San Francisco, Chicago, New York or Boston

Squall Leonhart · 13-05-2019 6:52am #1

Looking to arrange a holiday for my parents for first quarter of next year as a surprise.

They have been to New York before and loved it, it's been their only travel destination so far to the US.

Direct flights are key. I was thinking SF, but after a bit of a google I couldn't be sure where to book them into there that was vibrant, full of things to do, restaurants and bars etc. It looked like lots of suburbs rather than a city centre so was nervous of landing them somewhere a bit inconvenient.

NY seems the safest option, but definitely open to other cities if people can suggest good areas to stay etc.

Caranica · 13-05-2019 7:41am

I've been to all four. Love Chicago and New York, hated Boston and my overwhelming memory of San Francisco was that there were beggars everywhere.

Given that they've been to NY I would say Chicago to see somewhere new. I know there's so much you can do and see in NY but also Chicago. I've been to both many times.

How about Washington DC?

[Deleted User] · 13-05-2019 8:28am

San Francisco is a very long flight. Also, it is full of homeless & people with mental health issues.
I'd stick with Chicago or Boston for a new place

Mitzy · 13-05-2019 8:37am

What about Washington? I was there last year & absolutely loved it. It's a beautiful city and there is so much to do & see there. Plus there are direct flights.

I agree with what the others have said about San Francisco. There is a lot of issues with homeless with mental health issues & makes walking around the city feel very unsafe due to open drug taking etc plus its a VERY expensive city.

ncmc · 13-05-2019 8:48am

What a lovely surprise for them!

I haven’t been to Chicago so can’t comment on there, but have heard great things about it. But I have been to Boston, NYC and SF. I would probably rule out SF, based on the previous reasons given. I absolutely loved Boston, it’s a lot smaller and more manageable than NY and has an almost European feel. There is great history in it too with the freedom trail and the war of independence, so if they are history fans, that could be a bonus.

The one thing I will say, you mention the first quarter, Jan - March can be mind bogglingly cold on the east coast. You’re talking snow drifts that keep people indoors for days on end. Even if it’s not as bad as all that, it may very well be too cold for elderly people to comfortably sight see. I know a lot of people who have gone to NYC in those months because it is a lot cheaper (that’s why it’s cheaper!) and their holiday was really hampered by the cold.

I would say you can go wrong with Chicago NY, or Boston. But maybe try and delay it a month or two until April/May.

salmocab · 13-05-2019 8:55am

I’ve been to all 4,all great. I’d go with Chicago, it’s a great city with lots going on. Boston is lovely too but if it was a straight choice I’d plump for Chicago.

lawred2 · 13-05-2019 8:55am

Squall Leonhart wrote: »

Looking to arrange a holiday for my parents for first quarter of next year as a surprise.

They have been to New York before and loved it, it's been their only travel destination so far to the US.

Direct flights are key. I was thinking SF, but after a bit of a google I couldn't be sure where to book them into there that was vibrant, full of things to do, restaurants and bars etc. It looked like lots of suburbs rather than a city centre so was nervous of landing them somewhere a bit inconvenient.

NY seems the safest option, but definitely open to other cities if people can suggest good areas to stay etc.

Of the four - I've not been to Chicago.

Boston I lived and worked in and to be honest it's a fantastic living city and as a base in New England - not sure whether I would put it on a list for a city break however.

I was underwhelmed by SF and I felt the gap between rich and poor was even more visibly pronounced than NY. But we still had a great time there.

NY will always be my favourite of those three to visit.

Can't comment on Chicago but I've heard good things.

Squall Leonhart · 13-05-2019 9:15am

Based on all replies above, San Francisco is out!
I've been to Chicago myself and thought it was great, got to a live blues bar and it was really enjoyable.

I also got to Nashville and I think that they would absolutely love it, but too much travel I think. Anything involving transfers is something I know they'd shy away from, it'd be stressful and they wouldn't be confident with it. They're not elderly, one will be 60 by then, the other still late 50s.

