James: I wanted to start a reply thread to your post so it doesn't get lost! You have two weeks for your trip, but your itinerary is a little ambitious, and I wanted to give you some advise/suggestions. Here they are:

I think that 3 nights in Boston will be enough time for you to see the major sites. You don't say where you are staying, or if you have gotten that far, but you really should have a reservation for that time of year. It can be busy in Boston, although it is past the college graduations but it's the start of the tourist season. Please let us know if you need suggestions in that regard.

Next the Cape - again, have you thought about where you want to stay? If you want to go to MV, those ferries leave from Woods Hole (Falmouth) which is the "lower" cape (or the most western part). So you will be at the other end from Provincetown, Truro, Orleans, Eastham which, IMO, are the prettiest areas. Chatham (at the "elbow") is also lovely. It takes about an hour and one-half (no traffic) to drive from the Falmouth area to P-town at the eastern end, to give you an idea of the extent of the Cape. If you consider going to Nantucket instead (now I have to admit that I am a Nantucket fan and not a Vineyard person) you could stay more mid-cape as those ferries leave from Hyannis. Just a suggestion for you - if your DW is set on seeing the Vineyard, I don't want to change her mind.

One other comment, you have a lot of one night stays on your list. I would not include Providence on your list. Instead, you could spend an afternoon in Newport on your way back from the Cape en route to the Boston area and points north.

One other suggestion - if you like historic sites, scenery and walks, you may want to stay in Concord instead of Salem. Concord is a beautiful, historic town (again, I have to tell you that I live there so I am again partial) and you could easily fill a whole day there visiting the Wayside, Orchard House, Emerson's house, the North Bridge and Walden Pond. There is a nice, historic Inn right in the center of town (the Colonial Inn) that you might enjoy. You could spend the night in Concord on the way back from Newport/Cape Cod. Concord is right off of Route 128/95 and is about an hour and half from either Newport or the mid-Cape (again, no traffic).

I will let others join in about the NH/ME portions of your trip. The only comment that I have is that you might want to combine Portsmouth/Kennebunkport as they are fairly close to each other and you could spend the other night in Portland. The Old Port area is really fun and funky with lots of good restaurants and coffee shops. Some of the Harbor Islands are close to downtown Portland and interesting to explore, Peaks Island in particular. Again, just a suggestion to consider.

Lastly, there are lots of small motel chains throughout your route that should have availability to give you the flexibility.

One more thing - the weather during your trip can still be on the cool/rainy side or we can be in the throes of a hot/sunny summer.

Hope these suggestions will help you get started.

good advice from MarieF.
Salem MA to Portsmouth isn't very far. You could easily schedule a morning boat cruise from Portsmouth. The harbor or inland rivers cruise are interesting and a great opportunity to be on the water. Lunch in Portsmouth. Not sure if you would classify Strawbery Banke Historic area as a museum or historic site? From SB take Rt 1B out thru Newcastle. We don't spend much time on the southern coast of ME. You shouldn't have a problem finding a cookie cutter motel somewhere around Kennebunkport instead of staying in Portsmouth for the night. One reason for night in Portsmouth would be some evening entertainment at one of the theaters or music. I didn't check the calendar for June. Keep in mind that Kport, BH and Camden are all very popular weekend destinations for thousands which might make finding a motel a little more difficult but not impossible. Rt 1 all thru Maine has lots of motels. Don't miss the short hike to Owls Head light near Rockland ME nor the drive up Mt Battie in Camden. We typically plot our route to have lunch someplace with great lobster, preferably a small shack by the ocean. You could drive out to Pemaquid Point near Damariscotta for a lobster lunch and walk around the lighthouse but pay attention to miles because those beautiful drives take some time but well worth and exactly why we visit Maine.
I would choose Newport over Providence.

Ditto Newport over Providence.
Newport is very historic, with its waterfront area, scenic Cliff Walk and the wonderful mansions. There are many nice small inns, B&B's and good restaurants.IMO Newport is a must see for your first trip to New England!

I second Marie's advice, especially the suggestions of Concord over Salem and Newport over Providence. It sounds like a great trip--and you'll want to come back!

I agree with Newport over Providence as well....especially that time of year. If your husband really insists, I'd say spend the day in Newport and then head up to providence for the night, you can explore Providence a bit at night, and in the morning, then head up to Lexington.

Thanks for the comments.

