How To Surprise Someone With A Trip [How, When, Where + Tips]

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How to surprise someone (or your family) with a trip can be a daunting task. Not only do you you need know and schedule out the logistics of it, but also how you are going let that loved one know about the secret vacation! Here is the why, how, and additional tips and tricks on how to surprise someone with a trip!

How To Surprise Someone With A Trip [Complete Guide]
Exploring the dreamy Oceanside, California Mission

Why Plan a Surprise Trip

There are many reasons why you should plan a surprise trip. Some reasons include celebrating someones birthday, an epic Christmas gift, anniversary gift, or even a valentines day surprise. Or, it could be just simply wanting to surprise that loved one with a gift that they will cherish forever.

I planned a surprise trip for my husband to Hawaii and a graduation gift, and we enjoyed incredible outdoor activities while we were there!

Surprise trips are exciting, fun, and memorable. In addition, they provide the perfect opportunity to unexpectedly ditch the routine and recharge your batteries.

Just think, you could surprise someone with a trip to Alaska to escape the summer heat. Or maybe plan an epic surprise vacation to somewhere tropical during the dead of winter.

Click on a destination on the map to find a specific travel guide
Our Epic Weekend Getaway To Omaha, Nebraska

Tips On Keeping It A Surprise

The number one key of planning a surprise trip is keeping it a surprise! A few ways people drop the ball include not erasing your search history or keeping up their internet tabs that reveal all. The best way to avoid this? Plan everything using the incognito window on chrome.

Also, be careful about spilling the news if you share a bank account or credit card with that individual and they regularly check the statements. Instead, buy a visa gift card of the amount you plan to spend and purchase everything with that.

Lastly, when booking flights, don’t add their frequent flier miles to the booking. Nothing ruins a surprise better than that individual receiving the itinerary straight to their email.

How To Surprise Someone With A Trip [Complete Guide]
Checking off the U.S’s “Niagara Falls” from our bucket list

Scheduling a Surprise Trip

Scheduling a surprise trip is going to be one of the largest hurdles you face. Here’s a few tips of scheduling that epic vacation-

  • Check his/her schedule with their academic calendar if they are still in the university to see when their breaks are
  • Ask their friends/colleagues/co-workers more about their schedules
  • Depending on the job or company they work for, you can always go straight to their boss to request time off for them
  • Lastly, just ask them directly about their schedule around the time you are planning the trip

Additional Reading- How To To Travel With a Full-Time Job [Weekend Warrior Guide]

How To Surprise Someone With A Trip [Complete Guide]

Surprise Trip Reveals

9 Ways to reveal where you are going

Giving experiences as gifts is widely accepted as a wonderful alternative to giving material objects. But have you ever wondered how to give a trip as a gift, and have it still be fun to open? Make opening the gift an experience of it’s own! Here are several ideas of how to reveal a surprise trip-

10 Unforgettable Adventures in Oahu, Hawaii! These things are so great and I'm totally putting them on my list! I especially love the secret turtle beach, the amazing hikes, and the best beaches tips!
Exploring the Polynesian Cultural Center in Oahu
  1. Dress up as if you are in your vacation spot. For example, if you’re headed to the beach put on those flip flops and Hawaiian shirt before that loved one gets home. Going to Disneyland? Rock those mouse ears and that Disney t-shirt.
  2. Nothing says exciting like a good ole scavenger hunt. Leave little clues throughout the house that leads to the end prize of either flight tickets, a packed bag, you name it!
  3. Hand them a marked up travel guide of the future destination of places you’re going to see!
  4. Cook a meal that is local to the area you’ll be visiting. Not a good cook? Consider eating out at a restaurant that specializes in that cuisine.
  5. Gift them a new backpack or luggage set! Below is the best travel luggage on amazon.
  6. Buy them a camera that they can use to capture memories while on the surprise trip! Here is a complete guide to the best travel camera gear (all affordable options!)

Where To Go On Your Surprise Trip

You probably know the individual quite well so you’ll know where they prefer to go. Although Steve loved the trips I planned to this small island and this popular Mexican city, I know he prefers forested or mountain escapes (which is why we love visiting Idaho). So keep in mind your loved ones’ likes and plan accordingly.

fly fishing in swan valley
Exploring Swan Valley, Idaho

Still lost? Straight up ask them about their top three places they would like to visit someday. Or if you’re feeling adventurous, I like to use Skyscanner to find the cheapest airlines departing from my home airport and go there!

Here’s how to do it. Enter in your home airport. Then set your destination as “everywhere”. Next either choose the “cheapest month” or set a month of when you want to go. I’ve always scored the best flights deals while checking Skyscanner!

How To Surprise Someone With A Trip [Complete Guide]

When to Reveal the Surprise Trip

You have two options of when to reveal the surprise trip.

  • First, you can reveal the day of the trip! This one is risky yet incredible if pulled off correctly.
  • The next option is a little bit more safe by letting them know a little in advance.
Chasing incredible hot springs in Utah

Things To Plan For A Surprise Trip (That You Might Have Forgotten)

While you’re planning a surprise trip all by yourself can be quite overwhelming. Because you’ll most likely be planning your trip by yourself, you might worry that you are missing something. Here are a few travel tips while booking your trip of things not to forget about.

  • Flights– Like mentioned previously, I use Skyscanner to book my flights and always end up getting the best deals! You might consider purchasing flight cancellation coverage just in case.
  • Airport Parking– Know your airport, the fees, and the availability before arriving. You can find the cheapest airport parking with
  • Transportation when you get there. Do you plan on renting a car? Using public transportation? Or using an awesome tour bus?
  • Sightseeing/Plans– When we travel to a new city, I love purchasing the City Pass because it saves so much money on attractions, activities, and even food! Most U.S. cities are available on the City Pass.
  • Hotel or airbnb? If you are planning on booking a hotel, I recommend using this site. I always score the most incredible deals by using it! If you want to save a little money, then check out airbnb! Here’s a $40 coupon off of your stay!

Additional Reading: 5 Insanely Easy Ways To Eat Healthy While Traveling

Bear Lake Cabin, Utah
Enjoying our Cabin Retreat in Bear Lake

How To Document Your Surprise Trip

I’ve always said that the best souvenir is a travel photo! I recommend hiring a professional photographer is you are taking a special trip that you want to remember. Flytographer has great and affordable services! Use FLY25 for $25 off of your first booking.

Planning a surprise trip can be a bit scary, but if done correctly, can be an amazing gift that will be remembered forever.

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