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14-day Greek islands 1st-time Itinerary suggestions in May - THANKS!!

Hi, this is such an awesome forum! Thanks in advance to those who have any advice to offer! My husband and I are travelling to Greece for the first time for our 25th anniversary in May. We fly in/out of Athens, & excluding flight time from US mainland, have May 6-20 (14 days) for exploring the Greek islands. What would you suggest for an itinerary? We definitely want to see Santorini & Mykanos, and want to visit islands (and Athens, if you think it's worthwhile) that offer insight & experiences to Greek life. We are not big museum fans, nor do we like to lay out on the beach all day (although we're always up for relaxing for a few hours & people watching). We have the energy to see a lot in a small amount of time, but are open to your suggestions about enjoying a certain area, beach, town, etc and just soakin it up for what it is. We love to eat, enjoy hiking and seeing interesting & different things, scenic views, and want to experience local Greek life. We opted not to do a cruise for this trip because we want to spend more than one day on each island. We don't know anything about the ferry system, so any suggestions of an itinerary that simplifies ferry/etc travel between destinations would be greatly appreciated. Hotel recommendations with outstanding views in locations that provide easy access to exploring the area without renting a car would be great. If you highly suggest renting a car for a particular area, we're open to that as well (we've driven all over Europe & Australia so always up for the challenge). Also, if you have a suggestion for a tour or not-to-be-missed experience, please let us know. Some of our best trips involved off-the-beaten-path experiences. I've done some online research and got overwhelmed by the choices, so I'm hoping your responses narrow down our choices so we can book this thing! Thanks!!!!! Wendy

Posted by
91 posts

Just a couple of thoughts to get you started:
- Of course Athens is worth it, especially if you have never been. A couple of days at the end of your stay is highly recommended, to visit the Acropolis, 1 or 2 of the world-class museums, stroll around Plaka etc.. At the end as it's good to be in Athens the day before your International flight, in case of weather/ transport problems.

  • Why Mykonos? I don't think it's a good fit to your interests at all. It is always 'pushed', at the front of every US guidebook, it seems! I'd have another look, if I was you, there are so many islands that would suit you better. I wouldn't suggest more than 2 islands & Athens in 14 days, as the travelling time takes half a day each time, as well as the packing & unpacking, finding you hotel etc.

OR consider 12 days on Crete - it's a huge island, a country in itself really, with a big range of scenery, cities, mountains, beautiful beaches, lovely tiny traditional villages, Minoan sites etc etc. A hire car is best to get the most of it's beauty, in my opinion.

Posted by
1117 posts


first off, I think it's a wise choice not to do this by cruise. The cruise ship tourists, IMO, get to experience all islands at their very worst: in the midst of thousands of other cruise ship tourists who are set loose on the island all at the same time and crowd the same limited area that is within reach of their time limits. Restaurants and shopowners, in my experience, have learned to deal with this by offering overpriced and low quality service within that radius.

I think Santorini - though definitely touristy and crowded - is a must-see for a first time Greece visitor, so you've made the right choice there too.

Mykonos is nice and has Delos to go with it, but it's also a very crowded island and has a bit of a party island reputation.

The standard island recommendation you will get on this forum is Naxos, which is certainly nice and a much more "Greek" experience. Considering how often this recommendation is given here I would hesitate to call Naxos "off-the-beaten-path" though. If you want something more remote and more Greek, you might have a look at islands like Astypalea or Amorgos.

Now for your time frame: 14 days is not enough to do several islands plus Athens plus Crete. I personally would do Santorini + 1 other island + Athens within that time. People with a faster travel pace might add another island, but keep in mind that each change of location is going to cost you pretty much a whole travel day. Crete is so large that it's almost a country of its own, so I personally wouldn't find it worthwhile to combine that with other islands -- make that either one or the other.

If you can, try to get to your first destination (Santorini) directly without wasting a night in Athens if possible. Put your Athens stay at the end so you won't have to get nervous about catching your return flight in case some flight or ferry from the islands gets canceled.