Washington is somewhere to look into.
I hear ye about pushing it out a bit, something to keep in mind. Could potentially swing it to before Christmas either, Nov/Dec, but probably no better!

helimachoptor · 13-05-2019 9:20am

I've been to SF, NY and Boston.

Boston was very nice I'm going back in September for a week - but for work) and really looking forward to it.

Its obviously smaller but there's still a lot to do, huge amount of history to how the US came into being.

mx5ire · 13-05-2019 10:12am

As per previous poster, i have been to all 4 many times. We brought my parents in law to both NYC and Chicago a few years back, they liked NYC but loved Chicago. NYC was just too manic for them, Chicago more relaxed and in the summer it is just beautiful. Wouldn't do it in the deep Winter though. The shopping is great in both, but i suspect that they are not going for the shopping, and to be honest, i think that the US in general has become very expensive in the last 5 years. I am there regularly, and i just don't buy things there anymore.

You talk about 1st quarter, but when in Q1 would be important. All bar SF will be almost certainly really really cold in Jan, Feb, but March should be ok. I have walked around NYC and Boston in March in short sleeves, but it can be a little cooler in the evenings. NYC is a super place, and an absolute favourite of mine, but as they have been there before, maybe look at the others for a change. But NYC is a safe option, so much to do and see.

Not sure if flying time will be an issue, but obviously NYC and Boston are shorter, SF will be at least 3 more hours each way. Chicago maybe an extra hour and a half.

Chicago has a great waterfront, its lovely and clean to stroll around, take a boat trip up and down the river and out into the bay, museums, go up a couple of towers, take a trolley bus tour on the first day, and the jazz/blues bars in the evening are great. Restaurants to meet every need and taste. Just really relaxing, simply a great city. Stay around Michigan avenue, hotels will be a bit dearer, but very central and avoids cab fares.

As a Boston regular i really like it there, but again, its a summer city, very cold in winter. A stroll around the Common, browse boutiques on Newbury street, trolley tour etc. Lots of outdoor terrace restaurants to eat at, stroll around MIT campus, just a nice vibe to the place. As a smaller city, a little less to see and do than NYC though.

That leaves SF. We are split on it in our house, i really like it, my wife doesn't. She thinks that they all try too hard to be cool and alternative there, which i sort of agree with. We have family there, so have had some local knowledge to bring us around, which always helps, but you can manage fine without it. If walking up and down hills is an issue, skip it. Otherwise there is much to see and do. Downtown can be a little 'lived in', but worth strolling around, and i have seen plenty of beggars in my times there. But doing the usual tourist things, Alcatraz (must book in advance), walk/cycle over the golden gate and down into Sausalito, go out to Muir Woods and the see the massive redwood trees, thats well worth it. Go out to Tiburon on the ferry across the bay for lunch in the marina area, sit by the sea and enjoy the views of downtown. Take a cable car (trolley bus type) down to the seafront and walk along Crissy Field. Go around the old hippy areas in Haight Ashbury and see the famous painted ladie house, that you have seen from many movies etc. Go out to the cliff house hotel and stroll along Ocean beach. As a first timer, i think staying in Union Square or Nob hill would be best, shops, restaurants easy to get to, and then move around the the locations & sights above. Fishermans wharf is very touristy, which is fine, but i would prefer to stay downtown.

I think i have just talked myself into going back to SF......Hope that helps.

First Up · 13-05-2019 10:17am

Chicago for me too. Great from every angle. I like Boston too but Chicago has a special vibe. SF is sad these days - beggars and junkies.

mx5ire · 13-05-2019 10:21am

Oh man, lot of anti SF posts here - but honestly - i would not rule it out at all. I have never felt unsafe there, but common sense applies as per any big city. I would not hesitate to send my parents there, or go there with my own 12 year old daughter, no problem. As i said above, the flight is a bit longer at circa 10 hours, but don't let that put you off. Read a book, watch some moves, the time flies.

