Fall is upon us, and if you’re thinking about taking a winter vacation, it’s time to start planning.
Where will you go? What will you do? All questions that need answering before you can even begin to make a booking.
As someone who recently booked my own vacation, here are the steps I ended up following in my quest to find the perfect vacation.
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Steps on planning your perfect winter vacation
I recently went through the process of planning a winter vacation.
There’s a lot to consider, from what activities you want to do, keeping tabs on prices, and tricky booking processes. Here are 6 steps to follow to focus your line of thinking as to where you should go this winter.
1. Decide on what you want to do for your winter vacation
First, you need to decide on what you want to do with your vacation. It’s a straightforward question to answer.
For many, you’ll simply want to head somewhere warm and hit the pool or beach. Take a break from the cold that we experience all too much of in Canada.
Maybe you want a Disney World experience, or want to head to other major amusement parks.
Perhaps a golfing trip is more your thing, or you want to party in a place like Las Vegas.
And for others, you want to embrace the cold and do something like hit the slopes for a week.
Whatever you’re into, this is where to start.
For us, this was simple. We want a beach and pool vacation to get away from winter for a week.
2. Decide on where and when you want to go
Steps 2 and 3 go hand in hand, and may be repeated several times.
First, you have to decide on where you want to go. For some vacations, this is easy. If you want a Disney World vacation, well, you can skip ahead to the next step – you’re off to Orlando.
For others, it’s not so simple. For a Mexican/Caribbean beach holiday, this can be difficult to do. You’ve not only got a plethora of destinations, but multiple resorts to look at too.
First, whittle down exactly where you want to go, or at least make a short list of destinations to consider. If other family members are taking a vacation, that can help decide on where you want to go.
One other factor that can help decide – flights from your airport. This is especially true for sunny destinations. If you want a direct flight, you may be faced with limited options. If this is you, head to step 5 and check out your flight options. This alone can shrink down your list.
You’ll also have to decide on when you want to go. March break is the best choice for many so no one is missing a week of school. For others, it’s wide open. Step 3 can help, as prices (and crowding) will vary based on when you go. March is usually more expensive than other months.
Once that’s done, you can head to step 3.
Looking at flights from our airport helped us decide on destinations. Flying out of Moncton, we basically got these destinations to look at (if your curious, here’s their schedule for winter 2023):
- Varadero,
- Cayo Coco,
- Punta Cana,
- Montego Bay,
- Puerto Plata, and
- Cancun.
We knew we didn’t want to go to Cuba since we had been before, so that ruled out Varadero and Cayo Coco.
We also weren’t keen on Cancun or Puerto Plata, so that left us with Punta Cana and Montego Bay.
3. Decide on how much you want to spend
You now have to decide how much you want to spend. Set a budget for yourself and don’t spend more than you can afford.
With the destination you picked, start looking at various dates and skim the results and see what the prices are, just to get an idea. This can help decide when you want to go.
Let’s take the Carribean as an example – the prices you’ll pay can fluctuate wildly depending on where you want to go. Sure, Turks and Caicos is an excellent high-end destination, but you’ll also pay through the roof for it. We were curious about it, but didn’t want to spend US$10,000+ for a week (that didn’t include flights) when we could easily pay less than half of that elsewhere.
Another example is if you want to head to a ski resort. Take Mont Tremblant for instance. They have a lovely resort right on the hill, so you can ski in and out with ease. But that also costs more than staying somewhere else where you’ll have to drive to the hill.
How much you’re willing to spend can cut down where you want to go. In some cases, you may end up back at the drawing board and have to go back to step 2.
As for us, when looking at a few resorts in both places, Montego Bay was more expensive than Punta Cana, so it was decided right there. Punta Cana or bust!
4. Research hotels and resorts at your destination
This may be the hardest and most time consuming part – deciding on where you want to stay. No matter where you go, you’ll be faced with a plethora of options.
In some cases, this is where a travel agent can help out, particularly on those sunny destination vacations. Tell them what you want, and they can put together a few recommendations for you to think about. They get feedback from clients on where they want to stay and can help shape decisions for others. A travel agent helped us out on our last trip to Cuba.
It took us a while to pick, but we settled on a unique resort that had a large water park in it.
And yes, other extended family members were also going there, so that helped shape our decision.
5. Figure out your transportation (if required)
This may or may not be easy – figure out how you’re getting there.
If your trip is simply hopping in your car and heading out, skip to the last step.
For many, you’ll need to book some flights.
