Fabulous walk from Fira to Oia in Santorini

2 week Greece Itinerary in October

Nature
The wow factor for nature - does it show nature at its best? Doesn't need to be the wildebeest migration or diving with hundreds of hammerheads. Rather make you pause as you realise just how awesome the natural world can be
8
Culture
How much does this experience showcase some of the better and finer things that us humans can offer? Sure, it can be ancient ruins and renaissance churches, but it can also be festivals or soaking up some of the great modern cities of the world
10
Fun factor/activity
Very simple - was it fun? This is usually linked in with doing some kind of activity - i mean, walking along some cliffs is nice, but paragliding from them, now that is fun. Its a vastly underrated factor in a truly great experience
6
Avoid the crowds
Big tour groups and being surrounded by loud fellow tourists can sap the life out of even the greatest of travel experiences. This score is to reflect just how much you can avoid this. But. . . The score also takes into account if the crowds actually add to the experience, such as with a party town or a bustling local market
6
World famous
How world famous is the experience?
10
unique
How hard is it to have a similar experience in other places round the world?
10
Overall TE Score
The overall travel experiences score:  fun factor + avoid the crowds + (best of nature or culture) + (best of world famous or unique). Then convert into a score out of 100
80 *What the scores mean and where do they come from
RANKING
How this travel experience ranks compared to all the other experiences on this site, based on the travel experience (te) score
53rd/457
Top 20%
continent
Europe
country
Greece
Length of time
1-2 weeks
Typical daily price
This gives you a rough idea of the daily price based on 2 people travelling where they can split costs like accommodation. It excludes travel there and back, and factors in inflation the numbers in brackets show the price range for the full time of the experience (so not necessarily daily). It is a range to reflect different budget vs higher end
$200 (typically $100 - $290)
Time of year visited
October
Primary Tags
Click on any of the tags to see all travel experiences with the same tag
Ancient ruins Islands Old town
All Tags
Beach promenade Beaches Big city Boat trip Bustling restaurants Canyons Castles / Fortresses Cliffs Driving Forests Hiking Hilltop towns Local villages Mountains Partying / Lash Romans Rooftop Bars Sunsets UNESCO world heritage site Vineyards Volcanoes Wine
Wow Factor
Two scores: first is the wow factor which ranges from ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ to ⭐️, and a separate category for the truly "gash". The second is the more analytical travel experience score, which considers 6 varied criteria to give an overall score out of 100.
⭐⭐⭐

Summary

Greece is one of the best places to travel in Europe in October.  While the rest of Europe is starting to get the chills of winter and closing down, Greece is the standout for not only being open, but also still having the summer vibe pumping, especially in the islands.  This 2 week Greece itinerary gives you the “must dos” and the route to take.

 

Nutshell:

  • The mega wows are Santorini, the monasteries of Meteora and western Crete
  • Any Greece trip has a split between mainland Greece and the Greek Islands. If you only have a week, do one.  If 2 weeks, do both.
  • Athens will be the hub for the journey by ferry to the islands and by car through the mainland.
  • Islands – don’t miss Santorini. If pressed for time chose between Mykonos (high end fancy, lash, closer) and Crete (natural beauty, big nature, like a separate country).
  • Mainland – Delphi and Olympia are similar so, if pushed for time, go for Delphi as its closer to Meteora.

 

Table of Contents

Priorities for a 2 week Greece Itinerary in October

 

This website is all about rating the travel experiences.  The below is how each of the Greek pieces rate on the wow factor scale, and how you should prioritise:

#1 Santorini 🌟🌟🌟 (wow wow wow) – don’t fall for thinking its just the Instagram spot with the white villages.  The volcanic caldera is one of the most impressive sights I’ve seen, and the walk from Fira to Oia is magical.  In the whole world, its probably only the Sorrento Peninsular in Italy (see The Sorrento Peninsula – avoiding the crowds entry here) that manages to combine the uber chic with uber dramatic landscapes like Santorini does.  Rare to give a wow wow wow (less than 30 given out of 500+ experiences), but Santorini justifies it.  For more details, see this Santorini travel entry.

 

2 week Greece Itinerary in October

 

#2 The Monasteries of Meteora 🌟🌟 (wow wow) – how are these not more famous?!  We were blown away by how stunning the mountains are, the beauty of the monasteries perched on top, and just how well done it all was.  Driving the ridge road that links the monasteries was a real 🌟🌟🌟.  Yes, its a bit further to the north of Greece, but if you combine it with Olympia and Delphi its a big loop.  Do it!  For more details, seeThe monasteries of Meteora.

