Once upon a time, I posted a travel checklist that covered all the details I think about before I go on a trip. It was about managing my life so I was able to actually leave for the vacation! Now I’ll turn my attention to actual trip planning. Everyone has such different priorities, tastes, limitations and budgets when they travel. My choices are individual to me, but I’ll run through my thinking process. The way I see it, except for the super-rich, everyone has to balance convenience and cost. Do I want to travel cheap or travel smooth? I am always juggling the two.
Let’s say I have decided on a destination and made all my arrangements for taking time off work, cat care, and so on.
There are 6 things I spend a lot of time planning before I travel:
- Luggage
- Transportation
- Lodging
- Meals
- Attractions and Shows
- Record Keeping
I’ll throw in the disclaimer that I have never taken a cruise or a package tour, stayed at an all-inclusive resort or travelled in an RV! For the past 5 years, Rom and I have travelled to Toronto and London each year. In addition, we made one trip to Paris and one to New York. Making 12 trips in 5 years means that travel itself has become old-hat, and we have a lot of Standard Operating Procedures! The following are related to self-booked, independent travel.

All I can carry (minus the furry friend)
Luggage/Baggage
I keep 4 questions in mind:
- What are the necessities? (shoes for walking, a warm coat in November)
- How much can I manage? How much do I want to manage?
- How do I want to look?
I can manage one checked full-size wheeled suitcase (24”) and a carry-on backpack (large 34-litre size). On my last trip, my suitcase weighed 14 kg (31 lbs.) I know I can maneuver that much, even on stairs and in subways if I have to. So I don’t choose to travel lighter. It also gives me some room to buy a few gifts and souvenirs. Almost all of my vacations are to just one city / one hotel. When we travelled from London to Paris and back last year by Eurostar, it was not so easy. If I were making a grand tour, I would consider going carry-on only.
Because I like to travel to bigger cities and go to museums, art galleries, concerts and plays, I do like to dress non-touristy and have a variety of looks to choose from. I would not wear cargo pants, a windbreaker and sneakers in St. Germain 🙂 Call me vain.
I have never brought a second suitcase or paid for an over weight limit bag. However, I used to travel with an extra camera bag for a digital SLR and accessories. I gave it up and now travel with a super-zoom pocket digital camera, because the size/weight/awkwardness of the camera bag was too much. I do carry an empty purse or tote bag in my luggage and use it when I go out for the day.
Transportation
I live in a somewhat remote area, and getting anywhere is half the battle. We do have an international airport, train and bus service which enable us to connect to anywhere. Other than the nearby Maritime provinces, we fly to all of our destinations. Just for fun, I checked out the logistics of getting to Toronto (1800 km or 1120 miles):
- By air. 2.5 hours each way. Current prices are $1150 for 2 adults (direct) or $960 for a budget airline with a short stop. That includes baggage fees and prepaid seat selection.
- By car. Did this once with own car (not rental). 20 hours driving. Required overnight stay en route. The return trip cost $995 for gas, tolls, 1 night cheap motel each way, meals and coffee stops.
- By train. 28-29 hours each way. Cost $872 for 2 adults, plus meals. Very generous free baggage allowance.
- By bus. 25-26 hours each way if best connection is made. Cost $706 for 2 adults, including luggage fees but not meals.
I never have more than two weeks off to travel, so I don’t even consider travelling 24 hours, ten times longer than the flight time (besides, I could get to Sydney, Australia in 26 hours!) I am all for paying the convenience fee of air travel and arriving alert and ready for a day and night on the town. Despite this, because I book the lowest economy fares and I use a cash-back credit card instead of an air miles card, I never get any free flights.
Still in the transport category is local, ground travel after I arrive. Using Toronto as an example again, the flat rate for a cab from the airport to downtown is about $50. There are shuttles for about $22/person. Meanwhile, there is a new train service for only $24 (2 adults) followed by a slog from the downtown train station to the hotel by subway or cab. Guess which we choose?
While we are in the city, we would never rent a car because public transit is excellent (same in London, Paris and New York). In most cities, we stay somewhere central, walk most places, and take the subway. However, in London we stay at an inexpensive airport hotel (£65) and buy Oyster cards (top-up fare cards for the Tube) to travel into the city daily. It takes an hour each way, but saves buckets on hotel costs. The last time we were there, we stayed 5 nights, and bought weekly all-access passes, which cost far less than the daily fares. We just had to pay attention to the time so we didn’t miss the last evening stop at the hotel at 12:20 a.m.! In each city, we look at subway maps and get an overview of the routes before we travel. I need to feel oriented to the map when I go somewhere! The one time we didn’t, in Paris, we came close to getting lost in a vast, isolated area late at night.
