How to vacation like a VIP without spending a fortune

Two tickets to paradise

We’ll tip you off on the destinations where your dollars will go the farthest and how to take advantage of easy strategies that will stretch your budget.


Photo by Tom Byrom on Unsplash

There’s this misconception that travelling is expensive. But with a reasonable budget, two people can easily enjoy an epic adventure to some incredible destinations that will create lasting memories.

As someone who writes about both personal finance and travel, I’m often asked how much a vacation should cost. But that’s a personal choice. For some, spending $900 for a week-long vacation booked last-minute at an all-inclusive feels right. For others, a $9,000 on a luxury cruise through the Mediterranean is money well-spent.

There’s an almost endless range of prices when it comes to travel but in my experience, the sweet spot is about $5,000 per couple. With this budget, there’s no need to sacrifice comfort, and you can even enjoy a bit of luxury. It’s all about picking one of the destinations where your dollars go the furthest and taking advantage of some easy ways to save. Here are three top picks to get you started on plans for your next getaway.

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Portugal: An epic adventure on the cheap

One of Lisbon’s iconic trams, which have been getting residents and visitors around the city since 1873. (Photo: Barry Choi)

It may no longer be a hidden gem, but Portugal is still affordable compared to Spain, France and the U.K. This doesn’t mean you’ll get a lesser experience; in fact, when you come to visit, you’ll be wondering what took you so long.

There are multiple carriers that fly into Lisbon so prices can be competitive. You’ll pay about $500 to $700 from eastern Canada during the low season, but expect to pay closer to $1,000 in the summer. Once you’re on the ground, it shouldn’t be too hard to find a hotel or Airbnb for less than $150 CAD a night.

What makes Portugal appealing is its variety. You’ll most likely start in Lisbon, where you can soak in the culture and scenery from one of the city’s many lookout points. Explore the backstreets of Alfama and dine with the locals in the streets of Bairro Alto at night. Less than an hour away by train, the city of Sintra is home to multiple UNESCO World Heritage Sites such as the brightly coloured Pena Palace and the Castle of the Moors, which was built in the 8th and 9th centuries.

You won’t need more than a few days in Lisbon, so decide between the beaches to the south or culture to the north for your next destination. 

The southern coastline of Portugal is known as the Algarve. Where you stay depends on your travel style, but there’s everything from quiet retreats to bustling towns. While Lagos is the most popular overall, people travelling with children will be attracted to Praia da Luz, and Albufeira is for those who want to party. 

If you decide to head north, Porto is the next destination most people choose. Think of Porto as your home base and the gateway to the Douro Valley, where some of the best Portuguese wines come from. To get to the wineries you can rent a car, but many people prefer to book a tour that includes pickup from your hotel (try browsing the options at Another city worth a day trip is Braga which is close to Bom Jesus do Monte, a Portuguese sanctuary. You’ll need to climb 116 metres to get to the top, but it’ll be worth it as you pass by life-size statues that depict the day leading up to the crucifixion of Christ. (If you can’t or prefer not to do the walk, you can take the funicular instead.)

Food is relatively inexpensive and you really shouldn’t have an issue finding a nice meal for less than $20 CAD per person (much less if you’re grabbing food to go).

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Regina: Culture, food and the great Canadian outdoors

Regina’s Wascana Centre is larger than its more famous peers Stanley Park in Vancouver and Central Park in New York City. (Photo: Tourism Saskatchewan/Greg Haszar)

Many people put British Columbia, Ontario and Quebec on the top of their list when they want to travel within Canada, but Saskatchewan should be on your radar, too.

In Regina, the provincial capital, Wascana Centre is a star attraction. This 930-hectare park right in the middle of the city is larger than both Vancouver’s Stanley Park and New York City’s Central Park. Rent a Segway or kayak to tour the amazing green spaces, or check out the many attractions within the park. Start with a free tour of the Saskatchewan Legislative Building, where you can learn about the structure, which was completed in 1913, and the people who walked through its halls. Another free attraction (donations accepted) is the MacKenzie Art Gallery, where Picasso, Rodin and Munch represent among the more than 4,500 artworks. Especially if you’re travelling with dino-loving kids, you won’t want to miss Scotty, the world’s most massive T. rex, at the Royal Saskatchewan Museum.

One other attraction that’s a must-see is the RCMP Heritage Centre. Every officer is trained here and cadets hold a march every weekday at noon in the Sergeant Major’s Parade, which is open to the public. If you’re visiting in the summer, you can catch the Sunset Retreat Ceremony, a tradition that dates back to the 18th century.

As for where to sleep, the Hotel Saskatchewan is the best property in the city. Built by the Canadian Pacific Railroad to connect the people of Regina to the rest of Canada, the property preserves its history while offering modern comforts and service that is second to none.

While you’re in Saskatchewan, budget some time for Saskatoon. Head right for the Remai Modern, which has quickly become known as Canada’s modern art museum. It’s getting international recognition, too, as The New York Times featured it as one of their 52 places to go in 2018. 

For a look at 6,400 years of history, make the quick trip to the Wanuskewin Heritage Park, where you can learn about indigenous art, food, traditions and culture. The valley, which is currently shortlisted for UNESCO World Heritage List status (the first site in the province), hosts Han Wi-Moon dinners each month during the spring, summer and fall. The dinner combines a tour of the land with history, culture and food ingredients, such as chokecherry, dandelion greens and juniper, foraged from the valley below.

Speaking of food, Little Grouse on the Prairie is a popular local Italian eatery that cooks with Saskatchewan grains, while Black Fox Farm and Distillery is one of the few farm-to-flask distilleries in North America. 

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 St. Vincent and the Grenadines: Luxury within reach

Palm Island Resort & Spa sits in the middle of the Grenadines on a private island. (Photo: St. Vincent and the Grenadines Tourism)

Often thought of as a destination for the rich and famous, St. Vincent and the Grenadines is far from exclusive. You can find reasonably priced flights from Canada and plenty of value accommodations for a trip-of-a-lifetime experience without spending a fortune. 

Instead of booking an all-inclusive, look at hotels such as Beachcombers Hotel and Paradise Beach Hotel on the main island of St. Vincent, which are incredibly affordable and feel more like a home than a hotel. Both properties are steps from the beach, so you really can’t go wrong with either. If you’re looking for something a little more secluded and family-friendly, there’s the Bequia Beach Hotel located on Bequia island, an hour away from the main island by ferry. For those who prefer the all-inclusive experience, the Palm Island Resort & Spa sits in the middle of the Grenadines on a private island. 

Many hotels are available through Air Canada Vacations, in packages that also include flights. ACV frequently runs promotions, so it’s worth adding your name to their mailing list so you’ll be alerted when another deal comes up. The carrier only began offering year-round weekly flights in the summer and twice-weekly flights in the winter in 2017, so St. Vincent and the Grenadines is still well off the beaten path for Canadians.

You’ll need to fly into St. Vincent, so spend some time there before you start island-hopping. Here, you’ll be able to enjoy the capital of Kingstown and stunning botanical gardens which are the oldest of its kind in the Western hemisphere. For the best views, hike up La Soufrière volcano, or enjoy the two waterfalls of Dark View Falls.

As you can imagine, sailing, diving and eco-tourism adventures are the main draws regardless of where you’re staying; be sure to book an excursion to the Tobago Cays Marine Park, where you can snorkel through a protected wildlife reserve bordered by a horseshoe reef.

To get around the islands, you can book inter-island flights or take one of the ferries. You can also work with private companies, such as Fantasea Tours, that will help build your itinerary if you’re looking for something special.