Creating Unforgettable Multi-Generational Family Holidays

Bringing the whole family together for a trip is one of life’s greatest pleasures. From toddlers to grandparents, everyone shares in the memories, laughter, and stories that last for years. Planning truly memorable multi-generational family holidays means finding that perfect balance—where each person’s needs, interests, and comfort are taken into account. Done right, it’s an opportunity for everyone to enjoy quality time while still making space for individual moments.

Travelling with several generations doesn’t have to feel overwhelming. In fact, with the right approach, it can be more rewarding than you imagine. You get to celebrate milestones together, explore destinations at a shared pace, and watch bonds strengthen across ages.

And when your holiday is thoughtfully planned, everyone—from the youngest explorer to the most experienced traveller in the group—can have the time of their lives.

Planning Essentials for Multi-Generational Family Holidays

The secret to a successful trip with several age groups is thoughtful preparation. A well-planned itinerary makes the difference between a stressful getaway and one that flows naturally. Start by bringing everyone into the conversation early. This helps avoid misunderstandings and ensures that each person feels heard.

Create a shared list of must-haves and nice-to-haves. This could include activities, dining preferences, accessibility needs, and quiet spaces for rest. A family with young children may prioritise pool access and child-friendly dining, while grandparents might prefer cultural excursions or scenic train rides.

It’s worth thinking about pacing too. Instead of packing every day with activities, plan for a mix of group outings and relaxed downtime. This gives everyone the chance to recharge and enjoy moments at their own speed.

A realistic budget is another key part of the process. Agree on spending limits early, covering everything from accommodation to meals and activities. This avoids awkward conversations later and helps narrow down your destination choices.

When everyone is involved in the early stages, your itinerary becomes a reflection of the whole group’s interests, not just one or two voices. That shared sense of ownership can make the holiday even more meaningful.

Increasingly, parents are planning to travel with both their children and grandparents, as multi-generational holidays grow in popularity and offer something meaningful for every age group.

Choosing the Right Destination for Multi-Generational Family Holidays

Finding a destination that works for everyone is often the biggest decision of the planning process. The best multi-generational family holidays strike a balance between adventure, relaxation, and accessibility. You want somewhere with enough variety to keep different age groups engaged, yet manageable so no one feels left out.

Think about climate first. While sunny beach escapes are tempting, very young children and older relatives may prefer milder temperatures or destinations with shade and indoor options. Locations with a blend of natural beauty and modern amenities often work well, offering both outdoor activities and comfortable retreat spaces.

Travel time matters too. Long-haul flights can be challenging for toddlers and tiring for older travellers. Direct flights, shorter transfer times, or even UK-based breaks can make the journey part of the fun rather than a test of patience.

Safety and infrastructure should be on your checklist. Look for destinations with reliable healthcare facilities, family-friendly transport, and easy-to-reach attractions. Cities with walkable areas or resorts with everything on-site can simplify logistics and reduce stress.

Finally, don’t underestimate the charm of places with cultural depth. From small coastal villages to historic cities, destinations that encourage exploration can appeal to both curious youngsters and seasoned travellers. The shared discovery becomes a highlight in itself.

Accommodation Choices That Bring Everyone Together

Where you stay can make or break a multi-generational trip. The right accommodation isn’t just about beds and bathrooms — it’s about creating a comfortable base where everyone feels at home.

Villas are a popular choice for multi-generational family holidays because they combine privacy with shared living spaces. You can gather for breakfasts on the terrace, enjoy your own rooms for downtime, and even cook meals together. Many villas come with private pools, which are ideal for keeping younger travellers entertained while adults relax nearby.

Resorts offer the convenience of on-site dining, entertainment, and activities. Large properties often have kids’ clubs, teen lounges, and adult-only areas, giving each generation its own space to unwind. Look for resorts with accessible facilities so everyone can move around comfortably.

Hotels can work well too, especially in urban destinations. Booking adjoining rooms or suites gives families flexibility while keeping everyone close. Some hotels now specialise in family stays, offering cots, bottle warmers, and even babysitting services.

Self-catering apartments are another versatile option, especially for longer stays. They allow families to maintain familiar routines — a big plus for those travelling with babies or toddlers.

The key is to match accommodation style with your group’s priorities. Is it about convenience, privacy, or shared experiences? When that choice is right, your holiday feels effortless from the start.

