1st trip to Greece - Sept 2026 itinerary

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

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.

Thank you JoLui and Janet! You two are amazing. Truly appreciate the quick and detailed reply! Everything is so helpful. I am going to digest this information, secure our departure date and flight time for arrival in ATH and then write back with more detailed information. I like the tip about arriving in Santorini when the cruises are leaving so I will try to get a flight out on thursday or friday.

Because it's our first time in Greece, we really do want to experience the beauty of Santorini, and I've read great things about Naxos, and of course, have to experience the Acropolis and other sights/museums, so we will stick to these three destinations. We'll save Meteora, Hydra and others for another trip.

I will see if we can add 1 more day for a total of 13 nights and spend that in Naxos. I will try to book a flight that arrives in ATH before 2 on a Thursday or Friday, and our return flight from ATH to SFO will not be before 10am. I like to sleep in, have breakfast, finish packing and ease my way to the airport.
Thanks, again!

I disagree with Janet on the hike between Fira and Oia. We did the hike and thought the views were fantastic. We also hiked on Naxos. We went to top of Mt Zas which also had beautiful views.

Aegean, the Greek airline that flies from Athens to the islands, is a member of Star Alliance.

Check if you can find single-ticket flights from San Francisco to Santorini with other Star Alliance member airlines like United, Discover Airlines, or Lufthansa.

Santorini is a very popular tourist destination and is served from many European airports. For the outbound journey, you don't necessarily have to go through Athens.

On https://www.united.com/en/us/ I see flights from SFO to JTR (Santorini) via Munich, Frankfurt, or Zurich in mid-September (with Lufthansa).

I don't think the Fira-Oia and Mount Zeus hikes are really comparable. I've done both. In my opinion, they don't have much in common. Fira-Oia is mostly a long 10 km walk, more a scenic stroll along the cliffside with Caldera views. Mount Zeus on Naxos is more of a rugged mountain climb on rocky trails (there are two possible routes) where you'll encounter just as many goats as tourists.

You can do both!

Jo-Lui first again! now, some N American aspects.

OUTBOUND
It's a nice idea to be able to skip Athens en route to Santorini... but one must consider all factors:
• Sometimes Star Alliance bookings don't provide best price, if budget is an issue
• the loooong journey from West Coast is exhausting - you'd hope to have only 3 planes to reach Santorini: Options include (1) fly to East coast/ nonstop to ATH/domestic to Santorini (2) nonstop to European airport/ transfer to either ATH or (if lucky) Santo. The challenge w #2 is that transfers in Europe are usually late morning early afft, when most airport traffic-delays occur. Aim for a combo that gets you into Santo by 5 pm latest.
HOMEWARD
I totally agree w you in hating Dawn Departures... ruins one's last-night finale fun. Be aware that it can take 1 hour to airport, plus (formerly) required to be in line 2 hrs before Dep -- and now this newfangled EEC process seems to be causing big delays (groan). Keep an eye on this. Even so, a 10 AM Dep means leaving hotel @ 7 am. And homebound flights face headwinds - slower speed. You must weigh leisurely bkfst against a Dep time that only gets u to SF after midnight. Everything has its costs..

That said, plans sound good so far!

Janet, yeah I know, I just wanted to mention that option (whether it's a single ticket or not) in case the OP thinks they can only fly to Santorini from Athens. As for the rates and schedules from the West Coast, that's not my area of expertise Luckily, we aren't affected by this EES system either.

On the other hand, dawn departures for the Athens airport don't bother us at all. And we always have some sporting activities until 1:00 AM the night before our flight, which is usually around 8 or 9 AM the next day.

https://photos.app.goo.gl/yM5L2d7Q6F8L4tqbA

Yep, I always figured you for a party animal ... I'm a night owl /dawn-dreader myself, that's why the Greek timetable agrees with me so well. The OP seems to be the same... but late-departure can almost make it post-midnight arrivall for Pacific-dwellers.

Ah well... to keep it in perspective, my first trip abroad, NY - London, took 7+ hours on a turbo-prop.

