Planning Your Dream Holiday

A dream holiday is something that you have thought of for years and years. You’ve always wanted to imagine it coming true, then you take a leap of faith and book it.

This blog post contains gifted items.

You could have extravagant plans, or it’s simply to visit a far off place. Either way because it is a dream come true it takes a lot of planning.

I know this because pretty soon I am heading on my own dream holiday. Some would call it the trip of a lifetime, but I’m not using that term, as one day I hope to return.

For me a dream holiday is more than a beach and city break. It’s a longer time away from home, covers multiple things to do, and maybe involves travelling around.

I’ve had a lot of people ask me how I planned it so I thought I would share my main organising tips. I’ll hopefully share some things that’ll help you take the plunge and make your dream a reality.

California Dreaming

When growing up my favourite thing to watch were Musicals. I would even ask my Mum if we could move to the MGM studio lot like actors such as Gene Kelly, Debbie Reynolds & Judy Garland did when they were starting out.

I was obsessed with Old Hollywood, and still am. This grew in to asking more and more about California. My Mum (again) would tell me about a school pen pal she had that lived in Lodi, California. She would send her pictures of the beaches & palm trees out there.

This then led to me being introduced to music by The Beach Boys. A band that have remained one of my favourites for over 20 years now.

Then queue a moment in 2004 that changed my obsession with California to a dream that must come true one day. I remember being 15 years old and a new show started on Cable TV, The OC. This just cemented everything for me. I said to myself that before I am 30 I am going to visit the place I have always dreamed of seeing.

Where to Begin

I’d say the first things to think about are –

  • What is your budget?
  • Where are you going?
  • How long for?
  • Who are you going with?
  • What is your plan?


Knowing your budget is huge. This will help you stick to a plan. Once you have your budget in mind work out how much money you would need to put away each month to cover it. This doesn’t include spends yet.

From this moment on get your trip booked as soon as possible. I’d recommend booking a big trip at least a year in advance. This gives you time to make the monthly payments. These will be at a smaller cost due to spreading them out for longer.

Think about spends & what you want to do there. Start saving a little and often each month. Write yourself down a list of tourist/sightseeing things you want to do, as well as a savings tracker. Each time you put some money away tick a sightseeing activity off your list that you’ve saved enough to book.

I’ve loved doing this, and it’s reassured me that I can do what I had planned to do whilst away.

When and Where?

Where would your dream holiday be? I love hearing people’s choices. Mine has always been to the West Coast of the USA. California has been calling to me for years.

I can’t believe that in a few short weeks I’ll see Coachella festival, Venice Beach, The Golden Gate Bridge & the Neon Lights of Vegas (we’re hopping over state lines to Nevada).

Won’t this Cari’s Closet playsuit be perfect for the Cali weather!

Because the Coachella Festival has always been at the top of my Must-Do-Before-I’m-30 list this is what determined the start date of our trip.

Consider the best time of year to visit your destination. Is it rainy season, hurricane season, exceptionally hot? You don’t want any of these. So double check all of this before deciding on a place & month.

Once you’ve got your month and budget set in mind, think of how long you can afford to stay there. Things like work holidays, budget, spends etc can all determine how long you’ve got.

Who Are Your Travel Buddies?

I always travel with either my Mum, Sister or Husband. This time round we are going all together, plus my Sister’s boyfriend. This will be our 1st time travelling altogether.

Some may say we’re crazy, I say we’re all just up for a good time!

Picking your travel buddy is a big decision to make. You must get along well, be comfortable in silence together, have a laugh with one another, and the main one, be willing to let your guard down around them.

All kinds of things can happen on holiday so you have to be ready to experience that together. In close proximity.

My travel buddies are used to my excessive planning, claustrophobic panic attacks and my not so chirpy demeanour of a morning. So with all that in tow, and they still agreed to come with me, I’d say we’re on to a winner.

Have A Plan

I know people like to live in the moment and not plan too much, but seriously, if this is a dream trip then it’s going to take planning.

Appoint someone to be the main organiser. They can keep tabs of all the documents, pre booked tickets, and do a lot of the researching for you.

Planning out what you want to do will ensure that you make the most of your trip. It will also help with your budgeting.

Something I have done for our trip is print off blank calendars that cover the weeks we are away. I’ve written in where we are on each day, and then in a different coloured pen written in what we have/will have planned.

I told you I am an excessive planner!

This has helped us to figure out what days we can relax, and not feel like we’re going from pillar to post all the time.

Happy Planning

Once you have done all of these things you should feel like your dream trip is taking shape. This checklist helps put my mind at ease when I am planning, so I hope it does for you also.

I would love to hear if you have ever planned a dream holiday for yourselves. Please share your best tips with me, I’d love to hear them.

I am definitely going to be writing a more specific post about my American Trip planning, once I am home. But let’s not rush away the next few weeks.

You really must check out Cari’s Closet as well. This is where this beautiful playsuit* is from. It’s going straight in to my suitcase to be worn at Coachella and the beach!


Jessi xoxo

*The playsuit from Cari’s Closet was gifted to me. All images are my own. Blog post idea is my own.



  1. Bernadette
    27 March 2019 / 9:19 AM

    Another great blog Jess. Gary was saying just the other night his dream place would be Alaska.
    Loving the jumpsuit and your pics are so summery it really is a great piece for a summer wardrobe.
    Happy travelling ?

    • jessiloublog
      27 March 2019 / 4:20 PM

      Thanks so much Bernadette! Alaska would be amazing! A friend of mine used to work on a Cruise Ship that did Alaska tours & she said they were always her favourite! I hope you guys get there!

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