Itinerary and Ferries

I took Sea Jet, and Blue Star. High Speed versions of both. Had a great experience. Not sure what people are warning about (I did not experience more motion on one or the other that could lead to seasickness, with were clean and well serviced). The limitation is obviously causing you stress, Just take whatever ferry works.

The warnings are mostly about the instability of the much smaller SuperJet and SeaJet2, as well as Sea Jets overall poor performance reputation for breakdowns and late departures/arrivals. The larger Championjets don't seem to have any of the same problems.

It would be helpful if you gave us the dates you are planning on visiting. Just for fun I did a search in early June. There are 5 direct ferries Piraeus to Milos. Three in the morning and two in early afternoon. Two are Seajets and one of those is the Seajet 2 that Lee mentioned. So there are other options for you.

I just want to reiterate Seajets got a bad reputation because of the two smaller boats Lee mentioned. They are chronically late due to al the stops they make and they get bounced around in high waves. I can tell you we have used these boats when there were no other alternatives and we had no problem at all. But the sea was calm on both those occasions.
Blue Star does not service this route.

The Blue Star ferry is particularly promoted as the way to see the Santorini caldera because its in the Caldera for a good half hour and the views are spectacular. Blue star ships however are slower conventional ships so are slower in arriving at your next destination. You have to understand that Island hopping is a process and requires time. Realistically you use up a good 4 to 5 hours of a day when you realize you have to check out of your hotel, get to the ferry port wait for the ferry then the voyage then on your next island you have to get to your hotel and get checked in. For example the Blue Star from Paros to Naxos takes about an hour. We left our hotel by check out at 10 am. By the time we got to our hotel in Naxos it was 3PM before we hit the beach.

After numerous trips to Greece we have realized that time is the precious commodity not money. We always look for the fastest way to our next island. Seajets Championjet 1 and 2 are fast so they get to Santorini by mid morning. (They also have a back deck which is open so you can be outside for the caldera view) Mind you at 40 knots its a tad windy. I timed it and we were in the Caldera for 8 minutes and were past the outer ring of caldera islands in 15 minutes. The compelling factor was the Championjet (which is large and can hold up to 1800 passengers) departs Santorini around 11 AM and arrives in Naxos around 1PM . Blue star leaves Santorini around 3 PM and gets to Naxos around 5. My times may be a bit off but thats my recollection. I will always take an additional 4 to 5 hours on the beach in Naxos when there is a fast ferry that gets me there sooner.

On that thought I would fly to Milos. You will be there in 45 minutes. You will have to take the ferries to the other islands and you can fly back to Athens from Naxos. Often the cost of the flights are not significantly more expensive than the high speed ferry trip.

You mentioned that you can rearrange your schedule. Many experienced travelers to Greece prefer to do Athens at eh end of the trip not the beginning. Waking up on an island is way better than hot dusty busy Athens. Its also a good idea to be in Athens at least one night before your return flight so it just makes sense to catch a connecting flight to your first island immediately on arrival in Athens.

Have you been using GTP ferry schedule for ferry connections. Its very extensive and easy to use.

Thank you all for the tips and explaining the difference with the fast ferries. Like you said I would rather not waste time sailing from one island to the next, but also did not want to end up sick. Had it happen on a cruise after I took a small boat snorkling. I never ever want to relive that day. I am going to fly to Milos and then take the ferry to Sifnos. After that I will plan to take one of the ferries (hopefully the ones you mentioned) to Santorini and then to Naxos. Or would I be better off going to Naxos first and then fly out of Santorini to Athens? When I do look for the ferries I see a lot of the SuperJets. I do not see the ones you mentioned.

You can fly from Naxos to Athens. We did.

I looked at the ferry schedules (still don't know the dates)
Milos to Sifinos has 7 departures three of them on Seajets. One of them is on Naxos jet and its bigger than the two ferries mentioned by Lee. I have not heard anything bad about Naxos jet. There are however 4 additional options with other companies.

Sifinos to Santorini only had three departures with two seajets including Naxos Jet plus the Golden Star ferry. The two Championjets don't do these routes. They are too big for the limited demand and concentrate on the Crete, Santorini, Naxos/Paros Mykonos runs.

Santorini to Naxos has a pile of daily departures. This is where you will find the championjets.
You could go on the Seajets web site. They have a description of all their boats including size. number of passengers and speed. Compare the two boats mentioned by Lee with Naxos jet and the championjets and you will discover size difference. Another hint is buy your tickets for your next island when you arrive on the previous island. Local travel agents sell tickets. They will have the latest information on the weather, strikes and any other relevant information. If the seas are going to be calm on your hop day then even the small seajets are fine.

Sequence is important when hopping. There are three ferries from Sifinos to Naxos in June so it would be easy to bypass Santorini and place it at the end of the trip. As mentioned by Beth there are flights to Athens from Naxos but those flights fill up fast and there are only 5 or 6 flights a day. You will have a lot more options if you fly back to Athens from Santorini.