Going on a trip with your boyfriend is a ton of fun, but planning a surprise trip for you and your boyfriend takes the excitement to an entirely new level.
Whether it’s for his birthday or your anniversary, surprising him with a romantic getaway is a fantastic way to make more memories together.
But you don’t have to wait for a special occasion. Planning a trip for the two of you just because you feel like it is a surefire way to catch your boyfriend completely by surprise.
Your guy might love trips and going on vacation, but it’s likely that he doesn’t love the planning part (or the packing part)!
Your boyfriend will be super happy that you took the time to do all the planning to surprise him with a fun trip.
Let’s get planning!
1. Decide the length of the trip 📅
First things first, you need to figure out how long this trip is going to be. There are a few things to consider:
1. You’ll need to find out when it suits both of you to go on a trip. Try to plan your surprise at least one month in advance so you can figure out both of your schedules.
2. The longer the trip, the trickier it can be to pull off the surprise. If it’s your first time planning a surprise trip it might be a good idea to start with a long weekend away.
3. Deciding how many days you’ll be away will also help you choose where to go and how to get there. For example, if you’re taking a three day long weekend trip it’s not the best idea to go somewhere super far away that requires a layover or a ton of driving.
4. Usually, the longer the trip, the more money you’ll spend. Which brings us to…
2. Determine your budget 💵
When you’re planning a surprise trip for your boyfriend, it can be a bit tricky to set a budget.
You need to decide how much you are going to spend, and who is going to pay for what, without your boyfriend’s input.
If you are organizing a surprise vacation for your boyfriend’s birthday, you might decide to pay for the whole trip, or at least the accommodation and transport. If it’s for your anniversary, you might decide to book everything but then split the cost of the trip later.
You know your boyfriend better than anyone else, so trust yourself to set a budget that you’ll both be happy with.
3. Plan a cover-up story 🕵🏽♀️
Unless you have an “in” with his manager and can secretly request time off for him, you’re going to need to be clever to get him to take time off work.
If you have friends or family out of town, use them to your advantage. Let them in on the surprise and have them pretend that they are coming to visit you. You could say something like this to your boyfriend:
“Hey, so and so wants to come visit us for a few days and would love it if we could take some time off to show them around. What days work for you, and can you schedule that time off so I can let them know asap?”
This sneaky little trick gets you the scheduled time off, and he’ll be less likely to catch on now that he’s focused on the cover story!
3. Choose where you’re going to go 🌎
Now that you’ve got your dates planned, your budget set, and you’ve got a solid cover story, it’s time to pick a destination.
Researching where you’re going to go is one of the most exciting parts of planning a trip.
However, choosing a destination can be tricky when you have so many options. One way to make it easier is to first decide on the specific type of trip you want to go on with your boyfriend.
To help you out, here are some fun ideas for a three or four-day trip:
1. Play tourist
Pick a fun city you’ve never been to and just see where the weekend takes you. Enjoy being tourists and try not to over-plan things.
Highlight a few sites you’d love to check out and stop in anywhere that looks interesting along the way.
Try some delicious local foods, grab some cocktails, and stay in a popular area in the heart of the city so you can fully immerse yourself in the culture.
2. Ultimate relaxation
Have you ever come back from a trip and felt like you needed another vacation?
Plan a more laid-back getaway if you and your boyfriend could do with a break from your busy schedules to just relax.
Renting a beach house or a cozy little cottage in the woods is romantic and will leave you both feeling totally refreshed.
Who doesn’t love lounging by the beach or cozying up next to a fire with their man?
If you really want to go all out, you can book a retreat at a spa and enjoy being pampered together.
On an action-packed trip the fun doesn’t stop until you’re back home in your own bed!
If you and your boyfriend would rather be out adventuring than relaxing by a pool, pick a destination that has lots going on.
For example, flying into a city during an event like a weekend music festival is exhilarating.
This type of trip is all about the event or activities, so give yourself a full itinerary and ride that high together.
4. Plan an itinerary 📋
Once you’ve decided what type of trip you want to have and where you’re going to go, it’s time to start putting together an itinerary.
It could be a detailed schedule of what you are going to be doing at exact times each day, or just a rough plan of the activities you’re interested in.
You and your boyfriend might enjoy doing the same things, or have really different interests. It’s good to strike a balance between planning activities your boyfriend will really enjoy and things you want to do on the trip.
Even though you are planning a surprise trip for your boyfriend, it’s important that you have a great time too!
There are literally thousands of different things you could do on a trip with your boyfriend depending on where you decide to go. Here are just some ideas of activities to look into:
– Live events like concerts, shows, and festivals
– Amusement parks
– Sight seeing tours
– Outdoor sports and activities
– Museums and art galleries
– Relaxing experiences like massages or spa treatments
5. Plan how you’re going to get there ✈️
Depending on the length and destination of your trip, you’ll most likely be flying or driving.
If you do plan to drive, try to keep it a short distance or extend your trip, so you’re not spending the bulk of the time in the car.
However, an exception to that is if you both love long car rides or your surprise is a super fun road trip!
6. Start Booking 💻
The first thing you should always book are flights, if you are going to be flying. The price of flights can increase super quickly and there are usually limited options.
A close second is to book accommodation.
Booking.com is the best place to book hotels. You can read reviews, view photos, and you can often find better deals than what you’ll see on the hotels own website.
If you don’t want to stay in a hotel, Airbnb is great for finding really unique accommodation. Staying in a Airbnb will also help you get the authentic local experience while on your trip.
7. Get packing 🧳
If the surprise is going to be kept a secret right up until the last minute, you’re going to need to pack for your boyfriend.
You could ask a friend to take him out the night before your trip so you can pack while he’s away.
Another option is to offer to do the laundry and just pack his clean clothes along with whatever else you need into a suitcase instead of putting it away.
Taking care of packing for him allows you to keep the surprise for a little bit longer, making it even more exciting.
8. Plan the big reveal 🎉
How you reveal the surprise trip is entirely up to you.
If you’re driving somewhere, you can wait right up until you arrive at the destination, or you can start dropping hints leading up to your arrival.
If you’re flying, you can always choose to wait until you get to the airport, or you can surprise him the morning you leave.
Let’s say you’re surprising him with a trip to New York; you could always buy a tiny Statue of Liberty and place it next to his toothbrush with a note. Another option would be to hide the tickets in a drawer and ask him to grab something from there for you.
No matter how you choose to surprise him, he’s going to be super excited and you’re both going to have a blast.
Exploring new cities, trying new foods, seeing new things, and spending quality time together are all things that help couples connect and become closer.
Your boyfriend might love traveling, but guys aren’t always the best at organizing things. Your boyfriend will love it if you plan a surprise trip for the two of you, and all he has to do is enjoy it!
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