How to Plan a Holiday

Where To Go

The (obvious) first thing you have to do is decide where you want to go.

This can be easy or it can be difficult, and it depends on a range of factors. Some questions to ask yourself: How much time off do you have? What is your budget? Do you have a bucketlist? Are you traveling with anyone? What kind of weather do you want? Do you care about a language barrier? The answers to these types of questions can help you narrow down your search. If you do need some inspiration, Googling or Pinteresting things like “places to holiday in the sun” or “unusual holiday destinations” or “places to holiday on a budget” etc., etc. At the beginning of the year, I wrote this post all about ideas of where to travel this year, so if you’re stuck maybe it can help.

Personally, I have a bucketlist of places I want to visit. Some of these places are close, some far, some budget, some expensive. My bucketlist could be broken down into sub-bucketlists, if you will. For example, there are certain vacations that I want to put off taking until I have enough money saved up or am in a comfortable enough financial state to justify splashing out a bit – such as doing a long U.S. roadtrip, an African safari tour, or Australia. These are places where what I want to do will cost more money because of the exchange rate, the time I want to spend there, and the types of activities I want to do. Of course, there are ways to make each of these holidays budget, but I don’t want to. So, I will wait until I’m a bit older and have more money. In the meantime, there are other places on my bucketlist that make sense for where I’m at financially right now – Croatia, Spain, Thailand, and Austria.

So you know where you want to go – Great! Some questions to ask yourself once you’ve picked a place: Will you need a visa? Will you need vaccines? Are there travel advisories? Should you buy travel insurance? These questions aren’t fun ones, but they are important questions. Make sure to do the research about your destination so you don’t get turned away at the gate. Here’s a great resource from the British government that can help you answer these questions and more.

Stopped in Sedona, Arizona on my 10-day road trip from Ohio to California.

How To Get There

Now that you have picked a destination, you need to book travel.

It’s possible that this was part of the process for picking where you want to travel to. For example, the trains across Europe are convenient and a “green” way to travel, but they may take more time than flying. Are you going to drive? In the U.S., driving is the common mode of transportation (as most cities don’t have convenient public transport, some have none at all), but if you’re travelling in London driving doesn’t make much sense (public transport gets an A+).

If you’re looking to fly less (yay environment), then picking a destination closer to home may be better, or picking a destination that has good public transport is also a good option. If you have to fly but feel like you still want to do something for the environment, you could carbon offset your trip through companies like this one.

For booking flights, here is my guide. It varies depending on the time of year you travel – summer dates always cost more because it’s peak season. To get around this, you can book in reverse, meaning November – March is summer in the southern hemisphere so book warm vacations then to beat some peak prices.

London, UK

Where To Stay

I usually book accommodation after I book travel. Some questions to ask yourself: Do I want to stay in a hostel? What is my budget? How close to X do I want to stay? Is there a part of town I should not stay in for safety reasons? What kind of experience do I want? Who am I traveling with?

Hostels will most likely be the cheapest option, they can provide a social space, and are great for solo travelers or small groups. They can come with downsides – loud roommates, dirty (with so many people using the facilities this can happen), cheap (you get what you pay for). I suggest looking at the reviews on Hostel World.

Hotels can be great and can range in prices. Hotels can also be dodgy – looking at reviews on websites like and can help you weed out the bad ones. Hotels offer dining services and amenities (wifi, gym, pool, offices, printing, luggage storage, laundry, etc.), but can be isolating for solo travelers. For families or large groups, hotels are a great option.

Airbnb or home stays are also great options. Especially for groups bigger than two. In some places, Airbnb can be just as budget as hostels or just as expensive as hotels. Again, please read the reviews! So far, I have only had positive experiences with Airbnb, but that’s not always the case so definitely read the reviews. Also, more so for Airbnbs than hostels, you really tend to get what you paid for (relatively speaking per city).

Usually I do some research into all three options, especially if I’m traveling with someone/people. If I’m traveling solo, I tend to opt for hostels for the social aspect. Compare prices, amenities, locations, and reviews to get to the sweet spot for what you want to book.

Booked the Eiffel Tower in advance (saves money!).

What To Do

Some people are more spontaneous than others and don’t book anything ahead of time. Depending on where you are going, there may be some attractions that you have to book ahead of time, or that you will want to book ahead of time to avoid massive queues (like the Vatican Museums). In April, I’m going to a surf camp in Costa Rica – something I definitely had to book in advance, but I don’t have any other plans for my time there.

If you’re going for a specific purpose than obviously book ahead. Also major tourist attractions, I suggest you book ahead – such as the Eiffel Tower. Or, try to plan your days so you do the biggest tourist attractions in the morning to beat the long queues and then leave the rest of the day for wandering around exploring and being “spontaneous”. Or throw all caution to the wind, show up, and do you! It really depends on the type of traveler you are – Do you like to be prepared? Are you a planner? Do you want to pack in as much as possible? Are you going for only a short period of time? Are you going for quality or quantity? Is there anything you’re dying to do at your destination?

It also helps to be on the same page as anyone you are traveling with. For example, my best friend Emma and I went to Paris for four days – we are both planners and booked what we needed to in advance and made a general plan for the rest of the days to make sure we saw everything we wanted to. And we saw it all. That type of trip would have driven my boyfriend, Conor, insane. He is more the spontaneous type, doesn’t need to be awake at 7am every morning of the holiday, and likes to see what local gems we can stumble across. Both are amazing people to travel with. Knowing what type of traveler you’re traveling with and making compromises is essential to enjoying your holiday!

