I am planning an anniversary trip in late August and am looking at the Chatham Bars Inn and The Inn at Castle Hill. Both seem romantic and beautiful. I'd like to have quaint shops, galleries and things to do nearby. We may be interested in whale watching, beaches and hiking. Chatham seemed to be surrounded with a lot of things to do, but haven't found out much about Newport area. I've read other posts about Inn at Castle Hill being set apart from everything, but not sure if it would be a problem. FYI- we'll be flying into Boston and renting a car from there. Are the ferries able to carry cars or just people?

First of all, you won't need a ferry to get to either Newport or Chatham.

Newport is a bit more urban than Chatham, and is renowned or its fancy mansions and for being the home of the tennis hall of fame. Plenty of quaint shops etc., certainly more "to do" than Chatham.

The Inn at Castle Hill is about 10-15 minutes from downtown Newport. However, it is a really beautiful and scenic drive. If you're planning on going in August, the height of the tourist season, you might be a better off a bit removed from the hustle and bustle of downtown.

I've been to both and they are both lovely towns. I agree with Ellen, though, that there is quite a bit more to do in Newport. You can see the Mansions, do the cliff walk, visit shops, galleries, take a sailboat ride, etc.

Chatham is *very* quaint and we stayed at a lovely B&B there. You can see all the shops in town in an afternoon, though. I would think you'd also want to go to Provincetown (especially to do whale watching -- which was great) and take the ferry for a day to either Nantucket or Martha's Vineyard.

Lisa,
What B&B would you recommend in Newport? We love staying in them, but only with strong recs.

Tracy -- we didn't stay in a B&B in Newport, we stayed at the Hotel Viking. Here is a link to their website:

http://www.hotelviking.com/index.cfm

It is very well located and a nice hotel, but I thought it was VERY expensive for what it was (and I live in Manhattan). Our room was TINY (and I mean that there was no where, including a closet, to open the suitcase) and located right next door to the maid's room, where noisy activity begins around 6 am. You couldn't cuss a cat (as my mom would say) in the bathroom. All this for about $300 a night!

Tracy-
If you go to Chatham check out Vining's Bistro on the second floor of the building next to the Christian Science Reading Room on Main Street. Great food but unfortunately they don't take reservations.

While Newport has its moments it has become a party town for the 20 somethings and its not always very pretty.

Chatham has a center with quaint galleries, shops, et al as mentioned but it is not nearly as urban as Newport. (not that Newport is a big city...) However if you are really into the galleries you can hop into your car and visit Welfleet, Orleans Provincetown or anywhere on Rt 6a for plenty more.

I don't now much about ferries and cars but if you rent a car from Boston you can drive to either destination just avoid travelling to the Cape on Fridays 1-5:30, Saturdays 9-3, Sundays 3-7. These are very ugly traffic times at the Cape Cod Canal.

If you are a beach person, I would suggest Chatham. If you are looking for nightlife, I would go to Newport.

I absolutely love the Chatham Bars Inn, and Chatham. If you are going for your anniversary, chose Chatham. If you were single, I'd definitely go with Newport. Chatham is more beautiful, but no night life. Newport is a great party town. Lots of bars.

Are you planning on taking a car on the ferry to Nantucket or the Vineyard? If so, you will need a reservation. To take a car to Nantucket will run $ 330 Round trip (that doesn't include you, just the car). You're better off leaving the car at the docks and renting bikes when you get on island. There's really no need for a car for a car on either island, especially if you're not renting a house there.

The Cliffside Inn in Newport is lovely and located near the Cliff Walk between the downtown and the beach. There is also a small winery (with tours) in Middletown next door. I've stayed in both towns repeatedly, and would probably choose Newport for an anniversary stay.

Tracy -- I remembered the name of the B&B we stayed at in Chatham: Captain's House Inn. Here is a link to their website:

http://www.captainshouseinn.com/Default2.asp

It was absolutely wonderful! The house and grounds are beautiful. The room was large and well-appointed. Breakfast is filling and delicious and served at individual tables (my husband's strong preference). The host and the staff are all British or Irish and they are eager to attend to your every need. There are always brownies or other goodies (!) sitting out for you to sample. A thoroughly enjoyable experience.

Just to summarize what others have said and add my own comments: Newport is more sophisticated, with lots more bars, restaurants and nightlife after all it is a city, whereas Chatham is a small town with more appeal to families. Both places are in beautiful settings with awesome vistas.

Staying at the Inn at Castle Hill, you will have to drive to Newport attractions but you can walk to the center of Chatham from Chatham Bars Inn.

In Chatham you are on Cape Cod a 70 mile vacation peninsula with 14 other towns full of beaches, attractions and sightseeing. Although Newport has much more to do and see, once you leave the Newport area you are in plain old Rhode Island no different than any other non-descrip area of the USA.

Also there are no whale-watching boats from Newport that I know of. There are none from Chatham either but you can drive to Provincetown from Chatham (1 - 1.5 hour trip) where the best whale watch trips originate.