I know that I need reservations in Boston...still in sticker shock phase though. Suggestions welcome; considering Back Bay close to T. Maybe Priceline? I was also considering the mid Cape area of Yarmouth, Dennis, or Brewster (suggestions?)and hoping for Nantucket ferry vs. MV. We'll see.

Don't know if I can swap Newport for Prov. either, but could head to Concord the next AM and stay the night there after touring. (assuming I could get a 1 night stay in Newport on Friday?)

Salem was only a stopping point in my mind (might want to see 7 Gables house), but I chose Portsmouth for a Strawberry Banke visit.

Kennebunkport is a place I just want to see. Don't need to stay there and could just continue to Bar Harbor.

So, as of now:
Boston--3 nights
Cape--3 nights
Prov. or Newport--1 night
Concord/Lexington--1 night
Portsmouth--1 night
Bar Harbor--3 nights
Camden--2 nights

Better?

I would agree that your itinerary is quite ambitious and also that you will probably want to have a good idea of what you actually want to see/do in each location, along with being prepared to be flexible depending on the weather.

June weather can be positively beautiful, but could also be very rainy - or, of course, a combination of the two.

Highly recommend you research the "historical" sites and each town to determine which you and your wife would find more appealing, so on such a whirlwind tour you do not waste time at those you ultimately find disappointing and wish you had gone to others instead.

Though your destinations on the coast of Maine are popular weekend destinations, you shouldn't have any problem with last minute rooms in mid-late June. But, again, research really pays off. For example, I'd rather stay two nights on Wells Beach in an oceanfront room for half the price of lodging in Kennebunkport or Ogunquit, then visit each for a day.

Keep in mind that Bar Harbor could be totally fogged in for your entire visit, so you might want to change plans and spend more time in other spots.

And, for Boston hotels, I've always had terrific luck with Priceline and Hotwire. Though, weekend (Friday, Saturday, Sunday) rates tend to be much lower than weekday rates, so you may want to consider rearranging your itinerary accordingly. Hotel and parking rates in the Business/Financial district are much more favorable weekends. Otherwise, parking could add another $30-40/night. Or, wait to pick up your rental car when heading out of Boston rather than paying to park it.

Priceline is a great idea for the Boston hotels. Just be careful that you don't get misled as many hotels will advertise that they are in Boston when in fact they are in an inconvenient, outlying area that you don't want to stay in. A hotel in the Back Bay or Financial District is your best bet. There are many, many posts here about Priceline discussing this.

I thought of some additional suggestions for the Cape that you might enjoy. There is a lovely MA Audubon sanctuary on Route 6 in Wellfleet with scenic walking trails. The Marconi area of the Cape Cod National Seashore also has nice walks to explore (also on Route 6). If you go out to P-town, the Race Point area is beautiful as is Highland light in Truro which overlooks one of the oldest public golf courses in the US.

For lodging on the Cape, we've stayed at Holiday Hill on Route 28 in Dennis which is a basic, but clean motel. It's classic Cape Cod with mini-golf and ice cream.

I'm glad you are considering Nantucket, which is a historic whaling village with cobblestone streets. It's become a trendy (and expensive) summer resort but still worth considering.

There is so much to see in this area, that it's a tough choice to make where to go. Let us know if you have more questions, etc.

As mentioned by a previous poster, Chatham on Cape Cod is a lovely town. It is central Cape, so convenient ot everything, including Harwich Port, where you can pick up the ferry to Nantucket.

There are several nice inns and resorts in Chatham. Chatham Bars is very nice, but on the pricey side. Our favorite is the Captains House Inn.

MarieF is spot on.

If you're going to do a day trip from the Cape, I'd choose Nantucket over MV. The ferry docks right in town and there's lots to see within walking distance, it's more manageable for a day trip.

I've never tried Priceline but last Oct used Hotwire in Providence. I missed the deadline for the convention rate at the Westin. I was able to make a good guess that I was getting the Westin because of the hotel description and comparing it to other 4 star hotels. I ended up with a rate slightly cheaper than the convention rate which was a lot cheaper than the rack rate. Definitely be careful about hotel location in Boston because some will really be on route 1.
You might see the tail end of the lupines in bloom in the Camden to Bar Harbor stretch. Before you get to Bar Harbor there's an area called the Blue Hill Peninsula. One of the towns has a lupine festival. It's pretty much a local event but you can get a map to find the best fields. It's a fun way of traveling off the beaten path.
If you plan on any boat rides, it could be very cold that time of year on the water.