Help! Bad planner with itinerary questions :)

Tell us where you from and where, which airport
are you flying in and out of ?
Doing the perimeter is one thing
it would be better for you to pick
two of the provinces
say MUNSTER and CONNACHT
and workout a route using :
Google MAPS / SEE.....MYMAPS on Youtube

Thank you! We are flying from Boston into Dublin and are flying out of Dublin.

I think you need to do a bit of a search through the branch - there are lots and lots of 'itinerary' threads. In general, its better to keep things flexible according to weather, etc. Dublin is worth a few days, plenty of day trips and hikes you can do from the city, and plenty to see and do. Probably the simplest itinerary is to drive down to Cork and work your way along the west coast taking your own time. In general, you will not have to book ahead except perhaps during the weekend, but do check in at local tourist offices, if there is a festival or event on in an area things can book out very quickly.

Dublin is a very manageable city and is definitely not a sprawling metropolis. There are several attractievb suburbs along the dublin bay, including (from north to south) Howth, Malahide, Sandymount, Killiney, Dalky, Dun Laoghaire. There is a commuter train linking them all, so you could stay in Dun Laoghaire (pronounced dun LEER-ee) for example and make a trip to Killiney. There is good seafood and shopping in these towns, but they are not cheap.

After that, I would drive to Galway, its about three hours and explore Connemara and Mayo, or go south to Clare and Kerry.

Kinsale and Scull in Cork are also great.

To be honest, Ireland is not very big and once you start driving you won't be able to escape pretty coastal towns.

Thank you very much, everyone! We were hoping to wing it a bit, and having all of these great suggestions + knowing that we don't need to book ahead (expect weekends) really helps! :)

Does anyone have any thoughts regarding adding a trip to Scotland to this trip? We will be travelling for 17 days and I want to get the best out of Ireland. However, would going to Scotland be too much to add?

Connemara is in the west
checkout the following :

Youtube : AT YOUR SERVICE PART 1
followed by part 2 and part 3
enjoy.

If you plan to visit major places like Dublin, Cork, Galway and Belfast its most likely you will want to spend a couple of days at least in each, so thats 8 days gone already. If you add visiting small coastal villages,camping, major tourist sights, the odd museum and travelling between places you will probably find you may not have time for Scotland.
Ireland is small but there's still plenty to see and a complete coastal circuit ( if I understand you right ) is a lot of miles ( but still rewarding ) even if you skip a few places. Scotland isn't impossible by any means but you may end up rushing your trip and perhaps not doing Scotland justice. That's just my thoughts. It all depends on what kind of travellers you are and your interests.
I know Northern Ireland best so my post will deal with that so see others for Southern Ireland.
In Northern Ireland you can take the ferry ( with car ) from Belfast or Larne to Scotland in around 90 minutes. Glasgow would be no more than a couple of hours drive from where the ferry lands at Stranraer or Cairnryan
After Galway and the West of Ireland you could head to Enniskillen for the Marble Arch Caves and the Fermanagh Lakes. From here The Ulster American Folk Park in Omagh ( recommended ) is easy to reach for a half day trip. You could travel on to Londonderry/Derry from here or make your way into County Donegal first if you haven't seen enough wild country around Connemara. After Derry there's plenty to see along the North Antrim Coast and lots of pretty little Irish villages from Benone Beach to Larne.
If your heading to Downpatrick the most scenic route would be Belfast-Newtownards-Greyabbey ( Abbey Ruins ) - Kirkubbin ( typical irish village ) -Portaferry (fishing village)- 15 min charming little ferry across to Strangford - Saul ( Saint Patrick statue ) - Downpatrick ( said to be the burial place of ST Patrick.)
There is plenty of caravanning around this side of Strangford Lough and most will allow you to camp but check beforehand. I have camped at the caravan site at Cloughey ( one nearest the petrol station with small bar/restaurant on site ) You can pitch right by the water for around £10.There's a nice little beach turning left leaving the site by car around 2-3 miles.
From Downpatrick head to Ardglass ( small fishing village ) and check out Tyrella Beach a few miles ( nice views of the Mourne Mountains on a clear day ) further on the road towards Newcastle where you can explore the Mourne Mountains which has a huge selection of B&B's and camp sites. Tollymore is a good site in Newcastle. There are plenty of walks around the Mourne's but if your'e not into hiking it is at least worth going to the Silent Valley and the forests.
From here you could continue your circuit through Carlingford Lough or Newry and back to Dublin.
You could do the above places in Northern Ireland in 7 days quite comfortably ( not including exploring Donegal ) and I can recommend all of them.
That would give you 10 days in the Republic of Ireland at the beginning of your trip. For B&B's in Belfast try the streets around Botanic Avenue near Queens Univeristy. Booking may be required.
So you may think about spending 1 night in or around Enniskillen and Marble Arch Caves. Next morning visit caves and head to Ulster American Folk Park, Omagh in the afternoon before heading to Derry to spend the night. Next morning take a tour of the walled city and continue to Benone beach and Castlerock area then through Coleraine to Portstewart Strand, Dunluce Castle, Bushmills Whiskey Distillery, Giants Causeway, Ballintoy, Carrick-a-Rede Rope Bridge and stay the night in Ballycastle or nearby camp sites or further at Cushendall depending on time. Next day take the scenic route ( sign posted in brown ) through all the little villages ( stop at a cafe for an Ulster fry ) to Larne, stop at Carrickfergus Castle and on to Belfast for 2 nights. The hop on hop off bus tour and the Ulster Museum are 2 highlights as well as some great pubs. Early morning day 6 head to Downpatrick ( half day ) before heading to Newcastle for 2 nights. From here Dublin is around 2-2&1/2 hours drive.

I would advise against trying to fit in Scotland as well.