And there you have it – my ultimate guide to booking a holiday! Most of the time, planning my holiday happens in this order, but as you read the categories sometimes overlap or affect another. In order to keep track of everything, I keep everything I’ve book in a note on my computer (flight information, accommodation info and contact details, all confirmation numbers, and links to any websites) and flag any important emails (printing only what is necessary). I hope this helps you to have a great holiday!

Dana’s Do’s:

  1. Read the reviews!
  2. Understand the type of people you’re traveling with and adjust accordingly.
  3. Book the big tourist attractions in advance.
All around enjoying waking up at 7am to beat the Colosseum queues.

Packing Guide: Bahamas Cruise

Planning a spring break cruise and don’t know what to pack? I have you covered!

Bathing suits (duh)

This one is obvious if you’re going on a cruise, but how many should you bring? Well, that depends on how long your cruise is, how light you want to pack, and if you care about wearing the same suit twice. I lie somewhere in the middle of all of these, so for my seven day cruise, I packed three swim suits that were easy to mix and match. That way I didn’t overpack, but I also had enough options to mix it up on my Instagram.

Cover Up

For my coverup, I had a pair of red flowy pants (borrowed from a friend, bought from Target). For the most part, I didn’t need to cover up the top of my bikini on our boat, but I wanted to throw some pants on for some coverage. A cute pair of flowy pants, a lightweight dress, or even a kimono-like shawl will work! My advice would be to find something that can go from the beach to a restaurant so you don’t have to slip into jean shorts with wet bathing suit bottoms.

Sun dress

While this can double as a coverup, it’s also a good idea to bring regular clothes for when you’re not in a swim suit. Such as in the evenings when you’re eating dinner, at an on-board comedy show, or at the various clubs and bars on the cruise ship.

Shorts and Tank Top

For any excursions that don’t require a bathing suit! If you plan on hiking or going to see ruins or anything else remotely athletic, I suggest bringing a pair of shorts and a tank top (very versatile).

Senor Frogs will always have a place in my heart! Worst margaritas ever.

1 nice dinner outfit

There’s usually one nice restaurant on a cruise ship and it’s fun to get dressed up with your friends for one night. I brought a black romper and black heels, still warm weather clothes but nicer than my coverups.

Shoes: Sandals, sneakers, heels

You won’t need much, but sandals/flip flops are a must if you’re going to be by the pool or at the beach all day. Sneakers for any excursions. And heels to complement your nice dinner outfit.

Sunscreen, sunglasses, aloe vera (inevitable)

Sun protection is super important! Especially if you live in a place that hasn’t seen the sun much this winter. Sunscreen is expensive to buy once on board or on a tropical island so I suggest bringing your own. And, as is inevitable, pack some aloe vera for the sunburn. I was so good for the first four days about sunscreen and drinking water, but day five got the better of me and I ended up burning my chest pretty badly. And of course, sunglasses! But beware of falling asleep in them, no one wants those tan lines.

Making sure to stay covered after I got sun burnt but without missing the fun!

Pro-tip: pack less.

Really. I packed a full suitcase for my cruise and used maybe 1/3 of it. But hey, from one chronic overpacker to another – better to be safe than sorry, right? Well, if you pack less clothes you might have room to fit more alcohol so there’s that.

Dana’s Do’s:

  1. Pack sunscreen!
  2. One nice outfit can’t hurt, and it’s actually kind of fun.
  3. You don’t need as much as you think you do.

Packing Guide: Rome in the Winter

If you’re planning on traveling to Rome with just a carry-on, then I have the perfect packing list. I spent five days in Rome and came with just a backpack (thank you, Ryanair for your harsh restrictions). During December, Rome can be cold, but not too freezing. A good coat is all you need to stay warm. Since it’s a European city, it tends to be on the trendier side of fashion, so leave your athleisure at home. Below you’ll find all you need for a week or less in Rome, or anywhere else in Europe with a similar climate.

Weather in Rome: Dry, 10°C-15°C (50°F-60°F)

Basically, it was chilly but I wasn’t ever cold besides early in the morning.

What I wore on the plane: Heaviest items, but still comfortable

– White Coat

– Black leggings

– Black Sweater

– Sneakers

The rest of the list I packed in my backpack – black North Face Borealis Classic.


– 1 Pair of Jeans – black wide-leg cut-offs

– 1 grey sweater

– 1 white long sleeve

– 1 white short-sleeve crop

– 1 bra

– 1 pair of PJ’s

– 2 pairs of socks

– 6 pairs of underwear


– Toothbrush/Toothpaste

– Hairbrush

– Makeup Wipes

– Moisturiser


– BB Cream

– Mascara

– Blush, Highlighter, Bronzer


– Lonely Planet Guide

– Phone Charger

– Wallet – holds Passport, cards, cash, boarding pass

– Printed Documents – passport, visa, hostel and tour confirmations

– Purse – cross-body; can hold book, wallet, phone, charger

I saved space by re-wearing my jeans and leggings, just mix and matching with different tops. I also brought minimal makeup and toiletries because I was only gone for five days and I wasn’t planning on going anywhere too fancy. Since the flight was short, I was able to re-wear my outfit on the flight back as well, saving space.

My Air Force One’s are comfortable to walk in all day, even on all the old cobblestone streets in Rome, and cute enough to wear out in the evening, so there was no need to pack any other shoes. I only packed one short-sleeve, which I ended up wearing on the warmest day so that worked out.

I brought an extra cross-body bag so I could leave my backpack in the hostel locker during the day. That way I didn’t have to lug around extra weight, but I could still carry what I needed to.

Hopefully, this helps you realise you don’t need as much as you think you do – I say this as a recovering over-packer.

Dana’s Do’s:

  1. Plan what you pack to make the most of your space.
  2. Check the weather ahead of time.
  3. Choose cute but versatile pieces.