For us, this was simple, we knew our dates and had 2 flight options to choose between Sunwing and Air Transat. And that choice was simple – Air Transat had a much better flight schedule so they were our pick (travelling with small kids, I didn’t want to land in Moncton at 3:40 am). The prices were similar, so there was no issue in that regard.
As we stated in step 2, this may help when deciding on a short list of destinations.
6. Make your booking
You’re finally here – it’s time to make your bookings. You’ve picked out where you want to go and how you’re getting there.
For sunny destinations, there’s one more decision to make – booking a package versus booking your flights and resort separately. Most of the time, booking together is easier. You’ll probably get a better price and maybe even get a free transfer to your hotel.
But that’s not always the case. And in our case, Air Transat didn’t have a package option involving our chosen resort. However, Sunwing did.
But that wasn’t an issue. In fact, it worked out even better. It turned out that our resort was (I would say) secretly a Marriott hotel. And since we booked straight with them, we were set to earn a pile of Marriott points when we were done and we’d get Marriott Silver Elite benefits while we were there thanks to having the Marriott Bonvoy American Express Card.
Sure, we have to find our own way to the resort, but that’s more than offset in terms of what we’d be getting back.
So there you have it – your 6 step guide to a perfect winter vacation. And now you can relax, book your time off work, and start your countdown to when you leave.
Best credit cards you can get to help pay for any winter vacation
Vacations aren’t cheap. But luckily there’s a way to help pay for them – with a flexible rewards credit card.
Thanks to these credit cards, you can earn points on all your purchases, then use your points to help pay for your vacation.
Here are your best options.
We will point out if you’re absolutely certain you’ll be travelling on Air Canada or WestJet, then you’ll be excited for what their cards have to offer.
| Credit Card | Welcome Bonus | Earn Rates | Annual Fee, Income Requirements | Apply Now |
|---|---|---|---|---|
| American Express Cobalt | Up to 15,000 bonus points (terms) | * 5 points per $1 spent on eligible groceries and restaurants * 3 points per $1 spent on eligible streaming services * 2 points per $1 spent on eligible gas, transit, and ride share purchases * 1 point per $1 spent on foreign currency purchases * 1 point per $1 spent on all other purchases |
* $155.88 * None |
Apply Now |
| MBNA Rewards World Elite Mastercard |  $150 GC Boost + 30,000 bonus points (terms) |
* 5 points for every $1 spent on restaurants, groceries, and select recurring bills (up to $50,000 spent annually per category) * 1 point per $1 spent on all other purchases |
* $120 * $80K personal/$150K household |
Apply Now |
| National Bank World Elite Mastercard | None | * 5 points per $1 spent on groceries and restaurants * 2 points per $1 spent on gas, electric vehicle charging, recurring bills, and travel booked through À La Carte Rewards * 1 point per $1 spent on all other purchases |
* $150 * $80K personal/$150K household |
Apply Now |
| BMO Air Miles World Elite Mastercard | $150 GeniusCash + Up to 9,000 bonus miles, first year free (terms) |
* 1 Mile for every $12 spent * 3x the Miles for every $12 at participating Air Miles partners * 2x the Miles for every $12 spent at any eligible grocery, liquor, and wholesale stores |
* $120 * $80K personal/$150K household |
Apply Now |
| Scotiabank American Express | 7,500 bonus points (terms) | * 3 Scene+ points per $1 spent at Sobeys, Safeway, FreshCo and more * 2 Scene+ points per $1 spent on grocery, dining and entertainment, gas, daily transit, and select streaming services * 1 Scene+ point per $1 spent on all other purchases |
* $0 * $12K personal |
Apply Now |
1. The best travel credit card in Canada
Transfer points to Aeroplan and 7 other travel partners with Canada's #1 credit card.* Transfer points to Aeroplan and 7 other travel partners with Canada's #1 credit card.*
×8 Award winner 
8x Award winner
The best travel credit card is always a good place to start – the American Express Cobalt Card.
With this card, you’ll not only earn plenty of points, but get plenty of ways to redeem them for travel.
Here’s what you’ll earn:
- 5 points per $1 spent on eligible groceries and restaurants
- 3 points per $1 spent on eligible streaming services
- 2 points per $1 spent on eligible gas, transit, and ride share purchases
- 1 point per $1 spent on foreign currency purchases
- 1 point per $1 spent on all other purchases
But it’s also what your points are worth that matters here, and they’re worth quite a lot.
