How to Plan a Romantic Trip for First Timers (Step by Step)

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Wondering how to plan the romantic getaway of your dreams without selling a kidney and going prematurely bald?

As anyone who has ever planned a romantic trip will tell you, there’s much more to it than just dreamy harps and chocolate dipped strawberries. From picking the perfect romantic destination and accommodation to scheduling activities and making sure you don’t rip each other’s heads off… it’s a lot a pressure.

Luckily for you, I travel for a living and I’m a hopeless romantic, so this post is pretty much my calling. Today, I am going to walk you through step by step how to plan your own romantic trip, filled with disgustingly cute gestures and details that are guaranteed to make you swoon.

If you’re trying to plan a romantic trip, but don’t know where to start, then this one’s for you! Or feel free to send this to your non-planny partners as a not so subtle hint. There’s also a video version for you to watch here if you’d prefer.

PS: If you need extra help, I have a free romantic getaway workbook in my VIP Zone that walks you through each of the planning steps.

Save this Guide on How to Plan a Romantic Trip for Later!

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1. Decide When and Where You’re Going

The first step of romantic getaway planning? Choosing where to go. Granted, more so than any other trip, a romantic getaway is more about the company than it is about the destination.

….. but still, you don’t want to end up spooning in a ditch due to poor planning.

So here’s what you do, start with a big list, then narrow it down.

ACTION ITEM: Get a sheet of paper to write down a shortlist (or grab the free planner in my VIP zone for a template). Start with places you’ve always wanted to visit. If you’re planning this trip as a surprise, make sure to dig deep and think of times your partner has mentioned wanting to go to a certain place, or even ask their friends and consult their Pinterest boards.

Next, if you need more ideas, do a quick search on Google, TikTok and Pinterest to find ideas by searching “romantic destinations in _____” or “adventurous destinations in x _____”, “foodie destinations in _____” etc. depending on your interests as a couple.

You can also visit the websites and social media of tourism boards in your areas of interest because they often cover more than just the most popular spots.

With your full list in hand, I would then take a realistic look at your budget and time constraints and let that guide you. If you only have a weekend for instance you might want to do a staycation or somewhere just an hour or two away. Go through the list & cross out any unrealistic ones, until you have a shortlist of three choices max.

Typical Parisian street with the Eiffel Tower in the background with a pink sunset

With this shortlist in hand, if there’s no clear winner then I think you can move onto the next step in order to swing your decision, and that’s to….

2. Find Accommodation

Everybody has different preferences when they travel in terms of accommodation, so before you start your search, you should have a clear idea of what your priority is whether that’s having a really nice and lavish hotel that’s romantic or somewhere cheap and cheerful so you can focus on meals and experiences.

More so than on normal trips though I do think you should prioritize quality of accommodation because that’s really going to set the tone for your romantic getaway. 

ACTION ITEM: Assuming you want a place that has romantic vibes, I would again research on Google, TikTok and Pinterest to create a short list.

Some things to look out for might be…

  • A nice view 
  • Romantic on-site amenities like a spa and room service 
  • Late checkout 
  • A nice bathtub rather than just a shower 
  • Or even things like a rose pedal turndown service 

Googling hotels in your destination with these terms might help you narrow down your search e.g. “hotels in Paris with a nice view”.

NOTE: If you’re more budget conscious, I have a full guide on how to find the best deals on hotels so be sure to check that out for a step by step breakdown.

… And don’t worry – you don’t necessarily need to book an ultra pricey place just to make the stay feel romantic. There are plenty of ways to “romantify” a cheaper hotel e.g. bringing your own LED candles, chocolate, champagne, etc.

PRO TIP: If you want to enjoy spa amenities at a luxury hotel without booking an overnight stay, look into getting a day pass from ResortPass that gives you access to amenities without needing to stay there!

ACTION ITEM: The most important thing regardless of your budget is to read reviews. And I don’t just mean looking at the star rating, I mean going to reviews and sorting by “Newest” so you get the most recent possible feedback.

Sometimes, when you find good deals, it’s because of things like ongoing renovations or amenity closures, so sorting by ‘newest’ will be more helpful than just reading reviews from 3 years ago.

Once you’ve decided on the accommodation and therefore the destination, I would try to book as soon as possible, especially if it’s for a busy period like around Valentines Day.

If you are booking a hotel specifically for its amenities like a spa, I would also make sure to call them first and verify that you can book in for a treatment and that they’re not fully booked.

Depending on when you go, it’s possible that massages and treatments can book out in advance so if you’re booking a hotel for a specific perk you should definitely make sure that perk is available for your stay and organize that right away to avoid disappointment. 

Lastly, ALWAYS put in the booking box that you’re celebrating a special occasion to maximize the chance that you get a nice surprise in your room like chocolates or a bottle of wine. 

3. Book Transport

With the destination and accommodation decided, it’s time to book the transport for your romantic getaway!

This would include getting there, getting to your accommodation and then how you’ll get around your destination.

ACTION ITEM: Write down every portion of your trip that would require transportation and create a checklist so you get each one booked in.

If there’s flights involved, I always use Google Flights to find the best deals before booking with the airline directly. You can see my step by step process in this video.

If you’re exploring other options besides flying, then websites like Omio are great for showing you all the options from Point A to Point B at once.

And for car rentals, Discover Cars allows you to browse a bunch of companies at the same time. 

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Now in terms of what kind of transport to book, again this depends on your budget and where you’re going. But, I will say that you want to arrive refreshed and comfortable, so try to pick the option that’s most comfortable and convenient. 