Someone else mentioned Washington, and i completely agree. Great city to visit. Downtown is brilliant and compact. You do a lot of walking, (we did cycling tours which were so easy as its flat), but you can see so much, and its free into all Govt/Federal museums etc. All of the Smithsonian is free,and wandering around the mall, up to see Lincoln, and then back to the White house. Its great. Even the Zoo is well worth a visit. But cold weather warning applies there too. And on the unsafe topic, outside the main city centre, its really nasty in places. Out around Georgetown is really nice to stroll around, downtown can be a bit dead at night. Flight will be same as NYC and Boston.

Squall Leonhart · 13-05-2019 10:27am

Detailed post, thank you. That type of information about where to stay is gold.

I'm leaning towards Chicago, but not decided yet. I'll need some months of pulling together funds, so there's plenty of time to think.

mx5ire · 13-05-2019 10:39am

Squall Leonhart wrote: »

Detailed post, thank you. That type of information about where to stay is gold.

I'm leaning towards Chicago, but not decided yet. I'll need some months of pulling together funds, so there's plenty of time to think.

If the posts about beggars etc put you off, and the longer flight time, and you can push it out to April/May, then i would pick Chicago first. Really great city to go to, but not in the cold, either side of Christmas. Stay somewhere central near Michigan Ave, lots of good affordable choices. I put my folks in the Swissotel, which was a teeny bit dearer than a Courtyard or similar, but all very central. Get a trolly bus (hop on /off) tour from nearby Michigan Ave bridge.

As i said above, Washington is also a great option, and its free museums etc make it a quite a bit cheaper than somewhere like NYC.

First Up · 13-05-2019 1:37pm

mx5ire wrote:

Someone else mentioned Washington, and i completely agree. Great city to visit. Downtown is brilliant and compact. You do a lot of walking, (we did cycling tours which were so easy as its flat), but you can see so much, and its free into all Govt/Federal museums etc. All of the Smithsonian is free,and wandering around the mall, up to see Lincoln, and then back to the White house. Its great. Even the Zoo is well worth a visit. But cold weather warning applies there too. And on the unsafe topic, outside the main city centre, its really nasty in places. Out around Georgetown is really nice to stroll around, downtown can be a bit dead at night. Flight will be same as NYC and Boston.

I'd echo the advice on DC. The main bits are fine but it can be alarming to turn a corner and find yourself immediately in an unsavoury neighbourhood.

Make sure you know where you are, and where you are going.

First Up · 13-05-2019 1:40pm

mx5ire wrote:

If the posts about beggars etc put you off, and the longer flight time, and you can push it out to April/May, then i would pick Chicago first. Really great city to go to, but not in the cold, either side of Christmas. Stay somewhere central near Michigan Ave, lots of good affordable choices. I put my folks in the Swissotel, which was a teeny bit dearer than a Courtyard or similar, but all very central. Get a trolly bus (hop on /off) tour from nearby Michigan Ave bridge.

Yes avoid Chicago in winter. In the wind off the lake its the coldest I've ever felt and that includes Moscow in January.

deisemum · 14-05-2019 12:00am

I was in Philadelphia and Chicago over the Easter Holidays. We stayed 4 nights in Philadelphia in the Doubletree by Hilton on Broad Street and 5 nights in Chicago 4 of which were in Hotel Chicago Downtown Autograph Collection and the last night in the Crowne Plaza out near O'Hare Airport across the road from the outlets.

In hindsight we'd have been better spending more time in Philadelphia and less in Chicago. We've been to Boston, Washington and New York in the past but Philadelphia is our favourite of those cities. There's so much to do and see in Philly, it's the greenest city in the US with tree lined streets and parks of all sizes all over the place.

In Chicago I'd recommend the architectural boat tour, the views from the Willis Tower formerly Sears Tower are great. Our hotel was in a great location, the House of Blues, Dick's Last Resort and a couple of other restaurants are on the hotel's forecourt.

