Santorini has established itself as the latest cool trendy Mediterranean destination for couples, for backpackers, for families, and for weddings. So what does a package holiday on Santorini feel like? Does it deserve the hype?
Here are 10 observations that may help you decide if you want to follow the crowds to Santorini:
1. It is a small island and everything is accessible - transfers from the airport are short and all the island’s main towns are a short bus trip apart. The west side of the horseshoe-shaped island is the inside of a volcano and therefore has steep cliffs dropping down into deep waters. The east side is the outside of the volcano and is therefore less steeply shelving and has beaches of black volcanic sand. 
2. The airport is very close to one of the most popular tourist destinations - Kalmari - but this is not a problem because the planes tend to approach over the sea providing a distraction for sea-front diners and a great place for plane spotters. There is also something neat about bobbing around in the sea as an airliner comes in overhead.
3. In the posh resorts in the north west of the island you will come across weddings and bridal photoshoots. Brides look as if they are about to melt, even in September out of the peak heat of summer, so, unless you are a masochist, why would you dress up, and expect all your guests to dress up, in 30 degrees of heat?
4. The “wonderful” bus service has its limitations. You may not fit into the first coach that comes along, particularly if you get on a bus going to Oia just before sunset. Also buses fill with huge numbers of tourists from the cruise liners that call in to Fira. If you do fit in to the bus you may have to stand. This is a good workout for the upper body as you swing around hairpin bends holding on the overhead rails.
5. Whilst it is a “posh” island, expect to be in the minority if you don’t have multiple tattoos and a shaven head, particularly in the south-eastern resorts.
6. Restaurant prices are pretty similar, as are choices on menus, in any given area of any town. Some towns are more expensive than others but, when you are there, there seems to be a restaurant cartel that maintains a certain price level. You can always do the “Moussaka Test” (™) - as Moussaka is a staple of the local diet you can find it everywhere and use it as a “price benchmark”....9Euros was normal but I saw it for 16Euros in a restaurant (that I avoided). In Kalmari, for example you will have a huge choice of very similar restaurants along the front. How do you choose? It could boil down to the skill of the charming waiters, who are brilliant at engaging you in conversation and encouraging you to their restaurant over neighbouring ones.
Some restaurants do, however, offer different dishes. For example grilled octopus can be served by flame-grilling a boiled octopus or octopus dried in the sun for up to three days. The dried octopus has a denser texture. You can see which restaurants offer dried octopus by spotting the mesh cages with hanging octopus legs.
7. You will never see as many selfie-sticks as you will in Oia. The most amusing selfie takers tend to be pretty young women who have developed the art of the selfie into a contorted pouting and open-eyed caricature of a normal self-portrait.
8. Whilst Oia gets the hype, Fira, and in particular the walk between Imerovigli and Fira, is a far more interesting town. Oia is very crowded (think tube station at rush hour) and expensive but has a better view of the sunset - the sun dips into the water rather than behind an offshore island as it does if viewed from Fira. My tip - take a taxi from Fira to Imerovigli and walk down the hill past the beautiful boutique hotels just before sunset.
10. The boutique hotels of Imerovigli are impressive with their whitewashed walls, their infinity pools and their beautifully tended bougainvillea. But if you stay there would you always get “hotel envy” for the next-door establishment with that slightly better view, or the slightly bigger pool? Would you feel trapped in one of those tiny cave houses with streams of gawking tourists walking by, snapping away as you lie on your sun lounger? Wouldn’t you rather, at a fraction of the price, have a normal hotel on the other side of the island and BE one of those gawking tourists admiring the beauty of the boutique hotels? I guess you pay your money and take your choice.So I would say that Santorini is worth the hype. Just be prepared for crowds of tourists at every turn. In early September we sat in a beachside restaurant one hot evening and remarked to the waiter that his restaurant was busy, with most tables taken and people coming to eat all evening from around 6:00 till past 10:00p.m. He said “you should see it in August, there were 100 people waiting on the pavement for a table”...
