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There are a couple of ways for reaching Dubrovnik and from there, Šipan island. Here is a summary in short:
DUBROVNIK BY PLANE
A couple of major airlines in Europe offer flights to Dubrovnik during the summer tourist season. Some keep their offers open after the high season is over so there is a decent choice of options for getting to Dubrovnik by plane.
DUBROVNIK BY FERRY
There is a regular ferry line from Bari, Italy to Dubrovnik, Croatia that is operated by the croatian company Jadrolinija. The line operates from April till October each year, and during high season the ship departs almost every day from Bari at 22:00 o’clock, and arrives in Dubrovnik on the next morning at 7:00 o’clock. At the end of the busy season the departure dates may become more rare (once-twice a week) and the line will remain active until the end of October.
The prices for the ferry trip may vary from 50 EUR to appx. 100 EUR depending on whether you wish to travel more comfortably and get a cabin bed or simply purchase a deck space.
For more information on the prices, tickets and ticket reservations please visit the Jadrolinija web site.
DUBROVNIK BY BUS
Some travelers prefer to first fly to Montenegro’s city of Tivat and from there to get the bus to Dubrovnik. It is worth checking the low cost airlines for offers from major european cities to Tivat (also direct flights may be available). The bus ride from Tivat is a very advantageous trip that can cost you around 20 EUR per person in one direction, and lasts about 2,5 hours.
GETTING TO ŠIPAN ISLAND
Once you have arrived in Dubrovnik, your next and last trip will be from the port of Dubrovnik to the port of Suđurađ on Šipan.
If you arrived in Dubrovnik by plane, then you may want to get a shuttle bus or a cab/ an Uber car from the airport to the city of Dubrovnik. The end stop of the bus shuttle is the main bus station in Gruž which is a short walk away from the port. If your luggage is heavy or you are tired and don't feel like walking, then try any of the city buses departing from the main station. The port is just one bus stop away.
At the Dubrovnik port you can purchase tickets for the passengers' ship or the ferry to Šipan from the Jadrolinija office (right across the street).
For information on the sailing schedule, the prices and other details please visit the Jadrolinija web site.