Practical Tips for Group Holidays That Everyone Will Enjoy

Travelling with a large group is one of the best ways to share unforgettable moments, and it’s where great memories are made. But without a few smart steps in place, even the most exciting trip can feel stressful. That’s why having practical tips for group holidays makes all the difference. With the right approach, you can keep the planning simple, avoid unnecessary conflict, and ensure everyone enjoys the journey as much as the destination.

Why Planning Group Holidays Needs Extra Care

A group holiday has its own unique rhythm. Unlike travelling solo or as a couple, there are more personalities, preferences, and priorities to balance. The bigger the group, the more potential there is for both joy and frustration.

The good news? A little structure helps. You don’t need a complicated plan, but you do need a shared understanding. Everyone should feel heard before any bookings are made. This step might sound obvious, yet it’s often skipped.

When people agree early on, they’re more relaxed later. That means fewer arguments when it comes to money, activities, or even who gets the best bedroom in a villa.

So, take the extra time. It makes the whole trip smoother and far more enjoyable.

Start with Clear Conversations

Before diving into flights and accommodation, gather everyone together — even if it’s just a quick video call. Talk through the essentials:

• Budget – Set a realistic range so nobody feels left out.
• Destination type – Beach, city, ski, adventure? Keep the discussion open.
• Travel style – Relaxed and slow-paced, or full of activities?
• Dates – Match calendars early to avoid last-minute clashes.

This isn’t about making everything perfect. It’s about building a shared picture. One person may want luxury while another prefers budget-friendly. Talking it through avoids surprises later.

A simple tip: write everything down in a shared document or group chat. That way, agreements don’t get lost.

Clear conversations also create excitement. People feel invested because their voices are part of the plan. And when travellers feel included, they’re more likely to compromise later if needed.

Tips for Group Holidays When Choosing the Destination

Picking the right destination can set the tone for everything else. It’s not just about where looks beautiful on Instagram. It’s about what will actually work for your group.

Ask yourself:

• Is it affordable for everyone?
• How long will travel take?
• Does it offer enough variety to keep different interests happy?
• Is it accessible for all ages or anyone with mobility needs?

For some groups, a short-haul city break in Europe might be ideal. For others, a beach resort where everyone can relax without too many logistics works best.

You don’t need to satisfy every single wish. Instead, aim for a destination that offers balance. If half the group loves history and the other half just wants sunshine, somewhere like Lisbon or Barcelona can tick both boxes.

And remember, excitement builds when the choice feels inclusive. Share a shortlist, ask people to vote, and let the majority decide. It’s a fair and transparent way to keep everyone engaged.

Accommodation Matters More Than You Think

Where you stay can make or break a group holiday. The right choice creates comfort and connection, while the wrong one leads to stress. When booking accommodation for several people, it’s not just about price — it’s about space, flexibility, and convenience.

Here are a few popular options to consider:

• Private villas – Perfect for groups who value privacy and want shared living spaces.
• Hotels or resorts – Great when you want services like restaurants, spas, and organised activities.
• Apartments – Often budget-friendly and give a homely feel with kitchens for self-catering.
• Chalets or lodges – Ideal for ski trips or countryside retreats where everyone wants to be under one roof.

A villa works well for groups who like to cook together and enjoy evenings on a terrace. Resorts are better if you want entertainment on-site and dining sorted for you.

The key is matching the property to the group’s personality. A family gathering may love a spacious villa, while friends on a shorter break might prefer the facilities of a modern resort.

Tenerife Villas for Large Families

Tenerife is one of the most reliable destinations for sunshine all year round, and it has an impressive selection of villas built for larger groups. Many properties feature private pools, outdoor dining areas, and plenty of bedrooms so everyone has their own space. Staying in a villa also means you can set your own pace, whether that’s lazy mornings by the pool or a family-style barbecue at night.

