8 tips on how to plan a surprise holiday
Last updated on January 29th, 2026.
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 mamma, 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.
Naturally, 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 help you keep track of your progress.
8 tips on planning a surprise holiday
1. Choose the dates
When planning a surprise holiday, the first thing to do is decide the dates of the vacation.
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
My dad’s birthday falls in July, so I began making arrangements in January. This may sound like a lot of time in advance but I didn't want to leave things to the last minute.
There’s no set amount of time as to when you should start making preparations. For me, planning in advance gave me enough time to work out the best travel itinerary for my parents.
Better yet, it also gave me a head start to secure the best flight and hotel deals.
2. Create your budget
Now that you’ve decided on the dates, the next step is to create a budget.
Deciding how much you want to spend for the surprise vacation can help to condense your plans. A budget will also help you figure out how many days you can afford 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 traveled several times to Portugal, I knew it was a sufficient time-frame to see both cities. If they enjoyed this 'taster' visit, they could easily return for a longer trip in the future.
Who's going to pay
Another important point to factor into the budget is deciding who will pay for what.
In my situation, I’d arranged with my brother beforehand that he’d pay for accommodation, while I’d pay for flights and transfers.
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 planning 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.
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 big pain in the backside.
There are plenty of factors to consider when booking a destination as a surprise holiday. What kind of activities does the person/s like to do? Would they prefer staying by the beach or would they be more keen on exploring a city?
Would they prefer staying away from large crowds, or would they relish excitement of the urban jungle?
To and from the surprise holiday
When planning a surprise trip, it's also important to consider accessibility. A faraway, exotic destination may sound appealing, but not so much if the travel time is 13 hours.
With my parents being on the other side of 60, I wanted the trip to run as smoothly as possible. This included having easy access to airports and local transportation.
Having a home base in London gave me plenty of vacation options to choose from. The difficulty now was deciding on a destination where they’d both want to go.
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 visiting 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
My mamma 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 ending up choosing Portugal as the destination.
4. Take the lead
Assign 1 person in charge to avoid any conflicts that may arise in the planning process.
This person may already be obvious, for example, if you want to surprise your spouse. However, other situations can also arise, for example, other family members wanting to join the surprise vacation.
Be firm
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.
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 parents to have the same kind of experience in Portugal.
Select a few
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 at different price ranges.
This will help you figure out how much your budget will permit. Websites like Expedia.com, Booking.com, Hotels.com and Agoda will compare the best prices for your selected dates.
The smaller details when planning a 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 and bars nearby.
For Porto, we grabbed a great offer at OCA Flores Hotel Boutique.
Neither of my parents are keen on massages or facials, but the main selling point was its central location.
It’s around 5 minutes to reach attractions like Clerigos Tower (buy entry tickets), and the famous Lello bookshop (get tickets). 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.
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.
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.
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 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.
Travel insurance
Find out whether the person/s has sufficient (or any) 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
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.
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.
Like this post? Pin it!
I love the idea of a surprise vacation. Unfortunately or fortunately, I am usually a planner never the receiver 🙁 So this post is perfect for me. My boyfriend's birthday just went else I could have planned a surprise birthday vacation. But never mind I can plan for some other reason.
Use the post next time to plan a trip for him!
very nice sharing from you, love the captures here. I need a surprise trip too 😀
Great to know
This is great. I was planning a surprise trip for my husband for my anniversary. I am sure this will come in handy
That's great to know! Would love to know how it goes
Awe, I've never been presented with a surprise vacation! That would be so fun!
My dad thought so!
What a great gift! I would love to do this for my dad. Thanks for the tips.
You're welcome!
Our 13 yo has been dropping hints for us to plan one soon..ha ha
Brilliant, and they didn't have to read the post!
Now, I have to plan a vacation. The post is so tempting....
Great!
i have never tried it.. But thank you for this idea.. And I will try this year summer.
Good to know!
Such an awesome idea. You have some really great tips for planning too - great post 🙂
Thanks you!
So lovely that you planned a surprise trip for your Dad's 70th birthday! I also did that for my mum last year - though not quite as exotic as yours (it wasn't a "big" birthday for her LOL). We went to Croatia for a few days, to explore the Christmas markets - she didn't have a clue until she opened her birthday card x
That's really sweet Becca! It must have been a lovely surprise for her.
It's so sweet of you to surprise your father on a trip! I would like to go to the Clerigos Tower. Looks cool.
It's a stunning place, you must visit one day
Planning a surprise trip is a difficult task. I agree that whenever you are planning for a surprise trip, you should definitely plan your budget and the places you visit in advance. This will keep you away from unforeseen troubles.
Absolutely, a budget is key!
Great post. I plan to surprise my husband with a trip somewhere next year for his 40th!! I will have to bookmark this page so I can read again!!