We liked Washington and were there before 9/11 so not problem just queuing up and doing the White House and FBI tours which were very good.

We weren't gone on New York, think it's over-rated.

We were visiting family in Boston so we were able to be brought off outside the city which added to that trip.

While in Chicago we read a report on San Francisco and it's big problem with the homeless, it's now earned the name Brown Town because of the five-fold increase in the amount of human ****e on the footpaths from the beggars and the cost of cleaning it and the health risks because of it.

The weekend before and the weekend after Easter had snow and was bitterly cold on our first day in Chicago.

First Up · 14-05-2019 7:34am

deisemum wrote:

In Chicago I'd recommend the architectural boat tour, the views from the Willis Tower formerly Sears Tower are great. Our hotel was in a great location, the House of Blues, Dick's Last Resort and a couple of other restaurants are on the hotel's forecourt.

If you want to hear the blues in Chicago the place to go is Kingston Mines.

Nigel Fairservice · 14-05-2019 4:43pm

I've been to all 4 but seeing as they already have been to NYC (my favourite of them) I'd probably go with Chicago. Architecture tour along the river is fantastic as is the gangster tour.

Boston is very nice and a lovely city for strolling around. It's historical in terms of modern America. Much of New England is within easy reach of Boston so there's also good day trip potential from there.

I was initially taken aback with the homelessness in San Francisco but, and this sounds awful, you just tune it out after a while. I didn't encounter any aggression. I wouldn't let it overly influence a no decision.

Marcusm · 17-05-2019 6:45pm

Squall Leonhart wrote: »

Looking to arrange a holiday for my parents for first quarter of next year as a surprise.

They have been to New York before and loved it, it's been their only travel destination so far to the US.

Direct flights are key. I was thinking SF, but after a bit of a google I couldn't be sure where to book them into there that was vibrant, full of things to do, restaurants and bars etc. It looked like lots of suburbs rather than a city centre so was nervous of landing them somewhere a bit inconvenient.

NY seems the safest option, but definitely open to other cities if people can suggest good areas to stay etc.

First quarter can be hit/miss for NYC, Boston, Chicago and DC weatgerwise. Might be lovely, might be snowed in. If you can put it back to April you’ll likely avoid it all. What are they interested in? Boston has some decent historical aspects, as does DC but DC is a bit vanilla. Have you considered Philadelphia, the city of brotherly love but also the cradle of democracy. Stay in center city and walk the city. Independence Hall, constitutional centre, lots of little parks to rest as you walk. Huge immigration to PHL from Ireland. Lots of old streets, cobblestones etc. Great for food and live music in pubs, bars etc. A short trip to DC if they want to see those sights also.

Jimbob1977 · 17-05-2019 6:58pm

Never been to Boston or New York.

Lots to do in Chicago...

Willis (Sears) Tower
John Hancock Building
Art Institute of Chicago
Field Museum
Shedd Aquarium
Adler Planetarium

Grant Park
Buckingham Fountain
Lincoln Park
Navy Pier

Boat tours of the Chicago River and Lake Michigan are superb
Two baseball teams
The Bulls
The Bears
The Blackhawks

Michigan Avenue for shopping

Dangers: watch yourself on the West Side and South Side. High crime areas. Most tourists have zero reason to visit there.

San Francisco's setting is glorious. The steep streets. The Golden Gate Bridge over to Sausalito. Alcatraz out in the bay. Coit Tower, the street cars and Fisherman's Wharf. The various districts like Haight Ashbury, Castro and Nob Hill.

The real shame is the people from the 1960s and 1970s who never emerged from that decade. Now wandering the Tenderloin area and a few blocks from the tourist areas.

nice_guy80 · 17-05-2019 8:15pm

Seattle? anyone?
go out to Olympic national park for a day or two
mount rainier NP
San Juan islands for a day or two

lobbylad · 18-05-2019 12:08pm

Having been to all (except Chicago), I certainly wouldn't rule out SF because of the homeless/beggars. I've never experienced any hassle or aggression from them.

