I have gone to kalymnos every year since 2002 we travel in a group of family and friends which gets bigger every year 16 of us going this summer, we love the island, we always stay in massouri, and always end the night in fatalatis bar ( sakis) i take a young child and she loves it, they may be no big water parks or play areas or entertainment but my daughter (5) loves it, she is never bored, she plays in the sand and sea all day and plays with the bar owners grandchildren when in the bar or dances to the music in the livelier bars, i feel safe walking down the street and been in bars with children, all the people on the island are really friendly towards us all, you walk down the street and everyone says hello and fusses over the children.
The food is gorgeous never had a bad meal, if you like meat there are plenty of restaurants that have really big portions for really good prices you can get a joint of lamb with potatoes and rice for 2 people for 16 euro and most chicken meals are 6 euro.
I do recommend if you go to kalymnos to travel independently we book apartments with people we know over there once you have gone once you will get to know alot of people and book rooms through them at really good price some at 22 euro a night, the rooms are usually very basic and we usually stay at some apartments over mikes bikes there are 3 of them sharing one really large balcony, these are only cleaned twice a week but it seems enough and if something is not working properly they go out there way to get a replacement straight away. There are lots of apartments around they are some behind fatalatis bar that have family rooms.
There are not many pools around which can be a problem if you only like the pool, there is one over looking the beach called the plazahotel you can use this pool you just have to buy something from the pool bar, and we also got to babis pool down in myrtis which is near to the small harbour that has boots running every 10 mins to telendos which is a really nice place to visit and relax.
The island has not yet been taken over by loads of tourists it could do with afew more ( not too many don't want to spoli it ) as its quite sad when you walk past the deserted hotels and empty bars. Majority of the tourist their are regulars.
To us the island is like a second home and even though it is difficult to get to and even worse if you are delayed and miss a boat, It is all worth it in the end. We go for 18 nights that way we get our full holiday after travel time.
I do not think anyone you went there would go back disapointed with the island.
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