We often have a wide range of villa offers for Tenerife, and our team can advise you on the best choice to suit your group’s budget and style. Ask us about the latest options, and we’ll find something that fits perfectly.

All-Inclusive Resorts in Turkey

Turkey is known for its excellent value and generous all-inclusive resorts. Large groups love the convenience of knowing food, drinks, and entertainment are all taken care of. Resorts in Antalya and Bodrum are especially popular because they combine sandy beaches with excellent facilities like waterparks, spas, and family-friendly shows.

If your group includes a mix of ages, an all-inclusive resort keeps things simple. Younger guests can enjoy the activities while adults relax by the pool or take a trip to the local markets.

Jamie Wake Travel has access to a variety of resort offers in Turkey, so if your group prefers all-inclusive comfort, we can present you with the latest deals.

Ski Chalets in France

For groups who thrive on adventure, ski chalets in the French Alps are a brilliant choice. They’re designed for communal living, with cosy lounges, log fires, and easy access to the slopes. Some chalets even include catering, so you don’t have to worry about cooking after a long day skiing.

Group ski trips are a bonding experience, and having everyone in the same chalet makes it even more special. Plus, staying together often works out more affordable than booking individual rooms in separate hotels.

We’re able to share current chalet deals across top resorts in France, so if your group is considering a ski holiday, ask us for the best offers available now.

Tips for Group Holidays on Managing Money Smoothly

Money is one of the biggest reasons group trips fall out of sync. People often have different ideas about what’s reasonable to spend, and unspoken expectations can create tension. The solution is to make money a clear topic from the start.

One simple way is to set a shared budget. This doesn’t have to mean everyone pays the same amount, but it gives a framework for decisions. If the group agrees that meals should average £20 per person, it avoids anyone suggesting a pricey restaurant that feels uncomfortable for others.

To keep things smooth, consider these tools and ideas:

• Shared expense apps – Apps like Splitwise or Revolut make dividing bills straightforward.
• Group kitty – Collect a set amount from each person for basics like snacks, taxis, or tips.
• Agreed payment system – Rotate who pays, then settle up later to avoid awkward card shuffling at restaurants.

It’s not about tracking every penny. It’s about making sure nobody feels taken advantage of. A little clarity goes a long way.

Balancing Together Time and Personal Space

One of the most important tips for group holidays is recognising that not everyone needs to do everything together. In fact, a bit of freedom is healthy.

If the group spends every minute together, small annoyances quickly grow. That’s why downtime is so valuable. Encourage people to break into smaller groups or take solo time when needed.

For example, while some enjoy a guided tour, others might prefer a quiet afternoon at a café. Later, everyone can come back together for dinner and share stories from their day.

To make it easier, plan in advance which activities are “must-do” for the group, and which are optional. This balance means there’s no pressure and no guilt if someone wants to sit out.

Giving people space doesn’t weaken the group dynamic. It strengthens it, because everyone gets to enjoy the holiday in their own way.

Getting Around as a Group

Transport can be surprisingly tricky when you’re travelling with more than a few people. The goal is to make it simple and stress-free.

Private transfers are often worth the cost. Arriving at the airport and seeing a driver ready to take everyone together removes confusion. For shorter trips, hiring a minibus is another practical option. It means no waiting around for multiple taxis, and everyone arrives at the same time.

If your group prefers flexibility, hiring a few cars might be better. This allows smaller groups to explore at their own pace while still meeting up later. For city breaks, public transport often works well, especially if you buy group passes.

One smart move is to assign a “travel lead” who keeps track of times and bookings. This stops everyone from relying on one person and avoids the chaos of ten people trying to flag taxis at once.

Transport isn’t just about getting from A to B. It’s about keeping the group relaxed and moving smoothly, so energy stays focused on enjoying the trip.

Tips for Group Holidays With Food and Dining

Food is often the highlight of a holiday, but it can also be a source of stress when travelling with a group. Different tastes, dietary needs, and budgets can make dining decisions tricky. The good news is, with a little planning, meals can be one of the most enjoyable parts of the trip.

