You’d have to check the schedule for your specific dates but I think Santorini then Milos then Paros then Naxos and Athens would probably be the best order. 3 days in each sounds great. Or a small tweak: 2 days in Milos and then 4 days in Santorini (splitting time between 2 of the 4 caldera towns) or even 4 days in Paros (splitting time between Naousa and Parikia).
The so-called pearl of the French Caribbean, Guadeloupe is a butterfly-shaped archipelago of five main islands where volcanoes tower and 200-plus beaches come in shades from black and white to red and pink. Basse-Terre’s tropical forest and the bay of Grand-Cul-de-Sac Marin were declared a UNESCO Biosphere Reserve in 1993. From there, island-hop to discover Grande-Anse beach on Les Saintes; Marie-Galante’s rum estates (and old-fashioned oxcarts); and La Desirade’s 900-foot plateau.
Considering your interests (great food, hiking, beaches, nightlife unimportant) then Naxos should definitely be your other island. (And Naxos has many daily ferry connections with both Santorini and Athens.) Also, Athens needs at least one full day to explore so you should drop any thoughts about Delphi or Nafplio. Also, I would look into flights from Athens to Santorini on your night of arrival. If you could get to Santorini that night (and move your day in Athens to the end of your trip) you’d almost gain an entire day and could spend two nights on Naxos.
Private jet is the best new way for VIPs to travel south: Casa Marina, A Waldorf Astoria Resort, now offers direct seaplane air service with Key West Seaplanes from Florida airports to the property’s private beach pier. Slightly farther north on Key Largo, Playa Largo Resort & Spa debuted last summer with signature Sunshine State coral reefs and sea glass, plus 144 rooms and suites, 10 secluded bungalows and a standalone luxury guesthouse.
In many ways, the biggest winner in the deregulated environment was the air passenger. Although not exclusively attributable to deregulation, indeed the U.S. witnessed an explosive growth in demand for air travel. Many millions who had never or rarely flown before became regular fliers, even joining frequent flyer loyalty programs and receiving free flights and other benefits from their flying. New services and higher frequencies meant that business fliers could fly to another city, do business, and return the same day, from almost any point in the country. Air travel's advantages put long distance intercity railroad travel and bus lines under pressure, with most of the latter having withered away, whilst the former is still protected under nationalization through the continuing existence of Amtrak.
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).
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Ultimately, the federal government provided $4.6 billion in one-time, subject-to-income-tax cash payments to 427 U.S. air carriers, with no provision for repayment, essentially a gift from the taxpayers. (Passenger carriers operating scheduled service received approximately $4 billion, subject to tax.) In addition, the ATSB approved loan guarantees to six airlines totaling approximately $1.6 billion. Data from the U.S. Treasury Department show that the government recouped the $1.6 billion and a profit of $339 million from the fees, interest and purchase of discounted airline stock associated with loan guarantees.