Surprise holiday — 8 useful tips on planning a vacation




Giving the gift of a surprise holiday is one of the best things I’ve ever done.

When my dad turned 70, I knew immediately what to get him: a birthday surprise trip he’d always remember. Both he, and my mum, are keen travelers, so it was more a gift for them than just for him.

The following tips are based on my experience of how I planned his surprise birthday holiday.

That said, you’ll most likely have to tweak some details to fit your own plans. To make things less overwhelming, my FREE surprise trip planner will keep track of your progress.

1. Choose the dates

When planning a surprise holiday, the first thing to do is decide on when you want to book.

Are you planning a surprise birthday trip for your husband in March? Or are you planning to surprise your spouse for your wedding anniversary in November?

Whatever the occasion, knowing when you want to go allows plenty of time to sort out the details.

Planning ahead — surprise holiday

My dad’s birthday’s in July, so I began making arrangements in January.

There’s no set amount of time as to when you should start making preparations. However, for me, planning in advance gave me enough time to work out a travel itinerary.

Better yet, it also gave me a head start to secure the best flight and hotel deals.

Related post – A simple guide to Lisbon
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Booking a surprise holiday step 1: deciding when to go


2. Create your budget

Now that you’ve decided on the time to go, the next step is creating a budget.

Deciding upon how much you want to spend for the surprise vacation can help to condense your plans. A budget will also help figure out how many days you want to book for.

In the case of my dad’s birthday, we settled upon 7 days; 3 days in Porto and 4 in Lisbon. Having already traveled to Portugal, I knew it was enough time to sufficiently see both cities.

Another important point to factor into the budget is deciding who will pay for what.

In my situation, I’d arranged with my brother that he’d pay for accommodation, while I’d pay for flights and transfers.

Who’s going to pay — surprise holiday

Depending on your circumstances, you may be able to split the trip with a family member/s.

If you’re paying everything yourself and are on a tight budget, consider booking a short city break.It’s a good compromise where you can still give the gift of travel without running your funds into the ground.

Ultimately, the whole point of a surprise holiday isn’t about where you go. It’s about how who you’re with, how you celebrate, and how you make the most of your time. 
Having a budget also helps you think about the next step: the destination.

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Decide upon the budget for a surprise holiday


 “Giving the gift of a surprise vacation is one of the best things I’ve ever done.”

3. Choose a destination

Choosing a destination for a surprise birthday trip can be a lot of fun. On the flip side, it can also potentially be a pain in the backside.

The first thing to think about is accessibility. How easy it is for the person/persons to get from A to their surprise holiday destination?

Another factor to also think about is what kinds of activities they like to do. Are they more of a beach or a city person/s?

Would they prefer to stay away from large crowds, or do they relish excitement of the urban jungle?

In my case, my parents live in London, meaning I had plenty of vacation options to choose from. The difficulty was in deciding where they’d both want to go.

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The surprise trip destination winner: Portugal


Pick up on previous cues

Go over past conversations with the person/s in question.

Have they ever mentioned a certain city or country that they’d love to visit?

From speaking with my parents regarding my own travels, they’d always spoken fondly of Portugal and Ireland. Being devout Catholics, both countries satisfied not only their faith, but also their love of travel.  

What do they like to see and do — surprise holiday

My mum tends to enjoy a mixture of city and countryside, and loved my photos of County Kerry and Killarney.

My dad, on the other hand, simply likes to eat. He was immediately sold on Portugal after hearing about, and seeing photos of, my eating adventures in Lisbon and Porto.

He didn’t care whether it was by the beach or in the city center. His only concern was about trying all the delicious dishes I’d tried while I was there.

As the surprise holiday was for him, we chose Portugal as the destination. 

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Would they prefer the beach or city?


4. Take the lead

There should be 1 person in charge to avoid any conflicts that may arise in the planning process.

This person may already be obvious, ie you wanting to surprise your spouse. However, other situations can also arise, for example, other family members wanting to join the surprise vacation.

Be firm — surprise holiday

Decide whether this is something you want. If not, put your foot down and continue with planning the itinerary.

In my situation, I was the principal person in charge. It was an easy decision, given that I’d instigated the idea. I was very lucky with my family, in that there were no disagreements on any suggestions I put forward.

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How to book a surprise holiday – take the lead

5. Choose the hotel/s

In case it wasn’t obvious, I’m a big fan of staying at boutique, and budget permitting, luxury boutique hotels.

You not only get an individual sense of style at a boutique hotel, but also a personal level of service. And I wanted my dad, and mum, to have the same kind of experience in Portugal.