Posted by
3621 posts

Since you "...definitely want to see Santorini & Mykanos..." then do so. Better to regret (not likely) going there than regret (probably) not going there. We would not hesitate returning to either one or both. Delos (from Mykanos) is a wonder place and can be done as a day trip. Athens is definitely worthwhile. Just our opinion.

Posted by
2876 posts

For most efficiency our tested advice: when u land, connect ASAP (2 hr layover) with flight to Santorini. After 3 nights (I favor 48 hours max u may want a bit more), take Ferry 2 hrs to Naxos. A 10:30 AM fast-ferry Champion jet has back decks for caldera-leaving view; 3:30pm Blue Star has wide open decks for same. Avoid closed-in catamarans.

If u choose Santorini & Naxos you "have your cake and eat it too." Naxos has dedicated excursion boats for day trips. Mykonos 4-5 days a week, on the NAXOS STAR and MV ALEXANDER. I favor the Latter much larger vessel, smoother ride; 3 hours on Delos, 3 on Mykonos, back by 7pm, for leisurely "sundowner" before dinner.
Click my name, you'll probably find dozens of threads where I've responded at length with advice on lodgings, activities, foods etc on these 2 Islands I know well; Naxos 13 times, Santorini at least 5-6 ... most times with newcomers along, in your approximate age range, so I know what they've enjoyed most. Also, I've traveled in May on 11 of my trips.

SANTORINI -- Naturally, if possible you want a room on or near the Famous Caldera View. The village of OIA gets the most promotion for this, and accordingly the prices are considerably higher. FIRA Town is next for hotels on the Caldera. Both of these however get the Brunt of the Cruise Ship invasion from Mon-TH (sometimes 4 ships even in May) that dump 8-9,000 people on those 2 towns from 10-4. A good avoidance strategy is FIROSTEPHANI, which is in the "goldilocks" position -- many hotels on/near the view, but NO cruisers or tour busses; an easy 15-minute walk on the rim-path to FIRA, a quick bus-ride to OIA, no need for car rental. check this map - Check for availabilities in FIROSTEPHANI for May 6-7-8, (quickest overview - pick a hotel at random, click on google map & you'll see ALL hotels listed with this online site). If you can do without a pool the BEST bet is Hotel Mylos - €405 /3 nites w caldera view.. but only 1 room left. Also Agnadema Apartments (Pool!) Stefani Suites (pool!) Villa Maria Damigou, IRa Hotel. NOTE: DO NOT DELAY on booking hotels, because the best place are booking solid NOW (Bridezillas, you know). --unless u choose rock-bottom rate, you can book with FREE Cancellation, my recommend! If you can't decide, book 2, maybe on different online sites, then choose.

NAXOS -- In July I'd recommend a farther-out beach, but in May, the "goldilocks" location is ST.GEORGE/Ag. Giorgios beach, directly adjacent to port town. Best of both worlds, balcony view of sea ... handy for swims (shallow at edge, wade out to depths), wonderful for relaxing sunning and cafes, Just a 10-15 minute stroll to Naxos town's fascinating lanes, shops, museums, dining. NO need for car, Naxos has great bus system - I bus 2-3 times to swim at far-out beach or to hike in hills. To see the whole island do a all-day fascinating bus tour, from beaches to mountains, hill villages, ruins, ancient statues etc ... or book a car for a one-day whirl; I've done both. Naxos room-rates are 30-40% below Santorini caldera-area rooms. Right now on, St. George Beach area, some available places I like, May 10-15, include Kalergis (my top choice), and Ippokampos Beach Hotel. two that don't list on but u could contact direct are Hotel Asteria and Villa Naxia. 3 more "upscale" pool hotels in order of my choice are Naxos Resort beach hotel, Hotel Spiro, and Nissaki Beach. The latter 2 are a farther walk from town & beach, and many rooms have no ocean view. Nissaki is closest to town, but not best imho. But DO NOT DELAY! Book NOW at free-cancellation rate!

When you've booked, THEN we'll talk about activities, dining etc - but hotel bookings (AND that Santorini flight) come FIRST.

