rules for ultimate girls' trips

united we stand, divided by venmo we fall

Hey fam and welcome back to dumb rich! I hope everyone enjoyed the long weekend. Naturally, Wednesday came at us with zero chill because we had Monday “off”. Do you ever really get a day off when you work for yourself? Sure.

Since you asked, I had a fantastic MDW. My sister-in-law and I went to the Beyoncé concert — a religious experience, as expected. Nothing short of perfection. However, there was budgeting and there were logistics required. There was also a mutual vow that our selfies would never, ever see the light of day. All in all? Flawless execution (I think!?).

This week’s inspiration is also courtesy of my father-in-law (not my target audience, but my expert researcher) who sent me a Wall Street Journal article titled The Jaw-Dropping Cost of a Hamptons Girls’ Weekend. With inflation surging, bachelorette parties multiplying, and group chats popping off about summer plans, it got me thinking: How are friend groups actually having the “money talk”?

i pledge allegiance

The article? Seemed kind of unhinged. And yet… hauntingly accurate. It reflects the very real, very expensive reality of girls’ trips to the Hamptons. My hottest take (maybe ever) is that the Hamptons are overrated. There, I said it. One road. Eternal traffic. Zero cell service. Peak anxiety.

Let’s break down some of the items from the article’s “standard” weekend:

• $950 for bottle service

• $75 Tracy Anderson workout

• $16 chicken salad from Round Swamp (honestly worth it)

• $97 lobster salad (??)

• $1,500 accommodations (on the lower end imo)

• $550 for beauty prep

• $600 for groceries

They estimate the weekend total to be around $5,000 per person. If you’re not staying at someone’s house, the rentals and hotels are super costly because they often have minimum night stays.

First, I agree with the article that many trips are more subsidized than you think. No offense, your friend with an entry level job is not affording a $5,000 weekend easily. Perhaps their sugar daddy is subsidizing. Or maybe they’re going into credit card debt — which is an expensive price to pay just for the Instagram content.

Regardless of your tax bracket, every group trip needs two things: a budget convo and some planning realism. If expectations aren't aligned, friendships will be tested. Whether it’s a $5k Hamptons weekend, a $20k Amangiri splurge, or a $1k road trip, being on the same page is necessary.

So how do you plan a girls’ trip and keep your friends? Here are my rules (suggestions, but also... rules):

1. Budget first, book second - Before the flights get booked or the Airbnb gets locked in, have the money conversation. Everyone needs to express their ideal budget. If you want to make this anonymous, you could even do a group survey. Say your number. Stick to it. I would try to estimate as many of the costs up front as possible so there are no surprises.

2. Overcommunicate - If you have financial anxiety, you are not alone. Talk about it. If someone needs a bunk bed to afford the weekend, let them have their bunk bed moment! Make it okay to opt out of certain activities — or suggest cheaper alternatives. You don’t need to do everything together 24/7. I love having alone time on a trip. If you’re not interested in the expensive spa day, skip it! Read your book, go for a walk, do you. I bet others are feeling the same way, but it takes one person to express it.

3. Assign a CFO - There should be one person keeping track of all costs, and ideally it’s not the flakiest one in the group. Use Splitwise, Google Sheets, or one of those people who “just loves Excel” (we all have one!). Having a money manager avoids the passive-aggressive “did everyone Venmo me?” texts and makes sure no one ends up paying more than they meant to. For larger groups, I suggest splitting everything equally. For smaller groups, you could be a little bit looser and just alternate getting the Ubers, etc.

4. Cheesy, but remember why you’re doing this! - You’re not going on this trip to prove anything. It’s not a photoshoot. You’re there to connect with your friends, not cosplay as an influencer unless that’s your actual job. You don’t need a private chef for breakfast if all anyone wants is a bagel and gossip.

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Best Destinations
Majority of my best friends are long distance BFFs. The main perk here is we have the opportunity to travel together. This is a roundup of my favorite spots in no particular order and rated in price from $ - $$$:

1. Wildflower Farms in Hudson Valley, NY ($$$) — Haven’t been yet, but it’s booked. Going on a babymoon with my best friend (because yes, it’s my baby too). Seems like a dream: spa, good food, fresh air, endless gossip. I’ll report back.

2. Ocean View Hotel in Harbor Island, Bahamas ($$) — My personal favorite vacation spot. I went as my friend’s +1 to a wedding (let’s normalize bringing girlfriends as wedding guests!) and felt so lucky to discover the most magical place on earth. The island itself is super small and you can ride around it in your golf cart all day. They also have a sister hotel called “The Other Side” and you can take a boat day trip there to visit their pool (pictured below). A must do. Hotel is decently priced if timed right, but food is $$$ and getting there is a trek. Still: worth it.

   

3. Charleston, SC ($) — I’d suggest an Airbnb here. There are so many reasonable options and they can accommodate larger groups. This way, you can also get groceries from the amazing farmers markets and cook at home. I have done a few girls’ trips here and seen countless bachelorette parties while there. Incredible rooftop vibes, even better food, and every single thing is charming. If I wasn’t so obsessed with NY, I’d consider this lifestyle.

4. Faena Hotel in Miami, FL ($$) — If you’re going to do Miami, do it big. Faena is pure drama in the best way. The art deco, the pool umbrellas, the nightclub on property, velvet everything. Entirely over the top. We actually did my best friend’s baby shower here (she’s not just a regular mom, she’s a cool mom) and it was top notch — spa, food, beach, vibes, perfect people-watching, etc.

   

5. Aspen, CO ($$$+) — Yes, Aspen is expensive. But it’s also heaven. I did a mini bachelorette there with two of my best friends and it was my favorite weekend literally ever. Incredible shopping, skiing, food, etc. and most importantly, you get to lean into dressing for the mountain vibes. I stand by winter outfits ranking supreme. We stayed at The W which had a fantastic location and is a Marriott property if you're into using points. We visited Hotel Jerome for the hot chocolate which was borderline spiritual, so I imagine staying there is sublime.

   Okay fine, no West Coast recs this time. But Napa and Palm Springs are officially on my dumb rich to-do list. All in the name of research, obviously.

That’s all for this week. Thank you for your Money Makeover submissions!! If you want to be featured, you can email me at hello@ariellafond.com. Chat next week xoxo