1. Fly to Kos International Airport (KGS), then take the ferry from Kos to Kalymnos
This is what the majority of people do. Kos is a tourist island less than an hour away by ferry (main port to main port) offering an international airport. Between April and October and more recently even March to November, most major European airports offer charter and low cost flights to Kos. A few major European A/L like British A/W and Lufthansa also fly to Kos in season.
When you land in Kos, take a taxi to Mastichari port. Mastichari is the secondary port of Kos facing across the port of Kalymnos. From there, catch the next express boat to Kalymnos. Mastichari port is less than 10 minutes by taxi from Kos airport (7 km). Expect to pay €15-17 for the taxi ride (asking the driver beforehand is a good idea). There is also a bus from the airport of Kos to Mastichari port.
From Mastichari port, take the ferry to Kalymnos. Ferry tickets cost approximately €8.00–€10.00 per person. There are several connections between Kos and Kalymnos every day 5–10 crossings depending on the season, all year round.
When you arrive at Pothia (the port of Kalymnos) you will find taxis waiting. A taxi ride from Pothia to Myrties costs approximately € 12-14, to Massouri it costs approximately €15-16. Again, if in doubt, ask the driver about the price beforehand. Alternatively, if it is not too late in the day, you can rent a scooter or car at the port or you might want to prearrange and have the vehicle of your choice await for you at the port. There is also a bus, timetables are not always reliable, but if the tourist info office opposite the port is open, they can direct you to the nearest bus stop.
The sea connection between Kos and Kalymnos is disrupted only by very severe winds. This doesn’t happen often. When it does, the best—and usually only—option is to stay an additional day until sea travel is restored or check if there is a big ferry from the main port of Kos to Kalymnos later in the evening.
2. Fly to Athens, then fly directly to Kalymnos Airport (JKL)
Kalymnos airport is small and is connected to Athens airport a few times per week. The airline currently flying the Athens-Kalymnos-Athens route three or four times a week off season and almost every day in season is Sky Express. As with the ferries, flights to Kalymnos may be cancelled on very windy days. If that happens, try to get on a flight to Kos by the same airline; Kos airport is much bigger and not as sensitive to windy conditions. Then, take the ferry from Kos to Kalymnos as detailed above.
3. Fly to Athens, then go to Piraeus Port and take a ferry to Kalymnos
The ferries to Kalymnos depart from Piraeus, the port of Athens and main gateway to the Greek islands. From the Athens airport there are two ways to get to Piraeus: the city or suburban metro or the X96 express bus. The Athens airport has an excellent information desk; ask there and they will direct you.
Ferries from Piraeus to Kalymnos run now practically 5 times per week. The trip takes about 11-12 hours and it is often overnight. Ferries in Greece travel throughout the year however, timetables may change per season. So check the ferry timetable about a month prior to your travel dates to make sure you get the latest schedules. Sea travel in Greece is continuous, and it is only interrupted if the weather is very windy. This is infrequent and usually lasts no more than a day or two. The main ferry company on the Piraeus-Kalymnos route is Blue Star Ferries. If you are planning to take the ferry from Piraeus to Kalymnos anytime between April and September, we strongly recommend you book tickets ahead of time.
4. Fly to Rhodes (RHO), then take a ferry from Rhodes to Kalymnos
A less popular option is to fly to Rhodes, and from there take a ferry or the catamaran to Kalymnos. A charter flight to Rhodes (or Rodos) can be cheap, as Rhodes is one of the most popular destinations in Greece. There is the remote chance also that your city does not connect with Kos and connects with Rhodes. Once you arrive at Rhodes airport, you would have to go to its main port, Mandraki. From there, a ferry or catamaran takes you to Kalymnos. Between spring and autumn there is a daily catamaran (approx. 3 hours). In wintertime, ferries on the Rhodes-Piraeus line stopover at Kalymnos (approx. 5 hours). If you choose to travel via Rhodes, try to spend a few hours there and visit the Medieval City, a gorgeous UNESCO World Heritage site, before you set off for Kalymnos.