Smart Family Holiday Planning: A Guide for Extended Families

Family Holiday Planning begins with clear priorities and a personal touch. You want to bring everyone together, from toddlers to grandparents, while keeping things fun and simple. This post helps you plan a holiday that fits all ages, tastes, and needs.

Start with Open Conversation 

You begin by talking. Ask what each family member dreams about. Maybe some want time on the beach. Others want museum visits or relaxing by the pool. You might also feel pressure to fit everything in. Keep this in view. Start with a group chat or video call. That way, you know what each person hopes for.

This gives a solid start. A short sentence adds light rhythm. And you already have a rhythm shift.



Choose Shared Goals 

When you move beyond chat, set shared goals. Do you want relaxation? Adventure? Time with cousins?

You can even let younger family members suggest ideas. That adds fun and buy-in.

It’s helpful to offer options:

• Quiet time by the sea
• A local history walk
• Shared cooking in a villa

That gives you variety. It also lets you plan time on your own or together. A question to spark action: What’s one thing each small group would love to do?

Build Practical Ground Rules 

Next, set simple ground rules. Agree on budgets. Decide whether families share one house or stay in nearby rooms. Check how meals work—self-cater or eat out. Set expectations for days when people might split up, or choose their own pace. That helps avoid tension.

A short sentence hits the rhythm. Keep most sentences keyword-free. Use active voice. Keep it simple.

Jamie Says:

“With extended-family bookings, clear chat and flexible calm help make special memories.”

Jamie, Managing Director, Jamie Wake Travel

Agree on the Best Time to Travel

Picking the right date can make or break your plans. Extended families often have school terms, work shifts, and personal commitments to juggle. Aim for a window that works for everyone, even if it’s not peak season. Off-peak times can save money and mean fewer crowds.

A shared calendar works wonders here. Each person can mark when they’re free, and you’ll quickly spot overlapping dates. Once you have a shortlist, weigh the weather, local events, and travel costs before locking it in.

Match Accommodation to Your Group Size

Your choice of accommodation will shape the holiday’s feel. For a close-knit experience, a large villa or holiday home can be perfect. Hotels with adjoining rooms work well when families want more privacy.

Think about whether self-catering or all-inclusive best suits your group.

Consider:

• Space for children to play without disturbing others
• Accessible rooms for anyone with mobility concerns
• Communal areas for shared meals and evening chats

Choosing well here keeps everyone comfortable and happy.

Selecting the Right Destination Together 

The destination must balance varied interests. If you have beach lovers and city explorers in one group, look for somewhere offering both. Family Holiday Planning often means thinking about easy transfers, safety, and nearby attractions.

When possible, choose a location with:

• A range of activities within short travel distances
• Shops, cafés, and restaurants nearby
• Easy public transport or transfer services

And remember—while the perfect spot might not exist, the best choice is one where everyone feels included.

Your Holiday is Protected Every Step of the Way

When you book through Jamie Wake Travel, you’re not just getting a holiday — you’re getting peace of mind. We’re proud members of Protected Trust Services, and we hold a full ATOL licence. That means your money, and your trip, are fully secure.

Every tailor-made holiday we arrange comes with:

• Supplier Failure Insurance – If one of your holiday suppliers stops trading, you’re covered.
• Scheduled Airline Failure Insurance – Protection if your airline faces unexpected issues before or during travel.
• ATOL Protection – If something happens to your travel company or airline, you’ll be refunded or brought home without extra cost.

These layers of protection mean you can focus on making memories, knowing that your booking is safe.

With Jamie Wake Travel, Family Holiday Planning doesn’t stop at picking the perfect hotel — it includes making sure you’re supported from the moment you book until you’re back home.

Destinations That Work for Every Generation



Planning a trip for a large family means finding places that cater to all ages. The destinations below offer variety, comfort, and plenty of ways to enjoy time together or apart.

Algarve, Portugal

The Algarve is a firm favourite for extended families. Golden beaches, charming villages, and sunny weather make it a safe and relaxed choice. From coastal walks to water parks, there’s something for every generation.

Hotel suggestion: Tivoli Carvoeiro

This cliff-top hotel offers stunning ocean views, spacious rooms, and family-friendly facilities. There’s a kids’ club for younger travellers, a serene spa for adults, and dining options that keep everyone happy. The location makes exploring the Algarve’s coastline easy and enjoyable.

We often have exclusive offers for Algarve hotels and packages, and we can tailor them to suit your group’s needs — just ask us for the latest deals when you’re ready to plan.

Lake Garda, Italy

For families who enjoy scenery, culture, and leisurely days, Lake Garda is a perfect choice. The lakeside towns are beautiful, and day trips to Verona or Venice add variety.

Hotel suggestion: Aqualux Hotel Spa & Suite Bardolino

This eco-friendly hotel blends comfort with wellness. There are multiple pools, a spa, and suites ideal for families. The central location in Bardolino means cafés, restaurants, and the lake are within walking distance.

We work with a wide range of suppliers who offer Lake Garda holidays for families of all sizes, so we can help you create a package that balances rest and exploration.

Orlando, Florida

If your group is ready for adventure, Orlando’s theme parks are unbeatable. While the kids dive into Disney magic, grandparents can enjoy gardens, museums, and relaxing poolside afternoons.

Hotel suggestion: Loews Sapphire Falls Resort

Located within Universal Orlando, this resort offers spacious rooms, a tropical pool, and a water taxi to the parks. It’s designed to keep everyone comfortable, with dining options and activities for all ages.

