Tips for Planning Your First Holiday with Friends

Going on holiday with your friends is incredibly exciting, but it does mean finding the right people to go with, the correct destination, and accommodation everyone will full in love with and feel at home in. There is a lot to plan, but in the end, if everyone listens to one another and finds common ground, it should be one of the best holidays ever.

Firstly, find people who share the same interests as you. While you may want to go on holiday with your best friend, if they want to experience the nightlife in Ibiza while you want to see the Caribbean, it may be best not going abroad with them right now.


When and Where to Go

The world is your oyster. There are certain things you have to factor into the decision such as work commitments, personal interests, budget, time off and travel experience. However, the ultimate choice is all yours.

If you want to travel long distance, you’ll need more than a week; much closer to home and you’ll be able to have a peaceful week-long holiday. If this is your first holiday with friends, remember to take everyone’s opinions in; after all, it is a holiday for everyone. This means finding common ground, such as what you want to do and where to stay.  

Booking Your Accommodation

This depends on your budget, however, the possibilities are endless. There are hotels, bed and breakfasts and vacation rentals such as Caribbean villa holidays, but the latter is a great way to get quality time with your friends without being bothered by other tourists or hotel staff. Plus, you and your friends can cook on your own accord and laze around a pool without trying to find a free sun lounger.

It’s good to have a base from which to explore an area, and somewhere to come back to at the end of the day. If it’s relaxation you’re after, then make sure the accommodation you book has a pool, comfortable areas to chill out in, and somewhere warm and luxurious to lay your head at the end of a long day.

Creating a Travel Itinerary

This will probably be the most time-consuming part of planning your trip, but it can also be the most fun. Look into all the different attractions you can visit, the local markets and experiences you have to enjoy. The internet is a wonderful tool when you want to find out more about an area. It’ll help you identify the best time to arrive and how long a particular experience will take. If there are tour companies that operate in the area you’re, visiting review their itineraries for some ideas.  

There are other options if you’re not great at making plans. Look for organised tours of the local area instead. Don’t feel under pressure to pack as much as you can into your holiday. If you like a location, you’ve always got the option of returning.

Dining Out vs. Eating In


Of course, you’re going to want to sample the local cuisine, but don’t rule out shopping at the local produce markets and preparing something yourself. There are plenty of places to eat, but it can become too costly in the long run. Try and eat out, but do also remember that if you can cook at your own accommodation, that would also help you and your travel partners save some money that could be spent elsewhere.

Making New Acquaintances

Being on holiday is a great way to meet new people, regardless of the people you are currently travelling with. Remember, there are many travellers out there who may be on their own and who are looking for human interaction. Plus, if you ever head out on your own, it is always a good idea to learn how to approach people.

The most obvious places to meet people you can talk to are to eat at a local restaurant or drink at a local bar. If you’re a little nervous, it’s easy to break the ice with a simple question such as when does the bar close or open and what’s a recommended dish on the menu.

Booking a day tour is also a good way to minimise the feelings of loneliness. Spending a few hours with other people you have a connection with is a recipe for conversation. Wherever you go on holiday, there are going to be others around you who speak the same language. Keep an ear out for conversations going on around you. It’s much easier to break the ice with a fellow countryman or woman.

Essential Travel Tips

Travel Insurance – Always take out travel insurance, whether you’re travelling to the other side of the world or a country next door. You’ll be covered for cancellations, loss of luggage and medical care should you be injured or fall ill.

Keep in Touch – This is more for the peace of mind of friends and family, but it’s also for your own safety. How you do it is up to you as there are plenty of options.

Safe Surfing – Not to be confused with the sport, but instead, referring to Wi-Fi. It’s great if you want to look something up online, but making payments or doing your banking is not advisable if the connection is not secure.

Travel Apps – There are lots of different travel apps you can use when you’re on holiday. There are, however, a few that are recommended. WhatsApp and Skype, for example, allow you to text and call friends and family using Wi-Fi. Google Maps is another great app to have on your smartphone as it’ll help you find your way should you get lost. Keeping track of the weather is also a great idea. You’ll be able to check the night before whether it’s going to be OK weather for laying next to the pool all day.   

Going on holiday with friends is a positive experience for you to have as a young adult. It can open you up to new opportunities and change your outlook on life; it can also strengthen your friendships. Remember to have the best time, and not to worry too much.

Posted by

Cascade of Colour is a UK Male Lifestyle blog delving in to the world of Mens Fashion and Grooming, Food, Music, Design, Tech and Travel. Want to get in touch? Drop me an email at

One thought on “Tips for Planning Your First Holiday with Friends

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s