I am confused about "moderately expensive" including London; would you really want to fly ON in coach?

I am also not sure, given how varied your list is, how you are defining easy to navigate?

Your east coast roadtrip could include Sag Harbor, if not I would suggest SH and the Hamptons generally, after Labor Day.

San Francisco, esp if it includes driving up to Napa or S on the PCH, never disappoints.

Yeah, I don't have a budget set so I guess I can't define "moderately expensive". I am familiar with costs to fly to coach .. but didnt factor in that I have become accustomed to flying first class just to minneapolis. Good points. I really added it only because SO would love the trip.

Easy to navigate is specifically around my vision/depth perception issues.. but I kind of blow that with NYC and London also. I did ok in NYC on my last trip but I used uber vs mass transit or extended walking. Uber was super easy.

We'd both enjoy a beach but I nixed an island or eastern coastal destination due to hurricane season.

Any destinations you'd recommend adding?

If your heading to Maryland’s eastern shore, you should go to St. Michaels in the fall. Too hot and humid in summer for me.

If you would consider North Carolina, on the coast. add Bald Head Island to the list. I think its pretty easy to fly into Wilmington NC.

St Michaels would definitely be one of the eastern shore destinations... but that will be in late spring so I think the weather will be fine if not raining! I would likely take the boat from Annapolis and then stay for a day or 2.

It seems to me that being able to visit family, and go to a new destination, would tilt it to Asheville, Lake Lure, etc

For sure Asheville leads the list for me .. I also have family in the area (winstom-salem and wilmington depending on the time of year) and 2 of my employees.

I would like to add a few other destinations to the slide deck .. .to make it fun and spark a decision. In the end, I could just make the decision solo (I will do ALL the planning) but I want to make it fun.

If you want to add one to make it 5, Charleston? Savannah? Austin/SA?

Here are a few additions to make it fun:

Kentucky Bourbon Trail--fly into Louisville. KY is still very warm in September, but doable. The equestrian countryside, which you'll travel along the BT, is lovely. The history and process of bourbon making is culturally interesting, even if you don't imbibe. The small towns are quaint, and there are some excellent restaurants, particularly in Louisville and Lexington.

Big city alternatives to NY: Chicago, Toronto and Minneapolis (although I jump at the chance to visit SanF when I can). September is a beautiful time to visit these cities. Culture, history, great food, interesting neighborhoods, etc., and easily accessible. Each one has a variety of day trips to consider, too.

Following. These are wonderful destinations, may include them in the future for me😁

Can’t wait to hear which one you choose

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I could be wrong but I don't think SO will be into Charleston or Savannah.. but I think he'd love Austin/San Antonio.. Great idea!

Oh Feathers.. thank you! We've talked about the Bourbon trail.. and also the Blues Trail! We love bourbon but I lean to the Blues Trail (which will always include bourbon!)

LOL he is in Minneapolis ... I go there 2-3x a year. :) That said, other than 2 weeks in Dec/Jan I won't be going there next year. I was there for a month this past summer and we had so much fun! Maybe I plan the same this year but with a week in a resort or cottage up north... or a weekend in Chicago. I think I'll throw that in as a "joking/not joking" wild card.

Thank you for the ideas!

Wait, east coast road trip…north…come to Boston!

For the other trip, I highly recommend Asheville. So much to do, and lots of artsy stuff I think you’d like. Have they recovered from the last hurricane that hit? That would be my question.

Asheville is my vote. They are doing much better and major attractions are open but absolutely need tourists. The weather is very pleasant and there are other parts of western NC you can explore like Boone, Maggie Valley, Beech Mountain, etc.

The Pacific Coast Highway (PCH), also known as State Route 1, starts at its southern terminus near Dana Point in Orange County and runs north to its northern terminus near Leggett in Mendocino County. The PCH is a 656-mile highway that runs through or near San Francisco, though the main scenic portions that most people associate with the PCH are south of the city in places like Big Sur. San Francisco and the start of your PCH journey

• Visit California notes that San Francisco is a great starting point for a PCH road trip, which includes attractions like the Golden Gate Bridge and Fisherman's Wharf.
• If you are driving the PCH south from San Francisco, you can exit the city to follow the coastal route through locations like Muir Beach and Half Moon Bay.
• If you are driving the PCH north from Southern California, you can pass through San Francisco and make it your first stop

Asheville would probably work great for you.

I will say, we did a modified Bourbon Trail last year (not bourbon drinkers but still....) and I thought it was outstanding. I would love to go back and explore a bit more.

Instead of (or in addition to) Asheville, how about Highlands, NC? Cute, quaint little town. Easy to walk downtown area, nice little art museum, good restaurants. DH and I used to go in July or August. I’ve never stayed just a night or two there, so I can’t recommend a hotel. We would always rent a house.

Have you ever been to the Greenbrier in WV? I love it. We went in April. The food was wonderful. The Bunker Tour is not to be missed. We flew to Baltimore and took the train. I enjoyed it. The food on the train going was awful. But coming back was better because we had the Greenbrier pack lunches for us. Sooo good. (it has been a while, but I think it is a 6 hour train trip each way).

