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.
As in many mature industries, consolidation is a trend. Airline groupings may consist of limited bilateral partnerships, long-term, multi-faceted alliances between carriers, equity arrangements, mergers, or takeovers. Since governments often restrict ownership and merger between companies in different countries, most consolidation takes place within a country. In the U.S., over 200 airlines have merged, been taken over, or gone out of business since deregulation in 1978. Many international airline managers are lobbying their governments to permit greater consolidation to achieve higher economy and efficiency.

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]

Be cautious with Santorini and kids. Some hotels don’t do kids (check carefully) and not all hotels are suitable for kids along the caldera lip. Many steps, confined spaces and other guests who don’t actually want to hear kids … Here’s an idea – look for a child-friendly hotel (perhaps on the beach at Perissá) and base yourself where the kids will like it and then take them to the caldera scene. There are a couple of child-friendly hotels on the Caldera, but they get booked very early in the year. 

We are planning to come back at the start of September for 2 weeks to visit different islands for some beach and sun. To give you some background, we loved Santorini, Milos and the quieter / smaller places in Crete (Loutro, Falassarna, Samaria Gorge). We enjoy beach time, some hiking, site seeing, good wine / food and good / buzzy atmosphere at night for dinner / tavernas.
Congress passed the Air Transportation Safety and System Stabilization Act (P.L. 107-42) in response to a severe liquidity crisis facing the already-troubled airline industry in the aftermath of the September 11th terrorist attacks. Through the ATSB Congress sought to provide cash infusions to carriers for both the cost of the four-day federal shutdown of the airlines and the incremental losses incurred through December 31, 2001, as a result of the terrorist attacks. This resulted in the first government bailout of the 21st century.[44] Between 2000 and 2005 US airlines lost $30 billion with wage cuts of over $15 billion and 100,000 employees laid off.[45]
Transport between the three islands relies on local ferries and these are unsophisticated ‘landing-craft’ style boats that do little more than ferry passengers and vehicles in Spartan comfort, but they are very functional and vital to the inter-island communication. There is plenty of on the ground support excursions and infrastructure and the islands are well-used to tourism; the only exception is that travellers will need to use a bit of independence in getting between the islands. 

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.
Transport between them can be patchy, but a new service linking Zakynthos with Corfu which started this year now brings all the islands (bar Kythira) together. Zakynthos is otherwise linked to Kefallonia with an old-style open deck ‘slipper’ ferry; Kefallonia includes Ithaki on its local small ferry route to Nydri on Lefkada. There is no link (except for the new service) from Lefkada to Paxi/Corfu. Corfu has links to Paxi and its little know satellite islands just to the north. Kythira has an airport with flights to Athens and ferries to Crete (Kissamos) and the Peloponnese (Gythio, Kalamata, and Neapoli).

Also heralded for its seclusion — as well as its beaches, diving, and mountainous beauty — is Indonesia’s Lombok, an island just east of Bali that one reader dubbed “Romance Island.” In fact, Indonesia seems to have the joys of island life down to a science, laying claim to the top three spots people most enjoy visiting. Read on for the full list of 15 winners.
Hydra is great but it does take a bit of time and effort to get to from the Cyclades. You’ll need to ferry to Athens, then might have to overnight there, then ferry to Hydra. Whereas Naxos, Paros, Milos, Folegandros, etc. would all be one direct ferry from Santorini or Mykonos. If you do go to Hydra then Leto Hotel is a great choice close to the port and shops and restaurants.
Korcula Island (pronounced KOR-chu-la), also known as the Emerald Isle, is one of the absolute best islands near Dubrovnik. Located in southern Dalmatia, this small, 279-square-kilometer island is a favorite among travelers. A place of culture, history, beauty, and charm, the island of Korcula offers a variety of activities and unique traditions all surrounded by the stunning Adriatic sea and excellent Korcula weather.
The island doesn’t get many tourists and has therefore remained somewhat of an untouched paradise. Lastovo is renowned for its annual carnival, a celebration in which all residents participate by wearing elaborate folk costumes. Another notable attraction on the island is the unique cylindrical Lastovo chimneys, which look like mini-minarets (although no Turkish or Arab influences have ever reached the islands).
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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