The "best" time to buy international flights is 3-6 months out. We suggest monitoring the flight prices starting about 8 or 9 months out and buying when you feel comfortable.
There are several ways you can get to Dingle once you land in Ireland. Most flights from the US will take you to the main airport in Dublin. From here you can rent a car and drive (about 4 hours), take a train, hire a private driver, take a bus, or hop on another plane to take you to a closer airport. Please note that there are no airports in Dingle, so you will need transportation from the airport to the town.
Stay as long or as short as you would like! The only day you absolutely positively have to be in Dingle is May 27th ;)
Backwards, lol! When driving in Ireland you will be sitting on the right side of the car and driving in the left lane. It sounds crazy and daunting but we promise you'll get used to it! The highways are easy to navigate and operate just like they are in the US. They also have tolls on their highways so be prepared with coins. Things that are different from the US: 1. The passing lane on the highway is on the right and truly just used for passing. 2. The lanes are tiny... like "oh my gosh how are both cars going to fit on this road" tiny... and usually flanked on both sides by stone walls, cliffs, and/or thick brush. Just take it slow and you'll be fine. You'll also notice little pull-off areas every so often to let people pass. 3. The roundabouts are used correctly. In big cities (and small towns) the roundabouts can be 3 or 4 lanes. Pay attention to what exit you need to get off at and which lane will take you there. If you miss it and are in the wrong lane, no worries - it goes right back around! 4. Most cars are manual, so when you pull up behind someone on a hill, we recommend giving them some space. 5. You can park on either side of the street! You'll see a lot of cars that look like they are parked "going the wrong way".