How to plan an unforgettable surprise trip




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 details are based on my experience of booking a surprise birthday holiday. That said, you’ll most likely have to tweak some details to fit your own plans. However, you can download my FREE surprise trip planner to keep track of your progress.

Planning a surprise holiday – when to go?

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.

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 vacation step 1: deciding when to go


How to plan a surprise holiday – decide on a 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 long 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.

Depending on your circumstances, you may also 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. 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.”

Birthday surprise trip – where to go?

Choosing a destination for a surprise birthday trip can be a lot of fun. On the flip side, it can also have the potential of being a headache. 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 is to think about the 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 in the urban jungle?

In my case, my parents live in London, meaning tons of surprise vacation choices. The difficulty came in deciding where they’d want to go.

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The surprise trip destination winner: Portugal


Pick up on 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.  

Surprise holiday – what do they like to see/do?

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?


Take the lead – planning a surprise holiday

To avoid any conflicts that may arise in the planning process, there should be 1 person in charge. This person may already be obvious, ie the spouse wanting to surprise their partner. However, other situations can also arise, ie other family members wanting to join the surprise vacation. Decide whether this is something you want. If not, put your foot down and continue ahead 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

Surprise holiday – picking a hotel

In case it wasn’t obvious, I’m a 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.

The first thing to do is to look for the location. For example, when we’d chosen Porto and Lisbon, I started looking for boutique hotels in these cities. Choose at least 3 hotels in each place, and also at different price ranges.

This will help 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- how to plan a surprise holiday

Research other details such as the proximity of the hotel to main attractions, as well as the neighborhood itself. For Lisbon, I chose the 4-start 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 vacation: Clerigos Tower

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 views of Porto.

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.

The comfortability factor – a surprise holiday

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 mind 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 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 vacation – would they prefer quiet or touristy areas?

Booking flights for a surprise holiday

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.

The extras of planning a surprise holiday

What kind of extras 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.

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, travel insurance is higher given the likelihood of having certain medical conditions. Saying that, my parents take out an annual plan, and while it’s not cheap, it gives them peace of mind.

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 he’d 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.

Ultimately, planning a surprise vacation takes work, but the end result is completely worth it. My parents had an amazing time in Portugal, and it’s one birthday my dad will never forget.

Is there someone special you’d like to plan a surprise holiday for? Have you already booked one? If so, how did it go? Leave me a comment below!

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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