Five Destinations That Work for Three Generations at Once

A beautiful street in Lisbon

Most destinations are wonderful for one generation and hard work for another.

A lively beach town is fun at thirty and exhausting at seventy. A big kids resort is perfect with a five year old and a long week without one. A hiking destination is brilliant if you're fit, and miserable if your knees aren't what they were.

But some places work for every age at once. These are the five I come back to most for three generation trips.

1. The Italian Lakes

Lake Como is known for glamour and Lake Garda for activity. What people don't always realise is how well both work for every generation together.

The children get boat rides, lake swimming and gelato in every town. Teenagers can try sailing, kayaking or windsurfing on Garda. Parents get cycling, walking, wine and some of the best long lunches in Europe. And grandparents get views they can enjoy from a terrace, small towns to wander at their own pace, and a boat to take them everywhere, with no hiking required.

The best hotels here have quiet corners, excellent restaurants and rooms that suit older guests. Nobody is bored, and nobody is overwhelmed.

2. Portugal

Portugal gives you beauty, brilliant food and a gentler pace than much of Europe.

Lisbon is hilly, so I always build in a driver or a tuk tuk for anyone who needs it. The trains between Lisbon and Porto are comfortable and easy, so nobody has to do the driving. And the Algarve has beautiful beaches with quieter stretches, and resorts that take room placement seriously.

The food suits everyone too. The children can have their pasta, Grandpa can have his grilled fish, and the parents can have a proper dinner.

3. Spain

Spain has been welcoming families for a very long time, and it shows.

Barcelona has enough energy for teenagers and enough culture for the adults, with a beach at the end of the day. The Costa Brava, away from the busier resorts, has small walkable towns, lovely coves and boutique hotels that suit a family group far better than a sprawling resort. And Andalusia, with Seville, Granada and Córdoba, is wonderful for a trip built around the older generation. It's cultural, it's beautiful, and the late Spanish rhythm of long lunches and evening walks suits grandparents better than you'd think.

The secret is choosing the right town and the right hotel, which is where local knowledge matters.

4. Costa Rica

From California, Costa Rica is a manageable flight, which matters when you have grandparents and small children in the same row.

The pace is relaxed. The nature is extraordinary, and you don't need to be especially fit to see it. Sloths, monkeys and scarlet macaws can all be spotted on an easy walk with a good guide. The key is a split stay where best lodges and resorts combine the rainforest and the beach, so you get adventure for the children and a hammock for everyone else.

5. The Caribbean

Sometimes the right answer is simple: beautiful beach, reliable weather, and a resort that does everything well.

Turks and Caicos is calm and quiet, with some of the best beaches anywhere and resorts that are used to families of every age. St Lucia has more drama and personality, with the Pitons, rainforest and some very special hotels. And the Bahamas are a short flight from the East Coast, which makes them easy for grandparents flying in from elsewhere.

None of these are adventure trips. They aren't meant to be. They're places where three generations can simply be together.

What they have in common

The destinations that work for three generations aren't extreme in any direction. They aren't party towns or endurance adventures. They aren't so packed with culture that someone is worn out by lunchtime, or so built around children that the adults feel managed.

They have good food, a gentle pace and enough variety that everyone finds something. And, most importantly, they have hotels and villas that suit a family group: ground floor rooms, quiet corners, early and late dining, and activities that run at the same time.

Choose the destination first. Then choose the property very carefully. That's where the trip is made. Also these are not the only options for multigenerational travel.

If you'd like help with both, you can work directly with me here.

Quick answers

What is the best destination for a multigenerational trip? The Italian Lakes, Portugal, Spain, Costa Rica and the Caribbean all work well because they combine good food, a gentle pace and hotels suited to every age. That is not to say a trip to London, Scotland and Ireland cannot also deliver what everyone wants.

Is Europe good for a trip with grandparents and grandchildren? Yes, if you choose one or two bases rather than rushing between cities, and book hotels with lifts and ground floor rooms.

What makes a destination multigenerational friendly? A relaxed pace, easy travel between places, food everyone enjoys, and properties with separate spaces for different ages.