How to Plan a Vacation With Your Sweetheart, Boyfriend, Spouse, Partner, or Unicorn

Updated on March 12, 2019
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Andrea is a dating consultant who gives people advice on relationships and couple stuff. She's also a fan of traveling the world.

Traveling the World Together

When a relationship has really found a solid foundation, a vacation with your sweetheart is on the way. For some, this could be a process that's a total breeze and doesn't take much planning because the two of you know each other so well. But for many, a long-term adventure could be brand new territory, and there is nothing like some friendly advice to help you get on the right track.

This article is for couples and already established relationships, not so much for those who are dating and trying to figure things out.

Discuss Financial Scope of Trip

First, you need to discuss the scope of your trip. You'll need to discuss what time of year for you is ideal and roughly where your finances fall—this doesn't mean you open up your bank account and discuss every detail.

Think of it this way: If you want to save more money this year, then take a trip that's closer to home. If you have more to splurge and you're willing to splurge, then try traveling further away to somewhere more exotic. It's okay to say hey—I do want to go somewhere, but it can't be too far away. I would like to keep it closer to home so we can get away, but also so we don't spend too much money.

Both of you need to make lists or suggestions about where you want to go until someone comes up with an idea that both of you really feel like is a good fit. You might have to pitch a few ideas, so don't get bothered if your partner rejects the idea or puts it on the backburner. Really consider what are your interests and what kind of vacation you would like.

If you both like museums, history, and chocolate shops, maybe go somewhere on the East Coast. If you're both adventurous and like to be active, try Colorado or some nice hiking trails out in Peru.

Picking the right vacation spot also entails understanding your relationship and what makes it shine. In these early stages, you may want to consider the following:

  • What you'll do with your pets if you travel for a long time, and if the dog(s) can come with you.
  • If you'll need a passport and if it is time to update your passport.
  • How well you do outside your comfort zone.
  • Whether crowds are a good thing or would be better avoided.
  • What kind of activities bring you together.
  • Your comfort level around people who don't speak the same language or have a sharply different accent.
  • Any illnesses, food allergies, or other personal problems that could get in the way.
  • Who will be your emergency contact.
  • Favorite foods.
  • If you'll split the bills evenly or some of the bills.
  • How well the two of you share, compromise, and agree. You'll want to do activities you both like and also activities that maybe lean more toward one person's interests or the other's.

Taking Days Off

After deciding where you want to go together as a couple, you'll need to get some big-ticket items off the list. First, you'll need to get the time off with work. Some of you may have vacation PTO, while others of you have other working situations. As soon as you know what dates you want to take off, you need to get with your employer to ascertain that you get those days off.

This could take some extra thinking as not everyone has an 8–5 shift from Monday to Friday. Some of us work weekends and are off Tuesday and Wednesday, others of us work overnights, split shifts, or schedule our own time. It is important that you take some vacation time each year to relax. You need to step away from the job and trust that things are okay while you are gone at play. Your mental health needs it.

You might have to compromise on dates for your vacation. Also, consider big events that could be coming up in your life like your little sister's graduation or your best friend's wedding. You might need vacation days for those dates too.

Finding Accommodation

After you've secured the dates the next most important step is to secure lodging and any transportation costs. You can get a travel agent for advice, there are also several travel websites that can help you—and help you find incredible deals (like Travel Zoo or Travelocity).

Airbnb makes it easy for you to find a place wherever you want to go. People rent out their places for you to stay. I actually recommend going to a Bed and Breakfast. You'll be assured a meal, the hosts will be excellent guides for the know-how on the area, and they'll tell you about the things you should do in the area as opposed to what are the busts.

I highly recommend looking through Bed and Breakfasts online before looking at Airbnb or hotels. With Airbnb, you don't normally get a meal with it, but you do get much-wanted privacy. Hotels can sometimes be noisy and overpriced. Select carefully and diligently.

Travel agents can help you find a place when you want to travel overseas; I recommend this if you are not really sure how to scope out the area and don't want to fall prey to scams. Read Google reviews on anything and everything, so you get the best bang for your buck. (Great things to scope out on reviews first: hotels, bed and breakfasts, restaurants, travel apps, stores, and check crime maps.)

Booking Flights

For flights, I recommend Google Flights. You can put in your desired dates to any two airports and save the information so that when the best deal arrives, you'll get it in your email. Google Flights is also one of the better customization services. I recommend downloading several flight apps and trying them out to see what you like. There are certain days where deals tend to be better. Midweek flight hunting deals are better than on weekends. It's usually cheaper to fly certain days too. Airports tend to get more foot traffic on the weekends, so prices are higher. If you can leave on a weekday, it could save you some money, depending on what exactly you want out of your trip and your scheduling.

Most airlines are roughly the same experience. I don't recommend Spirit, and I prefer Delta and American over United. Not all trips come with a meal but usually a snack and beverage of your liking. If you have never flown, you may want to bring along motion sickness medicine just in case.

