Group Holidays Made Easy: Tips and Destinations

Travelling with friends, family, or like-minded travellers can turn an ordinary getaway into an extraordinary experience. But let’s be honest — group holidays come with their own set of challenges. From coordinating schedules to finding accommodation that suits everyone, it can feel like a puzzle. That’s where we come in.

At Jamie Wake Travel, we specialise in crafting tailor-made group holidays that take the stress away and put the fun back into travelling. As a member of Protected Trust Services, you’ll also have complete peace of mind that your money is 100% protected.

Why Choose Group Holidays?

There’s something special about sharing a holiday with people you know. Whether it’s a reunion, a birthday celebration abroad, a hen or stag do, or just a group of friends craving some sun, group travel brings shared memories and new experiences.

A group holiday gives you the chance to:

• Share costs and save money
• Enjoy exclusive group perks
• Strengthen bonds with the people you care about
• Explore destinations in a way that solo travel doesn’t allow

You can also leave the planning to someone else — like us.

Jamie Says:

“Group travel isn’t just about where you go — it’s about who you go with. We take pride in understanding what makes a great group holiday work, from start to finish.”

What Makes Group Holidays Work

The secret to stress-free group holidays lies in preparation. These are some of the key things to keep in mind:

1. Agree on the Basics Early

• Destination
• Budget
• Travel dates
• Preferred pace (relaxing vs action-packed)

A shared WhatsApp or group chat can help gather opinions. Once you’ve got a consensus, we can start building your ideal trip.

2. Choose Accommodation That Works for Everyone

Hotels, villas, apartments — each has pros and cons. We’ll help you find options that offer both private space and communal areas so your group can enjoy time together and apart.

Want something a bit different? Ask us about private resorts, glamping villages or exclusive-use properties.

3. Be Flexible with Activities

It’s okay if not everyone wants to do the same thing every day. Build in some free time. We can also suggest activities that suit mixed interests — from cultural tours and boat trips to wine tasting and spa days.

4. Let Us Handle the Logistics

We’ll take care of flights, transfers, activities, and even restaurant bookings. You focus on the fun stuff.

Top Destinations for Group Holidays

1. Costa del Sol, Spain

Sun, sea, and sangria — Costa del Sol remains one of our most popular destinations for group holidays. With resorts ranging from party towns like Marbella to tranquil villages in the hills, there’s something for every kind of group.

Ask us about our current group packages to Spain.

2. Greek Islands

From the whitewashed houses of Santorini to the hidden gems of Naxos and Milos , the Greek islands are great for group holidays. Enjoy beach time, hikes, culture, and food that everyone will rave about.

We can tailor trips to suit your group’s interests and pace.

3. New York City, USA

Perfect for small groups looking for a city break packed with sightseeing and experiences. Think Broadway shows, food tours, rooftop bars, and world-class museums.

We often have fantastic deals for group holidays in New York.

4. The Algarve, Portugal

Family-friendly, golf-friendly, foodie-friendly. The Algarve ticks a lot of boxes. Plus, many villas here are ideal for large groups, and the coastline is breathtaking.

Speak to us for exclusive group villa offers.

5. Lake District, UK

You don’t need to go far to enjoy a group escape. The Lake District is a fantastic option for walkers, nature lovers, and anyone looking to unwind. Great pubs, charming cottages, and jaw-dropping views.

We offer full UK accommodation packages for group holidays — just ask.

6. Iceland

Unique, dramatic, and unforgettable. Iceland is great for adventurous groups wanting to experience the Northern Lights, geothermal spas, volcanoes, and glaciers. Group excursions can include snowmobiling, hiking or whale watching.

Let us know if you’d like to plan an Icelandic adventure.

Tips for Planning the Perfect Group Holiday

• Nominate a main point of contact to streamline communication
• Book early, especially for school holidays or peak seasons
• Think about room arrangements before finalising the hotel
• Split payments fairly — we can often help manage this
• Get travel insurance that covers group bookings
• Build in flexibility — not everyone will want to do everything
• Use a trusted travel expert to avoid common pitfalls

The Jamie Wake Travel Difference

We don’t believe in a one-size-fits-all holiday. We:

• Get to know you and your group
• Suggest ideas you might not have considered
• Spot potential issues before they arise
• Offer full financial protection through PTS
• Work with suppliers that don’t list online

We’ve seen it all — the group booking that needed a last-minute villa upgrade, or the stag party that nearly missed their flight. Because we’re hands-on, we catch those problems before they become disasters.

Ideal Group Types We Work With

• Multi-generational families
• Friends celebrating birthdays or life events
• Church or choir groups
• Hobby or sports clubs
• LGBTQ+ travellers
• Corporate retreats and incentive travel

Whatever your reason for travelling together, we’ll make it happen.

Bonus: Hidden Gems for Group Holidays

Puglia, Italy

Beautiful beaches, baroque towns and olive groves. Less crowded than the Amalfi Coast but just as Instagrammable.

We often have villa offers available in this region.

Lapland, Finland

Great for families and festive groups. Think husky rides, snowy lodges, and a visit to see Santa. Magical doesn’t begin to cover it.

Let us help you plan a Christmas group break.

Kraków, Poland

Affordable and full of history, this compact city is ideal for short group holidays. Mix sightseeing with food markets, museums, and lively nightlife.

Check with us for our latest offers to Poland.

Final Thought

The right group holiday can create lifelong memories — but only if it’s done well. That’s where we come in. Whether you’re dreaming of beach bliss or cultural buzz, let Jamie Wake Travel take the stress out of planning.

Ready to Plan Your Group Holiday?

Let us take the hassle out of organising your group travel. With our tailored service, personal advice, and protected bookings, you’re in safe hands. Call us today on  01495 400005  or use the  holiday enquiry form  on our website. Let’s get your group talking about their next great escape.