View from the front portico

Very Dorothy Draper

Sorry, but no one in the north/central part of the state calls it the PCH north of about Ventura/Santa Barbara.. If you say that, you'll immediately be known as a foreigner. Your source was obviously from a non-Californian.

It was in ital; it was Google. Regardless, we drove from SF to LA once and it was lovely, whatever it was called, of course some spots more than others. We ON'd at a few different resorts along the way, and "massaged our way down the coast" as we called it.

If you say that, you'll immediately be known as a foreigner.Umm ok LOL

Sushipup is right about the local highway terminology:). When I lived in Laguna, we called it “Coast Highway”. Now I live in the Bay Area, and it’s called Hwy 1, or just “1”. Also, if you visit, please don’t call it Frisco or Cali, lol!! If you do wind up visiting Carmel and Big Sur, DO NOT MISS Point Lobos, just south of Carmel- arguably the most beautiful spot on the California coast. Be aware that as of now, Hwy 1 is still closed south of Big Sur, but it might be open by spring.

Thanks all for the ideas. For now, I am just putting together a slide deck at this point so more a concept review than planning. Perhaps a dumb idea given that my 2026 schedule isnt clear --but I am going to give it a go.

Well, research shows that most people enjoy the planning of vacation more than the vacations themselves so expanding the possibilities and turning it into a PPT is actually a very smart way to enhance your enjoyment of travel!

Recently, I was listening to Guy Raz (How I Built This) interview the guy who started Viator. He said the same as Mtn about planning (they obvs read the same research 😁). DD got a little snippy with all of my planning for the Iceland trip. But after it was over, she told me that it could not have been as enjoyable without all of my planning. I will admit that sometimes I over-research, but I hate getting home and realizing I was 2 miles from something spectacular.

Of course I agree! Especially traveling with a family. I like to have a list of things to do each day and we can pick and choose based on schedule, weather, or mood.

Well, I don't think planning more fun than the trip-- but I do like planning. SO does NOT.

I do not plan anywhere near as much as you all. I dont have itineraries or plans for each day. I plan OPTIONS and then take it day by day. Of course I make reservations etc... but not what to do each day.

Sometimes when at SO's place we get stuck with laziness or decision fatigue. On those days we can spend as much time talking about where to go/what to do as the time we actually spend there lol. (We would drive at least a few of you batty!) To combat that and have a little fun, I started a list to throw in a grab bag of plans if we're stuck. None require much preplanning. Some are new ideas .. some are old favorites, some are a little naughty or illicit.. ;) "explore the [...] neighborhood" .. "try a restaurant that opened in the last 6 months".. "Go to Coastal (Seafood) for lobster and make Lobster Bisque and lobster rolls" .. "Go to Gai Noi .. but order something you've never had" ... "Bundle up, grab coffee and stroll around the lake" .. "Live music bar hop" ... "Litt Pinball and cocktails"..

Well, I don't think planning more fun than the trip-

I don't either, but the research says that and I can guess why. Real life has disappointments, snafus, bad weather, jetlag, disagreements, etc. Planning is nothing but possibilities and the excitement of anticipation.

I dont have itineraries or plans for each day. I plan OPTIONS and then take it day by day.

I think that is what most of us mean by planning, unless you are with a tour group and then it really is a schedule.

I agree with the grab bag idea; somewhere I saw someone advertising a set of cards like that. I used to deal that with dinner planning too.

ok-- whew! I thought you all were much more detailed in your planning. I saw your post above after I posted so I saw you too plan "options".

I bought nieces and nephews one of those date night card sets a few years ago.. they came in a wood (balsam) box and then i paired them with gift cards. It went over pretty well.

@Funkyart, I love your ”grab bag” idea!

I plan so that I know what is available. Most of my trips these days include the grands. I do not schedule more than one thing in the morning and maybe one thing in the afternoon. Sometimes it is an actual reservation, sometimes it is just a goal. I try for an easy pace with lots of wiggle room in case something interesting catches our eye. In Reykjavik, we did a lot of stopping at neighborhood playgrounds.

Just as an aside and totally irrelevant to this convo, the twins are asking for a cruise for their 2026 trip. I’m pleased because I find it such an easy way to travel with kids.

Funky, have you thought of a cruise?

We have talked about a cruise .. I was not into the idea for well always but my sister and her DH took one last winter and they loved it and have booked another. She highly recommended -- but also gave me the caution that she thought it might be a challenge for me and my vision issues. Most especially having no depth perception. Some of my big issues are open stairs and walking (or even just standing) along a path with a steep drop or change in elevation. I am ok on ferry boats so maybe a cruise ship would be ok-- but even a hallway with glass windows in a high rise will give me vertigo, disorientation and nausea. Ive thought about trying a smaller boat-- like an alaskan cruise-- but it will make for a terrible trip if it is a problem.

Also, SO isnt sold on a cruise but did also show mild interest in an alaskan cruise.

How about Bora Bora. Just relax, get away from it all.

