Greece Sailing Tours & Trip Packages

Greece Sailing Tours & Trips

722 Greece trips. Tours from 153 tour companies. 1,033 reviews. 4.4/5 avg rating.

53 trips exactly matchall of the the filters you selected.
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Sailing
Sailing Greece - Mykonos to Santorini
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2/5 Disappointing
100+ reviews
Small Ship Cruise
Why we love them
They’ve partnered with well-known names like National Geographic and the Jane Goodall Institute to offer unique experiences unavailable elsewhere.
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Flexible schedule

Visits

Mykonos, Paro, Santorini

Highlights

  • 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

Themes

Cultural, Small Ship Cruise, Sailing

What travelers are saying

"We spent two wonderful weeks touring several of the best destinations in Portugal & Spain with a group of 16 people. Our guide (Fredy) was from Spain and intimately familiar with the region, including its rich history, attractions, and food/beverages. The tour was well-paced using a combinations of private vehicles (small buses and cabs), trains, and an airplane ride as well as a fair amount of walking to get around these two beautiful countries. We extended our stay in Lisbon to see more attractions and took a side trip to Fatima, Obidos, and Nazare that was also excellent. Would have liked to have a bit more time in a couple of the cities, but we'll just have to plan another trip!"

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Greece: Sparta, Monemvasia & the Peloponnesian Peninsula
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4.9/5 Excellent
100+ reviews
Group Tour
Why we love them
Their unique emphasis on immersive cultural experiences combined with active exploration with personalized cycling experiences.
Lodging level
Premium - 4 star
Physical level
Extreme
Trip pace
Full schedule

Visits

Athens, Crete, Santorini

Highlights

  • Uncover the treasures of the hillside medieval gem of Mystras, the Byzantine Empire’s cultural capital for nearly a millennium, with an expert archaeologist-guide.
  • Savor the recipes and the flavors of ancient Byzantine cuisine during a special dinner.
  • Walk through the maze of alleyways in the medieval castle town of Monemvasia, a crossroads of civilizations with Byzantine, Frankish, Venetian, and Ottoman influences.
  • Cruise around the monolithic Rock of Monemvasia.
  • Join a taverna owner on a shrimp-harvesting excursion, then join him for a cooking lesson and prepare garidopetoules—a savory shrimp pancake.

Themes

Cultural, Cycling & Biking, Nature & Wildlife, Sailing, Photography

What travelers are saying

"We just returned from our fifth VBT trip - this time to the Dolomites. It was a great trip and we are adding it to our "best" VBT trip list, along with the Czech Republic and the Tuscan Coast. Our friends at home thought we must be biking maniacs to bike in the Dolomite mountains, but we told them we would be in the flat valleys. Actually, we were wrong - much of the biking is not even flat, it is downhill! One day we started high in the valley above Merano, Italy, at scenic Lake Resia, and biked downhill back to Merano on a beautiful dedicated bike path along the Adige river. Our guides were fantastic. Martin is from Bolzano and is a font of information about the South Tyrol region. Christian, from the south, has a classic cheerful Italian personality and told us many facts (and jokes) about Italian idiosyncrasies. As always, the hotel accommodations (and breakfasts!) were excellent - better than we would sign up for if we on our own vacation."

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Greek Island Hopper
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By Interrailing Packages
Local Expert
Verified by Travelstride as locally operated and in the top of their field for customer reviews, local knowledge, and safety.
4.8/5 Excellent
100+ reviews
Self-Guided / Independent Tour
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Flexible schedule

Visits

Athens, Mykonos, Santorini

Highlights

  • Discover the captivating capital of Greece, exploring the ancient history, and modern charm.
  • Experience the ultimate vacation in stunning Mykonos
  • Visit Santorini
  • Greek island hopping

Themes

Cultural, High Adventure, Nature & Wildlife, Sailing, Photography

What travelers are saying

"Los funcionarios de Interraling son excelentes personas y atienden las inquietudes a tiempo y con amabilidad. Nos ayudaron a organizar nuestras vacaciones familiares en Europa, de acuerdo a nuestras solicitudes, las cuales llenaron todas nuestras expectativas. Gracias a ustedes disfrutamos al máximo este viajes. Las salidas de los trenes fueron en el horario previsto y los hoteles buenos y bien ubicados."

