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1st trip to Greece - Sept 2026 itinerary

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Hi experts!
I've been reading through the forum and appreciate all the info. Here's our plan:
When: Mid-Sept 2026 - leaving San Francisco (SFO) on 9/15 arriving Athens or Santorini or Naxos on 9/16 (we have flexibility within the month of Sept)
Length: 12 nights departing on the 13th day (9/28)
Who we are: I'm traveling with my cousin and we are both women in our late 50s, active and above average fitness level. We like to travel, sightsee, do cultural activities, some hiking, and some beach/relaxation/spa time.
We'd like to see: Athens, Santorini, Naxos and other sites but the RS road trip is too much driving for me.
Questions:

I've read here that many recommend exploring Athens last. If so, what island should we do first? What itinerary would you recommend and how many nights in each? I'm thinking 4 nights Athens and 4 in Naxos and 3 for Santorini? I think there's an extra night there but not sure where it would make sense?

Is it worth doing the day trip from Naxos to Mykonos or is Delos better? We're more interested in the historic sites than the party scene. If there's a reason to "not miss" Mykonos on your first trip, let me know.

Do we have enough time in Athens for a day trip to Meteora? Is it worth the drive and back? Or what would you recommend (Hydra, Napflio?)

Are the cooking classes in Naxos an authentic/nice experience or are they tourist traps? Recommendations would be great.

I'll keep this short for now and just focus on the order of the islands first. Would appreciate your thoughts and recommendations. Thank you!

Leah

Posted by
3853 posts

Based on what you described, you’ll be taking a connecting flight to Naxos or Santorini on Sept. 16.

Which island you choose depends entirely on what you prefer and the number of days to spend on an island depends first on the island itself and what you want to do there. There are no set rules. My personal rule is to stay at least 5 or 6 nights on an island (except for Mykonos and Santorini, which are unbearable nightmares for me).

Given the amount of time you have, you could potentially visit 2 islands and then return to Athens for 2 or 3 nights. There are over 20 islands you can visit in the Cyclades, but keep in mind that your choice for the second island will depend on the first, as you have to factor in ferry routes and schedules.

Forget about Meteora unless you add at least 2 nights to your trip.

Forget also about Hydra too. You can only get there by heading back to Athens, which means travel times that just don't fit your itinerary.

Nafplio is in the Peloponnese, so you'd also need to add at least 2 more nights and rent a car. (or skip other parts of your trip).

I have no idea about the quality of the cooking classes. I already have some Greek cooking skills so I don’t need them.. That said, I’m guessing they’re probably worth it most of the time.

A concrete example if you stick to Santorini and Naxos. Adjustable by +/- 1 night

  • September 16: fly to Santorini: 3 nights in Santorini.
  • September 19: Ferry to Naxos. 5 nights in Naxos
  • September 24: Ferry to Athens: 4 nights in Athens
  • September 28, flights home

Obviously, there are quite a few other possible options if you forget about Santorini and Naxos. Let's say that the Santorini-Naxos-Athens combination is a good one and easy from a logistical standpoint.

That said, in Santorini, be prepared for crowds. Huge crowds. My worst nightmare. LOL

Posted by
3759 posts

Ha Ha! Jo-Lui beat me to it with aq similar itinerary suggestion, tho as always more succinct.

KEY INFO -- with such a short visit, it is useful for helpers if lyou are very specific on exactly what HOUR you arrive in ATH on 9/16 ... and what HOUR you depart on 9/28. On short visits, every hour is precious, and affects your connections AND your stay at each destination. It's also helpful if you can say a llittle about what you expect/want at each stop. For instance, if you mainlly want to see the famous Santorini "caldera view", then 3 nights (2 days) should be enough, and makes the rest more do-able.

WISH-LIST & TIMING. 12 nights (really 11 days plus a few hours) is not long enough for Meteora. TIMING - Do you really mean you have "flexibility" for Sept dates? In that case, I would suggest arriving on either Thursday 9/ 17, IF your chosen airline arrives in afternoon or Friday 9/18, if your chosen flight arrives before noon. This is because your most transit-efficient itinerary would start with a 50 min. flight to SANTORINI. This jampacked destination. has the most megacruiser visits Mon - Friday noon, with far fewer on weekends ... Arrive when they leave & you'll have much better experience.

An Optional Itinerary
DaY# 1 - SANTORINI - Allow 3-hour layover (because of longer check=in process) - & take 1st available afternoon fllight via Aegean or Sky Express; I recommend staying FIROSTEPHANI (fab cliffside rooms, no tour mobs, v convenient ). Car service to hotel, sunset Dinner nearby ( try Remvi Cafe -- fab views, sane prices NO crowds).
Day 2 - (ajet-lag recovery day) pre-noon, Rimside walk from Firostephani to Fira ( Don't do Fira-Oia -- Naxos has better hikes)
check possible 6 pm wine-tasking at sunset-view winery)
Day 3 - book 7:30am taxi to OIA, to enjoy 2-3 hours exploring OIA, before cruise & package-tour armies invade. Many options for afternoon -- charming town of Pyrgos is tourgroup-free.
Day 4 - NAXOS - 10:30am Reserved-seat Champion-Jet fast-ferry; has rear-deck to see departing cliff view, Arr NAXOS around noon. Recommend booking beach-view balcony room on St. George beach adjoining Port Town... walk along shore line 1`5 mins to all the attraction of Naxos town- cafes, restaurants mseums, shops.. Hourly busses go to farther out beaches
Day 5 - 6 - 7- 8 -- Explore Naxos! Among the most scenic & history-rich, beach-blessed of all isles: ruins, charming hillside villages, amazing hikes, divine swims. Devote 1st day to Naxos Town, Fort, Castle etc, Next day This great tour http://www.naxosbustransfer.com/ takes u to all Naxos highlights, w noonday swim as well! The next 2 days, swim, hike, discover; and yes, there are genuine cooking/country farm experiences; others will give your their favorites.
Day 9 AM - ATHENS Take mornng fllight to ATH airport; to convenient Central Athens Hotel
Day 10 - 11 - 12 - Athens sightseeing.
Final note -- Lock in your intercontnental & domestic flights First -- only then, look at accomodaitons. you have plenty of time.

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