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Greece Sailing Tours & Trip Packages

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Greece: Sparta, Monemvasia & the Peloponnesian Peninsula

By VBT Bicycling Vacations

premier

Group Tour

Lodging level

Premium - 4 star

Physical level

Extreme

Trip pace

Full schedule

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

What travelers are saying

"This was the first organized tour my husband and I have ever joined, so we were not sure what to expect , but it turned out to be the best vacation we've ever had. The scenery and food were amazing. We stayed in beautiful hotels. Most of the riding was on paved bike paths so we hardly ever had to deal with car traffic. Our leaders, Andrea and Martin, were funny, informative , and so helpful. We are already planning to go back to Italy with VBT this summer."

Trip dates & details

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7 days From$3,845

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A Trip to Athens, Mykonos, Santorini, and Crete

By Greece Insiders

Local Expert

Verified by Travelstride as locally operated and in the top of their field for customer reviews, local knowledge, and safety.

Private Guided

Why we love them

Designing original, innovative, and out-of-the-box travel itineraries and incredible personalized service.

Lodging level

Standard - 3 star

Physical level

Easy

Trip pace

Balanced schedule

Highlights

Divine Delphi and Galaxidi Excursion
MykonosBeaches
Caldera Sunset Cruise Lagoon 560
Knossos and Archaeological Museum
Falassarna & Water Sports

Themes

Cultural, Culinary & Wine, Hiking & Walking, Local Immersion & Homestays, Sailing, High Adventure, Scuba Diving, Small Ship Cruise, Relaxing Retreats

What travelers are saying

"Normally, I don't feel like writing reviews, but I felt compelled to do it for Athens Insiders. I made the decision to travel to Athens in the summer of 2012 in order to avoid the commotion that was predicted to result from the Queen's jubilee. As usual, my work kept me busy right up to the last minute, so I ran out of time to do anything fun for my week-long trip. I learned about this young group of tour guides for Athens and its vicinity from a friend. I had a wonderful experience. I got in touch with Daphne, who gave me email recommendations for Athens attractions to see, inquired about my preferences for local cuisine, and then devised an itinerary for my trip. In addition to visiting the typical suspects in Athens (Acropolis, etc.), I also chose to travel to Delhi and spend a night at a campground there. And I had a great time, honestly. We visited the attractions when there were few visitors and spent the busiest times outside of Athens rather than being herded around like cattle. I was taken to incredible tiny eateries (the well-known tavernas), marketplaces, and other regional shops."

Trip dates & details

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$6,691

15 days From$4,956

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Sail Greece: Santorini to Mykonos

By Intrepid Travel

premier

Small Ship Cruise

Why we love them

They're highly committed to sustainable tourism and contribute to crucial initiatives like climate action, focusing on local cultures and more.

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.
See Santorini, where the blue and white villages cling to the rim of an ancient volcano – don't worry, the only fire you’ll see is in the island’s magnificent sunsets.
Break bread with locals in the sleepy fishing villages of the Small Cyclades islands, away from the typical tourist trail.
Taste rural life on the large island of Naxos – a mix of historic neighbourhoods and Kitron liqueur.
Explore a place where Europe’s chic and beautiful come to play – you’ll have plenty of time to soak up the beauty, charm and sunsets of Mykonos.

Themes

Sailing, Small Ship Cruise

What travelers are saying

"I went on the Intrepid 15 day "Best of Morocco" tour in 2025 and had such an amazing time that I wasn't ready to leave by the time the trip finished! It exceeded my expectations in so many ways: value for money, itinerary, a lot of included activities balanced with lots of rest stops on longer travel days, very caring & attentive local guides, and lots of optional activities. As a company, Intrepid was very easy to communicate with before the trip started (I had sent a few questions about optional activities). The website is also easy to navigate and simple for updating travel & health information. If you are considering doing a tour with Intrepid - make sure you read the Essential Trip Information they have on each tour page. It describes everything in detail so you'll know what to expect. While I LOVED my tour, I can see some people signing up for this without reading the description and then being surprised at some of the 2 star hotels (in this case it was the "Original" tour style). Overall, I am impressed at how this tour managed to simultaneously get us closer to Moroccan culture AND feel like an adventure AND feel like a vacation from day-to-day life back home. I would travel with Intrepid again."