Planning Activities for All Age Groups

The magic of multi-generational family holidays lies in shared moments. Yet those moments are easier to create when the schedule has something for everyone. Start by identifying activities that can be enjoyed together, then sprinkle in options tailored to specific age groups.

Group-friendly activities might include gentle boat trips, scenic walks, guided tours, or cooking classes where everyone can participate. These shared experiences often spark the best stories to retell at dinner.

For younger children, playgrounds, splash parks, and interactive museums keep energy levels high in a positive way. Teens may gravitate towards water sports, zip-lining, or exploring local markets. Adults might appreciate wine tastings, cultural performances, or a quiet afternoon in a spa.

A good approach is to plan mornings for active pursuits and afternoons for relaxation. This rhythm keeps energy balanced across the group. It also allows people to opt in or out without disrupting the rest of the day.

Don’t be afraid to build in “free time.” It’s in those unplanned hours that you’ll often find the most memorable moments — whether it’s an impromptu card game on the balcony or a stroll to a local café.

And remember: not every day needs to be full. The right blend of activity and rest makes the whole holiday more enjoyable for everyone.

Inspiring Destinations for Multi-Generational Family Holidays

Finding a destination that works for the whole family can be exciting once you start matching places with your group’s personality. Here are a few destinations that blend variety, comfort, and that special something which makes multi-generational family holidays unforgettable.

Tenerife – The Ritz-Carlton, Abama

Tenerife offers year-round sunshine, a friendly atmosphere, and attractions for every generation. The Ritz-Carlton, Abama sits on a clifftop overlooking the Atlantic, with lush gardens and direct access to a golden beach. Families will love the choice of swimming pools, the Ritz Kids programme, and the range of dining options from casual bites to Michelin-starred experiences. Golfers, spa lovers, and water-sports enthusiasts will all find something to enjoy without leaving the resort.

At Jamie Wake Travel, we have access to an impressive range of Tenerife offers, including family packages and seasonal specials. Speak to us to explore the latest deals and tailor a stay that suits your group’s needs.

Cornwall – Fowey Hall Hotel

For those who prefer to stay in the UK, Cornwall delivers coastal charm, fresh seafood, and stunning views. Fowey Hall Hotel combines historic elegance with family-friendly amenities. Overlooking the Fowey estuary, it offers spacious rooms, a children’s play area, and a spa for the grown-ups. The surrounding area is perfect for beach days, boat trips, and exploring charming fishing villages.

We can help you arrange a stay at Fowey Hall Hotel as part of a bespoke UK package, complete with travel arrangements, activities, and local experiences to make your time in Cornwall unforgettable.

Florida – Disney’s Grand Floridian Resort & Spa

Florida is a dream for families, and Disney’s Grand Floridian Resort & Spa adds a touch of luxury to the magic. With monorail access to the Magic Kingdom, elegant Victorian-style décor, and activities for all ages, it’s a perfect base for theme park adventures and poolside relaxation. Multiple dining options, character breakfasts, and a full-service spa mean no one misses out on the fun.

Jamie Wake Travel can secure exclusive offers for Florida family holidays, from park passes to room upgrades, ensuring your trip is as magical as possible.

Greece – Daios Cove Luxury Resort & Villas, Crete

Set in a private bay with spectacular views, Daios Cove is ideal for families wanting both privacy and first-class service. The villas and suites are spacious, many with private pools, and the resort offers a kids’ club, water sports, and a wellness centre. Dining is varied, with Greek specialities and international cuisine to suit all tastes.



We work closely with suppliers to secure competitive packages for Crete, whether you want a fully catered villa or a flexible half-board option at Daios Cove.

Italy – Borgo Egnazia, Puglia

Puglia’s sun-soaked coastline, whitewashed towns, and delicious cuisine make it a favourite for family getaways. Borgo Egnazia is a beautifully designed resort that feels like a traditional Italian village. It offers swimming pools, a beach club, a spa, and dedicated kids’ and teens’ clubs. The spacious villas give everyone room to spread out, while the cobbled lanes and gardens make the resort a joy to explore together.

We can arrange exclusive packages for Borgo Egnazia, from private transfers to dining experiences that showcase Puglia’s culinary traditions.