Start by asking if anyone has dietary requirements. Knowing this early avoids awkward moments at the table. Once that’s clear, you can look for restaurants that suit everyone. In popular destinations, it’s worth booking ahead — especially for large groups. Many restaurants are happy to prepare for bigger parties if they know in advance.

Self-catering is another great option. Cooking together in a villa or apartment can be just as fun as going out. A group barbecue or shared breakfast is often more memorable than a formal dinner. Plus, it keeps costs down.

Mix it up. Alternate between dining out and staying in. This keeps everyone satisfied and ensures meals don’t eat up too much of the budget.

Keeping Activities Flexible and Fun

Activities can bring people together, but over-planning can wear a group out. The best approach is to build a framework, not a strict schedule.

Make a shortlist of group-friendly activities. Think boat trips, wine tastings, cooking classes, walking tours, or beach days. Then, allow room for spontaneity. People might stumble upon a local festival or decide to spend the afternoon exploring markets.

One tip is to plan one “big” activity every couple of days. This gives the group something to look forward to without packing every day with obligations. Smaller optional activities can fill the gaps.

Flexibility also helps avoid conflict. If someone doesn’t fancy joining in, they don’t hold others back. Over time, these smaller choices keep the atmosphere light and enjoyable.

Remember, the goal isn’t to tick off a checklist. It’s to enjoy being together while giving each person the freedom to shape their own experience.

Protecting Your Holiday with Jamie Wake Travel

When organising a group holiday, peace of mind matters just as much as the destination itself. That’s why booking through Jamie Wake Travel gives you more than just choice — it gives you security.

Every tailor-made holiday we create includes Supplier Failure Insurance and Scheduled Airline Failure Insurance. This means that if a hotel, airline, or supplier were to stop trading, your holiday remains protected. You won’t lose your booking or your money.

We’re also proud members of Protected Trust Services (PTS) and hold an ATOL licence. These safeguards ensure your money is kept secure in a trust account until it is passed to the suppliers, giving you financial protection that online DIY bookings often lack.

For groups especially, this protection is essential. With multiple people involved, the financial commitment is higher, and unexpected problems could affect everyone. Knowing your holiday is backed by these protections takes the worry away, so you can focus on making memories.

In addition to our own protections, you can also check the latest destination advice via the UK government’s FCDO travel advice service to stay informed and safe before you go.

Jamie Says:

“From my experience, the best group holidays happen when people don’t try to control every detail. Give the trip structure, but leave space for those unexpected moments that often become the highlight. That’s where the real joy of travelling together shines through.”

Jamie Wake, Managing Director of Jamie Wake Travel

Why Use a Travel Agent for Group Holidays?

Planning a group holiday on your own takes time, and it can quickly become overwhelming. Coordinating flights, accommodation, transfers, activities, and payments for multiple people is no small task. That’s where a trusted travel agent like Jamie Wake Travel makes a difference.

We remove the stress by managing the details for you. Our access to a wide range of suppliers means more choice at better value, and our ATOL and PTS protection ensures peace of mind. For groups, the benefit is clear: you get expert support, exclusive offers, and one point of contact from start to finish.

Instead of juggling endless group messages about logistics, you can focus on enjoying the trip while we handle the rest.

Your Group Holiday, Tailored Your Way

A group holiday should be exciting, not exhausting. By using these tips and letting Jamie Wake Travel guide the planning, your group can enjoy the journey without the stress.

Whether you’d like us to design a tailor-made trip or prefer to create your own holiday using the search function on our website, the choice is yours. Every bespoke booking is “as unique as you are.”



You can call us today on 01495 400005 or use our online enquiry form to start planning. And if you’d rather leave the details in expert hands, we’re only a call or message away. With Jamie Wake Travel, your next group holiday is closer than you think.

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