First Trips with Your New Sig Other

First trips with your new sig other

Sometimes Moms just can’t help themselves. They just want to see you happy and part of things, no matter how old you are, and that means having that partner in life. Well, maybe Mom is onto something. That first trip can make or break your relationship, but no pressure; Regina and Christine have you covered. These are their ideas for where to vacation with your significant other.

Travel is a Big Step

You see inside someone’s soul when you travel with them. So that first trip away with your significant other will let you know at minimum if there’s real compatibility. Regina and Christine talk through what you need to think about when you’re planning where to vacation with your significant other. These are also some key takeaways to think about as you plan to give yourself the greatest chance of success.

The Destination List

The key to a first trip is to keep it easy, whatever that means to you. It’s nice to think that it doesn’t matter where to vacation with your significant other. However the truth is vacation time is scarce. So if you’re going away together, you might as well pick a place that you’ll enjoy. These are a few ideas to consider for that first trip, or even fiftieth.

The Islands

St. Barths

When an island exists to show you a good time, it becomes the perfect place to get away on a first trip. The hotels, food, service, shopping make the optimal base for where to vacation with your significant other. The best part of St. Barths is that you can return again and again. You almost can’t have anything but a perfect trip together.


Of all the Caribbean islands, this one is a sleeper hit. Besides having easy direct flights from cities all over the U.S., Barbados has everything you need for successful first vacation with your significant other. There are hotels of all premium budget levels (it is Barbados after all), that something will work. There’s also beautiful beaches, tennis, diving and activities for the sporty couple. Lastly, Barbados is an island where you can hop in the car and explore the quaint lunch, beach clubs and dinner spots. Or you can just do nothing and hang out at Sandy Lane.

The Brando

This one we’re throwing in there, because we know there’s someone out there who goes big. It doesn’t get bigger than The Brando, which really if you start here, there’s no place that you can honeymoon. The Brando is the ultimate place to go on vacation with your significant other. If you do find someone who is into grand gestures, this is where to go.

European Cities


There’s a reason that besides Virginia, Paris is for lovers too. And if you can’t find some common ground in Paris, chances are it’s not Paris that is the issue. From the hotels, to the restaurants, to just walking around and wandering through the city, there is plenty that will bring you closer together. It also doesn’t matter if it’s your first time in Paris or if it’s your fiftieth. Paris is a city where it can feel like a second home.


With no language barrier, London is a soft landing for where to vacation with your significant other. It also shines, literally, when the sun is shining, which it mostly does this summer. Like Paris, it’s a walking city where you can explore neighborhoods and also take in the fun London scene.


If you’re both intellectually curious and enjoy history, or just like Italy, Rome is where to vacation with your significant other. It’s also slightly  more gentle on the pocket than Paris and London right now, but has top hotels and restaurants too. The shopping is also a draw in Rome, as is the high romance factor as you walk through the city’s major landmarks.

Lake Como

It’s not just large cities in Europe that are a good idea for where to vacation with your significant other. Lake Como is one of the most romantic places in Europe that is lower key yet still glamorous. Just ask George and Amal, who while they can vacation anywhere, still come back to Lake Como every year.

Tips for Planning

The key is communication as you’re planning your first vacation with your significant other. The other piece of advice is set the expectation that you will need to compromise. Unless you like doormats, you’re probably with this person because you like and respect them. And at Galavante, we tend to attract a community of people who are successful and have strong personalities. Therefore these tips are considerations to think about, and to level set so that you have a successful and fun first trip away together.

  1. Establish a destination that you will both enjoy, that will be low-pressure.
  2. Talk about budgeting and expectations on who will pay for what.
  3. Choose a hotel that you know will be conducive to a first trip away.
  4. Plan the major meals and activities that will be sold out.
  5. Manage potential conflicts ahead of time.
  6. Leave some room for spontaneity.
  7. Have fun and don’t take any of this too seriously.

We know that we hyped up all the planning and did say that you see inside someone ‘s soul when you travel. But at the end of the day, the point is to enjoy yourself. Also when things go awry, as they often do in travel, it gives you a chance to see how you handle challenges as a team. If you’re meant to be, where to vacation with your significant other becomes less important than spending quality time together.

Other Articles You’ll Like

The Podcast: Where to Travel this Spring
Regina + Christine on Being Your Best Self 
Cool Places to Travel in 2024 

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