Syros is perhaps the easiest island in the Cyclades to get to from Pireaus. There is a ferrry leaving every day at around 7:30am year-round and in the summer several more during the day and sometimes in the evening.

The Highspeeds take about 2 hours from Pireaus, the regular ferry around four and a half. Because they are on the same ferry line Syros is a good island to combine with Mykonos and Tinos. There are also good connections to Paros, Naxos and Santorini in the summer. Remember that Syros is the capital of the Cyclades so there are connections to all the islands though some may only be once or twice a week. The NEL ferries Panagia Hozoviotissa (photo) and Panagia Tinou did this route in the past. They were old and slow but if you are the type who liked the old ferries with their wooden decks and classic design. It took us 6 hours to get from Kea to Syros but smoke was only coming out of one funnel so maybe they were trying to save fuel since there were only about a dozen people on the boat. Now they are using highspeeds but driving them at slow speed to save fuel. It doesn't matter. The Cyclades are close together. There are even connections to the Dodecanesos islands a couple times a week as well as Samos and Ikaria. There have been years where I have come to Syros to connect to Chios and Lesvos, though it is not a connection you can count on every summer.

There are also flights to Syros from Athens.

For hotels and transportation visit any of these agencies who all handle bookings on the island, car rentals, ferries and flights. I recommend them especially if you are including Syros with another island so they can coordinate hotels and ferries:
Fantasy Travel at www.fantasytravelofgreece.com
Aegean Thesaurus at www.greecetravel.com/aegean
Dolphin Hellas Travel at www.greecetravel.com/dolphinhellas

The best islands to combine with Syros are Mykonos and Tinos. Syros is the island of commerce. Tinos is the religious island. Mykonos is the party island. If you do all three you will have covered all the bases, especially if you throw in a daytrip to Delos which is the island with the richest history.

For hotels see Booking.com's Syros Pages or check out the Hotel Hermes in Hermoupolis where I stay whenever I go. You can't beat the location in the harbor and there is a beach in the back. If you want to stay outside of Hermoupolis see the Hotel Blue Sky on the beach at Galissas which is recommended by my pal Sakis at the Hotel Attalos in Athens who spent 2 weeks there.

Ferries returning from Syros are also returning from Tinos and Mykonos and are usually crowded. It would not hurt to arrange a taxi transfer for your arrival if you have a lot of luggage. Otherwise the boats dock pretty close to the Pireaus Metro Station. You an buy ferry tickets in Syros from Virginia Parissis of Parissis Shipping Agency in the harbor close to the Hotel Hermes.