I’m off to a wedding in September next year. Cape Cod, Massachusetts. I’ve got friends in St Louis, Chicago, and California and would like to visit all 4 places. I’ll be with my wife and 8 year old son.

What’s the best way to do something like that? And spend the least money?

Fly to Boston, hire a car, fly back from California?
Fly to Boston, internal flights to St Louis, Chicago, California, then fly back from California.

Also looking for any ways I can grab air miles to save money on costs. Are there any schemes out there that could help me – in the past have seen credit cards that give miles for every £x spent.

Mmmm, getting excited already.

What’s the best way to do something like that? And spend the least money?

touring bike, may take a while like but you’ll get a good sense of the place. Your wife n child may not enjoy it too much though (i’m only guessing here as i know neither your wife or offspring), probably best to leave them at home.

you don’t say how long you have to do this?

If you fancy a bit of an adventure take the train. I did San-Francisco-Portland-Seattle-Chicago-Boston in April last year. Chicago seems to be the main long-distance hub, relatively speaking given the limited number of train lines. It was suprisingly cheap at the time (around £200), not sure if September would count as peak season though. I went for the standard reclining seat (they’re quite large, about the size of a 1st class seat in the UK), a cabin would obviously be more expensive. Either way you’ll get to see some amazing scenary, and you don’t appreciate exactly how big the plains are until you’ve spent a day travelling across them.

Time-wise, let’s say I’ve got two weeks to do it.

Biking is out, definitely. Another time.

Fly to Califonia – visit friends.
Fly to St Louis – visit friends, go up arch.
Drive to Chicago (one road, aim north) – visit friends.
Fly to Boston – have wedding.
Fly home.

USA is big, and you’ll kill the holiday if you spend days and days just driving.

drive to chicago . . .fly to Cal . . fly cal to home

ignore friends in St Louis

How about trains? A great way to see stuff as you travel.

‘Merica is a big place; I assume that you recognize the shapes superimposed in the middle. 😉

Amtrak is the US passenger train entity.

Your 8 year old will die of boredom if you attempt this. Do you appreciate the distances you are proposing to cover and the time it takes? You’d waste most of your time travelling or recovering from travelling.

I’m touring the east coast end of the month, asked the same question. Im flying everywhere, internal flights in the US are buttons and save so much time.

As above fly between places but rent car to explore in Mass and California. Credit card airmiles, Amex is very good for BA but you need to decide which airline you’ll use.

Cape Cod is lovely, good for family. Explore a little the towns on the inner and outer coast plus you must see the dunes and take a whale watching trip from Provincetown (is season dependent). If you have time explore a bit, Newport, inland to Vermont possibly. Boston is a cool city, acquarium is great.

Chicago is fun city, enough to amuse you there without needing to venture too far. Lovely weather in the summer, absolutely arctic in the winter.

St Louis I don’t know but a fun contrast to other cities I imagine.

California is the huge variable, north or south you don’t say. I’d say spend the most time there and explore by car. LA, San Fran (and the home of mtb), wine lands, Yoesemiti ? People would easily spend 2 weeks touring just a part of California.

St Louis is nice, plenty to keep you occupied.

Forest park, the Zoo (free), Science Centre (free), Anheuser-Busch (free), the Arch, frozen custard at Ted Drewes on Route 66.

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If you’re planning on hiring a car in Chicago and seeing stuff roundabout I’d be tempted to drive to St Louis as well (~5 hours).

I’m going to be the voice of doom: two weeks is not enough for four locations far apart, ncluding a wedding. Yu’ll spend the whole time traveling and it’ll be crap. Lose California. Fly into Boston, do wedding, fly to St Louis, see your friends, drive to Chicago, see your friends, fly out.

How about trains? A great way to see stuff as you travel.

Amtrak? Four different locations? with an eight year old? Cheap? In two weeks? Are you quite mad?

I travelled New York, Washington, New Orleans, Memphis, Chicago, Niagara and back to New York in 2 weeks on the East Coast Rail Pass and quite enjoyed it.

😯