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Ionian Riviera
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5/5 Excellent
29 reviews
Small Group Tour
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Full schedule

Visits

Corfu

Highlights

  • Visit of of Old Town Corfu
  • Visit of Erota and Sidari
  • Visit of Porto Timoni and Ipsos-Saranda, Porto Palermo,Ipsos

Themes

Climbing & Mountaineering, Cultural, High Adventure, Hiking & Walking, Local Immersion & Homestays, Nature & Wildlife, Trekking & Expeditions, Sailing, Photography, Scuba Diving

What travelers are saying

"Although not a master in skiing this tour met all my expectations for a great holiday in Montenegro. Not only snow but also interior pools."

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Sail Greece: Santorini to Mykonos
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4.8/5 Excellent
100+ reviews
Small Ship Cruise
Why we love them
They’re very committed to sustainable and responsible tourism and contribute to important initiatives like climate action.
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Flexible schedule

Visits

Akrotiri, Mykonos, Santorini

Highlights

  • Spend your days island-hopping in the Cyclades, swimming in the clear waters of the Aegean and sleeping aboard a yacht
  • The blue and white villages of Santorini may cling to the rim of an ancient volcano, but the only fire you’ll see is in the island’s magnificent sunsets
  • In the sleepy fishing villages of the Small Cyclades islands, you’re more likely to break bread with a local than a tourist
  • A taste of rural life on the large island of Navos is a mix of historic neighbourhoods and Kitron liqueur
  • Stylish Mykonos is a place where Europe’s chic and beautiful come to play – offering an exclusive, boutique feel to the island

Themes

Small Ship Cruise, Sailing

What travelers are saying

"We joined the Intrepid “Real Italy Food Tour” and enjoyed it thoroughly. Our tour guide, Micol, was very knowledgeable and provided us with lots of good information. It seems Micol knew many of the staff of the venues we visited, including the pasta making class we attended. Our group of 11 travelers was extremely compatible, which greatly added to the fun and enjoyment."

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Greece Sailing Adventure: Cyclades Islands
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5/5 Excellent
100+ reviews
Small Ship Cruise
Why we love them
They’re very committed to sustainable and responsible tourism and contribute to important initiatives like climate action.
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Flexible schedule

Visits

Mykonos, Santorini

Highlights

  • A Santorini sunset around the caldera is a sight to behold. Walk along the volcanic rim of the island past white villages that cling to plunging cliffs and watch as day turns to night in the most stunning of ways.
  • Sail the Aegean Sea on your small group yacht and island-hop through the Cyclades, taking regular stops to swim off the side of your boat and letting the pitch and roll of the ocean help you sleep at night.
  • Feast on fresh seafood at a sleepy waterfront taverna in the Small Cyclades islands – far away from tourist crowds and deep in the local way of life. This is island living, Greek style.
  • Step back in time among the Venetian architecture of Naxos and consider learning about rural life with a daytrip to a country village – a couple of the many experiences to be had around the Cyclades.
  • No Greek island adventure is complete without a stop in Mykonos. Embrace your hedonistic side with its boutique culture and nightlife or relax on one of the many beaches dotted along the coast.

Themes

Small Ship Cruise, Sailing

What travelers are saying

"We joined the Intrepid “Real Italy Food Tour” and enjoyed it thoroughly. Our tour guide, Micol, was very knowledgeable and provided us with lots of good information. It seems Micol knew many of the staff of the venues we visited, including the pasta making class we attended. Our group of 11 travelers was extremely compatible, which greatly added to the fun and enjoyment."

