Eastern USA and Canada
 

We (family of 4 with 2 adult children) from Sydney, Australia plan to enjoy a vacation in the USA and Canada. 9 November to 23 December. Our itinerary:

1. Sydney-Los Angeles-Chicago (flights)
Issue: charged 4 separate times for tickets (each attracting a foreign transaction fee on my credit card) with Southwest despite paying a single amount at the time of booking for the Los Angeles to Chicago leg.

2. Chicago via Canada to Boston
Advice needed: one way car rental. Do I get a toll pass - offered by Alamo or do I buy a card in Chicago?

3. Boston to NYC
Advice needed: train and flights are similar in cost. Our hotel is near Newport in New Jersey (near Holland tunnel). Train or flight to Newark?

re Boston-NYC: The train is -- by far -- easier, more comfortable, and more reliable. The Jersey side of the Holland Tunnel is between midtown Manhattan and Newark, so you could take the train from Boston either to Newark and then taxi to the hotel, or, to save money, take the train to NYC (Penn Station) and then connect to the PATH train from Penn Station to Newport.

Also, a few cautions: In late November and December, you run a decent risk of encountering snow/ice en route from Chicago to Boston via Canada. Especially if you've not driven in these conditions, it's best to avoid them. Stay aware of weather forecasts, and be prepared to alter you schedules if needed. Finally, be sure to verify from you car rental agency that you are allowed to drive the rental car in Canada (that is, that your insurance is valid in Canada).

One way car rental with drop off may be expensive. Toll pass might be more expensive than just paying the tolls as you go, and may have extra charges for a rental car.
Flights would require getting to and from airports rather than taking a train that basically takes you to the center of the town you want.

1) your card was likely charged a foreign transaction fee for each ticket... the total amount is the same as the fees are based on the amount charged and not the number of transactions...

2) if money is a concern (see above) the easiest way through the tolls is an envelope full of $1 and 25 cent pieces... the tolls add up to about $50 and this will avoid the daily fees that come with the toll pass... your trip is quite long and those extra fees can add up to be higher than the tolls...

3) flights are so much easier and you can drop the car rental at the airport and save transfers...

2. Do not get a toll pass by Alamo. Many of the rental car companies charge you a surcharge for each and every day of the rental, regardless of whether you use the pass. As far as I know you do NOT need the pass, as you can pay with cash at any of the tolls.

You could also get a rental car in each area you stop... see the area and return the car... driving in the Chicago Boaton corridor during December could be challenging at the least...

Why is it difficult to drive from Chicago to Boston in December? The roads are open and unless it's actively snowing (which is not common in December), completely clear. If it is actively snowing, then smart drivers stay off the roads till the storm passes and the road crews have time to clear the roads.

They have 1.5mo, so plenty of time for a leisurely drive through Canada and the Northeast US from Chicago to Boston. Renting a car for that portion makes perfect sense to me. So does renting a car from Boston to NY if they have time to tour and not just transit from one city to another. There is a lot to see and do in that area, from the coast to historic villages to the mountains & valleys, and everything in between.

Dear J62, please avoid categorical statements.

We took our son from Boston to Montreal to look at universities over the Veterans Day weekend (November 11) some years ago.

It began to snow as we left Montreal. Hard. Neither Autoroute 10 nor I-91 were plowed until St Johnsbury, Vermont. Visibility was poor, and there was no visible difference between the roadway and the margins. Probably 10 inches of snow below the border. What should have taken 2.5 hours took more than 4, and we are experienced winter drivers with an AWD vehicle. In early November.

Likely, no. Possible, yes. Consequences, significant.

One more thing about the toll pass, if you get one for a rental car in the US it probably will not be good for tolls you pay in Canada (different system and different currency). Best to just use cash. FYI - tolls on bridges connecting US and Canada can usually be paid in either US or Canadian currency. Tolls on roads/bridges within the US have to be paid in US currency and tolls on roads/bridges with Canada have to be paid in Canadian currency.

Yup, if it's actively snowing you can have issues, and should stay off the road if there is any question.

You should also be aware of our US Thanksgiving holidays which may reduce hotel availability (and increase hotel prices) and increase traffic (especially getting in and out of major metropolitan areas on the Wednesday before the Thursday holiday and the Sunday after). This year US Thanksgiving is November 28. (Canada has a Thanksgiving holiday too but it is in October.)

Otherwise that time of year it should be easy enough to be flexible with your travel schedule to wait a day or so if you have bad weather.

A couple of notes;

Based on yuor plan you will be entering the US multiple times - make sure your visa allows for this.

Staying near the Holland Tunnel - this is an extremely unpleasant area and you really do not want to stay there. (Some of the motels charge by the hour - or used to - and it's really not tourist territory.) If you cannot afford Manhattan - and I would do everything possible to do so - you are better off in Long Island City - which is only a couple of subway stops from Manhattan. Granted it is a mixed use areas - but the motels are decent - check reviews thought - and not basically used by hookers or to house homeless as you can find by the Holland Tunnel.

I just want to chime in on a misunderstanding about "Newport" in Jersey City by nytraveler. This poster seems to be staying in the Newport area, also known as the waterfront area -- and is filled with hotels such as Doubletree, Courtyard by Marriott, Hyatt, and Westin. The Courtyard by Marriott is literally on top of the Newport PATH station, and therefore, the trip to Manhattan is approximately, oh, 15 minutes, which lets you out in Herald Square.

There's a bunch of nice restaurants in that neighborhood, and shops, and a lovely park along the water that has a gorgeous view of NYC all lit up at night.

NYTraveler, I know exactly which hotel you're talking about -- and you're right, that is a quite unpleasant, noisy area, across the street from the Holland Tunnel.

However, it seems to me -- and I lived in Jersey City for 4 years before moving in 2012 -- that he's staying on the waterfront. So this is totally OK.

<<Based on yuor plan you will be entering the US multiple times - make sure your visa allows for this.>>

Do NOT underestimate the importance of this advice. You CANNOT go from Sydney to LA to Chicago to (say) Detroit to Windsor-Toronto-Ottawa-Montreal and back into the United States unless you have a multiple-entry visa for the US.