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Boston, Portland, Charleston, or San Francisco?

I would like to plan a short vacation for September of this year. We are expecting our first child in April so we most likely will not be taking a long trip until the following year when she is slightly older. I would like to do a long weekend (4-5 days depending on how much time off DH can get) over one of the last two weekends of September.

Where would you go and why? I chose the US destinations because my husband accumulates lots of points through Southwest and has a companion pass so I can fly free this year anywhere he goes. Those are some of the top places I saw on their website I would be interested in visiting.

If we did either Boston or Portland (Oregon), would it be possible to do some day trips from around there or rent a car and drive the coastlines? I have always wanted to do a fall scenery tour on the east coast to see the beautiful foliage and pumpkin patches, etc but is that too early in the year?

 We both like good food, light hiking, exploring new places, breweries/wineries, beaches, etc. I am a major history buff so if there were interesting places to visit (museums, etc) I would be up for that too. TIA!

Re: Boston, Portland, Charleston, or San Francisco?

  • I think all four of your options are good choices. I have been to three (Boston, Portland, and San Francisco). Of those, all offer lots of options for day trips.

    In Boston you could drive to Plymouth, Salem, Lexington, Cape Cod etc. Late September would probably be too early to see the fall foliage in Boston but the weather would be very nice. I am not aware of any wineries in that area but there are lots of museums and historical sights to check out. I visited Boston a few years ago and have an entry in my old travel blog here.

    In Portland, you could day trip to the Oregon Coast (Cannon Beach is beautiful), Willamette Wine Valley, Multnomah Falls, or the Hood River Valley. My fiance and I traveled to Portland last year and I have two entries in my travel blog on sightseeing and dining. I also visited the Oregon Coast a few years back in 2007 with my ex-husband and have an entry in my old blog here.

    If you stayed in San Francisco, you could day trip out to Napa Valley or Sonoma County, but I would recommend actually spending the night in this area. Other options for day trips are Point Reyes National Seashore and Muir Woods National Monument. I also have entries in my old travel blog on a trip to San Francisco and Napa Valley/Sonoma County.

  • I also would agree that between Boston, Portland and San Francisco, you can find all your requirements for a city.  Having never been to Charleston, I can't attest to it.

    Have fun!

  • if i could only pick one id definitely go with san fran

    i love boston and portland but san fran better

  • image magsugar13:

    if i could only pick one id definitely go with san fran

    i love boston and portland but san fran better

    Ditto - I have been to Boston and San Francisco, and San Francisco would win hands favorite city in the US! 

    <a href="" target="_blank">Not Your Momma's Cookie: Cookie Decorating and More</a>
  • Thank you all for the input. I am going to check out your blog posts, too, travelingjen!
  • I've never been to Portland (drove near it on a road trip, if that counts?) But have been to Charleston & San Fran, and I live in Boston. I would vote for San Fran or Boston, they both have that old town charm. If you came the very last weekend of September, you might catch some apple picking and foliage, but you may have to travel an hour or two north for some traditional new england foliage. The weather has been so unusual lately here so it's hard to say for sure. You definitely catch some shoreline (If you do Portland, I don't think you can, but not sure). Boston is actually right on the water, and you can take a 2 hr ferry to provicetown too if you wanted, or rent a car and go up to the North Shore or down the south shore and/or Cape. There's also some wineries in Newport, RI/Southeastern, Mass if you like. The weather is usually perfect in September too :)

    I really like San Fran too and there's also the much nicer and famous wineries an hour or so north. There's so much to see and do, and I would say the weather would be comparable to Boston. I would vote for San Fran or Boston, I'm a little bias towards Boston obviously but I love San Fran- it's so quirky and fun! Can't go wrong.

  • I've lived in Boston and San Francisco.  Both are great cities.  Boston has pretty much everything you've outlined.  It beats SF on history and arguably breweries, but SF wins on wineries (you could drive up to Napa/Sonoma or just across the bay to Livermore). 

    San Francisco is not a beach town any time of the year.  I mean, you can go look at the beach, but it's pretty much never warm enough to "hang out" on the beach and no one really swims there.  It's not SoCal.  It will be too cold to do beaches in Boston in September.

    September is also too early for leaf peeping in Boston.  You'd have to go further north like Maine or New Hampshire as the colors move north to south.  October is the month for colors in Boston.

    You can certainly do day trips from either city.

    I'd rather be rock climbing or playing volleyball
    image image
  • September is a wonderful time to visit Portland, and i think it would be significantly cheaper than Boston or San Fran for hotels, rental cars, wine tasting, etc.  Portland is a 90 minute drive to the beach, and 60 minute drive to great wine tasting.
    Lilypie First Birthday tickers
  • I've been to all 4 and think they are all good choices.  I think I would choose either Boston or San Francisco before Charleston and Portland.  But again, I think all 4 are good choices.
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