Crete, Santorini, and Naxos look quite doable within the 12-day block, but Crete’s beaches are scattered throughout a very LARGE island, Santorini really only has Kamari and Perissá (and some southern coast bays) and Naxos does have nice places to swim. If you choose only to visit those three islands in your relatively short time, you will do well.
Excellent choice of islands, though getting between them presents one or two challenges (they are not as conveniently connected like the Cycladic or Dodecanese islands so island hopping is not as popular in this island group). All three islands are served by airports with year-round connections to Athens and in the Summer with international charter flights from Europe. Let’s take the pros and cons of each island.

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Nine weeks in Greece is a dream itinerary it certainly gives you lots of flexibility. As you seem to have Athens and the Peloponnese sorted, you just need to sort out your five weeks on the islands. What you need to realize, however, is that the islands are not all mutually interconnected, but rather they are ‘grouped’ – both administratively and from the point of view of transport routes. Here are the main groups.
This long and slender island is the most historic of the Out Islands, with the first English settlers arriving back in 1648.  Much of the architecture and way of life was influenced by these British Loyalists. Here you will find some of the island’s luxury resorts, massive coral reefs that create breathtaking backdrops, and miles and miles of beautiful beach that can often be enjoyed all to yourself, with many stretches of sand relatively deserted thanks to their secluded locales. Although Eleuthera is the fourth most populated island in The Bahamas, home to about 11,000, most who live here either fish for bounty or farm the rolling acres of pineapple plantations. The bakeries lure visitors in with their mouth-watering pineapple tarts from the island’s signature crop – Henry Sands homemade bread even won him an invitation to Princess Di’s wedding.

Unlike its luxurious Caribbean neighbors, here you’ll only find more budget-friendly hotels and guesthouses. Everything needs to come by ship or airplane, so it’s not super cheap. However, since no non-natives can own property there is no influx of overdevelopment, keeping the island simple but beautiful. For a more rustic, non-touristy getaway, this might be the island for you!
Under a constellation of dazzling lights, the Strip throngs with glamorous folk and star-struck visitors. The Eiffel Tower is illuminated against the night sky, boats punt along Venetian canals, and the roulette tables heat up with anticipation. Las Vegas is the city of fantasy, where dreams are realized and where fortunes are lost and won. It’s bold, brash, and it doesn’t hold back – you have to surrender to this exhilarating city and let it do with you whatever it desires.
I’m sorry if you covered this in another part of your site, (either I’m technically challenged or there just isn’t a search function for your site) but I’m curious about Corfu. From what I can tell, you mentioned it once in your site under your post about best beaches. The Paleokastritsa area is something that has caught my attention for a while and is on my list, and then I saw pictures of Nissakids Bay and that looked kind of amazing.
I’m sorry if you covered this in another part of your site, (either I’m technically challenged or there just isn’t a search function for your site) but I’m curious about Corfu. From what I can tell, you mentioned it once in your site under your post about best beaches. The Paleokastritsa area is something that has caught my attention for a while and is on my list, and then I saw pictures of Nissakids Bay and that looked kind of amazing.
I would recommend Naxos over Mykonos and with 12 days you could easily add Paros too. With Santorini, Paros, and Naxos you’ll get a good mix of different delights and some ferry island hopping too which is fun in itself. 1.5 days in Athens is perfect for most – 1 day for the Plaka, Parthenon, Acropolis Museum area; and a half-day to visit the Archaeological Museum which is a short drive or walk from the Plaka but hard to fit in one day along with the other sights.
Panama is an underrated destination in Central America, including the San Blas Islands. This is a popular spot for sailing and boat tours, though there are also some resorts in case you’re looking for a more luxurious stay. Generally, the islands are quite rustic and make for a great off-the-grid island getaway. There are tons of beautiful spots for good sailing, diving, and snorkeling.
Panama is an underrated destination in Central America, including the San Blas Islands. This is a popular spot for sailing and boat tours, though there are also some resorts in case you’re looking for a more luxurious stay. Generally, the islands are quite rustic and make for a great off-the-grid island getaway. There are tons of beautiful spots for good sailing, diving, and snorkeling.
Hi! I have fallen in love with the cyklades and have visited Santorini, Ios, Naxos and Folegandros in late june. Folegandros was the best, a fantastic island. We are now thinking about going to Paros the last week in September. Naoussa seem to be a great place. What’s the weather like in late September? Is it still quite warm? I also wonder about the sea conditions. May the sea be rough at that time of the year? I don’t like wavy ferry rides 😨 Thank you for a good sight!
To sum up: a lot depends on your own stamina because island hopping means packing and unpacking, getting on and off buses and ferries. Limit your choice of islands to perhaps one or two less than you think you can manage. Maximise transport links to avoid backtracking or port-transferring and since you are traveling high season be aware that you will usually need bookings ahead at most places. It is possible to turn up on an island and not find a place to stay or have to make do with a third-rate option.
The island’s next hotspot may be The Shore Club, the only development on Providenciales’ Long Bay Beach with 106 ocean view suites and six luxury villas on a nine-acre stretch. On popular, pristine Grace Bay Beach, Grace Bay Club’s tropical-chic redesign led by interior designer Thom Filicia includes redesigned lobby and guest rooms, the new Infiniti Restaurant and Raw Bar and The Residences, a trio of freestanding, beachfront villas. To get off the radar, the eco-conscious Sailrock Resort debuts this year on untouched South Caicos Island — secluded beaches are the buzz. 

