31/12/2018 06:00 GMT | Updated 31/12/2018 12:04 GMT

New Year's Resolution: In 2018, I Went On My 5-Week Dream Holiday – This Is How I Did It

"Each month when we got paid, we’d book a different part of the trip."

HuffPost UK

In this week-long series, we’re talking to HuffPost UK readers who set themselves a new year’s resolution last year that you may be considering for 2019 – and stuck to it. Their motivation could be your inspiration. Here, Olivia Tripp, 23, from Bristol shares her story

New year is definitely a time to think about travel – it’s having something to look forward to post-Christmas when everyone feels a bit bleak. I don’t know about you, but I like the sense of knowing what my year is going to look like. So, alongside the promises people make in January to exercise more and start a new hobby, mine was to book a dream trip – and boy did I book one. 

The trip was important for several reasons. We wanted a proper break, like an actual big chunk of time off. We’d both had really busy years so taking time away for headspace was exactly what we needed and I’m self-employed and was feeling burned out and unenthusiastic about work.

I like the idea of going on a longer holiday every couple of years – I guess I find it more of an exciting way to travel rather than taking a whole year off or going on one-week trips. I’ve done it before, too. The first was in Europe for two months in 2013 and the second was in California for six weeks in 2016. It was about time to do another.

The world is pretty huge, huh? My boyfriend and I opened a map, stared at it for several days and considered where we wanted to go. Visiting the US two years ago, we’d loved it so much, we decided to go back. 

Little Havana, Miami 

Everyone’s dream holiday will look totally different, but this was ours: Toronto - five nights; Niagara Falls - two nights; New York - six nights; Philadelphia - three nights; Washington DC - three nights; Miami - six nights; Florida Keys - seven nights; and Cuba - five nights. Pretty dreamy, if you ask me. We booked flights in January 2018 for the trip in September. 

It was a lot of work to organise and, add on the fact that we didn’t have the money to book it all in one go, you can imagine it became a pretty drawn-out process. Each month when we got paid, we’d book accommodation or some form of transport. It was an exciting build-up though and manageable, too, seeing as we had nine months to plan. 

[Read More: When To Take Annual Leave In 2019 To Get The Most Time Off Work]

I’m well aware not everyone is lucky enough to be able to do this. My business is in social media and marketing, so things were able to tick over while I was away with the help of a few freelancers (just a bit of checking emails). However, my boyfriend is a plumber so took the time off and had to sacrifice pay. 

In the last few months, I spent every spare moment researching places to visit, restaurants to eat at, bars to drink at. I enjoyed the organising but I’m not going to lie, it was like another job for a while. Come September, I was buzzing. The dream trip we had so meticulously planned out was finally here and, looking back now, it’s hard to sum up how amazing it was. 

Central Park, New York

We loved the variety of the different places we went to, especially how completely different one city was to another. Toronto is somewhere we would love to live – everyone was so friendly and it’s a super cool city. Visiting Havana in Cuba was extraordinary and like no where we’d ever been before.



We felt like proper tourists at Niagara Falls, and Central Park in New York was beautiful – I’d seen it on so many TV programmes, but until you’re there, you don’t quite know how incredible it is. Florida Keys had a completely chilled-out vibe and being able to just relax on the beach was what we needed near the end of our trip. 

The people, places, cities and memories were amazing, but it was also a great way to strengthen our relationship. To spend time not talking or thinking about work and just exploring together – and having all those memories brought us closer together. I’ll always remember everything we did on the trip. I’d so much rather spend money on experiences like these than on material things. 

Niagara Falls

I can honestly say coming back from the trip, I was in a completely different frame of mind. I was excited to start work again and make future plans.

Many people think big trips are out of reach, but it’s surprisingly manageable if you just have the confidence to book it. Money can be a limitation, but think of it this way: we did our first big trip when we were 18-years-old, with wages from my part-time job (20 hours a week in retail). It’s about planning in advance, and doing it bit-by-bit. It’s surprising what amazing things you can do on a limited budget.

As told to Amy Packham.

Cienfuegos, Cuba