It;s a beautiful city, and in addition to the sites mentioned earlier (Golden Gate Bridge, Alcatraz, Coit tower, steep streets, Sausalito etc), there's good places worth visiting on short day trips such as Napa Valley, coastal route down towards Carmel, Golden Gate national park).

If they're happy driving, then getting around SF and the whole area is relatively easy. Driving across the Golden gate and parking up, then walking the bridge is an experience! The Oakland bridge is good for views of the city skyline too.

I've stayed in hotels around Pacific Heights, and Mission/SOMA and no problems, also over across the Oakland bridge in Jack London Square area (Oakland itself isn't worth spending time in). Never had any problems.

If your parents are fit enough, then hiring a bike and going across the Golden Gate bridge, then back on the ferry from Sausalito (or Tiburon but this is a much longer cycle) is worth doing. The route is mostly cycle lanes.

Squall Leonhart · 18-05-2019 10:14pm

nice_guy80 wrote: »

Seattle? anyone?
go out to Olympic national park for a day or two
mount rainier NP
San Juan islands for a day or two

Seattle is out, simply because its not one flight from Ireland

Nigel Fairservice · 18-05-2019 10:18pm

Squall Leonhart wrote: »

Seattle is out, simply because its not one flight from Ireland

I think Aer Lingus are going direct from Dublin now to Seattle. Great spot too! Vancouver is nearby as well.

Arciphel · 18-05-2019 10:23pm

Was going to suggest Seattle as well...

tricky D · 19-05-2019 3:05pm

Squall Leonhart wrote: »

Seattle is out, simply because its not one flight from Ireland

3 per week and coming in around €710 for random Feb dates.

kerry4sam · 02-07-2019 6:00pm

Thread moved to where it would be better suited.

Thanks,
kerry4sam

Third_Echelon · 25-07-2019 11:47pm

I've been to all 4 and spent a good bit of time in each (Have lived in NY & SF). Currently living in the San Francisco Bay Area.

San Francisco is a great destination city. Like any large US city, it has problems with homelessness and crime. With SF, it's often more visible and on-show as a lot of it is in the Tenderloin district, which is right in the downtown. Most tourists consider the place to be and stay is right in downtown, where it's generally not the best advice for SF.

It is a great city to visit with plenty to do and plenty within 1 to 2 hours drive (as others have mentioned: Napa, Sonoma, Santa Cruz, Carmel, Monterrey, a little further Lake Tahoe and Yosemite too). SF is very unique with the hills and landscape, the bay, the bridges. I definitely wouldn't let any of the negative aspects put anyone off coming. Chicago has a worse reputation for crime and gun violence for example, but it's also still a great city to visit.

As for weather in SF area, it's a year-round destination. Summer (from what an Irish person would consider summer), is generally from around end of March to October. It will be anywhere from 18C to 35C with the peak heat in July and August. November to early march will have some rain and temperature during the day around 12 C to 15 C. San Francisco itself has its own weird little micro climate. It could be nice and warm outside then in a few minutes it could be a lot colder and foggy, so it's always advised to have a top with sleeves with you. Nothing too heavy, but just something to throw on you if it drops temperature.

Other's have mentioned Washington DC. Great city with the obvious sites like the White House and various monuments and museums being the big draws. I was working there for a few weeks and wasn't expecting much, but the weekends sightseeing were jam packed! Definitely recommend that, but again, weather is key. I was there in January and it was cold and we had some snow. Still enjoyed myself, but may be an issue for older parents.

endofrainbow · 26-07-2019 3:41pm

Another vote for Philadelphia - lots to see and do, great food and direct flights with Aer Lingus or American Airlines.

San Francisco, Chicago, New York or Boston

Comments