Trip dates & details

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$2,562

8 days From$1,898

Health Safety +

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The battle between mainland and the islands: Athens, Peloponnese & Corfu

By Eros and Psyche Travel

preferred

Private Guided

Why we love them

The husband-and-wife team behind Eros and Psyche specializes in couples' travel to Greece.

Lodging level

Luxury - 5 star

Physical level

Very Easy

Trip pace

Balanced schedule

Highlights

Staying in first-class hotels and reveling in their luxury and style.
Exploring the fascinating city of Athens and its archaeological sites
Visiting Nafplio, often considered the most romantic city in Greece.
Swimming in the crystal clear waters of Corfu.
Taking a guided tour across the UNESCO World Heritage Site of Mycenae.

Themes

Cultural, Sailing

What travelers are saying

"Seamless! Working with Eros + Psyche was seamless. From the moment we started planning to the minute we got home, our Greece honeymoon was perfect. The team took all our considerations into account when planning our itinerary and it was executed with no hiccups or anything! It was truly perfect. We spent time in Athens, Paros and Santorini and it was a very luxurious trip within our budget. I highly recommend working with Eros + Psyche for a trip to Greece."

Trip dates & details

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$1,139

10 days From$1,000

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Exploration of the Saronic Gulf

By Greece Insiders

Local Expert

Verified by Travelstride as locally operated and in the top of their field for customer reviews, local knowledge, and safety.

Private Guided

Why we love them

Designing original, innovative, and out-of-the-box travel itineraries and incredible personalized service.

Lodging level

Standard - 3 star

Physical level

Easy

Trip pace

Balanced schedule

Highlights

Explore Agistri and Moni with your private rib boat
Enjoy a day cruise around Hydra and Dokos
Enjoy an E-bike ride in Spetses
Hike in the mountain of Spetses

Themes

Cultural, Culinary & Wine, Cycling & Biking, Hiking & Walking, Small Ship Cruise, Relaxing Retreats

What travelers are saying

"Normally, I don't feel like writing reviews, but I felt compelled to do it for Athens Insiders. I made the decision to travel to Athens in the summer of 2012 in order to avoid the commotion that was predicted to result from the Queen's jubilee. As usual, my work kept me busy right up to the last minute, so I ran out of time to do anything fun for my week-long trip. I learned about this young group of tour guides for Athens and its vicinity from a friend. I had a wonderful experience. I got in touch with Daphne, who gave me email recommendations for Athens attractions to see, inquired about my preferences for local cuisine, and then devised an itinerary for my trip. In addition to visiting the typical suspects in Athens (Acropolis, etc.), I also chose to travel to Delhi and spend a night at a campground there. And I had a great time, honestly. We visited the attractions when there were few visitors and spent the busiest times outside of Athens rather than being herded around like cattle. I was taken to incredible tiny eateries (the well-known tavernas), marketplaces, and other regional shops."

Trip dates & details

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$3,187

10 days From$2,361

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Greece Sailing Adventure: Cyclades Islands

By Intrepid Travel

premier

Small Ship Cruise

Why we love them

They're highly committed to sustainable tourism and contribute to crucial initiatives like climate action, focusing on local cultures and more.

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

Sailing, Small Ship Cruise

What travelers are saying

"I went on the Intrepid 15 day "Best of Morocco" tour in 2025 and had such an amazing time that I wasn't ready to leave by the time the trip finished! It exceeded my expectations in so many ways: value for money, itinerary, a lot of included activities balanced with lots of rest stops on longer travel days, very caring & attentive local guides, and lots of optional activities. As a company, Intrepid was very easy to communicate with before the trip started (I had sent a few questions about optional activities). The website is also easy to navigate and simple for updating travel & health information. If you are considering doing a tour with Intrepid - make sure you read the Essential Trip Information they have on each tour page. It describes everything in detail so you'll know what to expect. While I LOVED my tour, I can see some people signing up for this without reading the description and then being surprised at some of the 2 star hotels (in this case it was the "Original" tour style). Overall, I am impressed at how this tour managed to simultaneously get us closer to Moroccan culture AND feel like an adventure AND feel like a vacation from day-to-day life back home. I would travel with Intrepid again."