Ahah, the first time I left NYC was to go to Los Angeles driving a Ford Country Squire Station Wagon. The journey took nearly four weeks. (I realize that has nothing to do with Greece.)

When one travels sometimes one has to make comprises on how to get to your destination and/or time of departure/arrival.

Flying from the West Coast will take time, lots of time plus at least one connection somewhere before arrival in Athens.

Then hope for a connection in a timely manner to Santorini or other island.

There's nothing wrong staying in Athens upon arrival if the schedule to Santorini or elsewhere doesn't work, either you missed a flight or the wait for the next one eats up valuable time sitting around in an airport after a super long flight to Greece.

I'm another who loathed the dreaded 6 a.m. departure from Athens back home. As Janet said it ruins your last night in Athens.

Fortunately for the past 5 years Delta Airlines now offers non-stop from Boston to Athens at wonderful departure/arrival times going and returning back home.

As for the "beauty of Santorini" there are numerous other islands that offer "beauty" without the hordes of tourists and at lower prices.

I've never been but I have been to a lot of other islands that for me offer beauty and a probably more "Greek Experience" rather than a tourist experience.

If you have your heart set on Santorini by all means do what your heart tells you.

Hello! Love everyone's commentary and your perspectives are all very helpful. Giving me food for thought. We are flying on United because we have the points to get us there and back. We do have to work around the star alliance connections because those most likely won't be covered by points but it's fine, I don't mind dishing out some $$ for reasonable flights. I am looking at routes that will get us to Santo without stopping in Athens. After a long haul, another 3 hour layover and 1 hour flight to Santo isn't very appealing. We can pretty much get to most of Europe on United and then find a connection to Santo on another airline. Will come back with a couple of options to see what you folks think. I'm not that familiar with the European airlines and their reliability.

Appreciate the info and comparisons on the hike as well! Maybe can do both, but not a long rugged hike. A short (2-3 miles) rugged hike would be ok though.

Thank you!

There are plenty of budget/low-cost airlines that fly to Santorini from Europe. In fact, that's the main reason many Europeans go to Santorini: because it's a gateway to other islands.

Ryanair is an Irish airline that has a really bad reputation but offers super low prices. However, they charge you for absolutely everything, even a glass of water. They've hired employees who get bonuses for catching passengers with oversized or overweight bags, so definitely watch out. Just 2 cm (less than an inch) too long or 200 grams over, and the price of your ticket will double. Also, since last November, they've gotten rid of printed boarding passes, only the mobile boarding pass on their app is free.

I've also flown with a few other low-cost carriers:

Volotea: (Spanish low-cost airline) It's barely any better, but it's more ethical than Ryanair.

EasyJet: A UK airline that's not too bad.

Transavia: The budget subsidiary of Air France/KLM, which is also fine.

None of these airlines are part of Star Alliance. Only Volotea has been operating codeshare flights with Aegean for the past two years.

For all of these carriers, make sure to carefully check their baggage, cancellation, and seat selection policies. Nothing is free.

Sky Express is a very good Greek airline that operates a few flights to and from Europe, but not to Santorini.

Regarding Mount Zeus, the shortest route is about 3 miles with an elevation gain of roughly 600 meters ( 2,000 ft). It’s nothing too difficult, as long as you start early and wear good shoes.

There are a few other easy hikes around Naxos. I've listed some of them on this map:

https://www.google.com/maps/d/edit?mid=1d7GZMjFODUlB8lf7EPSXQRwu-YXaKxw&usp=sharing

Use United to some airport in Europe.,,, except, since it's for a transfer, avoid ChasDeG at all costs ( sorry Jo-Lui, u don't want me to spell alll the reasons why not, and I'd avoid heathrow also). Pick another that has Santorini flights on Aegean ... and book. For heavens sake you are saving a bundle anyway on points. Aegean has been voted best European (nontranscontental) airlline for 5-6-7 years. Avoid those iffy outfits, you're not kids.

