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.
As a starter to explore ferry services, go to the Ferryhopper.com and punch in your route searches. Note: air travel between islands is not generally good. Air travel is normally only feasible between Athens (or other mainland destinations) and the island in question. Some exceptions do exist – Rhodes Kastellorizo, Kos-Leros-Astypalaia, Thessaloniki-Limnos-Ikaria etc. but again you will need bookings weeks in advance.
My boyfriend and I will be traveling to Greece on August 1-11th. We have 10 days. Is this a feasible itinerary for a couple in their early 30s who want beach, relaxation, good food, boating, and some history? Fly into Athens have one full day there then fly to Naxos for a day and a half, Milos for 3 nights, then Santorini for 3 nights, then back to Athens for our flight? We chose Milos over Naxos at first, but after reading your blog it seems the beaches in Naxos may be better? 

World War II, like World War I, brought new life to the airline industry. Many airlines in the Allied countries were flush from lease contracts to the military, and foresaw a future explosive demand for civil air transport, for both passengers and cargo. They were eager to invest in the newly emerging flagships of air travel such as the Boeing Stratocruiser, Lockheed Constellation, and Douglas DC-6. Most of these new aircraft were based on American bombers such as the B-29, which had spearheaded research into new technologies such as pressurization. Most offered increased efficiency from both added speed and greater payload.[32][33]
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.
The other groups are best tackled individually. For example, the Ionians have no ferry connections to the rest of the Greek islands; the same story with the Sporades and the Argo-Saronics. The NE Aegean islands do have a link to the Dodecanese and the Cyclades but are probably best left for another trip once you have got the feel of the rhythm of the Greek islands.
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.
Bermuda is recognized as one of the most elegant of the Caribbean islands, and also on the formal side. It has a strong British influence, and you can still find many places that serve traditional afternoon tea. Cricket matches are also easy to find. Bermuda is also a great destination for golfers, as the island has many world class courses. This island is extremely convenient to reach from the Eastern U.S. Flights from New York to Bermuda are only two hours.
Tony Jannus conducted the United States' first scheduled commercial airline flight on 1 January 1914 for the St. Petersburg-Tampa Airboat Line.[23] The 23-minute flight traveled between St. Petersburg, Florida and Tampa, Florida, passing some 50 feet (15 m) above Tampa Bay in Jannus' Benoist XIV wood and muslin biplane flying boat. His passenger was a former mayor of St. Petersburg, who paid $400 for the privilege of sitting on a wooden bench in the open cockpit. The Airboat line operated for about four months, carrying more than 1,200 passengers who paid $5 each.[24] Chalk's International Airlines began service between Miami and Bimini in the Bahamas in February 1919. Based in Ft. Lauderdale, Chalk's claimed to be the oldest continuously operating airline in the United States until its closure in 2008.[25]
We are two guys in our early 30s, we have 12 days for the Greek Islands. We like to swim, ride bikes, or drive on the islands to explore villages, culture, local life, love to eat local food, rest and have beers on beach, stroll and walk around in evening, etc. We will go to Santorini for 3 nights and select Fira according your suggestions, we are confused for next island between Crete and Naxos. Crete is huge but if we choose Naxos as it’s easy to reach from Santorini than does 8-9 days will be boredom in Naxos? Please suggest what’s best and on which place we should look for accommodation in either island you suggest..
Kefallonia was severely shaken by an earthquake in 1953 and thereafter lost its quaint gloss. The picturesque northern port of Fiskardo however, escaped much of the destruction and remains to this day one of the main focal points for visitors to the island, so is a good spot for a stay of 2-3 days. Pretty, waterfront cafés and restaurants and a cosy, folksy feel predominate. Asos, between Fiskardo and Argostoli is a west coast ‘resort’ village that pulls in its fair share of visitors and the view down to Asos from the main island road is one of the most photographed spots on Kefallonia. 

We are having trouble deciding on another island to go to besides Santorini (we both want to go there). I was hoping you might be able to make a suggestion. We are not really into late night partying/night life. We LOVE good food..quite possibly the most important item on our list. We also like to hike, my husband is very into history, we love beer/wine, we could definitely be into in a less populated/touristy type spot. Gorgeous beaches and great views are also a plus.
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