Trip dates & details

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$3,497

10 days From$2,590

Health Safety +

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The Complete Historical Panorama of Greece

By Greece Insiders

Local Expert

Verified by Travelstride as locally operated and in the top of their field for customer reviews, local knowledge, and safety.

Private Guided

Why we love them

Designing original, innovative, and out-of-the-box travel itineraries and incredible personalized service.

Lodging level

Standard - 3 star

Physical level

Easy

Trip pace

Balanced schedule

Highlights

Flavors of Athens - Food Tour - Private
Ancient Olympia Guided Tour - Private
Chania Local Cooking Class - Small Group
Knossos and Archaeological Museum Guided Tour - Private
Acropolis & Acropolis Museum Guided Tour - Private

Themes

Cultural, Nature & Wildlife, Culinary & Wine, Hiking & Walking, Sailing, Education / Learning, High Adventure, Relaxing Retreats

What travelers are saying

"Normally, I don't feel like writing reviews, but I felt compelled to do it for Athens Insiders. I made the decision to travel to Athens in the summer of 2012 in order to avoid the commotion that was predicted to result from the Queen's jubilee. As usual, my work kept me busy right up to the last minute, so I ran out of time to do anything fun for my week-long trip. I learned about this young group of tour guides for Athens and its vicinity from a friend. I had a wonderful experience. I got in touch with Daphne, who gave me email recommendations for Athens attractions to see, inquired about my preferences for local cuisine, and then devised an itinerary for my trip. In addition to visiting the typical suspects in Athens (Acropolis, etc.), I also chose to travel to Delhi and spend a night at a campground there. And I had a great time, honestly. We visited the attractions when there were few visitors and spent the busiest times outside of Athens rather than being herded around like cattle. I was taken to incredible tiny eateries (the well-known tavernas), marketplaces, and other regional shops."

Trip dates & details

Save this trip to your favorites or other list

$7,201

15 days From$5,334

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Greece Sailing Adventure: Corfu to Kefalonia

By Intrepid Travel

premier

Small Ship Cruise

Why we love them

They're highly committed to sustainable tourism and contribute to crucial initiatives like climate action, focusing on local cultures and more.

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.

Themes

Sailing, Small Ship Cruise

What travelers are saying

"I went on the Intrepid 15 day "Best of Morocco" tour in 2025 and had such an amazing time that I wasn't ready to leave by the time the trip finished! It exceeded my expectations in so many ways: value for money, itinerary, a lot of included activities balanced with lots of rest stops on longer travel days, very caring & attentive local guides, and lots of optional activities. As a company, Intrepid was very easy to communicate with before the trip started (I had sent a few questions about optional activities). The website is also easy to navigate and simple for updating travel & health information. If you are considering doing a tour with Intrepid - make sure you read the Essential Trip Information they have on each tour page. It describes everything in detail so you'll know what to expect. While I LOVED my tour, I can see some people signing up for this without reading the description and then being surprised at some of the 2 star hotels (in this case it was the "Original" tour style). Overall, I am impressed at how this tour managed to simultaneously get us closer to Moroccan culture AND feel like an adventure AND feel like a vacation from day-to-day life back home. I would travel with Intrepid again."

Trip dates & details

Save this trip to your favorites or other list

$3,507

8 days From$2,598

Health Safety +

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Greece Sailing Tours & Trips

38 Greece Sailing trips. Tours from 17 tour companies. 77 reviews. 1/5 avg rating.

Greece: Sparta, Monemvasia & the Peloponnesian Peninsula

A Trip to Athens, Mykonos, Santorini, and Crete

Sail Greece: Santorini to Mykonos

The battle between mainland and the islands: Athens, Peloponnese & Corfu

Exploration of the Saronic Gulf

Greece Sailing Adventure: Cyclades Islands

The Complete Historical Panorama of Greece

Greece Sailing Adventure: Corfu to Kefalonia

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Greece Sailing Reviews & Ratings

Easy booking, fast service, great travel experience. Amazing

I really enjoyed the trip

We were given more places to visit

It lived up to expectations in every

small Group and local guide