Select a few — surprise holiday

When we’d settled upon Porto and Lisbon, I immediately started looking for boutique hotels in those cities.

Choose at least 3 hotels in each place, and also at different price ranges.

This will help you figure out how much your budget will permit. Websites like HotelsCombined,, and Agoda will compare the best prices for your selected dates.

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Pick the best hotel your budget can buy

The smaller details — surprise holiday

Research other information such as the proximity of the hotel to main attractions, as well as the neighborhood itself.

For Lisbon, I chose the 4-star AlmaLusa Baixa/Chiado. It’s in a central part of the city, and within walking distance of many historic sites like Commerce Square.

What’s more, it’s a popular neighborhood of Lisbon, and with plenty of restaurants, cafes are bars nearby.

For Porto, we grabbed a great offer at Flores Village Hotel & SPA.

Neither of my parents are keen on massages or facials, but the main selling point was its central location.

Surprise holiday: Clerigos Tower

The red rooftops of Porto in Portugal


It’s around 5 minutes to reach attractions like the Clerigos Tower, and the famous Lello bookshop. There’s also an outdoor terrace where you can dine, drink a glass of wine and just enjoy the Porto views.

With both hotels in excellent locations, I was confident that my parents would enjoy it.

Choosing centrally-based hotels also means you don’t have to spend much money, or time, on transport.

Surprise holiday — is it suitable? 

Lastly, you also have to consider the comfortability factor when booking a surprise holiday.

Is the person/s able to walk around easily, or do they require transport? Would they enjoy staying in a local area, or prefer somewhere more touristic?

My parents are of a certain age, and would prefer being around other tourists and travelers, then in remote areas.

They also don’t usually hire a car when traveling, so this is something I had to consider before booking.

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Surprise holiday — would they prefer quiet or more touristy areas?

6. Book the flights

There are plenty of articles floating around on the internet suggesting the best time to book flights.

I don’t subscribe to this, as one size doesn’t fit all, and it really depends on your starting destination.

If the special occasion will take place during a peak time, like the school holidays, I’d suggest booking sooner.

For anything in the off-peak period, 5 weeks before the trip may be enough time.


surprise vacation - flights


Websites like Skyscanner and Expedia are good resources, and show flight comparisons ranking them in order of price.

As for last-minute flights, I don’t advocate them. I’ve always found them to be much more expensive and very limited too.

7. The extras

What other things would the person/s enjoy on the trip?

Would they go gaga over some relaxation time in a top spa? Or maybe they’d prefer to do a wine, food or walking tour?

While I’d advise against planning out the entire itinerary, adding one suggestion is a nice touch.

A surprise within a surprise — surprise holiday

As my dad would be celebrating his actual birthday in Lisbon, I contacted the hotel beforehand.

I asked whether they could send a slice of chocolate cake to their room on the day. My mum later told me, that they’d sent an entire cake and a bottle of champagne.

Needless to say, we both left raving reviews.


surprise vacation - travel insurance is a lifesaver

Travel insurance

Find out whether the person/s has sufficient travel insurance.

I never travel without, and I suggest you do the same. Travel insurance isn’t as costly as you may think, and it can be a lifesaver if anything goes wrong.

For travelers in my parents’ age group, the travel insurance premiums are higher. However, if you’re a younger person, with no existing medical conditions, you should be able to get a good deal.

Saying that, my parents take out an annual plan. While it’s not cheap, it gives them peace of mind whenever they travel.

8. How to reveal a birthday surprise trip

Now that you’ve arranged the flights, hotel and itinerary, what comes next is the best part: the reveal.

I won’t advise you on how to reveal the surprise vacation to your loved one, that’s down to you.

In my situation, we’d arranged a family dinner a week before the trip.

Once my dad had blown out the candles on his birthday cake, we presented him with an envelope. Inside was not only his birthday card, but also the e-tickets and hotel details.

I wish I’d taken a video of the event, as the look on his face is something I’ll never forget.

All worth it — surprise holiday

Ultimately, planning a surprise vacation takes work, but the end result is completely worth it. My parents had an amazing time in Portugal, and my dad got to try everything he set out to!

Is there someone special you’d like to plan a surprise holiday for? Have you already booked one, and if so, how did it go? Leave me a comment below, I’d love to hear from you.

Till next time, happy boutique travels x

Disclosure: This post may contain affiliate links, which means I may receive a commission if you click a link and purchase something that I’ve recommended. Thank you for your support.

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How to reveal a surprise vacation — the best bit

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Lisa R sitting in a wicker chair

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