Here are your various travel redemption options, and what you can expect to get for annual rewards.
| Redemption Option | Value Of 1 Point | Annual Rewards |
|---|---|---|
| Transfer Points 1:1 To Aeroplan | Up to 2 cents | $1,080 |
| Fixed Points Travel Program | Up to 1.75 cents | $945 |
| Transfer To Marriott Bonvoy 5:6 | Up to 1.164 cents | $626 |
| Redeem For Any Purchase | 2 cents | $540 |
That’s a lot of rewards on your spending for an annual fee of $155.88.
Want to learn more? Here’s our full guide to the American Express Membership Rewards program.
2. The best flexible rewards credit card
×4 Award winner 
GC: $125 + $25
4x Award winner
If you want to keep it simple, the MBNA Rewards World Elite Mastercard will offer you plenty of points on purchase anywhere, including Costco.
Here’s what you’ll get:
- 5 points for every $1 spent on restaurants, groceries, and select recurring bills (up to $50,000 spent annually per category)
- 1 point per $1 spent on all other purchases
You can use your points to redeem for any travel booked through MBNA Rewards, where each point is worth 1 cent. Based on a typical $2,000 monthly spend, you’re looking at annual rewards of $686.4.
3. A flexible rewards credit card with savings on travel fees
The National Bank World Elite Mastercard offers more than just rewards – you’ll also get savings while on your trip.
First, the rewards you’ll earn on purchases:
- 5 points per $1 spent on groceries and restaurants
- 2 points per $1 spent on gas, electric vehicle charging, recurring bills, and travel booked through À La Carte Rewards
- 1 point per $1 spent on all other purchases
When redeemed for flights and vacation packages through NBC Rewards, you’re looking at annual rewards of $552, as each point is worth 1 cent.
But there’s more. Every year you have the card, you’ll receive a $150 travel credit that can be used towards the following:
- airport parking,
- baggage fees,
- seat selection,
- airport lounge access, and
- airline seat upgrades.
Use the full amount, and you’ve offset the $150.
Finally, if you travel through Montreal, you’ll get free access to the National Bank lounge in the international departures area.
4. The best Air Miles credit card
×1 Award winner GC: $150
1x Award winner
For many, collecting Air Miles is a part of shopping. So to make them go farther, getting the BMO AIR MILES World Elite Mastercard is a must.
Here’s what you’ll earn for miles on purchases:
- 1 Mile for every $12 spent
- 3x the Miles for every $12 at participating Air Miles partners
- 2x the Miles for every $12 spent at any eligible grocery, liquor, and wholesale stores
Based on spending $2,000 per month, you would add 2,448 miles to your account every year.
To make the most of your miles, you’ll want to use them for flights. And this card comes with a major perk in this regard. You’ll receive a 25% discount on the number of reward miles you need to redeem for a rewards flight, up to 750 miles saved.
And of course, you can also use them for any part of your trip for varying value – hotels, car rentals, and vacation packages.
5. A no annual fee travel credit card
For the person who prefers no annual fees, the Scotiabank American Express Card is an excellent choice.
It’s a Scene+ credit card, so here’s what you’ll earn for rewards:
- 3 Scene+ points per $1 spent at Sobeys, Safeway, FreshCo and more
- 2 Scene+ points per $1 spent on grocery, dining and entertainment, gas, daily transit, and select streaming services
- 1 Scene+ point per $1 spent on all other purchases
You can redeem them either through the Scene+ Expedia portal or for travel from any provider. Either way, your points are worth $1, and will give you around $348 in annual rewards.
Here are a few other no fee credit cards you can also take a look at.
No foreign exchange fee credit cards
If your trip takes you out of the country or you have to pay for parts of your reservation in foreign currency, you’ll want a credit card that charges no foreign exchange fees.
This way, you can save an additional 2.5% on these purchases, on top of the rewards you’re earning.
Here are a few different cards you can look at in this regard.
×1 Award winner GC: $60
1x Award winner
GC: $30
Are you planning on taking a vacation this winter?
These are simply some pointers of things to think about, and hopefully will make it easier to plan your own vacation next year.
Are you planning on taking a vacation this winter?
Share your plans in the comments below.
FAQ
What are some things to consider for planning a winter vacation?
There are a few things to consider when planning a vacation. These include things like what you want to do, how much you want to spend, and ultimately, where you want to go.
What is the best credit card to earn points to get a free vacation?
To earn the most points to get a free vacation, the American Express Cobalt offers plenty of points, and multiple high value ways to use them.
What are some winter vacation ideas?
Here are a few winter vacation ideas:
- pool and beach vacation in Mexico/Caribbean,
- golfing,
- amusement parks, and
- skiing/snowboarding.
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