When I first got engaged, I had this picture-perfect idea of my bachelorette weekend: all my closest friends together, endless laughter, cute matching outfits and maybe a few too many cocktails. It felt like a rite of passage—one of those milestones splashed across Instagram with corny captions.
So I planned mine in the Hamptons, an easy three-hour drive from New York City, imagining it would be a gift: three days surrounded by the people I love most. But the reality was less rosy. Instead of feeling spoiled, I felt like a stressed-out host—guilty about the money, the dynamics and the pressure for everyone to have fun. (I’m a recovering people-pleaser.)
By the time it was over, I wasn’t basking in celebration—I was exhausted. With a few years of distance, I see it differently. The memory isn’t all bad; it’s not across-the-board regret. I don’t regret celebrating with my friends. But I do regret the format. If I could do it again, I’d ditch the bachelorette production altogether and plan a straightforward girls’ trip.
The myth of the “perfect” bachelorette party
What used to be a casual night out now often comes with the pressure of turning it into a full-scale production, complete with coordinating themes, matching outfits, hashtags, rentals and thousands of dollars in decor. It often feels less like celebrating friendship and more like staging content for Instagram.
On paper, mine looked ideal—Pinterest-worthy picnics on the beach, a packed itinerary and endless photo ops. In reality, every moment felt meticulously choreographed. The “relaxing weekend” vibe was replaced by a strict schedule. Instead of feeling celebrated, I found myself on edge—worried about whether everyone was having fun, getting along and smiling for social media.
The money guilt
There’s no way around it: Asking friends to spend hundreds (sometimes thousands) of dollars is uncomfortable. Even though we drove instead of flying, costs piled up—lodging, meals, drinks, rideshares, matching T-shirts and decorations.
Every time someone hesitated about splitting costs or ordered another cocktail, I felt responsible, like I’d forced them into an obligation they couldn’t escape. Instead of enjoying the moment, I worried about money that wasn’t even mine.
Friend group fusion is overrated
You imagine a bachelorette will unite all your circles but in reality, it’s often awkward. My college friends and childhood besties didn’t magically click just because I wanted them to.
So I spent the weekend in hostess mode—monitoring vibes, bridging conversations and making sure no one felt left out. By the end, I wasn’t energized; I was drained. It became clear almost immediately that I needed a vacation from my vacation.
Performance pressure
These weekends are designed to look good on social media. Decor, outfits, “Bride Tribe” moments—there’s unspoken pressure to make the weekend photograph well.
But behind the curated group shots were exhaustion, tension and long waits for everyone to be “camera ready.” At one point, I realized I was more focused on content than on whether I was actually having fun.
Why a girls’ trip would have been better
What I really wanted wasn’t a wedding-themed carnival—it was time with the women I love. A simple girls’ trip would have given me that: maybe a beach weekend, a mountain escape or a city adventure filled with good food and long conversations—no pressure, no matching outfits, no financial strain.
What I really wanted wasn’t a wedding-themed carnival—it was time with the women I love. A simple girls’ trip would have given me that, whether in the form of a beach weekend, a mountain escape or a city adventure. The appeal was straightforward: no pressure to perform, no themed dress codes and costs that felt clear and shared—without the extra weight of wedding expectations on everyone involved.
If I’d reframed my Hamptons weekend that way, it could have felt entirely different (read: way less stressful)—the same beaches and backdrops, but with fewer scheduled activities and more flexibility to actually wander, linger or do nothing at all. And with a smaller group of friends who already knew each other, there wouldn’t have been the same anxiety about mixing groups or playing social referee when tensions arose.
And maybe most importantly, a girls’ trip wouldn’t have been all about me (and for once, that would’ve been a relief). That shift is what would have mattered most. Instead of people feeling awkward about how much they were spending in honor of my relationship milestone, the cost would have gone toward a collective experience built on shared interests—something everyone could enjoy equally.
What I’ve learned from this is simple: a wedding-adjacent weekend can feel like an obligation, but a girls’ trip has the potential to feel like a gift—for everyone. And with that framing, there would have been far less pressure on me to make the whole thing perfect.
Girls’ trip ideas that aren’t lame (or overdone)
Finger Lakes, New York
Think of the Finger Lakes as New York’s answer to Napa—only with fewer crowds and none of the pretentiousness. Rent a lake house, go vineyard-hopping, hike to waterfalls or simply sit on a dock with takeout and vino.
If you only do one thing: Go chasing waterfalls—really—at Buttermilk Falls State Park.
Saint Michaels, Maryland
This tiny waterfront town on the Chesapeake Bay still feels like a secret—for now, at least. Days here are well spent sailing, feasting on crab cakes and strolling through the historic district, which is dotted with Victorian homes, boutiques and galleries. Evenings are quiet, with just enough restaurants and bars to keep things interesting.
If you only do one thing: Take a boat tour along the Chesapeake and bask in the water views. Sail Selina II offers themed sailings, including wine and beer tasting cruises, as well as private charters.
Marfa, Texas
Marfa has gained popularity in recent years, but it still feels more like a desert escape than a tourist trap. Between the eclectic installations and the eerie glow of the Marfa Lights, the vibe is equal parts surreal and grounding. There isn’t much to do, which is precisely the point. Instead, it’s about lingering over conversations that stretch long into the night.
If you only do one thing: Don’t miss the IG-famous Prada Marfa. Modeled after a Prada boutique, it’s an art installation filled with shoes, handbags and other luxury goods—though nothing is for sale.
Taos, New Mexico
For those craving a mountain getaway with an artsy twist, Taos delivers in spades. Its adobe architecture and walkable downtown area are rich with galleries and history, while the surrounding landscape offers year-round adventure opportunities. Hit the slopes in winter, hike in the summer, soak in nearby hot springs or go rafting down the Rio Grande if you’re up for it.
If you only do one thing: Carve out an afternoon to wander through Taos’ historic downtown, anchored by the Taos Plaza, which regularly hosts live music and farmers’ markets.
Oregon Coast
A trip to the Oregon Coast isn’t your ordinary beach getaway. Instead of palm trees and boardwalks, you’ll find otherworldly beaches, dramatic cliffs and rugged rock formations that look like they were pulled from another planet. Rent a beach house and pile on blankets as you post up on the couch overlooking the Pacific—ideally with a spread of snacks, a few bottles of wine within arm’s reach and your Bravo reality show of choice playing in the background.
If you only do one thing: Cannon Beach is world-famous for its 235-foot-tall Haystack Rock—where you can spot puffins from early spring to mid-summer—stroll along the sand and spot vibrant marine life in the tidal pools.