Planning a Surprise Trip for a Loved One

Since my lips are sealed on where I’m taking my boyfriend this year  (till July 🙂 ) I thought I would put together a list on how to plan a trip for a loved one. Whether your relationship is romantic or not- a trip will bring you two closer together by creating new memories.

Here are a few steps to get you started.

  1. Know Where They Want to Go

A great way to figure this out is to ASK. If you don’t feel comfortable asking, look for clues. Do they have a travel bucket list? Books on places? Brochures laying around? Would they like to visit a cosmopolitan environment or a remote location?  Is there a new restaurant they want to go to or a place far far away? Friends they have been meaning to see? You can also examine where you’d like to go- if you two have similar interests they’d probably like the same place as you!

       2. Know What They Want to Do

Does your loved one have a passion for a certain hobby or interest? Asking them ‘would you rather’ questions can help clarify activities that they’d want to pursue.  Are they into being outdoors or indoors? Do they enjoy a certain cuisine?

3. Get Creative! 

You don’t have to stay at a four-star hotel in a far far away place to create special memories. Find unique places to stay by using vacation rental sites. Find unique things to do by looking at visitor information sites for the location or state. City websites are immensely helpful in finding hotels, restaurants, etc.  TripAdvisor and locals are invaluable resources for determining what and what not to do!

      4. There’s No Such Thing as a Bad Vacation 

Although this seems rather silly, it’s a good thing to remind yourself when you start feeling the pressure to create the perfect experience for your loved one. Not only will your loved one feel flattered that you planned something special for them, you’ll also have the comfort of knowing, should everything go horribly wrong during your trip, it will be memorable!

5. Start early. 

This is an important tip no matter where you decide to go. Many accommodations and restaurants, especially hot destinations and popular local places will get booked up during the “on season”. Knowing when the peak traveling seasons are for the place you intend to go and planning accordingly will only benefit you both. If money is a concern, you can save on expenses by traveling in the “off season” and have the extra benefit of – lack of other tourists!

     6. Leave Room for the Spontaneous 

Whether you are going away for a day, or a few weeks- resist the urge to plan every minute of every day. Allow your loved one to make decisions about which activity they’d prefer or restaurant they’d like to visit. Eating food you wouldn’t normally eat, or doing activities that are more their style- will be a great experience for you two.


Thanks for reading. I’d love to hear how your trip goes, or if you’ve ever been the lucky recipient of a surprise getaway!

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