Finally, and this is perhaps the best tip of all – as it’s the old-style romantic one – book transport to and accommodation on one starter island (Paros is a good choice). Sail/fly there, sit down relax, pour cold drinks and eat healthy Greek foods for 4-5 days while working out where to go to next with your tablet under an umbrella on the beach. Book your next stop online and go there. Repeat the exercise. No hassles about being locked into a fixed itinerary and if you like a place, you stay longer. If not, you move on. You will generally find transport tickets for a day or three ahead and hotel owners often know someone on the next island who can fit you in. In Paros, Petres Hotel is a good starting point. Good luck and happy sailing!
I think that’s a great plan. Santorini is a must and Milos and Naxos are two islands that have both great beaches and lots to do and see away from the beach. Renting a car and exploring the interior villages of Naxos is a must-do and so is a boat tour around Milos. If you’re willing to cut Athens to 2 days, I would recommend Santorini 5 days, Milos 3 days, Naxos 3 days, and Athens 2 days.
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Chania is a great choice. A wonderful charming town. Elounda is great for a quiet laid back stop, Agios Nikolaos has a more interesting vibe and is more of a real town. Also very charming. I prefer Ag Nik but Elounda has more luxurious hotels. (Crete hotels.) Naxos has lots to see in the interior so if you didn’t explore then certainly consider that. Folegandros and Milos are both incredible. Folegandros is more suited to walking and relaxing (and has some top notch restaurants and hotels). On Milos you need to do a tour and get out and actively explore to do it justice. Geologically Milos is stunning. A little like Santorini but with better beaches.
Hydra is great but it does take a bit of time and effort to get to from the Cyclades. You’ll need to ferry to Athens, then might have to overnight there, then ferry to Hydra. Whereas Naxos, Paros, Milos, Folegandros, etc. would all be one direct ferry from Santorini or Mykonos. If you do go to Hydra then Leto Hotel is a great choice close to the port and shops and restaurants.

Drop-dead gorgeous Fiji is a filmmaker’s dream. Spy its Mamanuca island chain in Cast Away and Survivor; ogle its Yasawa archipelago in the 1980 version of Blue Lagoon. A dizzying amount of natural beauty — from mountains and mangroves to rivers and reefs — swathes Fiji’s 333 islands, and awe-inspiring wildlife (whales, sea turtles, dolphins, parrots) is the icing on the cake. For scenery with a side of luxury and exclusivity, reserve a bure (villa) at one of Fiji’s numerous private-island resorts.
The Greek islands have beautiful weather in the months just before and after peak season. It’s a great time to see the islands, save money, avoid the crowds, and still have great weather (though not as hot as July and August). If you want to see the super-popular islands of Santorini, Rhodes, Corfu, and Crete without the tourists then this is a great time to visit.

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I think that’s a great plan. Santorini is a must and Milos and Naxos are two islands that have both great beaches and lots to do and see away from the beach. Renting a car and exploring the interior villages of Naxos is a must-do and so is a boat tour around Milos. If you’re willing to cut Athens to 2 days, I would recommend Santorini 5 days, Milos 3 days, Naxos 3 days, and Athens 2 days.
Glass-bottom boats with thatched canopies ply shimmering lagoons. Tanned locals in pareus (sarongs) play ukuleles. Ridged velvet-green mountains punctuate the skyline. Palm trees reach higher than any roof. This is reality in the Cook Islands, a 15-isle archipelago marooned in the South Pacific. Go on a mountain safari on the main island of Rarotonga, or head to Aitutaki to stay in an overwater bungalow and motu-hop to deserted sugar beaches that beg to be Instagrammed. 

I am so disappointed that I was not there longer but I realize we could not do everything, if we were there for extra days. I think I will stay at a different resort on my next visit. We really enjoyed Vegas overall. I ate at various places to be sure I wasn't eating the same things. It was easy to access Uber/Lyft. This was the most appropriate method of traveling, just in case we partied too hard. We enjoyed the live music. There was a group performing R&B and then a gentleman mixing Reggae music. Everyone seemed to be enjoying it.

