Welcome to the sandwich generation! If you are the middle of the “sandwich,” you are caring for aging parents while also raising your own children. With three generations under your care, you have a lot of challenges, but thankfully, travelling as a group doesn’t have to be one of them. In fact, this large family dynamic can work in your favour!

Summer Shoes - Multi-generational travel

If you have young children, travelling with your parents gives you a built in babysitter. There are going to be times when you and your partner want to enjoy a little adult time on your vacation, such as a romantic stroll on a beach or a candlelit dinner for two. You also have an extra set of eyes and hands to keep the kids safe in busy theme parks or when playing in the ocean.

There are several types of vacations that make travelling as a large, extended family easy.

Multi-Generation Travel Tips:


Thanks to their need to sail with a full ship, you can book a full suite on a cruise ship for a very low cost through sites like vacationstogo.com. A cruise ship has something for everyone – pools and indoor play spaces for the kids; games, casinos, and musical entertainment for seniors; parties and classes for adults. When in port, there are a variety of excursions, such as on-shore cooking and dancing lessons, scuba diving, mini-sub exploration, and shopping in open air markets.

 With so much to do, see and experience, the whole family can disperse to do what they enjoy, but be under the same roof again that evening to compare notes over those famous cruise ship dinners.

disney magic exterior

Kids and parents alike love Disney. The Disney Magic embodies the Disney Cruise Line tradition of blending the elegant grace of early 20th century transatlantic ocean liners with contemporary design to create a stylish and spectacular cruise ship.  (Matt Stroshane, photographer)


Similar to cruise ships, all-inclusive family resorts have a host of activities for the young’uns, their parents, and the grandparents. Depending on the type of accommodations offered, you’ll find yourselves in a rental house or cabin, or in a lodge where you can get adjacent rooms, or a suite where the kids can have their own privacy (and so can the adults!). If one parent doesn’t like deep sea diving but the others (and the teens) do, that parent can indulge in beach volleyball or crafting with the grandparents while the other partner and kids peek at jellyfish and coral.

All-inclusive resorts have multiple dining locations, meaning grandpa can have his lobster feast on one night and the kids can have their fish and chips on another.

Escorted Tours:

If you don’t speak the language where you are but have an emergency, how can you get help? If you want to see a popular attraction but standing in line for hours will not be good for your kids or the grandparents, do you skip it? If your kids are young and you need a schedule so they can keep up with their meals and bedtimes, do you opt out of international travel? With escorted tours, you can have the vacation – and the peace of mind – you want.

Red Jeep Tours San Andreas Fault Palm Springs

Escorted tours come in all shapes and sizes, just like families! Adventuresome kids, parents and grandparents would love a desert tour in a bright red Jeep! 

If you have yet to discover the ease of travel that comes with escorted tours, you are in for a treat. Designed for every stage of traveller – those that need a guide for most of the day to those that just need someone and somewhere to check in with/to at the end of a day of solo exploration – escorted tours are a safety net when travelling internationally.  Your tour company often has preferred group access to attractions; can recommend the best places to dine (many supply most of the meals); chooses safe, clean accommodations; and allows downtime for solo exploration (or naps).

With escorted tours, all three generations can go beyond Canada’s borders with confidence. An added bonus? The tour packages save you hundreds when compared to booking fights, accommodations, attractions, and meals on your own.

There are pros and cons to being a sandwich middle, but when has being surrounded by a large, loving family ever been a bad thing in the long run? With a little advanced planning when booking the right trip, your loud, crazy, hyper, wonderful family can take all that joy on the road, together.