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Greece 8 Nights 9 Days Winter Escape Itinerary

Aryan Banoth

Curated by Aryan Banoth, planned 1543+ Greece trips

Helper
Sooper hit holidays
Why choose Pickyourtrail - Trust elements

Your Itinerary

Athens

2 nights

Day01

Arrive in Athens airport. Get transferred to your hotel.
Morning

Arrive in Athens airport. Get transferred to your hotel.

At leisure
Noon to Evening

At leisure

Add Activity

Day02

Athens: Discover Acropolis and Parthenon on a Guided Tour - Shared Group Tour without Entry Tickets
Morning

Athens: Discover Acropolis and Parthenon on a Guided Tour - Shared Group Tour without Entry Tickets

At leisure
Noon

At leisure

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Athens: City Sightseeing Hop-On Hop-Off Bus Tour - 24-Hour Hop-On Hop-Off Bus Tour - Athens Line
Evening

Athens: City Sightseeing Hop-On Hop-Off Bus Tour - 24-Hour Hop-On Hop-Off Bus Tour - Athens Line

Get transferred to Mykonos by ferry

Mykonos

2 nights

Day03

Check out of your hotel. Take the ferry to  Mykonos. Check-in to your new hotel.
Morning

Check out of your hotel. Take the ferry to Mykonos. Check-in to your new hotel.

At leisure
Noon

At leisure

Add Activity

Mykonos Old Town Historic and Cultural Walking Tour. - Mykonos Old Town Historic and Cultural Walking Tour.
Evening

Mykonos Old Town Historic and Cultural Walking Tour. - Mykonos Old Town Historic and Cultural Walking Tour.

Day04

Small Group Mykonos Walk with Cruise terminalpickup - Small Group Mykonos Walk with Cruise terminal pick up
Morning

Small Group Mykonos Walk with Cruise terminalpickup - Small Group Mykonos Walk with Cruise terminal pick up

At leisure
Noon to Evening

At leisure

Add Activity

Get transferred to Santorini by ferry

Santorini

2 nights

Day05

Check out of your hotel. Take the ferry to  Santorini. Check-in to your new hotel.
Morning to Noon

Check out of your hotel. Take the ferry to Santorini. Check-in to your new hotel.

Blue Dome Photo Stop & Oia Village Tour (Small Group) - Blue Dome Photo Stop & Oia Village Tour (Small Group)
Evening

Blue Dome Photo Stop & Oia Village Tour (Small Group) - Blue Dome Photo Stop & Oia Village Tour (Small Group)

Day06

5-Hour Winter Santorini Tour - 5-Hour Winter Santorini Tour
Morning to Noon

5-Hour Winter Santorini Tour - 5-Hour Winter Santorini Tour

At leisure
Evening

At leisure

Add Activity

Get transferred to Crete by ferry

Crete

2 nights

Day07

At leisure
Morning

At leisure

Add Activity

Check out of your hotel. Take the ferry to  Crete. Check-in to your new hotel.
Noon

Check out of your hotel. Take the ferry to Crete. Check-in to your new hotel.

At leisure
Evening

At leisure

Add Activity

Day08

From Chania: Elafonisi Pink Sand Beach & Elos Village Tour - Elafonisi Island Day Tour by Bus From Chania
Full Day

From Chania: Elafonisi Pink Sand Beach & Elos Village Tour - Elafonisi Island Day Tour by Bus From Chania

Day09

At leisure
Morning

At leisure

Add Activity

Time to head home with a full camera roll, a few souvenirs, and that Sooper hit holiday glow. The next journey awaits.
Noon to Evening

Time to head home with a full camera roll, a few souvenirs, and that Sooper hit holiday glow. The next journey awaits.

Your trip includes

Transfers, Visa & Insurance

Tell us your dates, travel group, and departure city to view all inclusion details

Hear from a traveller who chose a similar itinerary has to say

Ramesh K

A vacation to Greece was expertly prepared by the Pickyourtrail team! Very pleased with the timely visa assistance and on-trip service. These men are in their youth and are excellent planners. While travelling, you must have their app so you may mail them if you have any needs. When we had a few navigational questions, the support staff also assisted us. In Greece, we had a terrific time.

Ramesh K, Greece

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  1. Home
  2. Itineraries
  3. Greece 8 Nights 9 Days Winter Escape Itinerary

Greece in winter offers a unique charm, blending historical wonder with stunning landscapes. Imagine wandering through the ancient streets of Athens, where the Acropolis stands unyielding against the winter sky, or strolling along the dramatic cliffs of Santorini, with the caldera painted in hues of blue and white. The silence of winter transforms the islands into a tranquil retreat, making this 8-night journey an idyllic escape from the mundane. Let's embark on this enchanting adventure across Athens, Mykonos, Santorini, and Crete, soaking in culture, history, and breathtaking views.

Highlights of the Destination

  • Explore the UNESCO World Heritage-listed Acropolis and Parthenon in Athens, where ancient history comes alive.
  • Discover the captivating village of Oia in Santorini, renowned for its stunning sunsets and iconic blue-domed churches.
  • Experience the vibrant nightlife and beautiful beaches of Mykonos, where glamour meets traditional charm.
  • Relax on the pink sands of Elafonissi Beach in Crete, a natural paradise that beckons visitors year-round.

