I’m traveling to Greece for the first time, and I’m so fortunate to be staying for about 9 weeks (peak season, unfortunately, I’m an educator and it’s summer!). I have ample time planned in Athens, and the Peloponnese (with rental car). Here’s where I need some help and suggestions. I have 5 weeks saved for the islands and I’m still trying to figure out how to spend them. I’m not sure if I’d like to cover just a few islands and soak them in a bit deeper with longer stays…or to travel at a quicker pace covering several islands in each main area (the Cyclades, Ionians, Crete-Rhodes Dodecanese, Eastern Islands) I’m an easy traveler and enjoy diversity. I crave spending time with locals and interacting with families – home stays at times, I enjoy the water and I’m an avid diver, I like hiking and exploring. Also, want to perhaps relax a bit – food/wine tasting welcomed). I’m excited about the trip and my ideas are racing all over. Do you have some ideas and suggestions to share? A rough sketch itinerary for Greece? Thanks so much! 

Between Nydri and the next main tourism centre is the little port and beach of Mikros Gialos (small bay) that is a great little base for individual travellers for a day or three. The port village of Vasiliki on the southern underbelly of Lefkada is a haven for windsurfers: see this page or this one for more information. The little village is very pretty and is a good base for general holiday-making (as are the two other places). From Vasiliki there is a regular local ferry that runs to Fiskardo on Kefallonia (via Ithaca/Ithaki).
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.
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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. 

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Little by little, though, Milos is being discovered. Instagram is saturated with no-filter shots of the undulating cliffs at Sarakiniko, the bottle-green swimming hole at Papafragas, and colourful, rickety syrmata, tiny boat houses wedged between rock and sea. (You’ll find the best photo opportunities at Klima and Mandrakia). This painterly landscape was shaped by the minerals that have long been a source of wealth – obsidian, alum, barite and sulphur, which still bubbles up in the island’s many hot springs. As the 11,000-year-old mining industry is gradually giving way to tourism, several chic hotels have made an appearance. Go now, before the trickle of visitors turns into a tide.

I’m hoping you can help myself and a friend decide where to go. We are hoping to go away around mid August for 10 days-2 weeks. We’re looking for a sunny place and beaches to tan and relax during the day, with some big nightlife and a good strip (the odd daytime activity maybe too). However we are in mid 20s so want to go somewhere with the same age group or older. I’ve been to Zante and although it was super fun at the time (I was about 18) and loved having the strip etc, just don’t want to be the older people there anymore! Money is also fairly tight, so nothing too expensive (was thinking santorini maybe before hearing the price along with it).
Where to stay in Corfu: Rou Estate a hilltop hamlet transformed into a five-star retreat with an excellent spa. CV Villas has cornered the market in covetable villas on the north-east coast of Corfu. If you’d rather go all-inclusive, check into the smart Ikos Dassia, which opened in May 2018 in Dassia, a favourite haunt of The Durrells cast and crew. Guest perks include a Mini Cooper for cruising around the island.
Where to stay in Mykonos: Pale and interesting, Bill & Coo Coast on Agios Ioannis beach has dusky views across to Delos. Santa Marina resort tumbles down a private peninsula with a full-blown spa, a secret sandy beach, and a Riva to whisk you off to Nammos or Scorpios, if you can peel yourself off your canopied sunbed. If you prefer to be in the thick of it, The Belvedere is the gold standard in Chora, the glittering port capital.
In 2016, Stiniva beach on the island of Vis was named the best beach in Europe. One of the top beaches in Croatia, Stiniva is well hidden from the sea and not the easiest beach to access. It’s either a hike down to the beach or access by small boat, but a spectacular view will reward you for your effort. Although Vis has never really had large tourists numbers, it has become a popular stop for those sailing the Croatian islands.
Question: Is it worth taking the evening ferry on the 4th Sep to Crete (Heraklion) from Santorini, then the bus onto Chania so that we can do the Samaria Gorge on the 5th? Spending the full day in Chania on the 6th and taking the last flight out of Chania that night back to Athens? (or do you think this is trying to squeeze in too much in too little time)?
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!)
That all sounds good though I would recommend Naxos over Mykonos in March as there’s more to see and do there when not beach weather. And if you do decide to do Mykonos be sure there’s a ferry from Mykonos to Santorini for your dates. And same for Santorini to Crete. There should be ferry service but the route starts different times every year so you do want to be certain.
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.
While technically a subtropical island, the Azores make for a great getaway if you’re looking for something beyond the standard resort getaway. The islands boast tons of hiking and beautiful nature. Rent a car and explore the winding roads of the main island, São Miguel Island, taking it secluded beaches and picturesque waterfalls. Best of all, it’s close to both Europe and North America and makes for a great stopover point if you’re traveling between the two.

Where to stay in Crete: A 300-year-old hamlet surrounded by olive groves, Kapsaliana Village Hotel exudes peaceful authenticity. On a sandy bay just beyond Chania, Ammos Hotel smartly combines Scandi chic with a child-friendly vibe. Blue Palace Resort & Spa beats the (stiff) competition in Elounda with its spiral stone Isola Beach Club, thalassotherapy spa, and boat trips to Spinalonga island, a national monument just across Mirabello Bay.
I’m traveling to Greece for the first time, and I’m so fortunate to be staying for about 9 weeks (peak season, unfortunately, I’m an educator and it’s summer!). I have ample time planned in Athens, and the Peloponnese (with rental car). Here’s where I need some help and suggestions. I have 5 weeks saved for the islands and I’m still trying to figure out how to spend them. I’m not sure if I’d like to cover just a few islands and soak them in a bit deeper with longer stays…or to travel at a quicker pace covering several islands in each main area (the Cyclades, Ionians, Crete-Rhodes Dodecanese, Eastern Islands) I’m an easy traveler and enjoy diversity. I crave spending time with locals and interacting with families – home stays at times, I enjoy the water and I’m an avid diver, I like hiking and exploring. Also, want to perhaps relax a bit – food/wine tasting welcomed). I’m excited about the trip and my ideas are racing all over. Do you have some ideas and suggestions to share? A rough sketch itinerary for Greece? Thanks so much!

You’d have to check the schedule for your specific dates but I think Santorini then Milos then Paros then Naxos and Athens would probably be the best order. 3 days in each sounds great. Or a small tweak: 2 days in Milos and then 4 days in Santorini (splitting time between 2 of the 4 caldera towns) or even 4 days in Paros (splitting time between Naousa and Parikia).

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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 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!)

A limestone spike rising dramatically from the emerald waters of Phang Nga Bay, James Bond Island (Koh Tapu — Nail Island in Thai) earned its moniker from appearing in two 007 movies: The Man with the Golden Gun (1974) and Tomorrow Never Dies (1997). Excursions depart from the popular resort areas of Phuket, Khao Lak and Krabi on photogenic longtail boats. On the tour, explore secret lagoons, craggy sea caves and a floating village.
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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.
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