My parents tell my teenage son to, “go for it.” And, grinning broadly, he does. It’s a short run and then a sky-kicking jump as he leaps off the cliff at the “blue hole” at Island Gully Falls in Jamaica. His landing is an Olympic 10-worthy splash in the water below.

Now, all eyes are on me. I shrug, run, jump and fall with a flop into the water below before emerging, arms raised, to cheers.

Our brood of six includes my husband, our kids and my parents, and most days of this multigenerational vacation have been a combination of adventure, relaxation and fun—exactly as we’d hoped. Our goal was to find a vacation spot with activities to keep everyone engaged, while protecting the family budget. And, unlike the Rolling Stones’ tune, during Caribbean shoulder season, you can always get what you want.

Opting to vacation in the spring or fall has become a bit of a ritual for my family. And while Jamaica’s off-peak season includes the summer (running, for the most part, from May to mid-December), if you can take the heat, you’ll avoid the crowds by opting to pop in on either side of the winter crush.

Montego Bay, photograph by Lucky Photographer/iStock.

Rates on accommodations and activities can drop as much as 20 per cent in shoulder season, making it a good choice when you’ve got one eye on a beach vacation and the other on your finances. Of course, you’ll need to weigh your September and October trips against the region’s hurricane season.

The one wrinkle in off-peak travel is that it can mean taking the kids out of school, but we’ve found that a quick getaway, strategically planned around teachers’ professional development days, can keep absences to a minimum.

In Jamaica, families with young kids might want to consider all-inclusive resorts, such as Moon Palace, which offers a surf simulator on property but also puts you in close proximity to off-resort adventures such as horseback riding on the beach or climbing the famous Dunn’s River Falls.

In Ocho Rios, we opted for a home rental ( is one booking site) and found the costs were reasonable for a multigenerational trip. Plus, there is no shortage of activities in the area: try out the ATVs, cooking classes and Segway tours at Yaaman Adventure Park.

Our family opts to do it all, but also saves time for slower days filled with small group tours, swigging bottles of Ting on empty beaches, mid-day hammock swings and long, sun-weary family dinners. Unanimous grins tell the story of a budget-friendly vacation mission accomplished.

Shoulder-Season Solutions for Families

Marigot Bay Resort and Marina, photograph courtesy of Marigot Bay Resort and Marina.

Saint Lucia

Stay at Marigot Bay Resort and Marina, located on the western side of the island, where you’ll find complimentary daily activities that range from yoga and facial scrub-making classes to mini-massages for the whole family.


The Newstead Belmont Hills Golf Resort & Spa offers suites with balconies or terraces, a garden where kids can play and a seasonal shuttle service to nearby Coco Reef Beach. The resort offers complimentary transportation into Hamilton, the capital.

Cayman Islands

South Bay Beach Club offers quick access to the award-winning Seven Mile Beach and fully serviced apartments with kitchens and in-suite laundry. There are shops, water sports and car rentals within walking distance of the property.

[This story appears in the September 2019 edition of WestJet Magazine.]