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Group Trips for Women Over 40

Tyra Thompson • September 23, 2026

Group Trips for Women Over 40: Every Trip We're Taking in 2027 (and Which One Is Calling Your Name)

Okay, sis, real talk. How many times have you said "next year" about a trip?


Next year when work calms down. Next year when the kids are settled. Next year when you finally have the money, the time, and a friend whose schedule actually lines up with yours.


I'm going to lovingly stop you right there. Because 2027 is the year, and I've got group trips for women over 40 lined up across four continents and some of the best cities in the U.S. All you have to do is pick one. I'll handle the rest.


So grab your coffee (or your wine, no judgment), and let's find your trip.


First, Here's How We Travel

If you've never taken a group trip with me, here's what you're signing up for.


Small groups, big connection. You're not getting herded around with a flag and a megaphone. These are intimate groups of women who show up strangers and leave as a group chat that never goes quiet.


Everything's planned. You just show up. Hotels, tours, transfers, the restaurant everybody wants but nobody can get into. Handled. Your only job is to be present.


Coming solo? Good. Half my travelers book by themselves. Our Roommate Match Program pairs you with a travel sister, so you get the adventure without the lonely dinners.


Payment plans that make sense. Because a dream trip shouldn't require draining your savings in one shot.


The International Trips: Passports Out, Ladies

Japan 2027
Tokyo's neon, Kyoto's temples, Osaka's food scene, and a bullet train ride that'll have you grinning like a kid. This is the bucket list trip, and it holds space for every version of you: the adventurer, the foodie, the woman who just needs a quiet moment in a bamboo forest. 
See the Japan itinerary


Ghana 2027
Some trips you take. Some trips take you. Ghana is the second kind. Between the energy of Accra, the markets, the food, and the history at Cape Coast that stays with you forever, this is the trip your soul has been waiting for. 
See the Ghana itinerary


Costa Rica 2027
Pura vida, sis. Zip line through the rainforest in the morning, then melt into a hammock by the afternoon. Costa Rica is the perfect first international trip if you're new to traveling abroad, and the perfect reset if you're not. 
See the Costa Rica itinerary


Jamaica
No work, all play. Island time, grown-folks energy, jerk chicken that ruins every other jerk chicken for you, and a beach day that actually feels like a vacation. 
See the Jamaica trip


Belize (new!)
The Caribbean secret you haven't heard about yet. Crystal clear cayes, snorkeling that'll make you gasp, Mayan ruins in the jungle, and English is the official language, so it's easy from the moment you land. 
Join the Belize waitlist and get first dibs


South Africa 2028
Cape Town, the Winelands, and a safari where you're close enough to hear the elephants breathe. Yes, it's 2028. And yes, I'm telling you now on purpose. Big trips need a runway, and early birds get the best pricing. 
See the South Africa itinerary


Not ready to pick yet? That's okay. Join my email list and you'll be the first to hear when new trips open, when spots are running low, and when there's a deal worth jumping on. Join the list here


The U.S. Getaways: No Passport Required

These are the trips for when you want a real escape but don't have a week to spare. Long weekends, big memories.

Heads up, sis: the trips marked new aren't open for booking just yet. But waitlist ladies hear about them before anybody else, and first in line means first pick of rooms, roommates, and dates. Tap the waitlist link on any trip that has your heart and I'll let you know the minute it opens.


Napa Valley (new!)
Wine country for women who love wine and hate planning. Beautiful vineyards, incredible food, and tastings where nobody makes you feel silly for not knowing what "tannins" means. 
Join the Napa waitlist and get first dibs


Charleston (new!)
My backyard, so you're getting the local's version. Lowcountry food, rooftop drinks, and a side of the Holy City most visitors never see. 
Join the Charleston waitlist and get first dibs


New York City (new!)
Broadway, brunch, Harlem, and shopping, minus the tourist traps. This is NYC done the grown-woman way. 
Join the New York waitlist and get first dibs


Chicago (new!)
Chicago in the summer hits different. Architecture boat tours, lakefront views, rooftop nights, and the great pizza debate. 
Join the Chicago waitlist and get first dibs


Tennessee (new!)
Good music, hot chicken, and a whole lot of laughing. The girls' trip that's easy to get to and hard to forget. 
Join the Tennessee waitlist and get first dibs


Arizona (new!)
Red rocks, spa days, and sunrise moments that help you hear yourself think again. This one's a reset for your body, mind, and spirit. 
Join the Arizona waitlist and get first dibs


Martha's Vineyard (new!)
Oak Bluffs, Inkwell Beach, gingerbread cottages, and a summer tradition with so much history. Heads up: August books up by spring.  Join the
Martha's Vineyard Waitlist


So Which Trip Is Calling Your Name?

Still torn? Here's your cheat sheet:

  • You need to do absolutely nothing for a few days: Jamaica or Costa Rica
  • You want the trip of a lifetime: Japan or South Africa
  • You want a trip that moves you: Ghana
  • You only have a long weekend: Napa, Charleston, Tennessee, or Chicago
  • You need to reset your whole spirit: Arizona
  • You love a city with main-character energy: New York
  • You want something most people haven't done yet: Belize
  • You want summer at its most classic: Martha's Vineyard

Here's Your Nudge

You don't need the perfect time. The perfect time doesn't exist, and you know that better than anybody. What you need is to decide that you're worth the trip. Because you are.


So pick one. Click the link. Look at that itinerary and picture yourself there. And when you're ready, let's talk about getting you booked.

Found your trip but it's not open yet? Hop on the waitlist and I'll save you a seat at the front of the line.


Your paradise is waiting, sis. Let's go get it.


Travel. Sisterhood. Transformation.


Always,


Tyra

The Paradise Lounge


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