki, Mount Athos and Ammouliani Island
Thanasis K, Jul 2023
Unforgettable holidays
It is the best experience I had last years thanks a lot Yako Sailing for the places that we explore the boat is perfect as the captain and we had very beautiful family holidays Hope enjoy again your team
Read more
Great highlight trip of Santorini
New York City
2-Day Santorini Bus Tour with Volcanic Cruise
Rosalie, Oct 2022
Great highlight trip of Santorini
Great coverage of the highlights of Santorini. Really fun day on the boat. The hike up the volcano was great, some parts weren't easy but definitely doable. Our tour guide was great. The second day was a bus trip with some walking and it was also a fantastic day. Our tour guide was Athena and she was very thorough and knowledgeable.
Read more
Santorini,Mykonos ,Athens,Greece
New York City
4 Nights in the Greek Islands from Athens: Santorini, Mykonos and Syros
lipy1112000, Feb 2018
Santorini,Mykonos ,Athens,Greece
it is the best, you guys must visit those places .Me and my daughter like it so much ,we had so much fun,we went to more islands the name is very hard to say
Read more
Greece Tours
Attractions
Guides
Calendar
View more