Amazing! It'll be an incredible surprise for him!
I booked a surprise mini-vacation for my dad to a race he’d always wanted to go to. It was awesome. This post reminded me that I should do it again—this time to a place my mom would like to visit.
Aw that must have been a nice surprise! Portugal is beautiful, you must visit
Perfect story! And great pictures! Are all of them made by you? I am curious about one picture - the one with the caption "Would they prefer the beach or city?" What are these "tents" I have never seen them before.
That's not my photo sadly! It's from Portugal, and as I booked a surprise trip for my dad there, I thought it was fitting 🙂
There is a lot that goes into planning a surprise vacation especially if one's partner is working full time. But if you pull it off, it can be one of the best surprises you can give your partner 🙂
I couldn't agree with you more 😀
My friend's birthday is coming up next month. Thanks for the inspiration 🙂
You're welcome
Wow... if I had a chance to wish for this year's birthday, i would wish for this... a surprise vacation. ???
Aw send it to your husband/family/friends, you just never know!
Such a beautiful trip and great ideas. I will also plan a surprise for my mom on her upcoming birthday. You did a great job and the place is so beautiful
Thank you! I hope your mom also enjoys her surprise
i love these tips. we really need to plan a vacation soon, sending this to my husband
Perfect, that was the goal 😀
These are very useful tips for a surprise vacation! I hope my husband finds this article before our anniversary next month. 🙂
Lol so do I! Or you can just send it to him as a hint 😉
Here are some essential tips to follow for a surprise vacay I must say.
Thank you!
Thumbs up for these very helpful tips. You are very thoughtful and generous to your Dad. Have fun in your adventure there!
They had a lot of fun
A surprise vacation is such a great idea. My husband would be so happy if I surprised him a trip to Europe 🙂
Do it! It'll be a gift he'll never forget
Wow, such a detailed post that would be so helpful to plan a great surprise trip for my husband.
Use the planner, I've thought of everything 🙂
Great tips. I will use these when I plan my surprise vacation.
Great to know!
I do love the step by stem ideas. The idea of a surprise sounds like fun.
It's a good surprise for the person too!
Thank you for sharing! I have never planned a vacation much less a suprise one. Such good info. Thank you
You're welcome! Hope you get to plan one.
I'd love to go and visit the Castles in Lisbon. It had been a dream of mine since a little girl to live in one, so seeing one now up close as an adult, would be a dream come true.
You have to go, Sintra is so beautiful and romantic too!
Nice reading your tips. It will be quite useful for my future travel planning.
Thanks
Great tips. I learned a lot from this. However, its hard to keep secrets from my wife. She seems to have a power to know these things. Hence, I won't be able to give her a surprise trip.
She sounds like a bassett hound! Well, you can always try 😀
Very helpful guide thats works for some. Having a spa weekend is always good idea.
In my book, yes!
Wow, this would be so fun to put together. I don’t know if I would want to receive a surprise vacation, though, because I’m a planner haha!
Aw, you need to let yourself enjoy a surprise too 😉
A surprise vacation is such a lovely gift to give but requires plenty of planning. Thank you for the tips, they are very handy.
Download my free planner - it takes away half the hassle!
Awesome tips for planning a surprise vacation. I want to surprise my parents with something some day.
Thank you! You definitely should, the look on their faces was unforgettable!
this is such an unique and amazing post. I am not good at giving surprises so this is very useful for me. So nice of you to plan a surprise trip for your dad. I will download your free planner.
Thanks Sinjana! He was so happy when we handed him the envelope
I for one am a sucker for a great weekend getaway! Your dad is a lucky guy! So much fun!!
Tell me about it! He's very loved!
I would love one day to plan a trip to Italy...it has been a life long goal for me since that is where both my parents are from. Someday soon I hope...these are great tips and so inspiring!
Aw you have to go! I'm always there, and it's as great as it looks 🙂
What an amazing gift to give. We haven't planned a surprise getaway in a while. I think we are due!
Perfect! Feel free to download my planner to track your progress
Not just a slice of cake, the hotel sent an entire cake and a bottle of champagne to your parents' room. I'm sure it's one of the memorable birthday for your dad. This step by step really helps for planning a surprise vacation for someone you love. I will think about this when the time is come for me to plan one.
They were so incredible! And yes, giving a surprise birthday trip is one of the best gifts I've ever given 🙂
That is AMAZING!! I would love to be able to do this for someone one day - I bet that feeling was incredible!
It was! My dad was so happy and very surprised
I actually planned a surprise vacation for my husband for Father's Day last year. Packed up the car and everything. He had no idea.
How sweet! Where did you go? I bet he was happy 🙂
Surprise vacations are always the best! Definitely a bit hard to figure out the logistics and actually making it happen, but it's definitely a perfect way to make the surprisee feel appreciated
I couldn't agree with you more!
