Multi-Generational Trips: My FAVORITE ideas to get you started!!

Does the thought of planning a multi-generational trip fill you with dread? Questions like…Where would we go? What would we do? How could we possibly find something EVERYONE is interested in?... often plague the planner of such trips. Together, let’s consider a few really great options for multi-generational trips…


A villa or vacation home rental might be the perfect escape for your family. With varied and plentiful options (think idyllic seaside homes, European castles, mountainside stunners, or even secluded private islands), your family can choose the setting that offers the best mix of scenery and activities for them. As a travel agent, I have access to a few suppliers that do not sell directly to the public, and let me tell you, the options available are stunning. Property amenities can include the usual (pools, hot tubs, firepits) to the unique (private chef or butler, game rooms, or outdoor sports courts). The varied locales ensure that no matter where you’d like to vacation, there is sure to be an amazing option for you and your family. Honestly, the hardest part of all would be choosing just one place to go!


For a relaxing and stress-free vacation, All-Inclusive Resorts really can’t be beaten. They provide a complete package for families of all sizes and ages, and the only decision required is which lovely amenity should we take advantage of today! Additionally, with food, drinks, and activities (on the resort) all included in the price, All-Inclusives are an easy way to take a vacation that has a clear cost associated with it. Most All-Inclusive Resorts are located in Mexico and the Caribbean, but there are a few sprinkled throughout other parts of the world. Keep in mind that the considerations for which All-Inclusive Resort best fits your unique family situation are vast: Do you want amazing food? Or a waterpark for the kids? Or late-night activities for the adults? Or easy access to the local town? With so many choices, it can be hard to narrow down the field and pick, but hey, that’s what I’m here for! I’d love to understand what you are looking for and provide advice on which property will offer the best experience for you and your family.


Not completely unlike an All-Inclusive Resort (but potentially packed with way more physical activity!!) a Dude Ranch might be an experience your family didn’t know they were missing! Ranches are spread throughout the middle of the USA, with options from Montana to Texas, and many places in between. Most Dude Ranches are no longer sparse endeavors with cowboy food and uncomfortable accommodations. Luxury upgrades mean you sleep and eat well after your day of horseback riding, hiking, fly-fishing, steer roping, or learning new skills. Some posh Dude Ranches even offer pools, saunas, and spa services, but all promise to leave your family wishing they had been a real, live cowboy in the days of the Wild West.


A cruise vacation can be the perfect multi-generational vacation option, as it means families unpack once, but get to see and explore multiple destinations. Cruising often brings to mind hulking ships pulling into Caribbean Island destinations and while not untrue, this is only one of the many varied Cruising options. Cruises are available in some pretty exotic destinations (think Asia, Antarctica, or the British Isles) if the typical Caribbean itinerary is not what you were hoping for. Additionally, some cruise lines offer much smaller boats, which means they can often access unique ports that large ships cannot get to. There are even private yacht or sailboat options that would give your family complete privacy and control over the itinerary and stops. Overall, cruising can be a great multi-generational trip, and with the varied choices available, each family is sure to find an option they love.


If adventure and far-flung places are more your family's speed, a fully guided family trip might be the ticket. Companies such as G-Adventures and Backroads, run active, family-friendly trips to destinations all over the world. Your family could journey to Africa, Japan, or Iceland knowing that all the logistics were being overseen by a knowledgeable guide. Most trips include a mix of hiking or biking, local cultural exploration, and always a healthy dose of amazing food. With small group sizes of approximately 16 people, depending on your family size, you could have a private tour or join other families for the adventure of a lifetime. If the thought of adventuring with your family sounds thrilling, please reach out… finding and presenting the best options based on your preferences and budget is what I’m here for!

Which option do you think your multi-generational family would most enjoy? Personally, I have a list of the amazing Villas and Vacation Home rentals I found while writing this post and I hope to talk my family into a trip in the coming year! Will 2024 be the year YOUR family starts a new, epic tradition of multi-generational travel? I’m confident you’ll never regret the time you spent or the memories you’ll make! If you’d like to consider what a multi-generational trip would look like for your family, please reach out… Let’s find an option that works for you!

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Multi-Generational Trips: a few ideas to consider

Could 2024 be the year your family starts a new, epic tradition of travel?