Sister Trips Are the Best: Here's How to Plan One

In 2018, my older sister, Kelsey, flew to New York to visit me. The plan was just to hang out in the city for a few days, but at the last minute, we decided to head to a small beach town in New Jersey. Neither of us had even been to the state before, let alone that quaint little city along the coast, but that trip is responsible for some of my favorite memories with Kels. It was the getaway that made me catch the “travel with my sister” bug—and I’ll always be grateful for that.

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Soon after that New Jersey escape, sister trips became the norm, and now there’s no other type of vacation I would rather go on (or anyone else I’d rather travel with). Some of the destinations we’ve been to include a mountain resort in Aspen, a condo in Chicago, a high-rise in downtown Denver, a desert hotel in Scottsdale, and a waterside property in the Hamptons.

Each trip we go on seems to top the last—not necessarily because the destination gets better, but because we’re constantly getting closer. We could venture to a cabin in the middle of nowhere and we would still find a way to have the best time. I live for these moments with her, and if you have a sister that you’re close with, you likely know just how special it is to score some one-on-one time. Keep reading for everything you need to know about planning a sister trip of your own.

Source: Kara Thompson

How to Plan a Sister Trip

Below, you’ll find tips on booking your own sister getaway, complete with destinations, activities, and ideas for your itinerary.

Start with the logistics

The biggest factor in planning any type of vacation is landing on a destination. Some of my favorite sister trips with Kelsey took place in cities that I never thought would be at the top of my bucket list. Truthfully, there are a ton of touristy spots that feel overdone at this point—I’m mostly talking about the places that everyone goes to for bachelorette parties. While I won’t argue that those cities are fun to visit, I think there’s something incredibly special about picking a destination that’s more under the radar.

When planning your own sister getaway, research some smaller towns that you might not normally consider visiting with a larger group. One of the major perks to traveling with your sibling is that you have likely been to a lot of the same places already (thanks for the family vacations, Mom and Dad!) This opens up the perfect opportunity to cross some more unique destinations off your list, so be sure to take advantage.

Don’t overschedule activities

It’s obviously important to map out some activities you can do while on your trip, but I’d highly recommend leaving some free space in your itinerary. Until you get to your destination, it’s impossible to know exactly what the experience will feel like. Maybe the bar scene will be wildly better than people described, or maybe you’ll stumble upon a cute shopping area that you want to explore. Leaving some wiggle room in your itinerary will allow your trip to unfold in a more natural way, and it can result in some pretty great memories.

Create a stellar dining list

Full disclosure: My sister and I are major foodies. We also can’t turn down a good cocktail (a martini for her and a margarita for me). That means the bar and dining scene is always a major draw for us, regardless of the city we’re in. On our sister trips, we typically like to hit a bar before or after each dinner. We have met so many locals and have had such great conversations with other travelers just by going out and enjoying the nightlife. After all, it is a sister trip, so enjoy yourself!

As far as creating your dining list goes, my recommendation is to do the research together and then narrow it down. Once you’ve agreed on your restaurants, I’d suggest letting one person take the reins on making reservations. This just streamlines the process and makes it clear whose name each reservation is under.

Be open to the unexpected

I’m convinced that the best experiences happen when you least expect them. During our girls’ trip to New Jersey, Kelsey and I were lucky enough to meet the owners of the resort. We ended up having dinner together, then somehow wound up at their house for some astrology readings (LOL). When they took us back to the property, we pulled off the road a bit and did some old-school stargazing. It ended up being the most random night, but it was so special.

On our trip to the Hamptons, we signed up for tennis lessons on a whim and ended up with Roger Federer’s coach as our instructor. Considering the fact that neither of us had any tennis experience, it made for quite the outing. We (mainly me) missed balls left and right, but we laughed the entire time. Now it’s a memory I look back on with so much joy.

The point is: Be open to the unexpected during your sister trip. Whether that means striking up a conversation with a local or changing your plans at the last minute, it will yield better memories if you have an open mind.

Pack something fun

OK, I know that luggage space is sacred, and it’s already hard enough to squeeze your essentials in. However, there’s something so fun about bringing along a little surprise for your sis.

On our last trip to Scottsdale, I brought some quirky sunglasses along with me to complement the desert and pool vibes we were heading for. I gave her the glasses during our flight, and they became the perfect photo props and statement pieces for the weekend. A little something can go a long way—and it musters up excitement before the trip has even officially started.

Source: Kara Thompson

18 of the Best Destinations for Sister Trips

There are tons of girls’ trip destinations that go beyond Nashville or Austin. Here are some more out-of-the-box destinations that are worth considering for your sister trips. While each spot has a unique feel, they all offer lively dining scenes, cozy lodging, and a plethora of activities.