Starting in Toronto, Ending Up in Hawaii?

I've decided to give up living the adult life and go back to my backpacking ways to enjoy the last remaining bit of my 20s. So my house, cars, and everything I own is for sale, and of course... a road trip is in order!

Here are the plans so far:

I plan to leave the Toronto area with my fiancee and head over to Buffalo. We make a living online, so having WiFi is of the utmost importance everywhere we stay. However, I will also pick up an iPad 3G from Buffalo. Why? They come with a 3G sim card in the iPad itself, and because I can pop in credit card details on the device itself without needing to produce an American license or address etc. After being jailbroken, I can create a WiFi hotspot and we can tether our laptops to it, anywhere. Something tells me there is a gap between AT&T's network and how I'm picturing it though.

We don't have an exact timeframe or itinerary, as no road trip should, but we want to be able to check out various things in each city (food, first and foremost LOL), and take detours as we want.

Being a car aficionado and having owned a car from the age of 16 onwards, it's hard for me to picture how we're going to get around. I had originally envisioned us staying in city center-type areas for a few days at a time and using subways, but I realize now that I hate buses, and do not want to step foot on one. Taxis are too expensive, so that leaves car, rental car, train, subway and streetcar (where applicable). Small places like Buffalo pose a problem, because if we're staying 2-3 days, it'll even be hard to get food (can you tell I like food?). Should we buy a cheap car, like $2000, and maybe try to sell it towards the end of the road trip, or rent cars?

I'm also not too sure about where to leave our belongings. I was thinking about Motel 6ing it the whole way, with one night at a famous hotel if they exist in the city. The big-name hotel shoudn't be a problem, but is it safe to keep expensive laptops, cameras etc. in a motel room? If not there, then where? I don't want to carry a huge backpack with me everywhere I go.

Would you guys recommend Motel 6 most of the way? We want it to be cheap (of course), but want it to be clean and air-conditioned.

So the route itself: Thinking about taking a MEGABUS or a rental car from Toronto to Buffalo, where we'll do a bit of shopping, chill out a day or two.

From there we'll probably fly to Chicago, where we'll probably spend 3-5 days. We'll fly to NYC after that, where we'll spend about a week or so. This is where the real road trip will begin. I'm thinking about flying the previous routes, because, correct me if I'm wrong, but there isn't much to see along those routes, and also because it's a little similar to Ontario.


Here's the route we're thinking...

New York City

Philadelphia

Washington DC

Savannah

Jacksonville

Daytona Beach

Fort Lauderdale

Miami

Key Largo

Key West

Everglades

Tampa

Atlanta

New Orleans

Baton Rouge

Houston

Dallas/Fort Worth

Marfa

Roswell (not me, the gf)

San Diego

Los Angeles

Las Vegas

Area 51

Grand Canyon

San Francisco

Detour to Dubai, Egypt, Turkey and India for ~2 months

Back in LA

Hawaii


Would love to hear comments, feedback, criticism, opinions and/or advice!

2 issues - without a US address, you essentially can't buy, insure, and register a car here. You also can't rent a car in one country and drop it off in another.

My best suggestion would be for you to KEEP one of your cars and use it for the duration of your US road trip. Then buzz back across the border and sell it in Vancouver.

I don't think the Ipad and 3G are worth the expense - even Motel 6 has wifi now. Most of them charge 3 bucks a night per machine, but you could also stay at Super 8's, which all have free wifi. There are also other budget chains and most have wifi.

Hey glc! Actually there's a few car rental companies that let you rent here and drop off in ny state. Naturally they charge you a princely sum for it though lol!

Keeping one of my cars is not a bad idea though. I can probably get more for it in Vancouver too. Can I sell it in the States if I wanted to?

I could maybe use my brothers address in Georgia for insurance, but do I need an American license? You need a Canadian license to buy a car here.

I agree with GLC, I really think your best bet will far and away be to keep one of the cars you already have and sell it in Vancouver at the end of your trip.

Selling it in the US will generally not be possible - at least not in a practical sense. Importing a car for the purpose of selling it (which is what you'll be doing since you aren't planning to move here) is going to flag all sorts of red tape from customs - which will involve fees, taxes, etc. Not to mention, a Canadian car with its Metric Speedometer/Oddometer is going to fetch a significantly lower price in the US.

You generally need a state drivers license to register and insure a car. Having a brothers address will only be of limited help because, a- he lives in Georgia and you're looking at buying a car in the New York area, and b- you typically have to provide some sort of proof that you are actually living at that address by providing a utility bill, a lease, or some other proof (which may not be possible since you are visiting as a foreign tourist).

When you factor in all of those things, plus the likely un-reliability of a $2000 car, especially one you don't know the history of, I just think your life will be a whole lot more simple and you'll be able to spend much more time focusing on your actual trip if you just go with a car you already have.

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is it safe to keep expensive laptops, cameras etc. in a motel room? If not there, then where?

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I've never had a problem, but if you are concerned almost every motel will offer a safe - either in the room or behind the front desk.

Quite a few Super 8's have in room safes. They charge $1.50 a night for their use.

There's more than the metric speedometer and import issues, you will have issues trying to sell a Canadian car in California due to their emissions laws - it would have to have 50 state certification and it would have to pass a smog check prior to sale. Sell it in Vancouver and hop a flight to LA to go on to Hawaii.

Some legal issues - you may want to apply for a multiple entry visa due to the nature and length of your trip. If you plan on living in Hawaii, you are going to have to jump through hoops anyway. The standard visa waiver program will not be sufficient.

Yeah, I'm thinking car rental would be the way to go then... Not sure about going to Vancouver and selling it there. Car rental companies can negotiate good rates for weeks or months right? What can I expect?

I'd think renting a car would be more expensive than taking a car you already own, but it would have the advantage that you wouldn't have to worry about maintenance or selling it when you are ready to move on.

You will be looking at a one way drop off fee, which will raise your rental rate by several hundred dollars, but otherwise, you really have to shop around. There are just too many variables to try to guess what you might need to pay.