No need to be sorry Janet, I never fly from CDG for flights within Europe, flights to Santorini from Paris depart from Orly airport (and my usual airport is Toulouse anyway, the city of Airbus).

Thanks for the list of airlines! Will take your tips on avoiding CDG and Heathrow. Will look into Aegean too. It will take some coordination but I'm sure I can get it done. You two are the best.
I'm working today, but will have some options laid out by tomorrow. Stay tuned!

OK, so Aegean has a flight from Munich to Santo on Friday 9/18 departing at 14:55 and arriving Santo 18:35. Is that too late in the evening to arrive in Santo? Also, Aegean only offers this non-stop on certain days, so we're limited to this Friday flight. I've briefly checked other airlines but same (few non-stops). Will keep checking for a flight arriving earlier on Friday.

United has a ton of non-stops to Munich. We might stop there for 2 nights so we can have more options for flights to Santo.

Also, it appears that most of the direct flights from within Europe to Santorini are suspended starting September. So if the Aegean flight is too risky, maybe we should just fly into Athens are connect from there.
Thoughts?

My brother in law who joined us on our first trip to Greece flew from Munich to Santorini. I think it is a good option.

My twenty something kids took Ryan air to Santorini arriving at 11:30 pm. (We had a family group of 7). I arranged through hotel to have them picked up at airport. You could do the same.

I can't really comment on this kind of itinerary, but either way, if I had to choose between Ryanair and Aegean for the flight to Santorini, I wouldn't hesitate for a second—I'd go with Aegean.

If you have a reasonably priced option with just one layover on a single ticket, you will collect your checked bags, if you have any, in Santorini. If there is an issue with the first leg (a delay or something else) that causes you to miss your connecting flight to Santorini , the airline is required to find you a seat on the next available flight. If that flight is the next day, they must provide hotel accommodations, meals, and transportation at their own expense.

6:35 PM isn't too late to arrive in Santorini. There are flights arriving and departing until 1:00 or 2:00 AM, and some ferries even pull in the middle of the night. Everyone is used to it, including the hotels, which are totally accustomed to guests arriving at all hours of the day and night. In Greece, dinner time is around 9:00 PM. You'll see young kids playing outside until 11:00 PM, even when they have to go to school the next day.

I'd like to add, that if you like hiking you should definitely do the Fira - Oia hike (as it is really an amazing scenery) and in case you are hopping to Santorini directly, that you could even use your jetlag for your own benefit: It is often recommended to do the hike as early as possible to avoid the heat and crowds. Depends on your type (and as you are travelling eastwards), but it getting up reeeeaally earlier could be rather easy for you.

Instead of flying from Naxos to Athens I'd rather take a slow Blue Star ferry - it takes 5 hours, but is really relaxing in my opinion. Not that much longer than flying actually, becase you need about 1,5h on Naxos before flight and going to the airport, 45min flight, 30min baggage reclaim and getting to the bus/metro, then 1,5h to city center. Sums up to more than 4h. With the ferry, you just have a coffee at the port and walk over when the ferry comes in. Piraeus is just 30min from city center.
If you arrive in Athens, you could do a spontaneus trip to Hydra. There are many connections per day and it is not too far. Personally, that would be a too tight schedule for me, but it is worth keeping it an option.

Thank you, JoLui. Good to know that a late arrival in Santorini isn't an issue. I do feel safer with Aegean.
Thanks, Blackdog, for the info on the hike and the ferry from Naxos. It does sound like the same travel time either way. As long as the journey is pretty, relaxing, and I get a comfortable seat so I can read and eat I'll be happy. Will add that to the itinerary. Was going to ask for a recommendation on a ferry company, but I see that you mentioned Blue Star. Thanks!

To be honest, the journey is not that pretty actually, as most of the time its more or less open sea. The first hour, when sailing around Paros and docking there, is nice and when approaching Athens. It always gives me a sense of how travelling should be. In between, you can definitely find a nice place on deck (or wander around and switch between places), have a drink and watch the waves.