Posted by
4 posts

Thanks for your comments & advice! I booked a flight from Athens to Santorini upon arrival from the mainland on Ryan Air since it had a late flight departing 2+ hours after we arrive.

Now trying to figure out what to do in between Naxos & Athens.

- Would 4 nights in Hydra be too long? Heard it was a charming, relaxing village, but would it get boring?
- What about extending our stay in Naxos and doing day trips by ferry to neighboring islands like Mykonos, etc. Are ferry day trips expensive and time consuming? Was thinking we could use Naxos as a home base since it got lots of recommendations.
- What about arriving earlier in Athens & using it as a home base for day trips to Hydra/close islands?

Also, any strong opinions about Ryan Air? Should I fork out the extra $$ to stay overnight in Athens or book a more expensive airline? And is it a bad idea that we arrive into Santorini after midnight / hauling luggage around, or not a big deal (staying at Annio Flats)? Thanks!

Have this so far:
Day 1 - flight into Athens, late flight out to Santorini
Day 2 - Santorini
Day 3 - Santorini
Day 4 - Santorini
Day 5 - Ferry to Naxos
Day 6 - Naxos
Day 7 - Naxos
Day 8 - Naxos
Day 9 - Ferry to ??
Day 10-
Day 11 -
Day 12 -
Day 13- Ferry to Athens
Day 14 - Athens
Day 15 - Athens
Day 16 - fly back to mainland USA

Posted by
2876 posts

Congrats again on further work on the itinerary. Some added comments:

RYAN AIR - Yes does have iffy reviews ... but mainly from High Season, regarding Santorini package-tour crowds. Still, it may have departure delays. Thus, its prudent to arrange in advance for taxi/shuttle to your Imervogli place; it will cost at least €25+.

HYDRA - Why??? It's often promoted by RS Site, but mainly because it's part of some of his tours, its one of the few islands RS has visited in recent years and - most important - for people on very limited time, it can be a chance to see one island from Athens. I have a better alternative for an unforgettable 3-4 days:

NAFPLIO & ARGOLID -- This amazing adventure is only 2.5 hours away from ATH, by bus or rental car, on Greece's most modern divided highway, with scenic delights much of the way... The ARGOLID, just across Corinith Canal, is THE most densely historic area in the nation (landmarks everywhere!!) is centered on NAFPLIO, considered by Greeks to be the country's most beautiful OLd Town.. On a peninsula, a visual joy, check out this NONcommercial website created by a Scandinavian expat - Here's a great photo album of highlights, from another Nafplio fan, "stanbr" - - PLEASE click ALL links on Visit Nafplio, including How to Get there, and Important info: where to stay, eat, etc. To guide planning use this great online map : (click to enlarge) -- it shows ALL roads & terrain from Athens or ATH airport, to Nafplio & around.

TO GET THERE -- Easiest way would be to fly from NAXOS - there are usually 2 flights per day, one early, another about 11 AM, 45 mins vs 5-6 hrs on ferry. (Do not delay about booking because these are modern small planes, about 40 passengers and they fill up FAST). At Airport u can rent a car (about €35-40) & be on your way in minutes and not a single stop until after the Corinth Canal. If you like, a few miles onward, you can exit at "ANCIENT NEMEA" just off the highway and quickly see an wonderful "sacred games Site" -- the Runner-up to Olympia... but NO tour crowds! Its also in heart of BEST wine country, so in Nearby Nemea village you can visit an actuall bottling plant, and sample some Nemea Red (my fave). Then Onward to NAFPLIO ... in time to explore the town and have your first fab sunset (IMHO, better than Santorini). Town deserves a day, pllus u can explore around... with hikes, beaches etc. When time to return to Athens area, drive across the PEloponnese "thumb" to EPIDAURUS, just for its awesome ancient ampthitheatre, the world's best acoustics! Then go up coastal highway, jump off at ISTHMUS for 30 minutes, just to walk across the Old BRidge over the Canal (SO deep! SO skinny). You can return car at Airport & take a Bus or Metro into Central Athens for your hotel (you can also return car to a Central Athens office if you plan ahead and mark map thru the city maze of streets).