Ferries are not really cheap any more – certainly not like they used to be – but the vessel fleet is better, safer and faster than in previous years so the cost is justified. You can get exceptionally cheap deals on longer-haul routes if you are prepared to forego a booked seat: €14 v €40 on a run to a mid-distant island, but it’s probably wise to consider taking fast catamarans to get to core islands (Mykonos, Santorini, Paros etc.) and even then, go the extra 10/15% for Business or even VIP class for the extra comfort. On longer hauls it can be cheaper to fly if you seek out flights online and book beforehand.
My husband and I are planning a trip to Greece in late May/early April. We already plan to spend a few nights on Santorini, and are trying to choose one other island to pair with it (will have 3 nights on other island). We are in our late 20s and are more interested in outdoors (hiking, exploring, beaches, boat trips). I’d like to keep travel time to a minimum, so I have been looking at the closer islands – Milos, Paros, and Naxos. Do you have any recommendations or thoughts on a good island to pair with Santorini?
Went to Fiji for my honeymoon and i don’t think that trip can be topped. We wanted seclusion, privacy and romance and thats what we got. Our bure was 20 feet from the beach where we could relax and maybe see 1 or two people all day. It was incredible. The resort was called Matangi island resort. Great staff, great food…. It’s as close to perfect as you can get.
Located in southern Thailand, this semi-off-the-map island is one of my favorites and the month I spent here remains one of my most fond memories. Here on Ko Lipe, the super-friendly locals bring in the daily catch for amazing seafood, as the island’s water is teeming with life. Accommodation is still basic, and most places turn off the electricity around midnight.
Transport between the three islands relies on local ferries and these are unsophisticated ‘landing-craft’ style boats that do little more than ferry passengers and vehicles in Spartan comfort, but they are very functional and vital to the inter-island communication. There is plenty of on the ground support excursions and infrastructure and the islands are well-used to tourism; the only exception is that travellers will need to use a bit of independence in getting between the islands.
Im here in Vermont and love it here but want more and Im antsy to move in the future. I dont know where to start, but I do know I want a tropical place warm year round. I guess I need a break from this cold weather. I own and operate an herbal shop for I am a Holistic Practitioner , Master Herbalist, Nutritional consultant and much more. Iam looking to relocate my business and myself with my 2 boys!!! Anyone have any locations that I may visit that might be a new future location with a high call for my type of work please oh please let me know. Namaste! Cold here in Vermont!!!!

Located in southern Thailand, this semi-off-the-map island is one of my favorites and the month I spent here remains one of my most fond memories. Here on Ko Lipe, the super-friendly locals bring in the daily catch for amazing seafood, as the island’s water is teeming with life. Accommodation is still basic, and most places turn off the electricity around midnight.
Budgeting for Greece is always going to be subject to what your expectations and needs are. Assuming that you, like many travellers, like to eat a filling breakfast, savour maybe a light lunch and feast on a heavier dinner (or vice versa), enjoy a drink with your meals and are not totally vegetarian/vegan and prefer to sleep in comfort and cleanliness, then there is a set of figures that can be guesstimated.
I need to finalize plans for a mid-June trip, looking to stay 9-10 nights. Traveling with my wife and two sons (24 and 16). Definitely want to go to Santorini, Mykonos and Athens. Was considering 3 nights at each, but after reading on your site, I am thinking about stealing a night from Athens and spending 2 nights at Naxos. We want to see the major sights in Athens, can we do that in a day? Any comments on the itinerary given our group is welcome.
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