If I have a friend of mine visiting my island we would explore it all since it is not big but every place is unique.
First half day should be spent in Pothia the capital of the island situated in a valley and where the main port is.
A visit to at least one of the 2 museums both located in the center and walking distance (Archaelogical and Maritime), especially the Maritime Museum is a must
since we are in the island of the sponge divers. A small walk around the central square with the local shops and a sponge factory to buy some souvenirs and sponges too.
We should visit Agios Savvas the landmark church of Kalymnos located in a hill facing the main port where you can see the whole valley where Pothia is situated
and the port. After the capital it is time for all the small villages around Kalymnos where you can spend your day swimming and tasting the local food.
Vlychadia is a beautiful bay with 2 beaches and some restaurants and a museum of Sea Findings. Every Sunday there is a beach party from lunch time till late at night at Paradisio restaurant.
Next visit should be Vathy -a unique fjiord in a small picturesque village and the only green place in Kalymnos. At the small pier there is a kayak center for renting a kayak and explore all the areas around Vathy or do deep water solo. For swimming and relaxation is also Palionisos bay a remoted area but a very popular one with 3 restaurants and a beach or Emborios bay another village with beaches and some restaurants also popular for many yachts and not only.Of course there are some really nice beaches scattered around like Massouri, Plati Gialos,Melitsahas Kantouni with beach bars to spend the day there apart from the remoted ones all around the island. There are small traditional tavernas in all these places with tasty local food.
The night life hasn’t got many options is mostly in Kantouni where are some popular bars and Massouri with a night club and bouzoukia. Dinner at Aegean tavern in Massouri especially in sunset time is really amazing or a cocktail drink at Azul in Armeos .Also some Greek nights organized in different restaurants is another option for the night.
If you are more adventurous and you don’t want only relaxation swimming and good food then you can choose a climbing session after all Kalymnos is the top destination for this or diving in very interesting spots.
I am sure my friend would love to come again!