Looks wonderful.. but not a trip for 5-8 days in a busy year. That is a retirement trip.

A friend quit her job a few years ago and went to Bora Bora for what I think was 3 months? It was life changing for her as she needed to reevaluate where she was and what she wanted. I dont think I could do it but I admired her for it. That is the stuff of novels!

This might be a good ”test” cruise for you. It is on Virgin Voyages. If you totally hated it and it made you sick, you could probably fly home from Bermuda.

Virgin is adults only. I hear it is good value for your dollar because nearly everything is included. I also hear it is kind of raucous. The only cruise line that I know of that has a tattoo parlor on board. Do your research.

This is on Celebrity Silhouette. Celebrity is considered a premium cruise line but not a luxury line.

Celebrity Silhouette is the ship that we were on in Iceland. You can take the elevators instead of the stairs. There are some areas with large windows but I think you can avoid them.

Thanks Bbstx .. i appreciate the research and info. I was actually looking at bermuda earlier today but not a cruise. I think my biggest issue will be on deck-- with the change of elevation to the ocean and nothing on the horizon but I am open to try.

IDK, I'm always the planner in my family and I think it's stressful! It is exciting to think about it, but there are just so many choices and options and research to be done it gets kind of overwhelming to me. I'm planning a winter trip right now to an area I know nothing about and stressed already. Maybe because I always start late and it's that much harder to finalize plans that are still available:)

I'm happy to see the Greenbrier on here and that you had such a great visit @bbstx. It's in my neck of the woods so I've been many times - starting over 30 years ago for my engagement - but last time we visited several things went wrong and it made me sad. I have so many great memories there so I'm happy to see you enjoyed it. I do especially love it in the summer and fall and I love to stay in the cottages.

@legomom23, I appreciate what you are saying about planning. The Iceland trip took me a year to plan. We were planning a trip to Scotland in 2026, which has been overtaken by events and pushed out to 2027. Nevertheless, it seemed more overwhelming than any other trip I’ve planned. I’m not sure why. I’m happy that I’ve got a little breathing room now.

Just chiming in to say if you and SO decide on the Asheville area, I second bbstx's recommendation for a side trip to Highlands, NC. Super easy and lots to do for a short stay - wine tasting, easy hikes at nearby falls, cooking classes, shopping, fine dining, spas, etc. And my very favorite - the guy who makes the Stick Candles is based in Highlands!

I love those stick candles!

I have friends who went to the Highlands this fall and their pictures were absolutely stunning!

I am not sure if I mentioned ( search yields no results but I'll apologize if this is a repeat) that late August, DH and I did a little road trip within Pa. As you know, the state is so big and really does have interesting spots.

Milford Pa- gorgeous small town which has Grey Towers, National Historic Site which has beautiful land but also a mansion designed by Richard Morris Hunt who also designed the Biltmore and several other important structures. There is also Hotel Fauchere which was founded by a chef from Delmonico's. It's just a really neat town.

Scranton - I know eye roll, but we did the Anthracite Heritage Museum (ride in miner's car and go in the mines)

Eagles Mere. Stunning stunning small town.

Wellsboro- the "Pa Grand Canyon" and also adorable town.

Those are just some highlights, but we really enjoyed ...

I was just in Asheville this past weekend visiting the grandboy. It was much perkier than our previous visits this year and the downtown area is basically recovered from the hurricane. We didn't go by the river this time so I can't report on the river arts district.
Asheville is very walkable in the sense that there is a lot to see in a condensed area. But it is hilly, there are lots of curb cuts, the sidewalks are often buckled from trees and they can get crowded. I think I mentioned this to you before, I can't remember if those conditions would pose problems for you.

I've been watching "This Old House; Rebuilding NC". They're still doing clean up by the river....in the arts district. Hauling out tree branches, cars that were flooded. It looks OK...some of it's rebuilt. Don't know as I'd make it a vacay destination...yet. Link

Thankfully there is still plenty to do in Asheville besides visiting the River Arts District. And some places in the river area are open so putting it on your to do list won't be a total bust.

I don't want people to think that Asheville is not worth a visit because it absolutely is. And the area needs the tourist dollars.

https://www.riverartsdistrict.com/

We sre in Asheville at least yearly as its just over the mountains from us. it has greatly recovered. There is still work being done in the river district, but there is do my h more to see/do. Many, many good places to eat. You could easiky do day trips into yhe Smokies, or other cities in the atea too. (Tina Marie)

What about New Orleans? Definitely easy to fly into. We spent 5 days there in the spring. I'm sure fall would be good too. We had a great time and I was just recently thinking I would like to go back. I thought 5 days was the perfect length. Beignets for breakfast and absolutely delicious dinners every day.

I will add that we walked a lot. Like really a lot. So not sure that would work for you? I assume Uber or Lyft would be an option (we took Lyft to/from airport).

I've been wanting to plan a California trip. Some time in Napa, some time in San Fran (nephew lives there and I've never been) and some time in other places south of there. So if that is in your plans, would love to hear what you do/where you stay, etc.