Pack Light and Prioritize Comfort

For happy and successful flight traveling, wear comfortable shoes and dress in layers. You'll likely come across varying temperatures while walking through the airport(s) and while on the plane. If you wear contacts, I suggest having a glasses case in a spot where you can reach them comfortably. If you have a long trip, you might want to take out your contacts. I also recommend carrying around a toothbrush and some floss for long flights. Pack your luggage earlier than later and try to take fewer items than you intend. The less you carry with you on the trip, the better. If you can take a single carry-on without luggage, that's pretty amazing. Some lodging places will allow you to do laundry on site.

Don't bring more than one luggage case per person. Often these bags will cost $50 a pop. It'll also be a pain to drag that much luggage to your place of stay. Taxi drivers and hotel staff can only help you so far.

Here is a list of essentials for flying:

  • Passport. Make sure to put it in a spot that's easy for you to whip out but also difficult for someone to steal. ALWAYS PUT YOUR PASSPORT IN THE SAME SPOT, that way you don't lose it.
  • Tickets in hand for ease.
  • Book to read.
  • Any medicines.
  • Comfortable shoes.
  • Layers. Bring a sweater. Check the weather of your destination. Do you need an umbrella?
  • Toothbrush and floss.
  • An extra pair of clothes in your carry-on for emergency situations.
  • Wallet.
  • Charged cell phone with charging devices.
  • Save important emails about travel information. Check them before going to the airport.

Traveler's Insurance

Make sure you buy traveler's insurance for your trip in case something happens, like a hurricane that cancels flights or something of that nature.

It's a good idea to plan out your route from the airport to your place of stay. You might have more options than you realize: a bus, a rideshare option, taxis, boats, trains, and sometimes walking.

Road Trip Rules

If you plan to travel on the road and forgo flying, you'll have some different pros and cons. Your trip could last longer and you'll have to pay attention to the road, where you don't have to worry about other drivers while flying. You can also take more things while on the road, and it's easier to bring along the dog.

Many of the things you need while on a road trip are the same for a flight. I suggest packing some sandwiches and snacks to avoid wasting money on the road. Fill up on gas before leaving town, and switch out who pays for each round of gas so it doesn't all fall on the driver.

I suggest putting together in advance a playlist of your favorite tunes or new music. Podcast lists can also work, if you have similar interests with your sweetheart.

Check road conditions and weather before you set out on your journey. Also, make sure your car is up to date on all tags, insurance, and has no or little mechanical problems. Get your oil changed, your tires rotated, and brakes tested. You want to make sure your car is ready for a long haul.

Even though most of us use GPS now, it is a good idea to look at a map before setting out on your journey to get an idea of what's ahead. You might want to time out how long you'll drive from city to city or from state to state depending on your crossroad adventure.

Decide whether you're the couple that drives from point A to point B like they're on a mission or if stopping at things that look interesting is cool and groovy. Also, before traveling, know what your check-in times are at your place of lodging. Keep in touch with your host, so they know what to expect.

Avoid arguments on the road. Think before you speak. You don't have to be witty or right all the time.

Having Fun While on Location

Now that you've finally arrived there should be plenty of things to do. Hopefully the two of you have an idea of the kind of things you want to do before reaching your destination. Decide what days you'll do your favorite things you want to check out. Before going on the trip scope out good deals for those must hit items. Sometimes you can get free tickets to museums or dinner this way.

You don't have to have everything etched out in stone. It's okay to just relax and not really do anything some days... or all the days. Roughly know about how much you want to spend during the trip. Lodging and flights or other transportation should be bought in advance. Those will be your most expensive items.

You'll also want to budget for food and recreation.

If you're looking for romantic things to do, here are some ideas:

  • Some bed and breakfasts have packages for couples that include a spa day, candles, chocolates, wines, and soaps.
  • Look for deals on massages
  • Try out one of the fancier restaurants in town
  • Check out music venues in the area
  • Go to an observatory
  • Go to the beach at night
  • Hit up the hot tub
  • Wear fancy robes
  • Buy chocolates at fudge shops
  • Buy fancy soaps or bath bombs
  • Plan out something sweet and heartfelt yet simple
  • Look for couple deals in the area
  • Go to jewelry shops

Travel Tips for a Romantic Vacation

Remember—going on vacation is about having fun. Leave the work problems and the stress of everyday life behind. You'll be able to pick that stuff right back up when you get home, if you decide it's still a concern. Splurge a little and live life to the fullest. Have fun on the vacation and be willing to try new things.

Catching up on some sleep might be one of your highest priorities.

Try leaving negativity behind. Don't pick on your partner's flaws or nag about random things. Shove complaints aside. Go with the flow because no matter how much you plan with traveling strange things will still happen. Don't get upset over spilled milk. Enjoy the journey and be open to it. Do what helps you to relax and remember who you are despite all the other crazy things of adulthood.

Be excited for the adventure and expect that you might spend more than you intended. Try conserving your money as much as possible before the big vacation.

It also doesn't hurt to set goals before the vacation, like losing some weight, getting a new haircut, toning, tanning, something along these lines.

If you could travel anywhere it would be:

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