There's always Florida in the winter months. :) I think Boston to Orlando is a 2-3 hour flight. It's often beach weather in the winter (though the water is cold), and there are lots of things to do even if you aren't theme-park people.

Donna

Bermuda. In the winter it's not very tropical :) But still warm in October...

Dallas is beautiful in mid-October, just in time for the State Fair. And San Antonio: Riverwalk, old Spanish missions, Alamo. And Switzerland anytime!

Hurricane season in Oct makes Bermuda a little iffy.

I would start by looking at a fave hotel brand or resort brand and see if that sparks ideas. I know some people say a hotel "in only a place to sleep" but on the contrary I have gone places in part because I liked a particular hotel.

Look at Backroads -- I was always tempted by their Santa Barbara biking trip.

The Biltmore? Austin? Tulum?

Oh! Bermuda! How could I forget. But I think we may be going there next spring. We have been several times.

Good idea about searching hotels.

ETA I have been to Orlando the past 2 years for gymnastics meets...I will need a break from Orlando! But I know there are other areas of FL yet to be discovered. We have been to Amelia Island, Sanibel/Capitiva, Miami, and Orlando but that's it. I have been to Key West w/ girlfriends. Actually, if my DD does gymnastics as planned in college, most of our winter weekends will be spent traveling to her meets. Hopefully in some fun places to see!

I'd lean strongly towards what's already at the top of your list. Santa Fe and the surrounding area should be gorgeous late September / early October. We did the drive up to Taos in early October and had just missed the peak of the aspens turning gold, but it was nevertheless quite a gorgeous drive.

I agree on Asheville or else Boone/Blowing Rock, NC in fall or spring. They do get more snow in the mountains. You can fly into Asheville in a regional airport or else fly into Charlotte and drive 2 hours, but fairly easy drive in good weather. You probably need to avoid Appalachain State football weekends, though.

Assateague Isand...

San Francisco, Monterey Bay & Carmel - China Town in San Francisco then a drive along the coast to Monterey Bay where you can enjoy the aquarium and then kayak in the bay with sea otters. Shopping in Carmel...and 17 Mile Drive! Perfection.

Boston- Back Bay and all the historical sights then a drive for the day and a ferry ride to Martha’s Vinyard. Topped off by driving to NYC the MET, Central Park, Broadway Show! Wonderful.

Seattle for a few days then a cruise to Alaska!

Drive the whole coast of California.

I love a week in NOLA...not for everyone though it’s dirty, smelly...and wonderful on Frenchman Street, Magazine Street, The City Park, and The Garden District.

Also look into Denver. Though they can still get snow well into May!

September is perfect for CA wine country, the harvesting of the grapes. We are going next month, so I am biased! Are you and DH wine drinkers? Agree with sabbath 7 on seeing all of the above in CA. Although we have been several times, it never gets old.

I'd skip FL in the winter and head to the Caribbean. Some place like St. Kitts or Cozumel, either by air or by cruise line. There is no guarantee of warm weather in FL in the winter, which is why, after being disappointed a few times we fly either to Miami or San Juan and cruise as deep into the Caribbean as we can get.

DH and I had a similar plan when the girls were in college. We went away as much as we could. Sometimes I'd wake him up on a weekend with reservations in hand. Some of those were weekend trips to: Nantucket, Maine, Newport (a tank away.) Others were 4-5 days (we were both still working): We did Paris a few times, FL, New Orleans (family there).

I think you will find that even an empty house feels like being on vacation, because you are free to come and go as you wish, without worrying about someone's curfew. We just spent two nights in Boston (part of a friend's 65th birthday bash) and we had such a great time, we both said we must do this more often. We live in a great metro area, aren't we lucky?!

Enjoy the planning. Having something to look forward to is essential to cruising into the empty next-retirement phase of life. Of course, you have your lovely new home to keep you busy, or to just relax in.