 

 

#3 Western Crete 🌟 (wow).  Hania is the prettiest Old Town you’ll see on the trip, the beaches of Falasarna and Elafonsi are the best, and hiking the Samaria Gorge is the best outdoor experience.  Don’t be put off by Crete’s distance – its only an extra 3 hour or so ferry to factor in.  Base yourself in Hania for a 3-4 day magical stay.  See Staying in Chania’s Old Town, and Hiking the Samaria Gorge for more tips.

 

 

#4 Ancient Olympia – Worth it.  You get hit with the weight of history the moment you step inside Olympia.  Astonishing to think that the ancient games ran for  1169 years, the legacy it left us with the modern version and that the site represented the valley of the gods, home to The Statue of Zeus, one of the Seven Wonders of the Ancient World.  The ruins themselves are also just generally pretty atmospheric and beautifully set in the quiet valley to walk around, with enough standing columns, temples and foundations to fire the imagination.  Worth making the further drive west through the Peloponnese peninsular.  Ancient Olympia.

 

 

#5 Delphi – Worth It.  I can see what all the fuss is about walking through Delphi.  It’s not just the historical and cultural significance –  proclaimed by Zeus as the centre of the world, home of the oracle and temple of Apollo – but the gorgeous setting.  You can see why the ancient Greeks chose it – a bit like why the Inca chose Machu Picchu or the Nabataeans Petra – the setting on the slopes of Mt Parnassos is beautiful, and it must have been magnificent in its former glory.  Not toon far from Athens, so a must.  See Walking through Delphi.

 

 

#6 Athens and the Acropolis – Worth it.  The Acropolis is undeniably wow – one of the world’s great historical sites, set on a spectacular hilltop overlooking Athens. But it is RAMMED.  Honestly, they sort of ruined the experience for me and I found myself thinking how nice the likes of Delphi and Olympia were in comparison.  Reality is that you need to travel through Athens anyway, so you’re going to check it out and there are so many other attractions within Athens itself (the Panathenaic Stadium, Temple of Hephaestus and the Agora to name a few) that make the visit Worth it . . . just didn’t meet the “wow” criteria for me.  See Athens and the Acropolis for more detailed tips.

 

 

#7 Mykonos – Worth It.  The high-end party island for Greece – like Ibiza for the central Mediterranean or Seminyak in Bali – its oozing class, glam and lash … and with the prices to match.  Definitely include it as a highlight for the Cyclades islands – the Little Venice Old Town is worth it alone.  But … my suggestion is don’t prioritise it over Western Crete unless lash is the priority.  Mykonos.

 

 

#8 Crete’s Southern Coast – Worth It.  You can’t get much further south (or east) in Europe than Plakias on Crete’s south coast.  With a warm microclimate influenced by North Africa, the weather holds far better than northern Crete, the other Greek islands, or even southern Spain.  So, if your itinerary is eating into November, and want the summer to keep going, give this a go.  Beaches are fab, stunning hiking of the gorges and plenty of vineyards to keep you busy.  Chasing summer in November in Plakias on Crete’s South Coast for more tips.

 

 

#9 The Palace of Knossos – Meh.  Former capital of the Minoans, the first advanced civilization in Europe, and full of wonderful historical significance. The problem with Knossos though is that it is very hard to contextualize this history and bring it to life considering just how old it is.  To give context – its 1000+ years older than the Acropolis.  This is not a criticism of the restoration work that has been done, it is actually very impressive, more just the broad difficulties for a site quite this old.  Not a bad tag on when passing through Heraklion on the ferry to Crete.  The Palace of Knossos.

 

 

#10 The Palace of Mycenae – Meh.  Very similar to Knossos in that this is full of historical significance – the Mycenaeans were the precursor to classical Ancient Greece and this site was the home to, amongst others, the famous Agamemnon who led the Trojan War – but just hard to follow, especially compared to the some of the other wow spots around Greece.  That being said, also worth a brief stop as you travel from Athens over to Ancient Olympia.

 

 

Rough Itinerary for 2 weeks

Athens is the logical hub because that’s most likely where you will land, but also as it is the logical intersection for the two stages of a Greece Trip: Stage 1 mainland Greece, Stage 2 The Greek Islands.

