As I approach my milestone 60th birthday in April, I’ve been thinking about what kind of trip I’d like to take to celebrate. Ideally, I’d love to bring together multiple generations - our kids, grandkid, and my brother - for a trip filled with meaningful experiences. But when planning for a mix of ages, interests, and energy levels, finding the perfect destination can be tricky.
The best multi-generational travel destinations need to be immersive yet easy, offering a blend of adventure and relaxation, active experiences with cultural moments, and space for everyone to enjoy themselves in their own way.
Whether you’re planning a special birthday, anniversary trip, or a long-overdue family getaway, here are my top picks for destinations that work for all ages and travel styles.
1. Active & immersive river cruises with AmaWaterways & Avalon Waterways
Effortless travel with exciting activities for every generation
If I had to pick one of my favourite ways to bring family together in an easy yet exciting way, it would be a river cruise - specifically with AmaWaterways or Avalon Waterways. Unlike ocean cruises that can feel overwhelming with thousands of passengers, river cruises offer a much more intimate, immersive experience.
Both AmaWaterways and Avalon Waterways have fantastic itineraries that make them perfect for multi-generational travel. These cruises aren’t just about sitting back and watching the scenery pass by - they’re filled with activities like cycling through vineyard trails in France, hiking to medieval castles, chocolate workshop in Belgium (see pic) and kayaking along the Danube.
Why it works for families:
- Unpack once and enjoy different destinations without constant transfers.
- Excursions for every age group—bike tours and hikes for active travellers, cultural tours for history buffs, and wine tastings for adults.
- Spacious suites and interconnecting rooms so families can stay close but have their own space.
Tip: Consider AmaWaterways' "Christmas Markets on the Danube" for a festive family trip - it’s a magical way to experience the holidays together while exploring Austria, Germany, and Hungary.
2. Safari lodges in Africa: A bucket-list adventure for every generation
Wildlife, luxury, and unforgettable family moments
You already know I am obsessed with Africa so you had to expect it to be included! There’s something magical about seeing a herd of elephants crossing the plains at sunset or watching lions nap under an acacia tree - and sharing those moments with family makes it even more special. From the moment our granddaughter was born I have dreamt of the day I could take her on safari!
A luxury safari is surprisingly well-suited for multi-generational travel. Many high-end lodges in South Africa, Kenya, and Tanzania cater to families with private guides, shorter game drives for kids, and all-inclusive comfort.
Why it works for families:
- Malaria-free game reserves in South Africa and Tanzania make it easier for families with younger kids.
- No more than 6 in each safari vehicle so everyone has a Birds Eye view.
- Private safaris mean flexibility—no need to stick to rigid schedules.
- Many lodges offer special activities for kids, like wildlife tracking and cultural programs.
Tip: Book a lodge with a swimming pool and a family suite/tent—after morning game drives, kids can play while grandparents relax with a sundowner.
3. Hawaii: The ultimate no-stress island getaway that has never been so affordable
Beaches, volcanoes, and outdoor fun for all ages
Hawaii has long been a favourite for Canadian families, and for good reason. With stunning beaches, easy access with direct flights from Toronto and Vancouver, and a perfect mix of adventure and relaxation, it’s ideal for multi-generational trips.
Why it works for families:
- Resorts with villas provide space for the whole family without feeling crowded.
- Gentle activities for grandparents (like scenic drives and luaus) alongside thrills for kids (like snorkeling, surfing, and volcano hikes).
- Direct flights from Canada make it one of the easiest warm-weather getaways.
Tip: Skip the busy tourist spots and stay at a beachfront condo or private home on the Big Island or Maui for a more relaxed experience.
4. Villa stays in Europe: A home base for exploring together
Tuscany, Provence, or the Algarve—slow travel for the whole family
Rather than hopping from hotel to hotel, a villa stay in Europe is a fantastic way to keep the family together while allowing for independent adventures.
Why it works for families:
- A single home base means no constant packing and unpacking.
- Markets, vineyards, and historic towns offer plenty to explore without a packed schedule.
- You can hire a private chef or take turns cooking meals as a family.
Tip: Look for villas with pools, easy access to a small town, and multiple bathrooms - trust me, it makes a difference!
5. Japan: Surprisingly family friendly & ultra efficient
Temples, Sushi, and Bullet Trains—A fascinating mix of old and new
Japan might not be the first place you think of for multi-generational travel, but it should be! With its efficient transport, mix of cultural and modern attractions, and incredible food, it’s a fantastic choice for families.
Why it works for families:
- Bullet trains make travel effortless—perfect for avoiding long road trips.
- Temples, food markets, and theme parks mean everyone finds something they love.
- Japanese hospitality ensures a stress-free experience for all ages.
Tip: Get a Japan Rail Pass for unlimited train travel—it’s a game-changer for families!
Final tips for multi-generational travel success
Prioritize direct flights whenever possible. Layovers are exhausting for kids and older travellers alike.
Choose accommodations with extra space. Villas, connecting suites, or small cruise ships like AmaWaterways and Avalon make all the difference.
Plan meals ahead. A mix of restaurant meals and self-catering options ensures that everyone is happy.
Schedule downtime. Some travellers want to sight see all day, while others prefer an afternoon nap - build in flexibility.
Focus on shared experiences. The best part of multi-generational travel is the memories you create together - whether it’s spotting a leopard on safari, sharing a gelato in Florence, or watching the sunset over the Danube.
Where will you go next?
From African safaris to river cruises, Hawaii beaches to European villas, these destinations bring families together in the best possible way. If you’re thinking about your next big family adventure, I’d love to hear where you’re headed!
Have you ever taken a multi-generational trip? Where would you love to go next?
