As far as the Canadian part I would choose either PEI or Montreal and Quebec.
The roads arent scary either way.

I'll try and comment on some of your questions:
1. Boston and Portland are apples and oranges. Boston is a MUCH larger city. Both are great destinations but in a different way. If you want a big, bustling city with lots of history, shopping, dining, culture, etc, that's Boston. If you want a small waterfront city with lots of charm, a bit of grittyness, and some beautiful coastline nearby that's Portland. If you start from Boston, you are about an hour's drive to the Maine coast. You will pass thru New Hampshire's short coastline which is also quite nice. If you start from Portland, you will be in the heart of some beautiful coastal scenery.
2. There are dozens of towns that meet your description. Camden, Boothbay, Kennebunkport to name a few. You will be hard pressed to find a restaurant that doesn't serve lobster rolls. Unless you are driving during an ice storm, there are no scary roads. Maine is not like California, with cliffside highways. In fact much of Maine's route 1 along the coast is lined with motels, mini golf and restaurants.
3. I don't know, but I doubt it.
4. To where?
5. Both cities are fabulous. Like question 1, Montreal is a much bigger city with world class dining and shopping. Quebec City is extremely scenic, much like being in France. If you can swing it, try and do at least 2 nights in Montreal, 1 in Quebec City. I've never been to PEI, but I know it''s a very long drive. Go to the Canada forums for more info.

You will definitely want to rent a car except for your stays in Boston, Montreal and Quebec City. This is an easy part of the world to drive in except for summer traffic on rte 1 in Maine, or winter driving. Yes, there are windy roads heading out to some waterfront areas, but nothing challenging.
What time of year you go will have a big impact on your experience.

This is the Canada forum.

It is a full day drive from Boston to PEI. It would be another very full day drive from PEI to Quebec City. Easy drives on nice highways if you did the fast routes, but long drives.

One question I have is how much time do you have? Two weeks at least I'm hoping.

2) To add to recommendations by Zootsi, I'll add Charlottetown PEI for terrific seafood.
3) The only parts I could see a train even being feasible are: Boston-Portland, Quebec City-Montreal and possibly the once daily Moncton, New Brunswick (across Confederation Bridge from PEI)-Quebec City or Montreal train.
4) Ferries: If you just wanted to get out on the water on a boat, there is a slightly-out-of-the-way ferry from Nova Scotia to PEI that you could take, but you don't *need* to, as there's the Confederation Bridge. There may be other appealing day excursions, but that's all I can think of that's actually sort of "on your way". You'll need to be driving mostly though.
5) Both great cities and worth seeing if you have time, but if you had only let's say 2 days, I wouldn't do both, I'd stick with one.

If you were thinking about ferries from Maine to Nova Scotia, (like Portland-Yarmouth) there aren't any, any more.

I find the drive from Boston to PEI, around 12 hours, to be more than a full day. I wouldn't like to do that all in one go. When we did the trip we stopped at Acadia, and in New Brunswick. A stop someplace like Alma, New Brunswick would be a great place to have a lobster, and visit Hopewell Rocks, as well as Fundy National Park.

Consider Halifax, Nova Scotia instead of Quebec or Montreal if you want to add a Canadian city. While still not exactly on the way, it might fit your trip a little better.

How much time do you have, and what time of year?

Thank you so much. i had never been in this area so this information makes so much difference in planning. we are planning to go in late april and are trying to decide between 9-11 days. the cats start destroying the house on day 10 so we don't like to stay longer than that unless it's time for new furniture.....and it's not.
so, now what i am thinking is:
fly into Boston. spend the night.
day 2: Drive thru Camden and spend the night in Boothbay.
day 3 : drive to PEI
4, 5 PEI
Day 6 Drive to somewhere in Nova Scotia
Day 7 Quebec
Day 10 Back to Boston
Does this sound reasonable and any suggestions for nova Scotia?

This trip looks rather rushed & tiring to me. From this plan, I see essentially, you've decided not to explore either Boston or Portland to any significant extent. Given that you're zipping through Maine and Boston (Boston takes 4 days+ to really appreciate in my opinion) won't be much more than a place to crash, I think another airport would make more sense...I wouldn't want to deal with Boston traffic unless I were really going to sink my teeth into the city with a good several days there. Halifax, Montreal, Bangor, Burlington are some ideas of places to fly into, adjusting plans accordingly.

