My husband and I are planning a trip to Greece in May 2009. We will be taking our 16 month old with us and would like a relaxing family vacation. We like to be outside, meet locals, sunbathe, and partake in every water activity available.

Has anyone been to the island of Lesvos? If so, do you think this is the right island for us? We were also thinking of Sifnos, but for some reason we have been more pulled to Lesvos.

Please let me know your thoughts.

Also, this will be our first visit to Greece - will we regret skipping the major tourist destinations like Santorini, Mykonos, or Crete?

I can't give you the benefit of personal experience with Lesvos, but it is refreshing to see someone looking further afield than the well beaten path of Mykonos, Santorini, and Crete. Although you may miss some of the major tourist sights, you will see a bit of Greece far more traditional than the others.

Should you wish to avoid the long ferry ride with your 16 mo old, the airport on Lesvos is listed as Mytilene.

I will return from Lesvos May 3 and will be able to report first hand information. From everything I have read, it sounds like a Great place to vacation, plenty of variety, and family friendly. As for water sports, I seriously doubt the water in Greece will be warm enough for swimming before the end of May first of June.

Oops just saw this post, sorry.
Lesvos is half of my place of origin and i have been there plenty of times. Will you fly there directly? If not, there is an express ship that takes 6 hours to Mytilene (the port of the island) or many normal ones that take 12 hours. Personally i love the sea and the 12 hour evening route doesnt bother me at all, on the contrary i enjoy it, ther is plenty you can do on deck.. the best deal is if you get a cabin which is not that expensive, just have in mind that the best ship for the 12 hour journey is "Mytilini" with "Theofilos" left as a second choice-I wouldnt pick another one.
The benefit is that the island is quite green, has some great beaches (Vatera, Eressos)although the sea will still be a bit cold in May, it is not overrun by tourists but you will get the chance to meet many locals (get an english-greek translator-book with you, you might need it), you will get the feeling of "traditional" Greece and also of "religious" Greece, as some of the top sites on the island are monasteries and churches (Saint Raphael, Saint Taxiarhis monasteries and the Church of Virgin Mary in Petra and Agiassos) and the locals are quite religious people. There are also castles to see there in Mytilene, Molyvos, Sigri, the petrified forest (with scarce remainings) but the most important is the character of the place. This is not commercialised Greece, it is real Greek countryside. Just keep this in mind!
It is an inspiring place after all, you will get the chance to see yourself. So have a great time sunbathing, exploring and mixing up with the locals!!

P.S. Dont forget to buy ouzo... all great brands in Greece are produced in Lesvos!