The 20/30-Something Guide to Planning a Girls' Weekend

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In our 20/30-Something guides, we share our favorite shopping recommendations, dining destinations, and so much more with our readers.

Team SN is all about celebrating our favorite ladies, so today we are tackling how to plan an unforgettable girls' weekend. Read on for Sydney and Meghan's best tips, tricks, and ideas for a trip with your besties.

Sydney's 20-Something Guide

Image by Stan Dzugan via Getty Images

Where to Visit

The Hamptons, New York: I’ve pretty much grown up in the Hamptons and it is one of my favorite places, ever. There is nothing like being somewhere where you feel like you’re in the country and at the beach at the same time.

There are a lot of Airbnb, rental, and hotel options, so you can pick a place to stay based on what vibe you’re going for. If you want more of a party weekend, head to Montauk. If you want to relax, choose an Airbnb where you can BBQ and drink rosé with friends. Or, take the ferry to Sunset Beach on Shelter Island for a fun "beach to bar" day.

Miami, Florida: This is a no-brainer. It's a quick and easy flight from NYC, and the airport is a big hub in general so no matter where you are coming from you can always find flights! I went to college in Miami and now some of my family lives there as well, but even without those personal connections, Miami is a must-visit for a trip with girlfriends.

It has amazing restaurants, beautiful hotels and pools, and gorgeous beaches. You really get the vibe of being somewhere tropical, yet you're still in a city. There are endless options for dining and nightlife, and you can have a relaxing pool day or host a beach party depending on your group. It is literally impossible to be bored in Miami! 

What to Do

Head to a Fun Brunch: Because everyone loves brunch! It is the perfect daytime activity that can make your day fun, no matter if the weather is rain or shine. It's also a great way to transition your group from day drinking into your evening plans!

Host a Beach Bonfire or Picnic: There is so much to love about a get-together you put together yourself! I love planning a beach bonfire or a picnic with my girlfriends, and it’s generally a pretty low lift to make it happen. I always feel like it’s easier to have conversations and fun with your group in this setting rather than in a loud restaurant. Also, this is a perfect opportunity to get your golden hour Instagram photos–priorities!!

What to Pack

Something Comfy: This jumpsuit is good for lounging pre-dinner and it's perfect for a casual night on the beach with a sweater. It can also be thrown on with sneakers for a workout.

Something Casual: There has never been a time in my life where I don’t need a pair of white sneakers. I love these, and they go with everything.

Something Fancy: I always pack a versatile dress that I can either pair with a heel or a sneaker depending on where my day or night is taking me. I think the color of this one is so chic and elevated.

Something Necessary: No brainer…these under-eye patches are my holy grail after a night out when I need a little rejuvenation.

Meghan's 30-Something Guide

TraceRouda Via Getty Images

Where to Go

Laguna Beach, California: This is such a good girls' trip destination because you get it all: hiking, wine, great restaurants, fabulous views, a beautiful beach, and a bustling art scene. It's a perfect alternative to L.A., which can feel overdone and overly scene-y.

If you’re looking to indulge, stay at the Montage for the best view in town or at Casa Laguna, which was recently redecorated by Martin Lawrence Bullard (think: cozy, Moroccan vibes). Both are situated in prime locations!

Aspen, Colorado: Aspen is ideal for a summer, winter, or fall girls' trip. Aspen almost feels like a mini NYC these days, with all of its incredible shopping and culture. But it also has the most beautiful backdrop of mountains and open-air landscape to give you the fresh air you need!

If you book far enough in advance, you can find some great Airbnbs in town. If you’re looking for the ultimate luxury experience, stay at the Little Nell or Hotel Jerome. They also opened a W Hotel recently, which is a more affordable option with awesome views. My favorite must-do’s in Aspen include hiking Maroon Bells, getting a custom hat made at Kemosabe, breakfast at Little Nell, lunch at Ajax Tavern, and dinner at Casa Tua or Matsuhisa!

What to Do

Go for a Hike or Long Walk: I am a very active person and for me and most of my girlfriends, there is nothing better than taking an hourlong hike or walk to explore a new destination. It’s the best way to start your day and gets everyone’s endorphins surging. It's also a great way to experience and explore your destination!

Cocktail Hour With a View: Plan on having wine at 5 p.m. sharp to watch the sunset! Before dinner, my friends and I love to do wine and cheese on our girls’ trips. For us, it’s more about getting the opportunity to try another spot before dinner (we like to “hotel hop”).

In Laguna Beach, you absolutely must get a glass of wine or margarita at the Montage, where you can watch the sunset from their gorgeous terrace. In Aspen, try Hotel Jerome for wine and apps during happy hour–it’s such a cozy, chic cowboy scene!

What to Pack

Something to Keep You Warm: It gets chilly at night in both Laguna and Aspen and this jacket is the perfect weight to wear over a sweater or dress to keeping you warm. You will 100% be complimented on it.

Something to See In: No matter the time of year in these destinations, you absolutely need a good pair of sunglasses.

Something to Walk In: Like I mentioned, I always do a lot of walking on girls' getaways, so the most important item to pack is a pair of elevated sneakers that can be worn all day and into happy hour.

Something to Sleep In: On girls' trips, I tend to spend a lot of time in PJs. They're perfect for drinking wine or playing games like Code Names, so it’s always good to pack your softest matching set.