Lodgings

NYC
When travelling to cities, the airports are often distant from downtown which creates a dilemma: do you stay near the airport so it’s easy to get away when you leave, stay downtown near attractions but amidst the noise and haste, or stay somewhere in the suburbs where it is quiet and cheap?
I used to book inexpensive chain motels everywhere I went, because they are clean and sufficient. Now I prefer B&Bs because we can usually find centrally-located and charming rooms with wonderful breakfasts for the same or less cost. I am an early riser and I love breakfast! Call me squeamish, but I won’t share a bathroom with other travellers, except at a campground with shower stalls. So we have not booked rooms in hostels or student dorms. In NYC and Paris, we stayed at small independent hotels that served breakfast. In the past, on family trips, I have stayed in suites with kitchenettes (self-catering), shared cabins and campgrounds. I think the next time we stay in London, I will find an affordable place downtown on Trivago, and stay at the airport hotel on the last night to calm Rom’s nerves 🙂
As for amenities, even though I walk a lot when we travel (as much as 10 km a day), it doesn’t come close to my activity level at home where I do workouts most days. So if I can afford it, I like a place with a fitness room. I am 50/50 on hotel pools. Large hotels with nice pools are great, but I have been to some small motels with pretty sketchy-looking pool maintenance, so it is not a priority for me!

Fairmont Banff Springs
I will end by telling you about my best hotel pool experience. I was sent to Banff for a conference (poor me!) in the Canadian Rockies one November, and was even put up at the historic Banff Springs Hotel. The room was just average, but the hotel had a heated outdoor pool. My co-worker and I went for a swim, and a few minutes later it started to snow. So there we were, bathing in warm water on a cold night, surrounded by majestic mountains, with snowflakes dancing all around us. Unforgettable!
Next time: food, attractions, shows and…paperwork
Tell me how you like to travel!
Great post! For any trips 5 days or less I can manage a carry on with even a few spare items in the bag for fun which is great. I have a three week interrailing trip the end of the Summer which might be a bit more tricky to plan for though!
Thanks! I have never restricted my luggage to bare necessities. I wonder if I will ever have need of travelling light! Three weeks is a good long stretch – long enough to do laundry while away.
My primary school had an outdoor pool (heated!) Once we went to swim in it when it was snowing- it was amazing, even though there wasn’t a nice view or anything. I think the appreciation of the warm water when it’s snowing is enough to make it memorable! (It must have been between 21-25 years ago!)
As for travelling, generally I have to go for cheap (although as I am scared of driving on duel carriageways now, the cheapest option of car is not really available unless my bf drives us).
I’ve not travelled abroad for years, so most of my non-car travelling is done by train these days. When I last went to London for the day to see my friend tickets were about £25 I think because I bought them way in advance. I love the tube (though I am sure I would hate using it if it was my daily commute) as it is so convenient- out here (in a smallish town) we don’t have anything that good in terms of public transport. Luckily it’s small enough for me to walk into town, even though we live on the outskirts.
I also like to walk as much as I can- when we went to Paris a few years ago I got bad blisters on the first night because my shoes were not suitable for walking around the whole city in one go!
The train system in the UK is great – we have nothing like it (The Canadian National Railroad is just one line from coast to coast!) Yes, you are a good walker! It’s funny working out walking routes on a map. You don’t always know if you’ll encounter a rail yard or a ravine or who knows what! A few weeks ago when we went to London, we wanted to go up Primrose Hill and go to a restaurant on the other side. We debated whether the far side of Primrose Hill would be an impassable cliff face. After looking at pictures, we had a giggle because the hill is only 65 metres high 🙂
When we travel, the hotel room is definitely a place I don’t like to scrimp. My rationale is that our home where we have lived for almost 20 years is modest, paid for, and a “starter home” by US standards. It’s cheaper to book a nice fancy room a few times a year than to buy a new house! I would also rather eat fewer meals but order whatever I want 🎉
I like your rationale – I think I will borrow it! Our travel is limited and incurs no debt so I am OK with hotels vs hostels, and good meals too.
I take the same amount for one week, two weeks, or a month. It is just a matter of how often I get the laundry done! I pack with a maximum legal carry-on, and a day pack. So does Donna (although somehow she always gives me something extra to carry for her).
We stay in small hotels, inns, or b & bs. For Santa Fe and Taos I looked up reviews and then looked on line for discounts/best prices – usually it is better to look on line than to reserve directly. We are leaving for New Mexico tomorrow morning!
I tried to book a hotel room in Banff for this summer directly but struck out, and ended up using a booking site. Bon voyage – I’m sure you will love your trip!
Damn, and there I was getting excited about a trip for the furry friend! 😀
Ha ha! I used to take the cats to the kennel, but now my sister and I trade cat-sitting duties, so they have it pretty good.