Great post the planner is fab too it is my husbands 40th in a couple years and i would love to plan him a surprise trip great tips thanks
Thanks Katie! I hope it comes in handy when it comes time to planning x
Ahh nothing beats surprising a loved one with a holiday!! It's great to make memories together and it sounds like you had a fab time with your parents. I always try to pick up on cues to see where my partner wants to travel next so I have an idea for birthday or Christmas presents.
That's perfect! I love revealing the surprise, it's the best bit 😀
This is lovely, I have planned a semi-surprise vacation (mum knew Dad didn't) to France and they absolutely loved it.
Aw how sweet! I'm glad they loved it too!
I would LOVE to plan a surprise trip for my husband; he really deserves it! We live in the US, so a more financially feasible trip for us, would be somewhere within our country. You've given me great ideas; thank you!
The US has tons of great places, I'd like to see more myself! Would love to know if you book him a trip!
Our biggest financial hurdle is funding the flight from the US to overseas. From there, we can make it work, but saving up to get there in general has been so hard for us. These are really inspiring tips to help though!
You're welcome! I totally understand, it's the same for me flying to your side of the world. I hope you plan something one day soon x
I love the idea of a surprise vacation. I'm still waiting on mine. LOL But seriously, I think this would be the most amazing gift anyone could ever get.
Aw don't wait too long, it's one of the best gifts you can give!
I love planning a surprise vacation! I did it twice for my husband and he was very pleased with it. However, when he secretly planned one for our anniversary I wasn't to happy. He packed whatever clothes he thought I would need for a week in Hawaii. Unfortunately he packed all the wrong things, lol!
Lol oh dear! I should add that to the list! My dad knew a week before, so he could pack his own clothes 😀
Here are some essential tips to follow. It's really important to start planning and all arrangements a bit early to make the trip a successful one. I never thought for any surprise trip, it sounds like a cool idea should try once.
You really should!
Great tips! I don't know if I could do this- my husband and I usually plan everything together! But a surprise trip would be so fun!
Think about it for one day, it'd be an amazing surprise 😀
It is hard organising anything that this a surprise - whether it is a party or a vacation. There are some excellent tips here. We love Porto and it would have been a perfect destination for the surprise. A city that is walkable, safe, with great food and lots to do.
Absolutely! My parents loved both cities equally, but I'm keener on Porto 😀
So many great tips. I've never planned a surprise vacation as it seems so stressful, but these tips help a ton and help ease the stress 🙂 I hope to plan one someday for my parents.
Thank you! You should think about it for the future, it's not as stressful as you may think 🙂
I have never planned a surprise vacation. Trying to get all the details right always seemed challenging. The more you know the person, the easier it must be. But your tip about listening for cues is good. And worrying about comfort is important when travelling both with older adults and children. I am glad your surprise vacation for your dad turned out so well.
Aw thanks Linda! I really appreciate the feedback. Both my parents had an amazing time 😀
I planned a surprise vacation from my that time boyfriend and it was truly nice. However the bad was about the logistic. Being on a long distance relationship I didn't manage to buy easier flights fro him but I had to come to my town.
There's definitely no one size fits all when it comes to the planning process. I hope you still had a nice time 😀
What a lovely gift for your Dad’s birthday. My partner and I always get each other flights or experiences as gifts but it tends not to be much of a surprise. This year, I may just follow these tips as he has a big birthday coming up 🙂
Thank you, he loved it too! Let me know what you plan, I'd love to know the surprise 🙂
I must admit that you gave some great advice here. I'm always trying to plan my trip and make the most of it, but sometimes it just feels that something goes wrong and somehow I have some situations that I didn't plan. I will definitely try with those tips for my next trip 🙂
Excellent! Definitely download the free surprise trip plannner; it'll help keep track of your progress 😀
How wonderful Lisa! Well done on pulling off the surprise vacation for your father's bday. I absolutely love surpises and travel so this is like the best combination ever! What a great destination to celebrate his birthday and a nice gesture from the hotel for sending an entire cake. Every milestone should be celebrated and I'm gld your parents had a fantastic time!
Thanks Amy! They had an awesome time, and it was so sweet of the hotel to add those extra touches too 😀
My husband and I booked a surprise cruise for our families last Christmas and I feel like it's the best kind of gift that we can give them - the gift of adventure. Happy to learn more pointers here 🙂
That must have been a great gift! Thanks for reading 🙂
Awesome tips in this post! I have never planned a surprise trip, but I think it would be a lot of fun, and you provided some great advice! I can only imagine how special this must have been for your dad. Hopefully planning a surprise vacation is in my future. 🙂
Thanks Leah! I loved planning the surprise, and the look on his face was just wonderful 😀