
I have a long time client, who trusts my travel style, who emailed me and asked for trip ideas. Here were the parameters: something reasonable from the Pittsburgh area (no 12 hour flights, but plane rides are still acceptable); something a little unusual (“I don’t want a three day cruise to the Bahamas”); and must expose his family to new cultures and sightseeing.
Here are some fabulous suggestions I came up with. What do you think?
Taking the Canadian across the Rockies
This is always one of my top suggestions to clients who enjoy train travel. This train is so famous, called The Canadian, that it features on Canadian currency!

If you choose to do the whole trip, you start in Toronto (an easy drive from Pittsburgh) and end in Vancouver. This is not just any train ride. It rolls through some of the most stunning scenery in North America. You could even book individual legs if you wanted to stop in some of the towns and stay in a hotel for a night or two, or you can choose to just book it the whole way through.
There is a dining car onboard and travelers in sleeper car class or above automatically get all their meals included for free. Dine on china and white tablecloths with freshly cooked meals and Canadian specialties.
This is no ordinary train ride. In your spacious sleeper cabin, room attendants will make your seats into comfortable double beds in the evening. Room service and concierge service is even available for certain classes of travel. Park rangers get on and off the train periodically, making announcements when wildlife can be seen from the glass-domed observation cars. You’ll pass through prairies, plains, snow capped mountains, stunning lake vistas, and more.
Bermuda
Bermuda is less than 2 hours from the East Coast. There are direct flights from Washington DC, Newark, JFK-NYC, and Philadelphia. You can either fly from these cities to begin with or take a flight from Pittsburgh and connect through these cities. Even with a connection, you’re likely to be in Bermuda within 5 hours of leaving Pittsburgh – and there isn’t much of a time difference (1 hour) so there’s no jet lag! You can also take a cruise out of Baltimore and other East Coast ports, but if you’d like to spend the maximum amount of time on the islands, flying would be your best option.
Bermuda is often overlooked due to the cruise industry monopolizing advertisements for the Caribbean, but it’s a stunning destination. A recent friend who returned said, “East Coasters who dread the time and financial commitment of flights to Hawaii should really consider Bermuda!”
In 2015, Conde Nast Traveler Magazine named Bermuda one of the top 5 islands in the world! It’s safe, friendly, and stunningly beautiful. There is also a variety of things to do – not just its beautiful pink sandy beaches, but forts, museums, yummy food, water sports, aquariums, whitewashed houses, golfing, hiking, and so much more!
Quebec City
Quebec is one of the most underrated cities in North America – it’s only a 12 hour drive from Pittsburgh (I know this because I drove it!) OR what I would suggest is flying as you will then get more time actually in the city if your time is limited. There are flight sales periodically with a short layover in Toronto, for around $100 one-way, and even with a layover in Toronto you will still arrive in Quebec around lunchtime if you leave the airport early in the morning.
In Quebec, you’ll be surrounded by stunning architecture, incredible food, friendly people, and a wonderful culture that has made many travel writers note, “This is the closest you’ll get to Europe without leaving North America.” On my trip to Quebec, we wandered the narrow streets of the old city, drove to Montmorency Falls which are 1.5 times higher than Niagara Falls (they are within the city limits – just a 15 minute drive from the old city), explored old forts, and tried to go dog sledding (the snow was too slushy, hence the “tried”). If you have access to a car or want to venture out even deeper into Quebec province itself, not just Quebec City, you can be exposed to some top ski resorts, mountain homes, and amazing outdoor activities no matter what the season.
Francophiles will be happy here because although many Quebecois do speak English and are bilingual, French is still very much the preferred language and those wish to practice their French will be congratulated and gently encouraged.
You can also combine your trip to Quebec City with a stop in Montreal, which is about three hours drive away. This is what we did and the two cities are very different, so it’s good to get a feel for both. However, if you can only choose one, and you love the old Europe feel of winding streets, French language, Canadian hospitality, and historical buildings, I’d recommend Quebec for your first foray into this part of Canada.
New Orleans
There are now direct flights from Pittsburgh and other East Coast cities to New Orleans, and hear me out – there’s much more to see in Nola than just a mardi gras parade! (Don’t go during the summer months, however – it’s swampy, humid, and hot.) Historical plantations, Creole and Cajun food, museums (example: The National WWII Museum), Southern architecture, walking tours, exploring bayous and protected swamplands, jazz and musical performances… you’ll be guaranteed to have enough activities to keep you entertained. Packaged flight + hotel deals make this a great destination for the weekend. (Here’s my trip report from a long weekend in New Orleans.)
National Parks

You don’t have to leave the country to see amazing things. The USA is so large it has some of the most varied scenery in the world. Why not explore “from sea to shining sea” by exploring some of the stunning National Parks?
There are a variety of ways to do this – organized tour, train travel, self-drive. It’s so hard to pick the “best” national parks, so you’re only limited by time and budget – you’ll be sure to appreciate different things about each of our 58 National Parks. Some of the top visited parks include Yosemite in California, the Grand Canyon in Arizona (you could combine this with a trip to Vegas), Glacier National Park in Montana, Denali National Park in Alaska (you can also visit this on a cruise + land tour), Chaco Culture Park in New Mexico, Acadia National Park in Maine, Rocky Mountain National Park in Colorado, Mammoth Cave National Park in Kentucky, Olympic National Park in Washington, and Grand Teton in Wyoming. As you can see, you can find national parks in almost every corner of the USA!

We could do multiple blog posts on the National Parks, so we’ll just consider this a whetting of the appetite. (Check out 5 Reasons to Visit Glacier National Park here.) Amtrak Train Vacations offers some great package deals as well as some organized tours and packaged deals that allow you to see multiple parks in one visit. Or choose one park in detail and explore it to your heart’s content – you can easily spend multiple days in Yellowstone (and you can even visit Yellowstone in the winter and go on guided “Search for Wolves” walks and other fantastic explorations!).
A Fall Foliage Cruise

Although I initially didn’t want to include cruises on this list, these are so relatively few and unusual that it’s worth a mention. Just a few times a year, major cruise lines announce New England and Canada itineraries. Almost all of these are in September and October to coincide with incredible fall foliage – “leaf-peepers” will delight in this opportunity to see gorgeous colors along the coast. There are also some cruises that extend even further south – for instance, I found one that goes from Quebec City, along the coast of New England, and ends in Fort Lauderdale (perfect for snow-birds who have a winter home in Florida anyway!). You can also do 5-7 day roundtrip or one-way cruises out of New York and other gateways. Itineraries for New England and Canada vary – but some common ports of call include:
Quebec City, Quebec | Ville Saguenay, Quebec | Gaspe, Quebec | Charlottetown, Prince Edward Island, Canada | Sydney, Nova Scotia | Halifax, Nova Scotia | Saint John, New Brunswick (for the Bay of Fundy) | Bar Harbor, Maine | Boston, Massachusetts | New York City (Manhattan or Brooklyn), New York

Lengths of cruises can vary from 5 days to 14 days, within a wide variety of budgets, so contact me if you’d like me to give you more information about these.
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