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.
Hawaii’s biggest island has everything you could ever want to do and more. But what separates it from the other islands is Volcano National Park. Explore volcanoes, climb through old lava tubes, and watch as new lava oozes into the ocean. Then there are all the waterfalls on the island, too. Big Island has it all. I mean it’s Hawaii — how could you go wrong?!
Where to stay in Santorini: Trendier pretenders come and go, but Perivolas is still the most stylish and peaceful place to stay. If you have cash to splash, and can’t stand the crowds, take over Perivolas Hideaway, a waterfront villa on Santorini’s undiscovered offshoot, Thirassia, or Erosantorini, a stunning clifftop estate with a tiered pool plunging 1000 feet to the sea.
If you're wondering why this bountiful island (a two-hour ferry ride from Athens) isn't inundated with tourists, it's because the local ship-owners prefer to keep it quiet. They fraternise in country estates and neoclassical mansions in Hora. Floating on a slender peninsula, the stately capital is sprinkled with old-fashioned patisseries (Laskaris sells wonderful lemon-blossom preserves) and stylish boutiques (Waikiki Andros has gorgeous embroidered tunics and studded sandals). There's even a Museum of Contemporary Art, where the line-up might feature Man Ray or Miró.
Thank you for putting together such a great site. My husband and I are planning a trip to the Islands in May – neither of us have been and, honestly, have no idea where to even start putting together an itinerary. We have at least 14 nights to spend there (and may be able to push that to 17). I’m in my early 30s, my husband’s in his early 40s. Our priorities are culture and history, swimming, beautiful views, nice towns, and food and drink. We’re not interested in clubbing at all, but more laid-back late night bars definitely appeal. This is probably our one big holiday this year so while the budget is more mid-range than sky-high, we can push it a bit for the right places or experiences. We’re happy to take in quite a few islands, or with a mix of longer and shorter stays.