Having a new boyfriend can be an exciting time in your life. Whether or not he’s “the one,” it is important to do things right. Chances are if the two of you are planning to travel somewhere together, you are getting along and the relationship is solid. However, planning a trip too early in your relationship could pose some problems, including discovering you are not as comfortable with him as you may have thought. Not being comfortable with your new boyfriend could turn a well-planned trip into a disaster. The last thing you want is to not be yourself while traveling. Here are some tips to help you determine if it is the right time in your relationship to plan a trip together and how to plan one the two of you will enjoy.

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Before making any reservations, discuss both of your expectations. Determine if you will spend the entire time together or if you’ll separate for a bit to enjoy a few things alone. For example, find out if you will spend the day exploring the city together and then enjoy the city’s nightlife when the sun goes down. Or determine if he will go golfing while you go shopping or spend time at the spa.

These are important things to discuss before making plans to avoid any disappointment while away. The last thing you want to do is look forward to spending time together at the beach only to discover that he has scheduled tee times.

Another important expectation to discuss is technology limitations. This includes the checking of emails, taking phones calls and smart phone game playing. It is your first vacation together. Do not waste it talking to your girlfriends back home or watching as he plays games on his phone.

Comfort Levels

Make sure you two are completely comfortable with each other, or at least comfortable enough to spend time away, alone, together in the same hotel room. Avoid planning a getaway after just a few dates. Make sure you have bonded a little and are truly comfortable enough with each other.

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Destination Ideas

Select a destination the two of you can agree on without any debates. You do not want one of you upset because they were talked into going somewhere they really did not want to go.

To help find a destination, have each one of you make a list of places you would like to visit. They can be romantic or not, because you can turn any destination into a romantic getaway, just as long as you both agree on it.

When selecting a destination, choose one that will limit the amount of time you have to travel to get there. This will reduce the lengths of awkward silence when you two are having difficulties finding something to talk about. Longer flight times will be perfect once you two are established and have plenty to talk about.


Find a location that has a lot of things to do together. Many resort destinations offer everything you need in a single location, including dining, shopping and recreational activities. The more activities there are at your resort, the more time you can spend together without needing to find something to do.

A small hotel room may feel cramped after a few hours. Since this is your first time traveling together, consider getting a suite with separate sitting areas. This will give you plenty of room to walk around and space to escape and be alone for a few moments, even if it is just to take a quick nap or read a book.

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Group Travel

If you are still uncomfortable planning a vacation getaway with a new boyfriend, consider planning a group getaway. Keep in mind that a one-on-one trip is more intimate and gives you more control over your schedule than when traveling with others. However, a group trip will give you the security of knowing there will always be someone else there should you two run out of things to talk about or the trip does not go as smoothly as you hoped it would.

A group getaway also gives him the opportunity to get to know your friends or you his friends.

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Contact the hotel or the Convention and Visitors Bureau for the location of your getaway. Ask to be sent as much information as possible. Online searches and local magazines for the area are also great resources for planning things during your getaway.

Make plans to do fun and exciting activities together, such as wine tasting, zip lining, hiking, sea shell hunting and mountain climbing. Be creative and come up with activities that you two will not be able to do once you are home.

Dining Plans

What do you plan to eat while away together? Discuss both of your likes and dislikes. Discussing this before the getaway will reduce the time it takes to find a restaurant. It will also reduce the chances of hearing “I don’t know what I want. How about you?”

If desired, do an online search for romantic restaurants in the area, look at their menus and call ahead to make your reservations.


Do not worry about your first getaway not going as planned. Be flexible and willing to make last-minute itinerary changes. If something better comes up that he wants to do, go do it. Also, do not be afraid to offer suggestions when you discover something new in the area that you did not originally plan for.

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Do not overpack for your getaway. You want to make your trip as hassle free as possible and limiting your luggage will help do so. You also don’t want to wear the same outfit all weekend long so bring some variety.

Be creative with outfits. Dress up what you are wearing during the day with some cute heels and add a scarf. Once you do, you are ready for a night out on the town.

Pamper yourself before leaving on your first getaway. Go visit the salon or day spa and get all dolled up. Have your hair cut and colored. Wax areas of your body that need it. Get a pedicure and manicure.

All in all, keep your plans for your first trip together as simple as possible. Remember to not get upset when something you do doesn’t go as planned. If your trip with your new boyfriend goes smoothly and you both have a great time, you are sure to plan another trip together in the near future.

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Heather Landon is a freelance writer with more than 20 years of experience. She has combined two of her passions – writing and travel – to share her experiences with others. You can read more of her articles at Examiner.com.