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Greece Sailing Adventure: Corfu to Kefalonia
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4.5/5 Excellent
100+ reviews
Small Ship Cruise
Why we love them
They’re very committed to sustainable and responsible tourism and contribute to important initiatives like climate action.
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Full schedule

Visits

Corfu

Highlights

  • Begin your sailing adventure on one of the most beautiful islands in the Ionian Sea – the island of Corfu, filled with gorgeous Venetian architecture and boasting an azure sea.
  • Spend your nights on a sailing boat and fall asleep to the relaxing undulation of the waves below. Watch sunset every night from a nearby beach and wake up early to catch sunrise on the deck.
  • Explore the finest beaches in the Greek Islands at sister islands Paxos and Antipaxos, swimming in translucent waters and walking along pure white sand.
  • Take a dip near private islands seldom seen, like Skorpios – once home to Jacqueline Kennedy Onassis – and Atokos – uninhabited except by a few wandering goats.
  • Explore the seaside villages, hospitable locals, glittering bays, lush verdant hills and warm tavernas of Meganisi, Kastos, Kalamos and Ithaca – all at the desired pace of your group and friendly skipper.
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Themes

Small Ship Cruise, Sailing

What travelers are saying

"We joined the Intrepid “Real Italy Food Tour” and enjoyed it thoroughly. Our tour guide, Micol, was very knowledgeable and provided us with lots of good information. It seems Micol knew many of the staff of the venues we visited, including the pasta making class we attended. Our group of 11 travelers was extremely compatible, which greatly added to the fun and enjoyment."

Trip dates & details
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Greece Sailing Adventure: Kefalonia to Corfu
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4.5/5 Excellent
100+ reviews
Small Ship Cruise
Why we love them
They’re very committed to sustainable and responsible tourism and contribute to important initiatives like climate action.
Lodging level
Standard - 3 star
Physical level
Moderate

Visits

Corfu

Highlights

  • Begin your sailing adventure on the biggest and one of the most beautiful islands in the Ionian Sea – Kefalonia, famous for its delicious wine, sheer white cliff faces and world-famous beaches.    
  • Spend your nights on a sailing boat and fall asleep to the relaxing undulation of the waves below. Watch sunset every night from a nearby beach and wake up early to catch sunrise on the deck.    
  • Explore the finest beaches in the Greek Islands at sister islands Paxos and Antipaxos, swimming in translucent waters and walking along pure white sand.   
  • Take a dip near private islands seldom seen, like Skorpios – once home to Jacqueline Kennedy Onassis – and Atokos – uninhabited except by a few wandering goats.  
  • Explore the seaside villages, hospitable locals, glittering bays, lush verdant hills and warm tavernas of Meganisi, Kastos, Kalamos and Ithaca – all at the desired pace of your group and friendly skipper.
Show more

Themes

Small Ship Cruise, Sailing

What travelers are saying

"We joined the Intrepid “Real Italy Food Tour” and enjoyed it thoroughly. Our tour guide, Micol, was very knowledgeable and provided us with lots of good information. It seems Micol knew many of the staff of the venues we visited, including the pasta making class we attended. Our group of 11 travelers was extremely compatible, which greatly added to the fun and enjoyment."

Trip dates & details
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53 trips exactly matchall of the the filters you selected.
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Greece Reviews & Ratings

4.4/5  Great
1,033  Reviews
See all Greece tour reviews
Excellent
238
Great
85
Average
20
Disappointing
6
Terrible
13
M

Michael

Oct 2023

Written on

Best of Greece

The Rack Railway journey was excellent

D

Deborah

Oct 2023

Written on

Best of Greece

This trip had two guides, Katya for the first week through Delphi, Olympia, et. al., Peter guided in the second week through Naxos and Santorini and was spectacular....

W

Wendy

Jul 2023

Written on

Best of Greece

Well organised, good standard of hotels.