Other comments: Two days in PEI sounds ok for a taste. Day 6. I love Nova Scotia, but it seems a bit out-of-the-way in this case. Why not pick a spot in New Brunswick instead (maybe somewhere along the Acadian shoreline) which is more on the way to Quebec.

Best wishes whatever you decide, Daniel

Daniel, thank you. actually i meant New Brunswick, not Nova Scotia. and we really were just trying to find the northernmost point to fly into on a non-stop flight. hmmm. i may need to rethink.

You are doing a tremendous amount of driving - Boston to Camden is about 3.5-4 hours. Quebec City to Boston is another very long haul. I agree with Dan - if you are not going to experience Boston, why fly into & out of it. It might make more sense to fly into Portland and out of Montreal. Realize that late April can still be pretty chilly in this part of the country, bring some warm layers! Many places will not yet be open for the season. On the plus side, it will be blissfully uncrowded, and you'll see some beautiful coastline.

I really think you are covering too much ground and won't have time to see anything. Keep in mind that the driving between these places is NOT really scenic, unless you get off the highway. And then it becomes very slow.

Camden ME to Charlottetown PEI is 9 hours. That's a very long days driving, and while some of it is pretty, a lot of it is tree lined highway.


Now, here's your days 6,7,8 :
Charlottetown to Fredricton, NB is 4 hours
Alma to Quebec city, 8 hours.
Quebec City to Boston 7 hours.

Now, how are you going to see ANYthing in Quebec? Whats the point? You'll have dinner and breakfast and that's about it. Plus, I picked Fredericton because it shortened the route. it doesn't actually let you see the Bay of Fundy and the tides, I think that would add a couple of hours of drive time. So you don't get much at all out of those 3 days.

At least to me, this looks like a lot of driving, and very little seeing.

thank all of you for your help. after reading the above posts, we have checking into flying into Montreal, Quebec or Halifax. Then just going to PEI and Quebec. and hopefully a little nova scotia. haven't finished flight research. the non-stop under $300/ flight to Boston was the original allure.

Your last post is on the right track. I'd suggest concentrating on the coast of Maine plus Maritime Canada. Lots to see and much less windshield time. An alternative would be to fly to Montreal and concentrate on Quebec.

funny how a trip can totally change . Now, our plan is to fly int Halifax, take the slow road up the eastern coast, stop in a couple of places, spend the night, then up to Sydney and spend a couple of nights. Then to Charlottetown or Summerside for a couple of nights and back along the Bay of Fundy to Halifax. We are planning 9-10 days of slow travel. I have been reading scenic driving atlantic Canada to decide where to stop. Unfortunately, it makes every place sound enticing. anyone have any favorite towns or Inns along this route? and is this more doable? thank you.

This is much more my kind of trip now. I love Quebec (I live here) and New England (and you should plan a trip one day), but I think this is much better--you'll get a much greater appreciation of the Maritimes moving at this pace. I'm ashamed to say I've never been on the Cabot Trail, but by all accounts that's one place I'd definitely be focusing my energy on. I really like Halifax, I would allot 2-3 days there; Lunenburg, Mahone Bay and Peggy's Cove would be excursions you could do out of Halifax. In PEI, I'd recommend making downtown Charlottetown (over Summerside) a base, as quite a few sights as well as a gamut of terrific restaurants are within easy walking distance. I should warn you that I've been in Halifax and Charlottetown in June and needed my (Montreal) fall jacket or sweater, so since you're going in April, you may want to think what you might need as clothes for Houston in December.

Have a great trip! Daniel

Yes if you're going to Cape Breton you really need to see the Cabot Trail, especially through Cape Breton Highlands National Park - one of North America's top scenic drives. And instead of staying in Sidney, look into Baddeck, or possibly Ingonish area.

I'm not sure I would take the slow route from Halifax to Cape Breton. It's not unpleasant, and is scenic in some places, but I think the extra driving time could be better used exploring even more scenic areas, and your time is somewhat limited. You might stay a night or 2 in Halifax and use it as a base to explore down the Lighthouse Route for day-trips (as suggested by Daniel), e.g. charming historic Lunenburg, a scenic stop at dramatic Peggy's Cove, a walk around quaint Mahone Bay.

Some of the most dramatic vistas of the Bay of Fundy are along the New Brunswick Fundy Shore if you have time, e.g. Alma/Fundy National Park and Hopewell Rocks.

Do you have to go in April? June to October would be better.