All Our Annual Trips

osbornes

Buckle up, FAM! This is where we plan, laugh, reminisce, and get ridiculously excited about our annual family trip. Whether you need to check the itinerary, find out who’s pecan cookies (again, Momma?), or relive past travel shenanigans, you’re in the right place.

Jearlean-Osborne

Jearlean R. Osborne

About Our Matriarch

Mrs. Jearlean Osborne, beloved wife of the late Theadore Osborne Sr., is the heart and soul of our family. Her faith in God and family (in that order!) has shaped generations, and she’s the reason we all greet each other with warm hugs. A mother beyond measure, a Granny beyond compare, and quite possibly an actual angel, she is the glue that holds us together. To know her is to be loved unconditionally—and we are forever grateful.

A MESSAGE FROM OUR MATRIARCH: My dear Osborne family,

Another year, another adventure, another beautiful memory in the making! If there’s one thing I’ve learned in this life, it’s that the greatest treasures aren’t found in the places we visit but in the people we share them with. You—my children, my grandchildren, my family—are my greatest treasure. So wake up everyday and choose us. Choose FAMILY. . .

Upcoming Events:

The family email & upcoming Zoom meeting

Stay in the loop! We’ll keep this page fresh with all the must-know details, so check back often—because no one likes being the last to know!

 

family email

Ask to be added to the family email: 1(251) 202-3141 Theo Jr.

Zoom Meeting

Upcoming Zoom meeting will be announced soon.

Pricing Plan

Packages For All Attendees

$50

This amount is due every pay period (biweekly or twice a month, depending on your payroll schedule):  Adults 30yr old or older.
Adult & Married Couples

$50

This amount is due every pay period (biweekly or twice a month, depending on your payroll schedule):  Adults 22-29yr old working.
Young Working Adults

$25

This amount is due every pay period (biweekly or twice a month, depending on your payroll schedule):  Youths 21yr old or younger.
Young Adults

Where To This Year?

Be a part of the decision makers

The next Osborne family trip is in the works! If you’d like to help decide our destination, be sure to tune in for details on our first Zoom planning meeting!

The Extended Family

Yolunda Hayne's Family

Yolunda Haynes

The Caring Auntie

devonshae osborne

Everybody’s Baby

Whitney Payne

The Dancing Queen

Darius Haynes

Mr. Dairy Beatz

Shavonne (Turner) Osborne Family

Shavonne Osborne

The “Favorite” Auntie

Dennis Lovett

“That Dude”

Dontez Turner

Gentle Giant

Gabriel Turner

Super Dad!

Alessa Turner

Lil Hype

Elise Turner

Focused Cousin

The'ol King Family

The'ol King

The Crazy Uncle (No Real Talk 🤪)

Freda King

You know her, that’s Fatima’s Sister

Tru' King

Mr. Hard Worker

Mister' King

The Brainiac

Kalen Johnson

Mr. Laid Back

Fred McDonald

The Childhood Best Friend

Sonia Jacob's Family

Marco Robertson

Bowlegs

Sonia Jacobs

Nae Nae

Lyric Jacobs

The Serious One

Aarion Jacobs

Ms. TN Teen Petite

Nadine Jacobs

Too Hard Too Handle

Shaunte'el Osborne-Irving Family

Devin Irving
Devin Irving

Diesel

Shaunte'el Osborne-Irving
Shaunte'el Irving

Chuchi

Sabastian Irving
Stefan Irving

Bug

Athena Irving
Athena Irving

Tootie Bird

Stefan Irving
Sebastian Irving

Little Diesel

Tony Conerly's Family

Tony Cornerly

Pastor

Jackie Cornerly

First Lady

TJ Cornerly

“TJ”

Family Videos: Xmas '90

Christmas 1990: This is one of several Xmas family gathering at Momma’s house. The location this particular Xmas is Caillvet Street. People Present: Jearlean Osborne, Nadine Osborne, Shavonne & Johnny Turner, Dontez Turner, Gabe Turner, Yolunda Haynes (Payne) Osborne, Chris Payne, Devonshae Osborne, and Theo Osborne
Special Appearance: Mrs. Nancy Redmon

Family Videos: Qwebes Tribe

Event: Step Competiton
Location: Red Gym, Biloxi, MS
Date: 1992
Significances: The Qwebes TRIBE step for the fist time alone and dominated the show.

Question

Helpful answers to your questions.

Where are we going? Well, that’s up to you! But before you start dreaming about a Hawaiian getaway, remember this—our destination must be within an 8-hour drive from Biloxi, MS. Why? Because our beloved elder, Jearlean Osborne, is handling the most important cargo: the food! And trust, no one wants to take this trip without her legendary cooking. So, if you want a say in where we end up, make sure you’re at the first Zoom meeting to cast your vote!

If you’ve got Osborne blood running through your veins or have survived one of our family game nights without flipping the table, congratulations—you qualify for this trip! Pack your bags, bring your good vibes, and get ready for an adventure.

Alright, folks—let’s talk dollars and sense (yes, we meant to spell it that way!). To keep this trip affordable, we’re asking each adult to chip in $50 per pay period, while young adults who are unemployed contribute $25 per pay period. This covers lodging, group activities, and all the fun we’re about to have together.

Now, listen up, elder adults—do not, we repeat, DO NOT pay for your grown kids! Here’s why: when people put their own money into something, they’re way less likely to pull a last-minute “Oops, I can’t make it” stunt. Trust us, this is wisdom. Or at least really good common sense. We want a full house, not a bunch of empty beds because someone suddenly “forgot they had plans."

So, let’s all pitch in, commit, and get ready for another unforgettable Osborne adventure!

We’re booking as a group to make things easier and more affordable. A few family members will coordinate reservations, and we’ll share payment details soon. If you have specific requests, let us know!

The itinerary will include a mix of planned activities, free time, and a few family traditions. If you have ideas for fun things to do, we’d love to hear them! Bring your suggestions to the Zoom meeting or send them our way.

A link to the Zoom meeting will be shared via email, text, and our family group chat. Be sure to check your messages for details on the date and time!

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