Naturally, there are some amazing coral reefs for snorkeling and diving and pristine beaches (my favorite is Whitehaven Beach). Upon arrival, you’ll instantly see why this is one of the best tropical islands in the world — and why over half a million people visit a year. One of the most popular way to see the islands is via a multi-day sailing tour (which is what I did when I visited). It was an amazing experience — especially diving! Prices start around 450 AUD for multi-day sailing tours.
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Known as the Cradle of Polynesia, Samoa is notable for its Fa’a Samoa way of life — a 3,000-year-old social code that prizes family, tradition and the environment. Happily, the landscape is as lovely as the local culture. On the main island of Upolu, a plunge into the To Sua Ocean Trench swimming grotto is a must. On Savaii, Samoa’s largest island, visit caves, waterfalls, blowholes and the Saleaula lava field, formed by a 1905 volcanic eruption that buried five villages.

You seem to have your heart set on Zakynthos but I have to say it’s not a good use of time for a sort-of overrated payoff. Your time is much better spent (in my opinion) seeing another Greek island in the cyclades (maybe taking a ferry to Naxos or Paros sitting outside on the deck drinking a bottle of wine) rather than taking a bus and connecting flights. Zakynthos and Santorini/Mykonos are on opposite sides of the country and the only way from one to the other is by flying (or some combination of bus and ferry). So, my recommendation is to consider spending those Zakynthos days in Naxos, Paros, Milos, or some other Cycladic island.


Every imaginable shade of blue manifests in the lagoon of Bora Bora, aka, the Jewel of the South Seas. Coral motus ring the main island like a sandy sash, and beneath the surface, dolphins, rays, sharks, turtles and colorful fish throng. Presiding over it all is the moss-green volcanic peak of Mount Otemanu, where god descended to the island on a rainbow, according to local lore. Timeless grass-skirted dancers and exotic overwater bungalows round out the sublime scene.
Yes, I would agree that 8 or 9 days is too long for Naxos – unless you’re happy sitting at the beach for several of those days. But if you’re looking to be semi-active and explore then you’d be best to add Paros and spend 4/5 days on each. Crete, on the other hand, would be perfect for an 8/9 day road trip. Start in Heraklion (where the ferry arrives from Santorini) head east and then south and finally ending up in the western town of Chania where you can fly up home from.
It’s best to visit Greek islands within the same group. For example, I wouldn’t recommend visiting Corfu and Santorini on the same trip as they’re on opposite sides of the country. Instead, visit islands in the same island group: the Cyclades, the Sporades, the Dodecanese, the Ionian, the Saronic, and the Northeastern Aegean. For one, they’re close to each other. And two, they have frequent ferry connections with each other. For first time visitors to Greece, the Cyclades make the most natural and convenient introduction. 

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?

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Fabulous site Dave! I am taking my daughter to Greece for 12 days in late May 2017 as a grad gift (yeah I know…, I think my Dad gave me a Timex watch, but I digress) and we are flying into Santorini expecting to spend 5-6 days there then ferrying over to Mykonos (not really sure why?) for a couple days. A couple days there and then flying into Athens for 2-2.5 days to inject some culture into what is otherwise somewhat hedonistic trip. I was wondering, after reading about other islands whether it is worth going to Mykonos. I’d love to go to Crete but it seems to be tough to squeeze that in. The original plan was to go to Istanbul for a couple days but it seems really sketchy right now. So is Naxos a better idea than Mykonos? Should we stay longer in Santorini? Is 2.5 days too much for Athens? Any and all info is appreciated.
Wowzers! Tahiti is beautiful! The sunset just completes the picture along with tahiti’s beautiful scenery! All of these destinations are extremely beautiful but my choice out of all of them would definitely be tahiti! I love tahiti because you get your own little hut to stay in! The huts are placed on top of the the bay of water and it would be so beautiful to wake up in the morning to an ocean right beside you! You’d look down and all you would see is ocean! Its so amazing how gorgeous things are! Tahiti will definitely be on my wish list of places to go in the future. Just need a little more money!
Hi Dave. Thank you for your amazing website! We (30’s / 40’s couple – no kids) used your recommendations last year in September and visited Santorini (7days), Milos (3days) and Crete (12days) before spending 3 days in Athens. The trip was amazing and Greece is calling us to go back again this year! We have a conundrum which we are hoping you can assist (well, many of them really!)
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