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The May 2025 Rewind

The May 2025 Rewind

Maycember in all its glory - and some exciting news!

Rachel Lipson's avatar
Rachel Lipson
Jun 02, 2025
∙ Paid
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Brooklyn Family Travelers
Brooklyn Family Travelers
The May 2025 Rewind
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Make sure to click “view entire message” if you’re reading this via email or check this post out in a browser so you don’t miss anything!

It’s June!

The amount of things that somehow got packed into May is dizzying to think about. But, it’s over now and we’re in the homestretch before summer break! I’ve got a lot of travel plans on the horizon (on brand!) and so much to share with you all.

Big News 🥁 …

We have a NEW points class!

If you are one of the many people who took advantage of that 100K elevated offer that was out last month, you may be wondering…what now?? Or maybe you already have 100K points (or plan to have some soon)?

Well, here is your answer! May I introduce to you:

LIVE: June 17th at 1pm ET

You’ve got the points - now learn how to use them. This class covers the basics behind turning points into actual travel with a focus on tips and tricks for families.

We’ll talk about smarter ways to book, where the real value is, which cards to use and when, and what to avoid.

The class will be recorded if you can’t make it live (and the recording will be available for 14 days from date of class). This will likely not be available long term so don’t miss this! It’s a one-off!

Q&A at the end if you attend live.

Open to all - beginners welcome!

Annual subscribers receive 50% off. Scroll to the end of this email for the code!

REGISTER HERE!

How to Spend 100K Points (Wisely)!

If you are interested in other classes, click here for more info!

Need help figuring out which welcome bonus to go for next? Fill this out and I’ll help you find the right card. Thank you for using my links when you apply!

Don’t miss out!

Before I get into the review for May, I want to remind you that Steward, the modern estate planning company I hosted the webinar on, has generously extended a $500 discount to our community.

Get $500 off

If you are still interested in watching the webinar, you can access it through the registration link below.

Don’t forget to mention Brooklyn Family Travelers for your $500 off when you sign up for their comprehensive estate plan!

Register here for the free webinar!

May flowers at the Park Hyatt NY 😍

A tip for earning extra points!

The shopping portal Rakuten has a bonus of $30/3K points for signing up. Today, a lot of brands are offering 10x which is an amazing way to rack up points/cash through regular purchases. If you haven’t signed up yet, please use my link here! If you already have it and want to switch to points back instead of cash back, comment or message me and I will help you! Don’t miss this.

Get $30

And now…the MAY rewind! A few highlights:

1. I checked myself into a hotel for Mother’s Day

I thought I’d feel guilty, I was worried I’d miss the kids and Kamali — especially if I saw others with their families. NOPE. It was the best 24 hours ever. No one asked me questions, I didn’t have to wrangle anyone and I got an actual break.

I headed back to the Park Hyatt NY for a little solo staycation and it was the best decision. I walked around Central Park, ordered room service, got myself a last minute ticket to see Hell’s Kitchen on Broadway (so fun!) and spent the next day actually sleeping in, catching up on some emails and strolling around the city before heading back at 4pm when I had to check out. One of the best perks of having hotel status with Hyatt is late check out! The other is free breakfast and I took advantage of both.

More on hotel status

The pool and jacuzzi on the top floor of this Billionaires' Row hotel made it a perfect choice for a staycation. The cost for a night at this hotel would have been over $2,000 with the upgrade I got, but instead, it was 45K points which made it VERY worth it. I transferred these points from my favorite card to Hyatt to book this hotel for $0 🙌

This isn’t an ad, just keeping you up to date on how I am using my points :)

2. The best card for points travel came out with a 100K offer and it ended 😢

I posted about this so many times that — even though it is my favorite card (if I could only have one, this would be it — even I got sick of hearing about it ;)

But, I know many of you are here because you want to learn the ins and outs of points travel — and using the Brooklyn Family Travelers links supports my work — so I felt compelled to continue to share this once in a blue moon offer!

