Strange name for an island, isn't it?
Anyways, to get there, we took the Steamship Authority ferry from Woods Hole to Vineyard Haven. Because some ferries go to Oak Bluffs instead, you end up with about a ferry every hour. So no matter when you arrive at the terminal, you don't (usually) have to wait too long. The ferry is HUGE (three decks of total comfort) so even in the middle of summer, don't see any problem with boarding even if you're late (they recommend coming 1/2 hour before departure in the off-season and 1 hour in the summer, but not sure you really have to). Now, the fun part is that (assuming you're just gonna board yourself and your loved ones) you leave your car at a parking lot in the boonies and take a shuttle bus to the ferry terminal. The one we left the car at is called Cataumet and is right before Falmouth (cost = $10, shuttle is complimentary of course). Don't worry, there are signs on road 28 for the parking lots (have no idea where the other parking lots are). Almost forgot, the cost for a ticket round-trip is a mere $15 and it takes 45 minutes to cross.
There is an another ferry company called the Island Queen that only takes passengers (hmm, maybe it's not a ferry then) that operates from Falmouth to Oak Bluffs. We took that one before and we would have taken it again but the website was saying that the annual Falmouth road race would disrupt traffic. Their parking lots are located within walking distance of their terminal but their ships are much smaller (and less comfortable) than the giant Steamship Authority ferries (they fill pretty quick). The cost for a round-trip ticket is $16 and it takes just 35 minutes to reach your destination.
Once you arrive in Vineyard Haven, you can go straight to Oak Bluffs (or whatever other town you want to check out) using the local bus system. The brochure says it's $1 from town to town, but to go from Vineyard Haven (aka Tisbury) to Oak Bluffs, it's gonna cost you $2 per person. If you plan on taking the bus a whole lot, not a bad idea to buy the day pass for $6. Besides the harbor and main street, not much to see, in my opinion, in Vineyard Haven.
When we arrived in Oak Bluffs, we went straight to the former Methodist campsite (former as in Victorian times). In the middle of it all, there is the Tabernacle, a pretty big steel canopy-like structure that serves as a church on sundays. There are tons of little cottages around the tabernacle, about 300 from what I've heard. The most photographed is probably the Pink House but it is a bit out of the way (we found it without really looking for it and said to ourselves: oooh, that's the Pink House everybody is writing about or at least, I did).
When you step out of the bus, you have the beach on one side and the marina on the other. The beach is not that great to be honest but the marina is full of nice leisure boats (wouldn't call them yachts but there are some nice big boats). Not sure what the owners do all day but there seems to be a lot of beer drinking going on but maybe it's just an impression.
There are tons of restaurants on the main street, which happens to be called Circuit Avenue. We chose the Island House for a nice lobster dinner, which was followed later on by a nice little cup of homemade ice cream.
Other places of interest on the Island are Edgartown and Aquinnah. We went to Edgartown before but can't remember a thing about it beside some old whaling captain houses here and there. Maybe next time, we'll revisit.