 

If you’ve got the two weeks 📆, go for this (if want to prioritise lash, switch Mykonos with Crete):

  • Day 1 & 2 – Athens.  Land in Athens, visit the Acropolis and generally get settled.
  • Day 3 & 4 – Olympia and the Peloponnese.  Drive to Olympia (3.5hrs) and stay there for 2 nights, via the Acropolis of Mycenae.
  • Day 4 & 5 – Monasteries of Meteora.  Drive to Kastraki (5hrs) and stay there for 2 nights.
  • Day 6 – Delphi.  Drive to Delphi (2.5hrs) and stay there for the night, via Thermopylae if a history fan.
  • Day 7 – back to Athens for ferry to the islands.
  • Day 8, 9 & 10 – Santorini.  Give yourself the full 3 nights so you can walk from Fira to Oia, get a couple of sunsets in and take a boat trip through the magnificent caldera.  Depart on the final day for Iraklion in Crete.
  • Day 11 & 12 & 13 – Western Crete.  Base yourself in Chania (Hania) for the wonderful Old Town, the beaches to the west and the Samaria Gorge Hike.
  • Day 14 – ferry back to Athens.  Either from Hania or via Iraklion on the overnight ferry.

 

If you’ve got full energy and want to adrenaline-shot this 🎢, you could do it in a week with some sacrifices.  You’ll be knackered, but do-able:

  • Day 1 – Athens.  Land in Athens, visit the Acropolis and get going.
  • Day 2 – Olympia and the Peloponnese.  Drive to Olympia (3.5hrs) in the morning and see Olympia in the afternoon.
  • Day 3 – Monasteries of Meteora.  Drive to Kastraki (5hrs) in the morning and catch the 2 monasteries before they close, and enjoy the views along the road connecting for the sunsets.
  • Day 4 – Delphi and get to Mykonos.  Drive to Delphi (2.5hrs), check it out and then drive back to Athens for one of the later Mykonos ferries (2.75hrs) and push on for lash in the evening.
  • Day 5 – Mykonos.  Enjoy Little Venice and maybe even a beach afternoon at Ornos.  Get a late ferry to Santorini (2.5hrs)
  • Day 6 – Santorini.  Prioritise the walk from Fira to Oia, and enjoy the famous sunset from either. Stay in Santorini for 2 nights.
  • Day 7 – ferry back to Athens. 5hrs.

 

General Tips for a 2 week Greece Itinerary in October

 

Prices vary dramatically – be aware that Greece displays not just the classic split of international high tourism prices vs cheap as chips prices outside the main tourist areas . . . but also goes into another gear for the likes of Mykonos and Santorini which are some of the most expensive places on the planet.  Heaps of ways round this, but golden rule is try not to stay in the daft expensive places.  In the cases of Mykonos and Santorini, its really easy to stay 5mins away from the likes of Little Venice and Oia, and see prices drop 75%.

 

Prices for AirBnB and Booking.com will drop significantly in October, so shop around.  We were blown away by some of the discounts.

 

Whats the weather and vibe like in October and early November?  We started the trip around 10th October and finished around 10th November.  Whole time the temperature was kind of perfect for travelling and general tourist things but with one caveat – if looking for the summer beach vibe, it tends to drop off towards the end of October with the exception of southern Crete.  Because of the microclimate there influenced by North Africa, you can squeeze out an extra couple of weeks or so on the beach.

 

Best spots we found to eat:

Athens: Dionysos Zonar’s restaurant is right next to the Acropolis entry spot and with nice views.  For dinner, the Hill Athens Rooftop Restaurant was great food and wonderful evening views of the Acropolis as it shifted from sunset to it being lit up at night.

Chania – for water views and generally good food Amphora Taverna and Canale; for atmospheric courtyard Senal Chania; for wonderful meat dishes Christostomos.

Santorini – in Oia we loved Fanari and Emphasis.  For Fira , Idol Restaurant and VR Cafe had great views . . . and definitely get a terrace to avoid chaotic views.

Experiences Nearby

Wow Factor Score Two scores: first is the wow factor which ranges from ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ to ⭐️, and a separate category for the truly "gash". The second is the more analytical travel experience score, which considers 6 varied criteria to give an overall score out of 100. LowHigh
  • Elite, unmissable
  • World-class, downsides
  • Meets the Wow Factor
  • Worth it
  • Meh
  • Gash

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Score Detail

The scores above are the real point of this site.

Over 20+ years and 100+ countries, I’ve tried to rank the world’s best travel experiences - from genuinely mind-blowing ⭐⭐⭐⭐⭐ to the properly gash.

Every one of the 500+ places on this site has both a Wow Factor rating and a more analytical Travel Experience (TE) score based on the things that actually make travel memorable.

If you're curious about the thinking behind it, head to the About page.

Otherwise, explore the map above or on the Home page and see which places truly deliver maximum wow.

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