We can source special packages for Orlando holidays that combine flights, accommodation, and park tickets in one easy booking — making your Family Holiday Planning simple and stress-free.

Balancing Togetherness and Personal Space

One of the biggest challenges in Family Holiday Planning is keeping everyone happy without feeling tied together all the time. Large groups can benefit from a mix of shared activities and smaller, optional outings.

Plan for:

• Group days – beach trips, guided tours, or family meals.
• Split days – where smaller groups choose activities they enjoy.
• Downtime – so no one feels rushed or worn out.

Respecting personal space is just as important as sharing moments. Not everyone will want to be together every hour, and that’s okay. In fact, having that balance often makes the shared time feel more special.

It’s all about choice.

Mealtimes Made Simple

Food is often at the heart of family holidays, but it can be tricky with different tastes, budgets, and dietary needs in the mix. Think about mealtimes before you go. Will you eat out most days? Cook together in your accommodation? Or mix the two?

Some families enjoy setting a rota for cooking or deciding in advance which nights will be for group meals. This way, everyone gets a turn to relax while still enjoying shared moments around the table.

Where possible, book restaurants ahead — especially if you’re a large party. This avoids last-minute stress and ensures everyone gets a seat.

Keep Travel Days Smooth

Getting to and from your destination with a big group can be the most stressful part of the trip. The trick is to plan the journey just as carefully as the holiday itself.

Check flight times to avoid awkward layovers or late arrivals. Arrange transfers or car hire in advance, especially if you have young children or older relatives who prefer minimal waiting around. If travelling by train or ferry, consider reserving seats together for a more relaxed start and finish to the trip.

A well-planned journey sets the tone for the holiday — and gets everyone off to the right start.

Budgeting and Cost-Sharing Without Awkwardness

Talking about money early makes everything smoother. In Family Holiday Planning, clear cost expectations prevent misunderstandings later. Decide together what the main budget will cover — flights, accommodation, shared meals, and activities — and what will be down to individual spending.

Some families prefer to pool funds for certain expenses, like food shopping or day trips. Others keep everything separate and settle up as they go. There’s no one right way, but agreeing on it before the holiday helps keep the mood light.

Apps can make tracking shared costs simple. With a quick update each day, everyone knows where they stand without awkward end-of-trip calculations.

Activities for All Ages

The joy of extended-family travel is in creating moments everyone remembers. But not all activities suit all ages. The secret is variety.

For younger children:

• Pool games or kids’ clubs
• Theme park days
• Simple nature walks

For teenagers:

• Watersports or adventure parks
• Local market visits
• Cultural activities with an interactive twist

For adults:

• Wine tastings or cooking classes
• Historic sites and museums
• Spa afternoons

Mixing activities means everyone has something to look forward to. You might find the best memories come from unexpected moments — like a sunset stroll or a group picnic in a scenic spot.

More Destinations Your Whole Family Will Love

The right location can bring everyone together and still leave space for individual adventures. Here are more destinations that work beautifully for extended families.

Cornwall, UK

Cornwall is perfect if you want to avoid long flights but still enjoy stunning scenery. With its mix of sandy beaches, fishing villages, and coastal trails, it offers a relaxed pace and plenty of family-friendly attractions.

Hotel suggestion: The Headland Hotel & Spa, Newquay

This Victorian-style hotel sits above Fistral Beach and blends classic charm with modern comfort. It offers family suites, an award-winning spa, and direct beach access. The hotel’s restaurant focuses on fresh, local produce — ideal for sharing great meals together.

We often have seasonal offers for Cornwall getaways, and can arrange stays that suit groups of all sizes. Ask us for the latest deals when planning your trip.

Tenerife, Canary Islands

Year-round sunshine and a mix of activities make Tenerife a solid choice for extended families. You’ll find beaches, water parks, volcanic landscapes, and charming old towns all within easy reach.

Hotel suggestion: Bahia del Duque

Set in lush gardens by the beach, this resort offers a village-style layout with pools, restaurants, and plenty of activities. Its spacious rooms and villas work well for larger family groups, and there’s a kids’ club plus quiet spaces for adults.

We work closely with Tenerife suppliers to secure exclusive holiday packages, so let us know if you’d like to see our current options for this stunning island.

Dubai, UAE

For those seeking a mix of luxury, adventure, and cultural experiences, Dubai ticks all the boxes. From desert safaris to theme parks and incredible shopping, there’s something to entertain every generation.

Hotel suggestion: Atlantis The Palm

This iconic resort offers waterpark access, marine animal encounters, and a wide range of dining. The family suites are spacious, and the service is designed to make guests feel truly looked after.

We can create Dubai packages that combine flights, transfers, and accommodation for a smooth, stress-free experience. Ask us about offers that fit your travel dates and preferences.

Turning Plans into Memories

Family Holiday Planning is about more than picking a place and packing a suitcase. It’s about finding a balance between shared moments and personal space, giving everyone a say, and making sure every age group feels included. Whether you’re imagining sandy beaches, cultural city breaks, or a mix of both, the key is starting early, communicating clearly, and leaving room for flexibility.

At Jamie Wake Travel, we know that every family is different. That’s why we tailor-make holidays “as unique as you are,” backed by ATOL protection, Supplier Failure Insurance, and Scheduled Airline Failure Insurance. You can leave the hard work to us, or you can use our easy online search tool to build your own bespoke holiday — available on every page of our website.

If you’d rather sit back and let us do the planning, we’re only a call or message away. Ring us on 01495 400005 or use our holiday enquiry form to get started. We’ll bring your extended family together in the perfect way — so all you have to do is enjoy the memories.

Frequently Asked Questions