Travel Tips for Greece

  • Visit major attractions early in the morning to avoid crowds, especially in Athens.
  • Dress in layers; winter temperatures may vary significantly between day and night.
  • Don’t forget cash; while many places accept cards, some local spots prefer cash transactions.
  • Embrace local cuisine with traditional dishes like moussaka and baklava at local tavernas for an authentic dining experience.

Conclusion

With its historical treasures and captivating landscapes, Greece is a gem waiting to be uncovered, especially during the quiet beauty of winter. This 8-night itinerary allows you to capture the essence of this magnificent country while enjoying its serene atmosphere. Whether you are exploring ancient ruins, wandering through picturesque villages, or relaxing by the sea, each moment is a reminder of Greece's timeless allure.

Customer Reviews

4.6

From 65+
countries

5

4

3

2

1

Ramesh K-Profile

Ramesh K

Reviewed on: 18 Jun 2026

A vacation to Greece was expertly prepared by the Pickyourtrail team! Very pleased with the timely visa assistance and on-trip service. These men are in their youth and are excellent planners. While travelling, you must have their app so you may mail them if you have any needs. When we had a few navigational questions, the support staff also assisted us. In Greece, we had a terrific time.

Vishal Shekhar-Profile

Vishal Shekhar

Reviewed on: 18 Jun 2026

Prices were competitive and got a great deal. Our requests were accommodated. Great work by Sowmya at PYT. Definately opting for PYT for next trip. 2nd Trip Edit- Had a great trip to Greece. Loved the on-trip support. Akshay really helped me plan the best customized package and was proactive in responding to all my queries. Had good visa support from Afroz as well. Keep up the good work.

Prathi-Profile

Prathi

Reviewed on: 11 Dec 2025

We had a wonderful experience with Pickyourtrail with our Greece holiday, everything was planned well according to our choices, during the trip constant support was offered, all the hotels, activities were great and we had a wonderful time. Would definitely love to book more holidays with Pickyourtrail, highly recommend

Kalpakam Gopalakrishnan-Profile

Kalpakam Gopalakrishnan

Reviewed on: 11 Feb 2025

Our Greece trip with pickyourtrail was amazing. Service during the trip was commendable. Although there was a timing mismatch from vendors end, pickyourtrail ensured that our plans went thru. Their team connected with us to see that everything was smooth. They compensated us for the last minute charges. For a short while when there was some problem with my app, the team established alternative connectivity thru my whatsapp. Overall, I felt it was very trustworthy and felt at ease to travel with them in future.

P Varun Kajava-Profile

P Varun Kajava

Reviewed on: 04 Oct 2024

Pickyourtrail I am using their services for 2nd time this time it was Greece and the team entirely supported through the journey. Great support throughout the journey. Always recommended

Namita Rao-Profile

Namita Rao

Reviewed on: 09 Sep 2024

Pick Your Trail turned out to be good choice to plan our vacation (for 4 friends from 4 different locations) to Greece right from drafting the itinerary to visa guidance, ticketing and on ground support in Greece. But for their app which created initial hurdles, their executives were friendly, approachable guided us well at all stages. I would certainly suggest PYT to my friends and relatives.Thank you PYT for making our vacation special.

Hemalatha Sridhar-Profile

Hemalatha Sridhar

Reviewed on: 04 Sep 2023

Pickyourtrail and their team arranged a wonderful holiday in greece, covering Athens, Mykonos and Santorini for 9 days. The arrangements were to the tee and spot on. And no where did we fell stranded or shortchanged. I am impressed with their attention to detail and constant checking on us and customised the itenary to our needs. Their 24/7 support system through their app is impressive and this was a new pleasant experience for us. greece of course was beautiful as ever and i have no problem recommending them to others if travelling abroad. I wish then all the best

Subrat-Profile

Subrat

Reviewed on: 06 Jul 2023

We had a very pleasant experience with Pick Your Trail for our recent vacation to Greece. Starting from the pickup cabs to booking cruise to ferry tickets, everything was very well arranged. The support team was constantly available over chat to acknowledge any help that was needed. The hotels had the best view and were present at the best location.The only thing which was a little less convenient was that the pickup points scheduled for us for various activities were a little far from our hotels, so we had to book either a taxi or walk down/up the hills to be at our scheduled points.

Amith M-Profile

Amith M

Reviewed on: 06 May 2023

Awesome Guys. Without your support I don’t think so I could plan my 🇬🇷Greece vacation planned so memorable. Thanks a lot

Ramesh K-Profile

Ramesh K

Reviewed on: 15 Jul 2022

A vacation to Greece was expertly prepared by the Pickyourtrail team! Very pleased with the timely visa assistance and on-trip service. These men are in their youth and are excellent planners. While travelling, you must have their app so you may mail them if you have any needs. When we had a few navigational questions, the support staff also assisted us. In Greece, we had a terrific time.

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