Banff looks so beautiful. That was hard luck, having to go there for a conference! I don’t like to be geographically naïve but I had *no* idea that Toronto was so incredibly far away from Halifax. I’ve looked at that part of the world many times on maps (especially back when we were going to move to Toronto.) Somehow (without checking), I thought it was about a 2 hour drive, not flight! It brings home how massive Canada is.
I think your luggage solution is very sensible – we mostly travel ‘light’ with air-travel to allow for last-minute, ‘budget’ airline bookings and weight limits. We don’t often look at B&Bs. I had the impression they were a lot more expensive and maybe not kid-friendly. Might have to review that on our next trip!
OK, I looked up a point of reference for you: the distance from Halifax to Toronto is about the same as going from Melbourne to Sydney AND BACK, or the distance from Canberra to Sydney to Adelaide 🙂 If Link lived a 2-hour drive away we’d probably see each other twice a month instead of twice a year 😦 I’m not sure about B&Bs and kids – often the rooms are small and may not have a second bed, or space for a sofabed or fold-away bed. In my experience, they are mostly less expensive than hotels, and comparable in price to inexpensive roadside motels.
I just looked it all up again…driving distance from Halifax to Toronto is roughly the same as Melbourne to Brisbane (Gold Coast.) I had *no* idea it was that far! And it just looks like a fraction of the map of Canada. You live in a gigantic land! We did the Melbourne to Brisbane drive over Easter on our Road Trip, so I’ll always have a good idea now how far the Halifax/Toronto drive would be.
Yes, that’s exactly the distance! The worst part is that we consider Toronto “near to us” and still part of the “east” 🙂 In the summer I’ll travel to Calgary which is a 5.5 hour flight. I have been to Vancouver a couple of times (8 hour flight) which is the furthest east-west mainland destination. Of course I’d love to go “up north” someday.
Never realised how big Canada is. This puts it in perspective. I thought Toronto was east-ish and close to Nova Scotia. We might be close with global connectedness but we are really distant in reality too.
We do consider Toronto to be east-ish and close to Nova Scotia. What’s 1800 km between friends?
My husband & I have 2 kids, I like booking airbnb places that are an apartment or house so that we have a kitchen, nice to have hearty breakfast, quiet dinner, not force to eat meals out all the time: sitting/living room, etc, more roomy and comfortable than hotel rooms, everyone has private corner to retreat to…
My husband and his friends are divers, so an annual vacation to various warm locales with all inclusive resorts are great, no cooking or cleaning, meals available most any time (sad to admit that one time in one week I gained 10 pounds), activities for kids, places seem popular, stayed in Curauco (so?), Costa Rica, Cozumel, Playa, Dominican Republic, surprised that so many European tourists too, must be a relative bargain for them as well
I would like to do an all-inclusive resort holiday someday. Most people I know have been to Cuba or the Dominican (some every winter!) I have also never booked an Air B&B but should try it for comparison purposes!
I second Fiona’s comment. I knew Canadacwas wide but those times are mind-blowing. Even more so are the costs. It’s the same for those in regional Australia. I’m spoiled for cheap flights coming from Sydney. Except I can’t visit my sister without a $1,200 return flight. I can fly to London for that!!!
My debate on accommodation when in a city is the same – central, expensive, save time travelling; outer area: costs and time transferred to daily travel. I’m currently researching my trip for next Sept to France. Hard when you know little about places but especially the local transport.
I’d love to be in a pool with the snow falling. Like those Japanese monkeys, I wouldn’t want to get out.
I can only imagine the costs to go anywhere if you lived in Perth! We don’t get many visitors because, as you say, for the airfare to Halifax they could go to New York or London. Do you have a must-see list in France: will you be centred in Paris or travelling around the country? I forgot about those macaques and their hot springs 🙂
I have some must sees inFrance but more in a general way. We are doing a bus trip to the WWI battlefields and Brugge. I’m currently researching my lists of things, especially Brittany.
Perth is actually OK. They get cheap flights and can fly cheaper to Bali. It’s the regional centres that cost so much.
Perth is only three hours to Bali, which the BF misses (it’s about 7hrs from Sydney).
