The destinations that you list are quiet this time of year uinless you are interested in a foliage tour. For clebratory occasions, you are better served to remain in Boston at this time of year. There are hundreds of things to do and enjoy from professional and college sporting events, restaurants, bars, museums, shopping, etc. Read the last 20 - 50 postings on this forum to obtain ideas.
If you want to visit someplace in New England outside of Boston, with some fun nightlife for 30 somethings, you should try Newport, RI. There are lots of clubs and bars, etc, and it's a fun place to visit and hang out with your friends. Providence is also worth visiting. They have a lot of great restaurants and clubs and it's fun for hanging out, especially on the East Side, near Brown University and RI School of Design.
October on Cape Cod is very pretty, and very quiet. Most of the restaurants/bars have closed for the season by then. If you want solitude, maybe walks along empty beaches, etc., you could try it, but it strikes my mind as a more romantic getaway than a buddies one.
The same goes for Bar Harbor. Portland is a very nice little city, which is not a summer resort, so it will be lively and active that time of year.
I used to live in Providence on the East Side but moved back to Boston because it was so boring.
Portland? nice place to take a date.
Bar Harbor - too far, nothing but foliage up there.
Cape Cod? Good for old folks.
Single guys? Boston definitely. This town is PACKED with babes. Newbury St by day. Landsdowne St or downtown by night. Harvard Sq anytime.
You might like spooky fun in Salem around this time of year. The witches are just fabulous!
Anyway the hire car probably wouldn't be allowed north of the border.
Any suggestions for cool hotels and special occasion restaurants in Boston?
First, I have to disagree with the Providence comment. There's plenty of cool, fun things to do in Providence, and most of it comes without the high costs and attitude you can sometimes find in Boston.
I think we were all giving you advice in the mindset of 4 young guys out on the town, and we were all thinking of babes, drinks, and nightlife.
If you really would like to see some of New England countryside while you are here, rent a car and drive West or North. You don't need to go all the way to Burlington. The rental car contract will be good for anywhere in the area, but probably not to drive into Canada.
If you wanted, you could drive up Interstate 93 towards Concord NH and into the Franconia Notch area, which is quite pretty, although the foliage will be gone by the time you get here.
As far as places to go in Boston, definitely check out Landsdowne St., which is next to Fenway Park. Lots of big dance clubs, pool halls and nightspots there.
Also, the area around the Banknorth Garden. Causeway St., Friend St., Canal St., and the surrounding areas are packed with bars and clubs with dancing, etc. The other hot spot is the Quincy Market area, which tends towards Irish pubs and bar life, not so much the large dance club scene.
If you are looking for hot waitresses, you should try out Hooters, which is on Friend St. They make great Buffalo wings. Their claim to fame is a hot waitstaff wearing short shorts and very tight t shirts stretched over their very large "Hooters"...
Forgot about the cool hotels. You might want to try the Kimpton Onyx hotel, which is "staggering distance" from all the clubs in the Garden area. It's got a very funky vibe and Kimpton hotels are always well run and very trendy.
Another idea is the Marriott Custom House hotel, which is in a Boston skyline landmark, and has fantastic views from the rooms on the upper floors. It's also centrally-located to all the Quincy Market and Waterfront tourist areas.
London and Boston have a lot in common Dan. We have a lot of nice parks just like you guys. We have a lot of beautiful women, just like London. Boston is a little more stuffy attitude wise than London - London has a decadent side. Boston is thoroughly puritan. What is an ironic twist of fate of course is (from what I saw) Boston is more historically preserved than London. That of course is no fault of the Brits, it is obviously a misfortune brought to us courtesy of Herman Goering. I found it very sad walking around London seeing obviously how much history was destroyed there. Anyways not to mope...
I guess I'm just a city boy Dan, that's why I find Providence and Burlington dull. There's no crowds on the streets, no action. Too small. But hey, different strokes for different folks! The Green Mountains of VT are nice, I agree Franconia Notch in New Hampshire is better. Providence does have a few niceties. The Historic area Benefit St, College Hill, and Downcity are cute, maybe you'll like. It's a cute little city, the people are sweet, the food is good but you won't see much going on.
To me if you come from overseas to the Northeast, you should see Boston, NY, and Montreal. Sure stop in Burlington for a few hours on your way to Montreal. Stop in Providence for a few hours on your way back from NYC.
I agree with Beantown Man. "Cool" hotels is not really part of the fabric of "Boston Society". Elegant, fashionable, yes - "cool"? For "cool" you need to go to Miami. All the hotels there are cool.
The only curious spot I know of in Boston is I do believe the ONYX Hotel actually has a "Britney Spears Room"! So uhh bring your dolls and perfume.... :-)
Special Occasion dinners? Well, we definitely have plenty of good food to choose from. You guys kick our butts with the Indian food. A few interesting places -
Top of the Hub restaurant: elegant live Jazz on floor 52 of the Pru. Go for lunch or dessert to save a few bucks.
Steak at the Castle: Park Plaza
Union Oyster House:200 year old restaurant.
Quincy Market: Anything you want, all moderate, all good.
Mike's pastries, North End: To die for finger pastries on a sweet street.
Brown Sugar Cafe, Jersey St: Taste this Thai food and you'll never want Chinese again.
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