If you want to take things up a notch, transport might also be a fun opportunity to surprise your partner.

Let’s say you’re planning the trip together and have decided to catch a shuttle bus to the hotel, if budget allows, it would be really cute to surprise them with a private driver who has their name written on card, even better if it’s a silly nickname or inside joke. I can recommend Welcome Pickups for this. Or, take things a step further by surprising them with upgraded seats on the flight. 

… But honestly, don’t pressure yourself to do this if you’re on a budget.

There are plenty of ways to “romantify” even bus travel, whether that’s surprising your partner with their favourite snacks or whipping out a custom playlist curated specifically for the journey. Yes, I realize this is an unhinged level of cheesiness, but with romantic getaways, it’s often the thought that counts, so embrace the cheese.

4. Figure Out Visas and Documents

Next, a very important step in planning a romantic getaway: don’t forget about visas and entry requirements!

Granted, this only applies if you are going abroad and obviously it’ll depend on where you go, so I won’t go into detail here, but please remember that you may need to secure visas or the right documents before your trip (or even before booking the trip).

The next step in planning a romantic getaway is to… 

5. Plan Activities

When it comes to activities, the most important thing is that you tailor your romantic getaway itinerary to what you and your partner like to do, meaning you should stay away from copying generic ‘one size fits all’ itineraries.

And, if this is a surprise getaway you’re organizing, then I would advise tailoring things more to the person you’re surprising rather than yourself….

But if it’s a joint effort then I’d recommend the following…

ACTION ITEM: Independently make a list each of what you want to do, then compare and make sure you do the ones that overlap, while also having one compromise activity for each person that only they want to do. 

Of course, it may be good to add some overtly romantic activities as well. 

Some things I might want to research would be…

  • Nice restaurants with a view 
  • Nice bars with a view 
  • Photogenic spots where you could get some cute photos together

Honestly, TikTok is by far the best app for finding these kinds of activities. The search capabilities on Instagram are mediocre at best, while Google isn’t very curated. On the other hand, I’ve had a lot of success finding nice food spots and bars by searching them on TikTok.

Just remember that when you do choose a place to go, if it’s possible to, make a reservation. If that’s not possible, then make sure you have a backup plan of somewhere else you could go in case they’re full or closed. 

In addition to that, for optimal romance points, I would add two more things…

First – organize one unexpected surprise.

I love a good surprise and think that’s a key element to making a trip feel more romantic.

So here’s what you do: look at your partner’s list of things they want to do, and see if there’s a way to enhance that experience and take it to the next level. E.g. If there’s an attraction they want to see, check if they do private after hours experiences, or if they want to see a lake, see if you can book a surprise boat ride on that lake. 

And again this doesn’t have to be expensive, what matters most is that you put thought into it. 

The second thing is to create a moment where it’s just you two... where it feels like you’ve escaped the crowds and it’s super romantic because you have a place all to yourself. This could be as easy as waking up early and going for a walk before the crowds arrive, staying up late so you have the city to yourself as you walk home, or planning a picnic somewhere quiet. 

With those two additions to the itinerary – you’re golden. 

ACTION ITEM: Aim to plan at least one big activity per day so that even if you decide to sleep in or don’t end up doing anything crazy, that day will still feel worthwhile. 

6. Go on the trip

This part is pretty self explanatory and will depend completely on your specific trip but the main thing I want to emphasize is that you should be taking active measures to prevent arguments… because nothing kills the romantic mood on a trip more than random spats.

And the best way to prevent these spats is to really just recognize where potential tension points will be on your trip, and diffuse them before they explode.

Some common points of tension include…

  • One person being the planner and the other one having no idea what the itinerary is
  • One person being unhelpful with making decisions
  • Different expectations of what the trip would be (for example a very common argument I’ve heard from couple trips is when one person wants photos and the other wants to be in the moment and just relax)

Honestly, the things you fight about at home are probably the things you might fight about on a trip, so recognize those weak points in advance and make sure you’re not doing anything to feed into those patterns. 

Remember – communication is key. Do not assume anything. Plus, travel is often a stressful experience just in itself so remember to exercise a little extra patience as well. 

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7. Make a memento of the trip

Finally, as a bonus tip, do remember to get lots of mementos from your trip. Get cute photos, sure but also hold onto little things like receipts and travel tickets because the very last bonus step that will just take this romantic getaway from good to unforgettable is….

Gifting your partner a sentimental gift related to the trip!

Trust me, it doesn’t have to be fancy – a framed photo, a shadow box, a custom piece of art featuring memories you collected – whatever it is… if you can find a way to commemorate the trip afterwards you’ll be taking in brownie points for a very long time.

Adorable Travel-Themed Illustration

This ultra cute and thoughtful piece of art is customized according to your specifications with 6 potential places to feature.

Photo via PlacesAndSpacesArtCo on Etsy

I Hope You Enjoyed That Guide to Booking a Romantic Getaway!

Let me know in the comments if you have any questions or need extra guidance.

My Go-To Travel Favourites:

🧳 Eagle Creek: My favourite packing cubes

💳 Wise: For FREE travel friendly credit cards

🍯 Airalo: My go-to eSIM

🏨 For searching hotels

📷 Sony A7IV: My (amazing) camera

✈️ Google Flights: For finding flight deals

🌎 WorldNomads: For travel insurance

🎉 GetYourGuide: For booking activities

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