Ah, you are so organized, also in your head. Many good thoughts, most I notice I actually already do do (I am happy to say), just never quite think of it. I also do what Jamie Ray above does, I bring two changes of clothes and laundry detergent. Usually light weight, quick dry clothing and since I travel in Europe and mostly in France, nothing can ever look casual, camping or touristy. I agree with you – Nono-no to cargo trousers, chequered shirts or sandals with open toes (if not with heals and I do not need them). It is not about vanity, it is about accepting and adapting where I go. The man and I once hiked in France through woods and countryside with fully loaded backpacks when we very sweaty arrived in a village where we had the chance of a very-very-very nice three course lunch (€70 p.p. without wine, just to give you an idea). With a quick wash we were perfectly presentable! (And it was lovely!) Rome is the same. Not even here in Amsterdam does anybody except American tourists and students wear shorts in the city. Ever! However even I will happily wear sandals and socks in the Bavarian mountains… 😉
I have never experienced a lunch that deluxe 🙂 And especially not after hiking. My maximum (so far) was 40 GBP p.p.! We North Americans have a weird idea that work clothes are uncomfortable, and that true comfort means T-shirts, shorts and sneakers. There are lots of other clothes that are just as comfortable but appropriate to more settings. I suppose the real issue is caring: labelling oneself as a tourist kind of gives permission to gawk and to see local people and places as “not like us.” I would not want to slavishly copy the people I’m visiting, but I wouldn’t want to ignore local custom either.
Smooth – but still cheap. It’s in my nature to aim for cheap, but I do think Rich has really helped me ‘lifestyle upgrade’ as part of the whole ‘we earn enough’ and I also consider a future where we may not have the same funds (kids, maybe one without a job etc).
So I would go for hostels when I was travelling alone. It was just cheaper and easier – hotels can be lonely, particularly for a longer period. My parents are pretty thrifty with accommodation, which is how I set off on the budget. But over time, I’ve seen some of the errors in their bargain basement ways (sinks falling off walls, toilets flooding).
When we went to Phuket for Easter 2015, we booked a package and we were then told there’d be an additional fee for Easter week. So we asked for a refund, and I used that to find somewhere else. Alas, the standard wasn’t as high as I or Rich would have been comfortable with (I am SO detail conscious in hotels – what’s not cleaned or maintained). I have to say, our hotel was perfectly fine though!! At that stage, we had a chat about what I *should* have expected at what price points… so it was a good discussion for future planning. In the US more recently, LA hotel was only choice in walking proximity to my brother (passable). Chicago was his company’s choice (Hard Rock – AMAZING!) and in SF we went for an AirBnB as it’s such an expensive place with a short booking timeframe. We were going to risk an app for lastminute accom and may have ended up more centrally and swankier… Our AirBnB was good for other reasons – multi rooms (a very recently emerging preference of Rich’s! He’s away overnight in an ‘apartment’!); parking for a hire car we decided on as the days passed, proximity to local resturants and mini mart and laudromat. SF is good with Uber and Lyft too, so between those and buses and the hire car for a short time, we got around pretty easily and competitively.
Planning my Jul/Aug Europe trip, I’ve started with best ranked TripAdvisor, and then price. It’s really worked, especially as central Europe isn’t easy to know what the price points are. But we (I’m going with my brother) are staying in a private room in one hostel, as it came well recommended, and I can see why. As my brother is only one or two years out of school, I’ve told him he’ll pay a fixed cost per night, and I’ll cover the difference, given my pricier choices!
I am really conscious of room cleanliness, and also safety of the building. I wouldn’t knowingly compromise those. I’d like to stay in a Hard Rock some time! Multiple rooms would be good if one of you had work to do, or liked to stay up later than the other to watch YouTube etc! If I were travelling with someone else on a lower budget, I would offer the same as you: to have them pay a fixed rate and then top it up (also if I wanted a nice meal out!)
My dad offered the same brother the deal and is still waiting ‘reimbursement’ though…!
🙂
I prefer to travel fairly light – a 20″ case that I check – even though I could legally take it onboard its too difficult for me to manage since I’m very short and walk with a cane. I take a tote bag onboard with a change of clothes and nightwear just in case anything goes missing.
I find that I can pack enough to last two weeks with maybe a small hand wash done along the way. I also save old undies & t-shirts/shirts throughout the year, take them along and throw them out as I go – this leaves room to bring home a few things.
I stick to one colour scheme so that everything mixes and matches and always lean towards dressy/casual rather than sloppy/touristy – I like to blend in, not stand out like a sore thumb.
I have stayed in some lovely B&B’s but prefer a nice hotel that is centrally located – I like to be able to walk to as many sites as possible and always use public transit when I can’t walk.
I like a good breakfast and will often eat a late lunch rather than a big supper – I find locales like museums & galleries often have lovely and reasonably priced restaurants and then I can pick up a sandwich or salad at a supermarket to eat in my hotel room later – after a busy day of sightseeing, something easy and light is my preference.
Hi Margie, I have never had any luggage lost, or brought a change of clothes on board a flight. I suppose someday my luck will run out. Wearing and tossing old clothes is a novel idea! I usually stick with one colour scheme, only because I don’t want to bring extra shoes to match anything! I have managed to find B&Bs centrally located often, but not always, including good ones in Toronto! I like museum and gallery cafes when they are not heaving with people and long lineups – I really like the one at the ROM which is run by Druxy’s Deli.