I’m a Maui native and it is not that expensive! You just need to do it the smart way, avoid tourist traps and ABC stores, stop at Costco to stock up on supplies before you reach your hotel. Many of the best things Hawaii has to offer are free: beaches, sunsets, hikes, snorkeling, walking the streets of small beach towns. Condos are also way cheaper than hotels and they are usually beachfront.
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.
With its pastel villages, rolling olive groves and grand manor houses, the rest of the island recalls Tuscany - but with far better beaches. The smart set stay on Corfu's north-east coast (nicknamed Kensington-on-Sea) where the Rothschilds like to unwind. It's wall-to-wall Sloanes and speedboats at Agni, a tiny fishing village with three rival tavernas (Toula's is the best). From here, you can rent a boat and putter to your own cove: perhaps Nissaki, Agios Stefanos or Kerasia. These idyllic bays still resemble the 'delectable landscape' that Lawrence Durrell fell for in the 1930s — now back in vogue thanks to the ITV series, The Durrells. Or venture inland to Ambelonas, an enchanting winery, restaurant and cooking school that specialises in Corfiot dishes, such as squid with chickpea and turmeric mousse and rose petal jelly. Steer clear of the south, especially Kavos. Unless you happen to like wet T-shirt contests.
U.S. citizens don’t need a passport to explore this trio of Caribbean islands (St. Thomas, St. John and St. Croix). While the 133-square-mile chain has history in spades — Christopher Columbus touched down in 1493 — 2017 marks a banner year as the USVI celebrates its Centennial, with special events (festivals, parades and presumably lots of rum cake) continuing throughout the year. Also historic, Caneel Bay, the 60-year-old, 170-acre escape in St. John’s Virgin Islands National Park founded by environmentalist and preservationist Laurance Rockefeller, just celebrated its diamond anniversary. The property is bringing back the original beauty of its pared-down, 1950s-inspired Scandinavian style.
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. 

Yachts moor in the deep, sheltered harbour of Vathy, or Kioni, a miniature port where you’ll find Spavento, the perfect pier-side café-bar. Go any time of day or night for ice-cream sundaes, excellent cocktails, and a soundtrack to make your heart sing. Ideal for low-key family holidays or retreats, rugged little Ithaca is somewhere you can still disappear. 
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