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. 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!)
  6. Gift them a new backpack or luggage set! Below is the best travel luggage on amazon.

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?
  • Comfortable Travel Items- There are some things that make the traveling experience that much better (like having your favorite snack on the flight). My top thing to not forget at home is a reliable travel pillow! I absolutely love mine from PineTales. It has a designer bamboo pillowcase and offers better support because it’s filled with premium buckwheat. It’s great to travel with through the airport, plane and even makes a great knee pillow for the hotel (they never provide enough pillows anyway!)
  • 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.

Booking A Surprise Trip With A Company

Instead of planning a surprise trip yourself, there are also surprise trip companies that will completley do all the heavy lifting for you! There are several reasons why I would reccomend booking a surprise trip with a company-

  • You also want to enjoy the experience of a surprise trip (you don’t really get to be surprised if you’re the one booking the getaway)
  • You don’t want to worry about the logistics of picking a destination, booking a flight + hotel, planning things to do, finding restaurants, etc.
  • You don’t consider yourself a good planner and want someone else to do it for you

What Surprise Trip Company Should You Book With?

There are several surprise trip companies out there but I would recommend booking your trip with Next Where! The mission of Next Where is to “set-up your perfect weekend at an unforgettable destination. We’ll send you to places you would otherwise never visit. Or maybe you would – but with Next-Where you will travel under a completely different mindset, or at least we hope so.”

Our Surprise Vacation Experience With Next Where

We booked a trip with Next Where for a weekend getaway in February and were blown away with how much we loved the experience! Next Where coordinated our fights, hotels, and even gave us recommendations of what to do, see and eat while we were in Denver, Colorado. The best part of this experience is that we had no idea where we were going until we got to the airport!

Once at the airport, we first opened up the envelope that told us where we were going to be flying to. In our case, it was Denver. Next, we opened up the envelope of where we would be staying. We were so impressed with the hotel that they choose- The Hyatt Regency Denver At Colorado Convention Center. Lastly, we opened up the envelope that had recommendations, based on our interests, of things we could do and places where we could eat!

The flights went really smoothly and we were so happy once we arrived to Denver and checked into our hotel. As mentioned above, we stayed at the Hyatt Regency Denver At Colorado Convention Center that was in the ideal location to do some sight-seeing!

In addition to the location, the hotel provided excellent views of the city and surrounding mountains, had an amazing fitness center, pool, and rooftop hot tub! (If you ever find yourself in Denver, don’t hesitate to book a stay at this hotel!)

What I also loved about this hotel was that they had on-site dining options. We had the opportunity to dine at the Former Saint Denver for both breakfast and dinner and were impressed with the atmosphere, seating options, and most importantly, the food!

For breakfast, we enjoyed the nutella pancakes and salmon eggs benedict and for dinner we feasted on perfectly cooked chicken and lamb. Seriously, the next time that you are in Denver you need to stop at this restaurant whether you stay at the hotel or not!

The entire weekend we spend walking around the Lodo District and exploring famous sites such as Union Station, the 16th street mall, and the Capitol building. All of these places that we visited were found in the third envelope that we opened.

Overall, we would give Next Where a 10/10 for the surprise trip experience that they provided us! If you have more questions about booking a surprise trip with Next Where, you can visit their FAQ page.

Is A Surprise Trip For You?

In the words of Next Where, “If you are a spontaneous, open-minded traveler seeking a break from day-to-day stress, you are at the right place.

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