For September and a longer trip, I'd consider Montreal and Quebec; or totally different, Utah, i.e. Arches, Zion, fly into Las Vegas and explore the national parks nearby. https://www.zionnationalpark.com/about/southern-utah/other-areas/

It's not as sexy as some of the other locations suggested-- but the Laurel Highlands in western PA is beautiful in the fall and you can see FLW's Falling Water -- and there are so many great places to hike and ride bikes and it's a photographer's dream! I've only stayed at Nemacolin resort which is very nice. I believe Seven Springs has more outdoor activities and is more relaxed and "fun".. but it doesn't have the same level of luxury as Nemacolin. Not really bucket list material unless you haven't seen Falling Water... but a good 4 day weekend from Boston.

ETA I loved NM and it would be top of my list-- great for adventure, romance, photography, hiking, shopping and eating!

Some ideas for shorter, closer trips:

One of my favorite places to visit is the PA/DE area around the brandywine river...longwood gardens, hagley museum, brandywine river museum, De Nemours mansion, Winterthur and great restaurants in the area... and not far from valley forge if you're into history.

If you haven't done a trip to tour DC, it's wonderful with so many museums, the zoo, historical sights, monuments, etc. The best part is you can fly in to Reagan and just use the metro to get around...no rental car needed.

Heading up to NH to see Mt Washington, Lake Winnipesauki, Franconia Notch and other wonderful sights to see.

Lots to see and do along the Hudson river from bear mountain and westpoint to all the mansions including FDR's place, Vanderbilt's, love Olana, Boscobel, Lyndhurst Castle and if you like antiquing, Cold Spring is a great place for it, plus incredible views of the river.

Years ago, DH and I took a short trip to Dearborn MI to see the Greenfield Village which is a most incredible museum.

And, of course, Acadia is quite spectacular...so many different environments packed into such a small area, from bald mountains to alpine forests to rocky coasts...quite something.

We enjoyed going to VA to see Williamsburg and there was this incredible pottery place nearby back then....we were there so long ago. I think we stopped at Robert E Lee's house on one of the necks along the VA coast as I recall...where we had to use a rope to climb up the steep trail on our hike on his property. The house was lovely.

We also did a long weekend in Charleston which was nice.

I've not been (other than work) but people rave about what a fun place Nashville is to visit so perhaps we'll get there eventually.

San Francisco, Monterey Bay & Carmel - China Town in San Francisco then a drive along the coast to Monterey Bay where you can enjoy the aquarium and then kayak in the bay with sea otters. Shopping in Carmel...and 17 Mile Drive! Perfection.

-- We did exactly this probably 8 years ago. I would love to go back. But for the extended fall trip, I'd love to go somewhere we haven't been.

DC! yes! So funny because it's such a quick flight, but I have only been once, and DH and I haven't been together. So definitely on the weekend-away list.

National parks...yes. We have been to Yosemite, Yellowstone, Grand Canyon, Bryce, Zion... with DS now living in Tucson, we can combine a visit with him with a visit to some parks too.

There is a chance DD will go to college in PA, so we could have 4 years' worth of excuses to explore that area.

Annie, I went to Nashville with friends -- so fun, especially if you like music.

Definitely do DC. In addition to museums and cool restaurants, we actually have some very impressive parks and trails for hiking or biking. Very close to the city is the Great Falls Park.

Do you like to walk in nature? The Finger Lakes District of NY is beautiful, Ithaca! And an assortment of cruises on the lake, including wine tastings from the local vineyards.

I forgot how wonderful DC is!! The Smithsonian alone....

This is a great thread, really. :)

Bp, my son just graduated from Syracuse so we’ve explored a lot of that area! I love Skaneateles.

The first weekend in April look at going to Seattle then driving up I-5 to the Skagit Valley for the Tulip Festival. DH and I happened upon it once and I’ve never forgotten it!

Are Cape Breton and Prince Edward Island (Malpeque oysters!) close enough to Boston for a long weekend trip?

When going to DC, try to avoid weekends that coincide with school holidays. We took DH’s grands one year for Spring Break and it was a zoo!

Do an Elvis tour of Memphis. I had an acquaintance from Scotland who spent 4 days in Memphis seeing all things Elvis, including a tour of his early childhood home in Tupelo. She said it was fantastic, but she is a serious Elvis fan, so she may be a tad biased.

