The Great Girlfriends Getaway: Expert Tips For How To Have A Successful Group Trip


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“We should take a trip together.”

It’s akin to getting to third base in a friendship. You’ve realized the energy matches, you’ve had your share of late nights on the town as a group, and you genuinely enjoy each other’s company. It’s now time to take this circle of girlfriends to the next level.

For some, a group trip has come to symbolize the place or point where friendships go to die. The drama can begin before the plane even takes off when the size of the group headed to a chosen destination quickly dwindles from 10 to only four who paid the final deposit. Then, when you arrive at your destination, there are the constant battles over spending and activities; some want to lay on the beach while the others want to go ziplining. 

The group trip does not have to be the end of your friendship. It’s not an episode of Survivor where there’s only one participant left standing. Traveling together is this incredible chance to bond at a deeper intimate level and it allows you to create memories that years later will still bring a smile to your faces. Added bonus? You get to see the world.

Alea Simone, also known as The Travel Taurus, knows plenty about seeing the world.  

“I was going through a period where I did not like the trajectory of my life. After my dad died, I realized I should really be doing something that I’m actually proud of, so I just went for the thing I was most passionate about at that time and it was travel,” she tells ESSENCE. “I quit my job and traveled for four months. It was my first solo trip. From May until September, I went to 13 countries in Europe and spent the final two months across Asia. When the money ran out and I went back home, I knew I wanted to keep traveling.”

Simone’s travels led to growing popularity on Instagram and from there she created a website where she answers questions for those interested in adventures, which she has now turned into a full-scale travel agency where she hosts group trips internationally.

We want that group trip to not only make it out of the group chat but for everyone to also come back home excited for the next getaway. With that in mind, Simone offered some advice on the keys to making these assembled adventures work.

Set Expectations

Everyone’s travel style is different. Someone who has traveled to 30 countries solo is going to have a different travel experience than somebody who has never traveled out of the country before. Keep that in mind and be upfront about whether it’s an adventure, educational or relaxation trip you’re seeking.

Keep the Lines of Communication Open

As a group trip planner, Simone not only plans out an itinerary but she also requires participants to read all of the details by following up and having conversations during every stage, from planning to take off and during the trip. A planned itinerary allows people the chance to opt out of certain activities that they’re not interested in and make alternative plans. That gives travelers freedom and sets the expectation that just because you’re on a group trip doesn’t mean you all have to do the same thing all of the time.

Personalities Don’t Magically Change Because You’re Traveling

When it comes to traveling with your family or friends, you really have to think about what that person’s personality is like before you even invite them. I know that’s your friend. I know it’s your family, but is that someone you really want to go out of the country with? If it’s a friend who is known to become aggressive or irritated easily and they don’t do well in unknown environments, that may not be someone you really want to be stuck with for a few days or longer.

Planning Ahead Is Key for Big Group Trips

The more people you have the more organized you need to be. Everything needs to be streamlined and finances should be in order. Get a travel agent involved if you’ve been tasked with most of the organizing. They can take some of the stress off of you, offer ideas and solve problems you might not have considered.

If you want to take a big family trip, cruises are a great idea. The entire group is still in one space, but they still have the freedom to do what they want. It also helps with people not feeling alone and yet, also makes it easy for those who want to do solo activities.

Get Travel Insurance

Travel insurance is required to travel during Simone’s group trips. And while people think that travel insurance is a scam, it covers you if you lose your luggage, have a flight delay, and if you have to spend the night at a hotel they’ll reimburse you. A friend of mine came down with a fever when she was traveling last year and had to stay in a hospital in Bali. It cost nearly $7,000, but because she had travel insurance, the stay was covered.


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