The offer is gone now, but it’s important to know that while taking advantage of an elevated bonus is a nice to have, it’s not a necessity. This card in particular is STILL worth getting even with the regular 60K offer. That’s because you’re eligible for the bonus every 4 years. If you wait to apply, you’re waiting to start that clock which is a big mistake. And this is the #1 card for points travel.

Did you miss it? Not too late to get 60K! Click “our favorite cards” and it’s the first one there:

Get 60K points

If you already met the minimum spend and got the welcome bonus, and you’re ready for another card, message me for a recommendation.

You can also fill out a FREE wallet edit so I can see what other cards you have to make the best rec!

Get a free wallet edit!

3. I am launching a chat group for paid subscribers

This is going to be coming out in the next couple of weeks and I am so excited about it! If you’re already a paid subscriber, stay tuned for the link to join the group. If not, what are you waiting for?

4. Getting to 200 paid subscribers

For my birthday, I vowed to get to 200k paid subscribers and indeed many of you have stepped up (thank you)! I would love to get there by the end of the month. If you’ve been on the fence about becoming a paid subscriber, now is a great time. I will celebrate by gifting a free 1:1 coaching session to the 200th subscriber :)

The 10% off ends Friday, so don’t delay!

Get 10% off!

Some of my highlights from the month of May:

  • I attended a benefit for an incredible non-profit I serve on the advisory board for called The Service Learning Project (SLP) at my friend LeAnn’s bar Talea in Cobble Hill. SLP helps kids become change-makers in their own communities and it’s an organization I am so proud to be a part of. Crystal Hudson, a local city council person was our honoree — who made history as one of the first out gay Black woman ever elected in New York City. It was such a fun night.

Thanks for coming, Crystal Hudson!
  • I recorded a podcast on friendship for The Significance of Others which I’ll share with you once it airs! I am so fortunate to have some really special, close friendships — and for this podcast, I got to talk about friendship with my dear friend Crystal Granderson Reid of Brooklyn Chateau Lifestyle.

  • I watched A LOT of baseball games in Prospect Park. Even with 6 innings in little league it’s just soooo long! But the kids’ teams are both undefeated so on with baseball we go!

  • I wrote a song 🖤

  • The spread at a spring Soirée hosted by our dear friends Alex and Chondita has made me re-think the standard cheese plate 😮

    Chondita’s Grazing Table was so perfect
  • We got to go see my friend Jeb Brown starring in Dead Outlaw on Broadway. Don’t miss it!

  • An old friend reached out for business coaching and I got to help propel her business in a clearer direction.

  • I watched more little league games 😁

  • My annual weekend in Nashville for the Blue Balloon Songwriting School showcase (Nashville edition) was the most fun as always. I watched 20+ kids perform original songs on stage and spent the weekend with my dear friend and business partner (and wildly talented singer/songwriter) Lauren. A recap on Nashville to come!

  • I co-hosted a webinar with Steward on estate planning and many of you took advantage of their incredibly generous offer to our community (still going - now $500 off!).

  • I went to so many great restaurants for my birthday and dinners with friends: Ernesto’s, I Sodi, Leland Eating and Drinking House (with

    Jennifer Cook
    of Mom Friend!), Popina and more.

  • Went to my friend Leah’s inaugural Spark Society Party the night before the big Blue Balloon showcase (more on that in two seconds) — the first time I’ve ever gone out before the showcase in all 16 years of having them!

  • I spent the last 48 hours on my feet, hosting 130 children performing one original song each at City Winery NYC for the 16th Annual Blue Balloon Songwriting School Showcase. Truly the highlight of my month to see young creativity blooming. This is my business of 16 years that I am so deeply proud of. It’s almost an adult!

I am exhausted just reading all of this - but what a month!

ICYMI: Some posts you may have missed!

A chance to check out some of the stuff you may have breezed past.

One thing that can make points even more valuable

One thing that can make points even more valuable

Rachel Lipson
·
May 1
Read full story

This is hands down always the most popular topic. Read this if nothing else!

