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.
Can you see all the major sights in Athens in one day? No. But you can see the Acropolis, Acropolis Museum, and the top historical sites of the Plaka in one day. If you had an extra half-day then visit the Archaeological Museum in Exarcheia. That still leaves many great sights but you will have seen all of the iconic Athens attractions. Adding Naxos is always a good idea. You might even enjoy it more than Mykonos (but no nightlife like Mykonos).
Christened the Garden Island, Kauai’s splendor extends from its vermillion Waimea Canyon, plunging down 3,600 feet, to its rugged Napali Cliffs, stretching up 4,000 feet. Often dotted with dozing monk seals, Kauai’s Poipu Beach has appeared on Dr. Beach’s esteemed list of America’s Best Beaches. Rivers, rainforests and waterfalls garnish the interior; don’t miss a photo op of Wailua Falls, famously featured in the opening credits of Fantasy Island, which aired from 1977 to 1984.
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.
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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.
Where to stay in Crete: Adults-only Casa Cook is a chic little number that breaks all the rules about package holidays (you’d never know it was created by Thomas Cook). The Marco Polo is a 15th-century mansion decorated like a pasha's harem, with an enchanting garden restaurant. Ottoman-style suites at Melenos Lindos have hand-painted ceilings and carved platform beds.
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.
Blaca Hermitage in the south of the island is a must-visit, as well as Vidova Gora Mountain, which is the highest peak on the island, offering you stunning views across the Adriatic and to neighboring islands on a clear day. Brač is also where you’ll find the famous Zlatni Rat Beach, one of the absolute best Croatia beaches (and even in all of Europe) and a wonderful place to spend a day. This all makes Brač one of the best islands near Split, a perfect day trip from Croatia’s second-largest city.
Sarah-Jane — Thanks for another helpful article (this one on planning an island-hopping trip). Chasingthedonkey.com is a great website and my first go-to place for information on Croatia. I have scheduled my third 3-month-long stay and still have so much to do and see in Croatia. Personally, my favorite times to visit are in the “shoulder” seasons …. September-November and March-May.
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.