Portugal – Martinhal Sagres Beach Family Resort

Perched on the Algarve coast, Martinhal Sagres is built with families in mind. Its modern villas and townhouses have sea views, and the resort features multiple pools, kids’ clubs, sports academies, and even a babysitting service. The sandy beach is just steps away, perfect for days spent building sandcastles or trying paddleboarding.

Ask us about our current Portugal offers, including flexible dining options and activity packages at Martinhal Sagres Beach Family Resort.

Thailand – SAii Laguna Phuket

Thailand combines exotic scenery, friendly locals, and rich cultural experiences. SAii Laguna Phuket sits along Bang Tao Beach, offering direct access to golden sands and calm waters. The resort includes family rooms, a kids’ club, and easy access to island-hopping excursions. Adults can enjoy beachfront dining and spa treatments while the younger members of the family try Thai cooking classes or water sports.

We can tailor a Thailand itinerary that includes SAii Laguna Phuket as part of a wider adventure, complete with internal flights and guided experiences.

Peace of Mind When You Book with Jamie Wake Travel

One of the biggest advantages of booking multi-generational family holidays with Jamie Wake Travel is knowing that every trip comes with built-in protection. We’re members of Protected Trust Services (PTS), which means all customer payments are held securely in a trust account until your holiday is delivered. This gives you complete financial security from the moment you book.

We also hold an ATOL licence, so if your holiday includes flights, you’re covered by the UK’s most recognised travel protection scheme. Should anything happen to your airline or travel provider before or during your trip, ATOL ensures that you’re not left out of pocket and can either continue your holiday or return home without extra costs.

Every tailor-made holiday with us includes Supplier Failure Insurance and Scheduled Airline Failure Insurance. This means that even if a supplier unexpectedly ceases trading, your arrangements are protected, and we can secure suitable alternatives without added stress.

By combining our personal travel service with these protections, we make sure your holiday is not only memorable but also worry-free. You can focus on enjoying your time together while we take care of every detail behind the scenes.

Tips for Smooth Multi-Generational Family Holidays

A successful trip with several generations comes down to planning and flexibility. Here are some tried-and-tested tips to keep your holiday running smoothly from start to finish.

• Appoint a trip organiser – Having one person oversee communications, collect preferences, and keep track of bookings avoids confusion.
• Mix group and solo time – Allow for moments where people can do their own thing, whether it’s a morning walk or an evening out.
• Build in rest days – Avoid scheduling activities every single day. Downtime keeps everyone refreshed.
• Plan for different meal needs – Check dining options in advance, especially if your group includes vegetarians, vegans, or those with food allergies.
• Think about accessibility – Ensure accommodation and excursions are manageable for grandparents or anyone with mobility considerations.
• Set realistic expectations – Not everything will go to plan, and that’s okay. A little flexibility goes a long way.
• Bring entertainment for the journey – Books, games, and downloaded films can make long transfers or flights more pleasant for everyone.
• Share responsibilities – From keeping an eye on children to organising snacks, spreading the load makes the trip easier for all.

Jamie Says:

“When I help families plan multi-generational holidays, I always look for destinations and accommodations that give everyone the freedom to enjoy their own moments while still coming together for shared experiences. Those little pockets of connection — a beach walk, a late-night chat on the balcony — are what people remember most.”

Your Next Family Adventure Starts Here

Bringing the whole family together for a shared holiday is a rare and special opportunity. With the right destination, comfortable accommodation, and a thoughtful itinerary, multi-generational family holidays can become the stories you talk about for years. It’s about finding that sweet spot where everyone’s needs are met — and where the laughter comes easily.

At Jamie Wake Travel, we’re here to make that happen. Whether you want us to design your holiday from the ground up or prefer to explore and book through our website’s search function, we’ll ensure your trip is as unique as you are. Every page of our site gives you the tools to build your own bespoke holiday, but we’re only ever a call or message away if you’d rather leave the planning to us.

From ATOL protection and Supplier Failure Insurance to our network of trusted suppliers, we handle the details so you can focus on enjoying your time together. All you need to do is gather your loved ones and decide where you’d like to go.

If you’re ready to start planning, call us on 01495 400005 or use our holiday enquiry form on the website. Your next family adventure is waiting — let’s make it one to remember.

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