Thank you for all the responses! We've nailed it down! We're flying to Munich non-stop. Staying 2 nights and then flying Aegean non-stop to Santo arriving on Friday 9/18. I know Munich will be a different vibe from Greece but we're happy to get a taste of Germany.

3 nights in Santorini. If you haven't already, please provide your top lodging recommendations. I know Janet recommended staying in Firostefani. Mid-price is ok.
4 nights in Naxos. Any area recommendations close to a nice beach?
3 nights in Athens. We have a hotel already and will follow most of Rick's walking tours and other suggestions. Will leave from Athens for SFO on a flight that doesn't leave too early and arrives SFO around 7:30pm.

Will use inter-island ferries. Would appreciate restaurant recommendations, local eats, beaches with easy access and any other tips you wish to share. Thank you!

Glad to hear you've "pulled the trigger" & havve your fllights. Here are some reccommends -- and remember, if you book at the "cancel without penalty" rate, it's a NO-RISK , if you decide to swtich to something else, or "tweak" your dates. So if you see something good, Pounce! Good valuers/locations book up increasingly early... not like the old days.

SANTORINI - FIROSTEPHANI -- Places with rooms w caldera-view balconies -- Best buy is Hotel Mylos w view balconies ... also check Agnadema Apts (actually a hotel - has pool on shared terrace... Hotel Sunset has large shared terrace w bg wicker couches... DINING - In Firostephani, don't miss the Oldest Taverna (restaurant) on island! Aktaion, https://www.aktaionsantorini.com/ .. right beside the rimside path For sunset dining without crowds, fine traditonal menu at sane prices, great views -- check Remvi Cafe == https://santorinidave.com/santorini-restaurant-remvi

NAXOS - For Mid-Sept, when outer beach activity is closing down, the great solution is to stay at Ag Giorgios (St. George) Beach directly adjacent to Port Town... 10-15 min walk along seafront to all attractions, cafes, nightlife etc of Naxos Town. For rooms right on sand w sea view, Look at Studios Kalergis,, of Hotel Palatia (upper floor), Studios Thomais, Studios Diogenes, (all on booking dot com & other online agencies) ... also Villa Naxia, must be contacted direct/ Dining -- walk up to top of town, To Kastro, great sunset views, Right on port promenade Looing out at Ferry pier, Balcony up 1 flight - Boulamatsis -- GrEAT fish n chips!! A good Grill House right on seafront promenade, Cozi. For 2 you'll need reservations for, Metaxi Mas and To Elliniko.. the latter dovted to classic Greek menu. 2 out on Plaka Beach are special -- NIkolas & Maria,, tables in the sand at water's edge, and Petrino's, this is top Naxian restaurant, modern take on best Greek dishes, features Naxian products. U can take bus out htere for sunset dinner but in advance, book taxi to come get you back to your hotel.
-- The St. George beach is shallow at edge, but wade out 100 yard and sudden drop-off for great swims... If you want another beach, my fave is Plaka. Take a bus out, ask for a stop at Aegean Land (a beachside hotel)... it has beach sunloungers, no cost if you buy a bev or snack, plus a pool & a changing area. NOTE: Buy all bus tix in advance at kiosk by ferry pier & get tmetable.

Thank you, Janet! We got our room at Hotel Mylos. Pics look nice. Will check your recommendations for Naxos.

Just back from Naxos yesterday. It certainly ticks all your wants. This year we stayed at St George beach to be close to Naxos town. but you can easily take a bus excursion available from the KTEL bus office at the port so you can get up into the mountains and see the countryside.
If you do not like escorted bus trips just use the KTEL bus and take in one of the mountain villages at your own pace. We always like to get to Aparanthos and Chalki. These mountain villages are a treat to explore.
I have not had time to edit my Photos of Naxos however these images were taken on our visit last year.
https://www.flickr.com/photos/stanbr54/albums/72177720329571437/

You're back! will expect pix soon, expertly displayed by the Family Organizer ... I'm currently helping out another Canadian who's planning a long wished-for trip... your savvy will be called upon stanbr.