That's a trip I'd like to do this fall--to drive across NY state on old routes 5 and 20 through the finger lakes district. If your library can get a copy, there's an old book called Slim Fingers Beckon by Arch Merrill, a writer for the Rochester Democrat who was a sort of proto-Charles Kuralt for western NY back in the 40s and 50s when all that area was thriving with little local industries. It makes an interesting contrast to how it's changed since, and includes a lot of local history, too.

Although last September is possible past the peak leaf viewing time, I'm fond of the trip through Vermont, New Hampshire and into Quebec (if Canada isn't too international for your) to Montreal and Quebec City (and Maine as well).

If you have not done the PNW, then hitting Seattle and the parks is still do-able in late September. They tend to have the weather hold through September, and there are leaf-peeping opportunities in the northern Cascades as well, and hopping the border to Victoria and Vancouver is also easy.

Weekend wise, after you sort out your DD's meet schedule, you could begin to hit places like San Diego, Palm Springs in the winter, New Orleans... or easterly, how about Savannah and Key West?

New York State is so beautiful....But I'm biased having lived there.

If you're going to Quebec City, consider a side trip for whale watching in Tadoussac. Late September is an active time of the year for whales.

Just left the Cliff House where we had couples massages. It is just lovely, you should come back for a weekend, esp in the fall when they have bargains.

Also, I know you haven't tried Air BnB but they have such cool and interesting places to stay --- might inspire you.

Jackson, Wyoming? It's just right for a few days' stay. In the shadow of the stunning Grand Tetons, you can hike, ride horses, go rafting down a calm stretch of the Snake River, dine in the lodge overlooking Jenny Lake (two lakes, not sure which one), or just bask on the balcony of your resort or Air Bnb, and appreciate those incomparable views. We drove off into the prairie down a gravel road and parked at a distance, so that I could just look at the Tetons and think about Shane.

Jackson is a cute Western town, but maybe don't go in high summer; it will be crammed with tourists. And Yellowstone is just up the road through a mountain pass.

Jackson was the first destination that came to my mind, too. We go every couple of years in early fall and it's lovely.

We’ve just returned from a trip to Nashville. We were there two years ago for a medical seminar, but spent the majority of time inside the incredible, gorgeous Gaylord Opryland Resort. This time, we rented a house through AirBnB in the Edgehill neighborhood of Nashville. Although we love Country music and very much enjoyed our tour of the Grand Ole Opry, had great meals out, and saw the beautiful surrounding towns of Franklin, etc., overall it was just so congested everywhere! The roads, the entire downtown area, seemed so crowded, just as it was when we were there last. The majority of the homes in the. Nashville area seem to be without garages, which may be fine for the area but as a result, every street ( in both business and residential areas) was lined on both sides with bumper to bumper parked cars. Thank goodness DH can parallel park or we would have been in serious trouble (LOL)! We did end up driving 3 hours to Knoxville one day, which is a lovely city. If we’d had more time we would have loved to have spent some time in Asheville. In retrospect, I’m glad we went, but any future trips to Nashville will be to the Gaylord, with hired drivers dropping us off to see anything.

How about Park City, Utah? The mountains are gorgeous in autumn, the downtown is vibrant and there are plenty of outdoor activities, from mountain biking to horse back riding and hiking. Might be too far for a long weekend, though.

Thanks for all these great ideas. We have decided to go to Santa Fe next fall. It’s been on my list for sooo long. I’m excited.

We have been to Seattle and Vancouver and Jackson...loved them all. We’d love to go back to Jackson at some point, as it’s been about 5 years or so since we’ve been there. Lots of great ideas above for the long weekend trips, too.

Mtn, we have stayed at AirBnB a couple of times — in upstate NY (family trip) and in Austin (girlfriends trip). Both were good experiences.

Lynn, I went to Nashville last March and didn’t have the same experience, so maybe if you go back, try a less busy time of year?

Lynn, wonder if you got caught in “move-in” traffic. Nashville has several universities near the Edgehill area and kids are already starting to move in. 21st Ave as it runs past Vanderbilt is always a high traffic zoo!

I'm not sure this would work for a 4-day week end, but you might consider the west coast of Canada - Jasper, Banff, Lake Louise, Waterton, Victoria, Whistler, Tofino, etc. The drive from Edmonton - Jasper - Lake Louise - Banff - Calgary (in part via the Icefields Parkway) is truly spectacular.