One of the great things about traveling is that it offers you a lot of options for surprising someone you love.
Over the past several years, I’ve been able to pull off a number of (mostly successful) surprises for other people that were truly worth all of the effort.
I’ll break down some of the different surprise ideas that you might think about for romantic surprises for your partner and some special surprises for your family and friends.
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The “circle back” surprise
One of the coolest surprises to do when traveling is what I call the “circle back” surprise.
This is whenever you notice that your partner is infatuated by a site and you figure out a way to return back to that site while also surprising them.
The best example of this for me was doing a helicopter ride in Kauai, Hawaii. We flew over the Waimea Canyon and Brad noticed a small picnic table on the edge of the canyon.
It looked like the perfect picnic spot to catch a view and relax from a hike. So I looked up how to access that picnic table and found out that it was on the route of a hiking trail.
We did the hike but I did not mention to Brad that our destination was going to be that ultra scenic picnic table and once we stumbled upon it he was speechless.
This type of surprise really shows your partner that you are always paying attention to what they say and even the simplest sites like a basic picnic table can end up being a great surprise.
But this is also one of the hardest surprises to pull off because you’re probably working with limited time and you really have to be paying attention and thinking ahead to pick up on these.
The pick up surprise
One of the easiest surprises to pull off is the pick up surprise.
All you have to do is arrange to be picked up from the airport or your hotel in some type of special vehicle that your partner will love. Luxury properties usually have a lineup of vehicles you can choose from and very high-end hotels even offer options like a Rolls-Royce.
If getting picked up from a hotel, make sure that you alert the hotel staff about your plans because my surprise almost got spoiled when a hotel agent rushed up to me to tell me that our ride was slightly delayed.
The welcome gift surprise
Another easy surprise idea is a welcome gift.
For special birthdays or anniversaries, you can often arrange for the hotel to deliver something special to your room.
Some hotels might actually provide this for free especially if they are a true luxury property and you have high elite status.
Other times, you can just order things like chocolate covered strawberries and champagne for a price. The key with these things is to time the delivery.
It’s usually pretty easy to ask them to deliver these things about 30 minutes after you arrive so that you can get a little bit settled but don’t have to sit around your hotel room waiting for the delivery.
Other times you may want to make it a little bit more romantic at the hotel and have them deliver it when you know you will be in for the night or at sunset. The hotel might be willing to privately text you so that can be an easy way to get it done without ruining the surprise.
Romantic decorations for the hotel room
You can take the above surprise a step further and request for the hotel to decorate your room romantically before you arrive. This would typically be with things like rose petals and the like.
This is not always doable for a few reasons, though.
For one, a hotel simply may not be willing to work with you for something like this.
And sometimes they have good reasons. They could be worried that the rose petals could stain the bedding for example. Other times candles may be a fire hazard.
But some hotels will work with you to do something and it often will involve some type of delivery like the above surprise.
The first class cabin celebration
If you’re ever flying first class on an international airline that is known for great service like Singapore Airlines or Emirates and flying on a birthday, anniversary, or honeymoon, that is an amazing opportunity to surprise your partner.
Even if you are a same-sex couple and potentially worried about receiving push back certain airlines, some of these airlines can actually be more progressive than you would think.
Singapore Airlines helped me pull off a first class surprise for Bradley for our anniversary and they brought us a cake, stuffed animals with our names stitched on them, and a huge card signed by everyone on the crew.
There’s nothing like a surprise celebration in the sky!
The under-hyped hotel room
One of the easier surprises is what I called the under hyped hotel room.
This one is easy to do because you basically just downplay the quality of your hotel room so that your partner does not have great expectations.
Then, whenever you show up at your hotel room your partner can be amazed by the awesome view, beautiful suite, etc.
I recently did this on a trip to Hawaii but by accident.
I was downplaying our room because I had our hotels mixed up and truly thought that we were not going to have that great of a room.
Then once we arrived at our room I realized that it was much nicer than anticipated. So did Brad.
It then clicked to me that this would be an easy way to add another surprise to our travels in the future. It’s the whole under promise, over deliver principal.
The post-travel food delivery
One thing that most people love about travel is the ability to try out different foods, especially local hot spots.
And now, with service is like Gold Belly it’s super easy to get those amazing foods delivered to your doorstep.
Brad recently surprised me on my birthday with lobster rolls from Maine which he noticed I fell in love with during a recent trip. It’s amazing how fresh these foods can be even when delivered from across the country.
Biting into those lobster rolls instantly took me back to my Northeast travels and it’s a great way to deal with the travel bug when perhaps you’re not able to travel at the moment.
So pay special attention to what your partner is into when it comes to cuisine and you’ll find it to be a great way to surprise them in the future.
The concierge surprise
If you have a premium credit card like an American Express Platinum Card you can utilize the concierge to help you arrange a surprise.
This is a great thing to do if you have no idea what you would want to surprise your partner with but you have a day or two of planning time.
If you are going to find it difficult to get away from your partner and have a phone call with the concierge to verify the gift sometimes you can just tell them to find something within a certain category and within a certain price range.
You can tell them something like “I want an edible arrangement under $100” and they will find something for you.
Then when the gift arrives the both of you will be surprised!
Of course, you can also utilize the concierge at a hotel to help you with things like this as well.
The surprise return
This surprise is more for people living abroad or for people just spending a lot of time abroad. Whenever you return home that’s always a great opportunity to give your family or friends a surprise.
The best examples of these in my opinion are when military members return home but even if you have just been traveling abroad for a long time the surprises are still priceless.
The best way to do this is to surprise them whenever they are in a setting where they would not expect you to arrive.
After living in the UK for several months we made a return visit to surprise my mom. We met up at a Mexican restaurant while they were in the middle of a meal and she had no idea what was coming!
Don’t let your surprises get ruined!
If you really want to pull off the perfect surprise, think through all the situations that could ruin your surprise.
Brad was recently infatuated with the rare sight of the green flashing light at sunset which you can usually only see when viewing the sunset on an uninterrupted horizon, such as an open ocean or mountain peak.
I booked us an astronomy night on top of a mountain which included giving us the chance to see this amazing natural phenomenon and looked forward to surprising Brad with it.
The problem is we found ourselves in an information center beforehand with a guy who had recently done the astronomy night.
Literally, one of the first things he mentioned was the AMAZING green flashing light that they train you to see and the surprise was no longer on the table.
So try to think through different situations where your surprise might be revealed by someone other than yourself. It’s the one time in your relationship it pays to be sneaky!
Final word
Finding ways to surprise your partner is a tremendous way to add excitement to your travels and to your overall relationship.
It’s a great feeling whenever you never know what your partner is going to try to pull off next. And it feels amazing to pull off the perfect surprise for your partner.
The ideas above should hopefully give you some inspiration for pulling off some surprises of your own and hopefully you’ll have success!
Daniel Gillaspia is the Founder of UponArriving.com and the credit card app, WalletFlo. He is a former attorney turned travel expert covering destinations along with TSA, airline, and hotel policies. Since 2014, his content has been featured in publications such as National Geographic, Smithsonian Magazine, and CNBC. Read my bio.