Meeting internet friends IRL

Meeting internet friends IRL

Rachel Lipson
·
May 8
Read full story

I got to sit down with

Jennifer Cook
of Mom Friend and chat about life and travel!

What is a saver fare?

What is a saver fare?

Rachel Lipson
·
May 12
Read full story

This is one of the most important elements of points bookings that many people are totally in the dark about.

3 of the most confusing things about points explained

3 of the most confusing things about points explained

Rachel Lipson
·
May 16
Read full story

And three more things that you need to know!

How to book a free stopover

How to book a free stopover

Rachel Lipson
·
May 21
Read full story

This was a post I was asked by many to write. It’s a confusing idea but one that can save you a fortune AND make trips more interesting and fun.

Happy Birthday to me!

Happy Birthday to me!

Rachel Lipson
·
May 27
Read full story

I am not usually one for celebrating my birthday publicly but this time did it with gifts for YOU!

Have you heard about the TikTok trend "Airport Theory"?

Have you heard about the TikTok trend "Airport Theory"?

Rachel Lipson
·
May 28
Read full story

Talking to PureWow about this polarizing trend was super fun. So happy to share it! What do you think about Airport Theory. Would you try it? I am not suggesting it lol.

Leave a comment

And a few top posts from last month:

There is no “we” in credit card land

There is no “we” in credit card land

Rachel Lipson
·
Apr 7
Read full story

True story! You may think you both have one card but the truth is that one of you is the cardholder and the other isn’t!

Do you know your 5/24 status?

Do you know your 5/24 status?

Rachel Lipson
·
Apr 9
Read full story

Important info that can make or break your ability to earn points.

The #1 non-points related travel tip that's changed how we travel

The #1 non-points related travel tip that's changed how we travel

Rachel Lipson
·
Apr 13
Read full story

It’s not always all about points :)

How to spend 100k points (wisely)

How to spend 100k points (wisely)

Rachel Lipson
·
Apr 18
Read full story

So popular I made a class about this one!

What to do if your credit card application gets denied

What to do if your credit card application gets denied

Rachel Lipson
·
Apr 21
Read full story

A denial is NOT the end. Read this for info on what to do next!

How much are points actually worth?

How much are points actually worth?

Rachel Lipson
·
Apr 28
Read full story

The most popular post. Don’t miss!

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What’s on the horizon?

This month was really exciting as I continue to build this super fun and rewarding business and create more offerings and content to share with you all.

  • Less talking about cards (ha) and more talking about how to use them for travel!

  • More trip reports and city edits as we start to look ahead to summer. I have so much to share with you on this front and look forward to quieter days when I can put these together for you!

  • Lots of great points and miles posts to help you earn more points and spend them wisely. There are so many tips and tricks and it’s so fun sharing them with you all!

  • A posting schedule! I am working on this but you can always expect:

    • A minimum of one in-depth post a week on points and miles (usually more!)

    • At least one city edit per month

    • A monthly recap

    • Other posts when I can’t help myself

If you’re not already a paid subscriber, you are missing out! Subscribe here to access the intel, invaluable info and countless posts I’m cooking up for you all. I love what I do and I hope you do too. 🖤

Have an idea for a post or something you’ve been wondering about? Send me a message and I’ll consider it for an upcoming newsletter!

And just a note to say thanks for being here. Looking at the subscriber count (and the paid subscriber count!) going (way!) up reminds me that the work I’m doing is helpful and important. I appreciate the trust you’ve put in me and look forward to continuing to grow this wonderful community.

Have a friend who would love Brooklyn Family Travelers? Please invite them to subscribe!

A solo trip to the Thompson Nashville! April 2025. Here’s the dress (in a different print) and jacket 🖤

Refer a friend

If you’re not yet a paying subscriber, I hope you’ll consider it. I spend a lot of time on these posts to bring valuable info to you. I’m deeply committed to making sure that a subscription to Brooklyn Family Travelers saves you a lot of money in the long run. Thanks for being here and happy travels!

Code for 50% off the class on how to spend 100K points below the paywall :)

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