Sad to leave Naxos and Crete but happy to be home again.

Thank you stanbr! Beautiful pics. I'm excited! Do you (or anyone else) have more recommendations for lodging in Naxos?
Unfortunately, all of Janet's recs are booked for our dates. Thanks!

I’m going to go against the grain here and say that we never stay in Naxos Town or the surrounding areas like Agios Prokopios, Plaka, or Agios Georgios. During over 15 days, we only spent a few hours there. So, since you're having trouble finding a place to stay, I just wanted to point out that 90% of the accommodations on the island are actually outside of that zone.

Granted, it’s much quieter, for sure you won't find tons of shops or dozens of restaurants but the sandy beaches stretch on forever and are practically deserted (and no paid sunbeds!). Just start your search around Mikri Vigla and keep heading south along the coast.

And if beaches aren't really your thing, there are dozens of spots in the inland villages that are totally worth staying in. Of course, this usually means you'll need a rental car and wanting to explore the island.

Thank you JoLui. I will search around Mikri Vigla. I would like to lounge on the beach a couple of mornings in Naxos so I hope it's close. I think we will need a car for one day to explore.

A little south of Mikri Viglia is the village of Kastraki, which offers a few options for accommodations, taverns, and beach bars right on Kastraki Beach.

You can check out places like Coralli Beach Apartments:

https://www.coralli-naxos.gr/

Or Kastraki Dunes: (from approximately €90 per night for a room with kitchenette, terrace, and sea view)
https://kastrakidunes.gr/

It's right on the Naxos Town–Pyrgaki bus route:

https://naxosbuses.com/routes/pyrgaki/

There is also a mini-market right next to the Kastraki bus stop.

Here is the Naxos bus route map:

https://naxosbuses.com/wp-content/uploads/2025/06/busmap-1.png

And not far away, there's an excellent tavern serving local Naxos specialties called Apolafsi:

https://www.apolafsinaxos.gr/en/

I think we will need a car for one day to explore.

Naxos is a huge island. Renting a car for just one day won't be nearly enough time, and on top of that, many car rental companies won't even let you book for less than 2 or 3 days.

Don't forget that you can also rent e-bikes: https://naxosbikes.com/our-bikes/

Unless you are committed to car rental for whole trip, I still think staying in Ag Giorgios (St George) beach area is best for you. And believe it or not, these days, June is late for having widest choice for hotel. Your best bet may be, not to hunt up individually, but put your dates nto This "clean" llink to St G -- https://www.booking.com/district/gr/naxos/agiosgeorgiosbeach.html (BTW, I suggest using your "private " or "anonymous" browser window option, so the online agency won't "cookie" you & show you a llimited list)

When u put in dates of Sept 21 to AM 25, you get a list... but instead click "show on map" & you'll see exact location of places that still have available double rooms -- U have 2 problems limiting your choirce • you probably want free cancellation and • you need twin beds -- SO many Greek rooms have only double or queen. You also have not shared your preferred budget. For future, remember that's thoughtful when asking adivce. With the above link, I see 3 w free cncellation I'd say to check: • STUDIOS KALERGIS - top location, right on sand, all units balcony on sea, but $162 per night • NAXOS DREAM APHRODITE - off sands, balcony w side street view, but twin beds, looks nice • Azure Mare- also a bit off beach but looks nice, balcony, twin beds $ 82 per night

Thank you both! I'll look into your recommendations. Appreciate the booking tips and link. Our budget for hotels in Naxos is under $200/night. I think closer to $150 can get us a nice clean place. I've seen some under $100 and they just don't look clean (and I've checked reviews).
We're not that high maintenance but I do worry about bedbugs.
Not sure we will need a car for the whole stay in Naxos but will do some research and check prices to see if it makes sense.
Thanks!

For Naxos beach places, the price thing is often location-based ... In naxos, i've always found nce clean small places -- best ones, like htese, are usually family run, 12 - 20 units. Often the linens are line-dried, and snowy-white, crispy-fresh. One forget that, in these days of machine-everything.