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Greece 8 Nights 9 Days Luxury Winter Escape Itinerary

Curated by Naveen, planned 4502+ Greece trips



Your Itinerary
Athens
2 nights
Day01

Arrive in Athens airport. Get transferred to your hotel.

At leisure
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Day02

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

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
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.

At leisure
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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

At leisure
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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.

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

At leisure
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Get transferred to Crete by ferry
Crete
2 nights
Day07

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

At leisure
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Day08

From Chania: Elafonisi Pink Sand Beach & Elos Village Tour - Elafonisi Island Day Tour by Bus From Chania
Day09

At leisure
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Time to head home with a full camera roll, a few souvenirs, and that Sooper hit holiday glow. The next journey awaits.
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/ person
Excluding Applicable Taxes
Your route
Arrival at ATH
Athens
2N
Transfer by ferry
Mykonos
2N
Transfer by ferry
Santorini
2N
Transfer by ferry
Crete
2N
Departure at CHQ
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

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
GET ASSISTANCE
Not sure if this plan is right for you? Let our experts fine-tune it to match your style.
Embark on a luxurious 9-day winter escape to Greece, where sun-drenched landscapes greet you at every turn, and rich history whispers from the ruins. This itinerary invites you to explore the timeless beauty of Athens, the glamour of Mykonos, the stunning vistas of Santorini, and the diverse terrains of Crete. Picture yourself standing at the Parthenon, savoring delectable dishes in seaside taverns, and soaking in breathtaking sunsets that paint the horizon in vibrant hues.
Highlights of the Destination
- Discover Athens' ancient treasures, from the majestic Acropolis to vibrant street markets.
- Unwind on the celebrity-studded beaches of Mykonos while dancing the night away.
- Immerse yourself in the iconic charm of Santorini, with its whitewashed buildings clinging to cliffs.
- Experience Crete's dramatic landscapes and mythological sites, including the birthplace of Zeus.
Travel Tips for Greece
- Visit museums during weekdays to avoid the weekend crowd and for a more intimate experience.
- Consider taking guided tours in Athens to delve deeper into the rich history and stories behind each landmark.
- Create your own walking food tour in Mykonos—don't miss local delicacies like louza and kopanisti.
- Bring comfortable walking shoes for exploring the charming alleys of Santorini and Crete.
Conclusion
Your 9-day journey through Greece is not just a trip; it’s an immersion into a land rich with history, culture, and breathtaking landscapes. Each moment, from sipping ouzo by the beaches of Mykonos to watching the sunset over Oia, etches memories that linger long after your return home. Whether you're indulging in luxurious accommodations or exploring remote beaches, this winter escape promises to be an adventure of a lifetime.
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Customer Reviews
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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
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
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
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
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
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
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
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
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
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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