Greece Sailing Cruises & Packages Tours & Trips

20 Greece Sailing Cruises & Packages trips. Tours from 10 tour companies. 77 reviews.

20 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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By Topdeck
premier
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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Yachting in Greece
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Small Ship Cruise
Why we love them
They’ve been recognized by major travel publications for their pioneering adventure travel expertise that spans back to their founding in 1979.
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Flexible schedule

Highlights

  • Explore the island of Homer
  • Visit Santorini
  • Visit Paros, one of the most beautiful islands of the Cyclades
  • Explore Myconos - the most cosmopolitan island with dazzling white houses
  • Visit the church of PARAPORTIANI is considered to be an architectural masterpiece
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Themes

Sailing, High Adventure, Small Ship Cruise

What travelers are saying

"I have travelled with ROW numerous times, including four trips on the Rogue River. Every trip has been wonderful and every person associated with ROW has been nice, knowledgeable, professional and fun. The Rogue is a great river and the trip is an excellent one for two people or a large group—and I have done both. I’ve taken both of my kids, one time each, and have organized groups of colleagues twice; most recently in 2019 when 14 of us gathered. The guides at ROW are great and help to make the trip very enjoyable. The scenery, lodging and the wonderful outdoors including warm air and refreshing water, make for a wonderful escape from the everyday routine. The fact that this trip offers beds and indoor plumbing is a nice benefit and allows those who have an aversion to camping a chance to see the wilderness. I have recommended ROW and the Rogue trip more times than I can count and my group has already reserved our trip for 2021. What are you waiting for?"

Trip dates & details
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Jewels of the Cyclades
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Small Ship Cruise
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Flexible schedule

Highlights

  • Explore the Aegean Islands
  • Paros and Folegandros
  • Excursions in Santorini and Delos, nighlife in Mykonos
  • Visit old Greece atmosphere in Folegandros and swim stops in some secluded bays to swim from the boat

Themes

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

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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Greece Sailing Cruises & 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

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