F

Francis

May 2023

Written on

Best of Greece

Impossible to choose just a single highlight, but Sapfo was extraordinarily good.

L

Linda

May 2023

Written on

Best of Greece

Santorini sunset tour and the tour keader

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Greece Tour Selection Trips

  • While visiting the Acropolis is a must, you really don’t need a lot of time in Athens. Flights will fly right into Athens so spending 1-2 days at the beginning or end of your trip is usually sufficient.
  • There are many options for getting between the islands — flying, taking a ferry or chartering a boat. The waters can be a little rough at times, so flying between the farther islands might be a good option for those who get sea sick.
  • While on the map the islands look close, they are quite a distance from the mainland. The “closer” islands of Mykonos, Santorini and Crete are all over 4 hours on a ferry, so if you are looking to visit multiple islands, be sure to know the distances so you make sure to have enough time in each island.
  • Each island has its own culture and attractions: Santorini has the iconic photos you see of the blue-topped churches on the cliff and the lava-black sand beaches. Mykonos is the “party” island with lots of day beach clubs and a robust nightlife. Koufanisis is the off-the-beaten-path island with a small, country feel. Naxos is also a less-traveled island with abundant shops and restaurants and a beautiful castle.

Additional details

Experiencing Ancient Greece on Your Tour

The Ancient Greeks founded democracy, created theater, the key principles of modern architecture, philosophy, trial by jury, instituted a mythology still taught to every generation, standardized medicine, and generally provided the foundation to all of Western Civilization.

As a result, we have a couple things to thank them for -- and there is no better way to do this than to visit the many Ancient archaeological sites that stand to this day in Greece. Here are some of the best archaeological sites in Greece:

1. The Acropolis.

This UNESCO world heritage site is a worldwide symbol for the contributions of Ancient Greece to modernity. Some of its most notable features include the theatre of Herod Atticus, the Parthenon, the Temple of Nike Athena, and the Pinacotheca.

2. The Parthenon.

Perhaps the most iconic symbol of Greece, this temple sits in the heart of Athens. Originally dedicated to the goddess Athena, it housed various statues. This massive building, one of the most impressive architectural feats of its time, is truly awe inspiring to see in person.

3. Monolithos Castle in Rhodes.

 Climbing the tall rock that the castle sits on will not only give you a peek at the two 15th century chapels inside of Monolithos, but gorgeous views of the entire island. One interesting feature of the Monolithos castle is that it was built on the foundations of an even older castle, which is easily seen at the spot.

4. Mycenae.

This late Bronze Age city was once one of the epicenters of Greek civilization, and remains remarkably intact.

5. Acropolis of Rhodes.

Made up of the ruins of multiple temples, a small odeion, and other buildings, a guided tour of this spot can offer deep insight into Ancient Grecian life. The surrounding natural sights make the trip particularly enjoyable.

6. Temple of Apollo, Delphi.

Although perhaps not so physically impressive, this spot is overwhelmed with spiritual and historical significance. The home of the Oracle of Delphi, this site plays a role in dozens of ancient myths and modern stories.

Facts about Greece

  • The official name of Greece is the Hellenic Republic.
  • The saying “taking the bull by its horns” comes from the Greek myth of Hercules saving Crete from a raging bull by seizing its horns
  • 80% of Greece is mountainous.
  • Continuously inhabited for over 7,000 years, Athens is one of the oldest cities in Europe. It is also the birthplace of democracy, Western philosophy, the Olympic Games, political science, Western literature, historiography, major mathematical principles, and Western theories of tragedy and comedy.
  • Greece has more archaeological museums than any other country in the world.
  • Greece’s currency, the drachma, was 2,650 years old and Europe’s oldest currency. The drachma was replaced with the Euro in 2002.
  • Make sure to try Greece's national dish: moussaka. 
  • Voting is required by law for every citizen who is 18 or older.
  • Greek people wave with a closed hand as it is considered rude to show your palm of your hand in public.

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