Greece Sailing Trips & Packages Tours & Trips

45 Greece Sailing Trips & Packages trips. Tours from 22 tour companies. 82 reviews.

45 Trips match your criteria (1 - 20 shown)

Sail Greece: Santorini to Mykonos
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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

"Michelle Middleton is an asset to the customer care team. Easy and honest communication throughout!"

Trip dates & details
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Greece Sailing Adventure: Cyclades Islands
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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

"Michelle Middleton is an asset to the customer care team. Easy and honest communication throughout!"

Trip dates & details
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Greece Sailing Adventure: Corfu to Kefalonia
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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.
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Themes

Sailing, Small Ship Cruise

What travelers are saying

"Michelle Middleton is an asset to the customer care team. Easy and honest communication throughout!"

Trip dates & details
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Custom Designed Trip
Lodging level
lodgingLevelName
Physical level
N/A

Highlights

  • Fully customized trip based on preferences
  • Matched with a local specialist
  • From $150 per person per day
Self-Guided / Independent Tour
Greece Sailing Adventure: Kefalonia to Corfu
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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

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.
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Themes

Sailing, Small Ship Cruise

What travelers are saying

"Michelle Middleton is an asset to the customer care team. Easy and honest communication throughout!"

Trip dates & details
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Sail Greece: Mykonos to Santorini
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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

  • Tour the iconic Cyclades Islands by yacht – is there any better way? Swim in the Aegean Sea off the side of the boat and let the waves rock you to sleep each night.
  • Visit the chic waterfront bars that line the beaches of Mykonos, serving authentic Greek food and cocktails as the sun goes down. This is a great place to eat well and relax!
  • Explore the 11th-century monastery of Moni Hozoviotissis, wedged between the dramatic cliffs of Amorgos.
  • Pass the bleached-white villages that cling to plunging cliffs along the rim of a volcano –Santorini has some of the most distinctive and attractive landscapes in the world.
  • Head away from the tourist trail to the remote Small Cyclades islands, chock-full of tavernas serving fresh seafood and small villages to explore.

Themes

Sailing, Small Ship Cruise

What travelers are saying

"Michelle Middleton is an asset to the customer care team. Easy and honest communication throughout!"

Trip dates & details
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Sail & Swim: Greece 2025
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Small Ship Cruise
Why we love them
Their trips perfectly balance epic experiences and free time for exploring in the most popular backpacking destinations.
Lodging level
Standard - 3 star
Physical level
Moderate

Visits

Aegina, Athens

Highlights

  • -Orientation walk of Aegina with Trip Leader
  • -Orientation walk of Poros with Trip Leader
  • -Orientation walk of Ermioni with Trip Leader
  • -Orientation walk of Spetses with Trip Leader
  • -Orientation walk of Hydra with Trip Leader
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Themes

Sailing, Small Ship Cruise

What travelers are saying

"Last review doesn’t know what they’re talking about. Myself and my friends had an AMAZING trip on the Moja Maja, G** our tour guide was incredible and so so fun to be around. Food was really good, better than I expected for being on a sailboat. I don’t know what the negative reviews are talking about because I would find it really hard to find any faults with the trip that we had. Crew were really friendly and made the trip even better. 5 Stars easy."

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The battle between mainland and the islands: Athens, Peloponnese & Corfu
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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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A Story of history and wine: Athens & Santorini
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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

  • Exploring the historical city of Athens
  • Delighting in a sunset wine experience in Santorini.
  • Staying in luxury hotels & enjoying the services of the friendly staff.
  • Strolling the cobblestone streets & admiring the trademark Cycladic aesthetic.
  • Sunbathing by the pool with a refreshing drink in hand.

Themes

Culinary & Wine, 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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Greece Sailing Trips & Packages Reviews

G

Graziella

Oct 2015

Written on

Easy booking, fast service, great travel experience. Amazing

Easy booking, fast service, great travel experience. Amazing trip & skipper, see below.

S

Sheridan

Oct 2015

Written on

We were given more places to visit

We were given more places to visit than what was on our itinerary such as an extra island n great night at sea. The skipper taught us how to sail sharing his boat k...

F

Fiona

Oct 2015

Written on

I really enjoyed the trip

I really enjoyed the trip

L

Lorraine

Sep 2015

Written on

It lived up to expectations in every

It lived up to expectations in every way

I

Isabelle

Sep 2015

Written on

small Group and local guide

small Group and local guide

Write a Review

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