IF you don't want to drive, on arrival you can take a bus from ATH airport to the KTEL (intercity) bus station on Kifissou Street and get a modern reserved-seat bus to Nafplio (€13 1-way), 2.5 hours, just not able to stop enroute. When in Nafplio it's easy to rent a car for 1-2 days for about €35 ... in either case, before leaving, stop at AAA for 20 minutes to get an INternational Driving Permit for about $25. (U do know to bring along your regular license as well).

FINAL ITEMS -- I see you have 3 days or so in ATHENS ... I'd also advise booking NOW for best locations, for walkability to the major sights. I myself prefer places on SOUTH side of Acropolis, quieter, more scenic. If you do choose Nafplio, and/or have not yet booked for Athens, I can suggest moderate-rate places for both... but DO NOT delay -- smart travelers already are filling up my favorites!

Posted by
4 posts

@ Janet - love your suggestion! You sold me on Nafplio and Argolid! Looks beautiful, romantic, and we like our wine.

Would appreciate some suggestions for hotels there? I don't mind driving and sounds like there's lots to see to/from Athens.

I did put 2 hotels on hold in Athens - Andromeda Downtown Suites, and Athenaeum Grand Hotel. Your thoughts or other suggestions?


Posted by
4 posts

@ Janet -- the reason we considered Hydra is because my brother in law spent time there and thought we'd enjoy it. I can do it as a last minute day trip from Athens if we have time.

I forgot to mention that we did see the Olympia ruins as a day tour from a cruise years ago. And we've visited many ancient Roman ruins, churches, and most major museums in Paris on previous trips -- so sometimes it's hit or miss for us on historical sites. The island of Hydra with the donkeys and no cars allowed sounded refreshing and different. :)

Posted by
2876 posts

NAFPLIO HOTELS -- I just checked for double w. balcony 3 nites check-in May 14 - check out Th May 17 -- and found a few. The BEST location (hotel AGAMEMMNON) right ON the water has balc room but with city view not sea; OMORFO POLI, a Super Pension, facing a darling flower-garland lane, has a double w. balcony ... AND, right on the (marble-paved) square ATHENA HOTEL has 2 rooms w balcony with view (the "deluxe" one has a queen bed) ... on a weekend it might be over-lively, but midweek is perfect. Upscale a bit is GAMBELLO LUXURY ROOMS ... new to me, but location is great, and they have a "superior ROom with Sea view" (but no balcony)

If you want to stay up above, looking down on town and sea, a quaint place at VERY moderate rates (€ 147-160 for THREE nights) - and that's at the higher free-cancellation rate... PensionEleni. Eleni doesn't speak much English but is warm & welcoming! Friends have stayed there & enjoyed much. 2-3 choices, balconies with view of lane and some w. ocen views. You drive up a curving road & park in a small square; Pension is right on its corner. You walk down stairstep lanes to the sea level. I used to stay next door at Hotel Leto & looooved it; it was sold to dumb new peope, called Hotel Leto Nuevo, tacky Moderne decor, I don't recommend.

For all sea-level lodgings, at midweek parking is a snap ... the whole seafront is a wide-open free parking lot. As before, I urge booking NOW ... if u cant decide, book 2 and then choose, Also if you decide to "tweak it" a day one way or the other later, most hoteliers will go out of their way to fix it.

RE HYDRA -- I understand -- but peple who can stay there like it best, they have access to a pool. Some well-known people have houses there... most of them hidden behind high walls. Also, I am a big one for swims, and Hydra has almost no beaches, you swim off rocks. But to each his own. If I wanted an island outside of Athens for a day or Overnight, I'd choose Aegina; have been there 2. Here's an interesting photo album of a day trip to Aegina on a conventional open-deck ferry (avoid hydrofoils, u are trapped inside in assigned seats, NO view at all). Aegina is just an hour's ride, but such an enjoyable sea-scape! Huge freighters, cruise liners, ferries, and tiny sloops... once i even saw a dolphin! Interesting island, half the time or less to get there as Hydra.