Madison Rolley

Directions Website

✈️ Helping you travel like an insider
🎤Leading voice in travel & tech 📲 250K+ on TT 📍Nashville based
💌[email protected]

10/15/2026

📲 Send this to your travel buddies because Travel Tuesday 2026 is coming, and the best time to prepare for the travel deals is before they start dropping. ✈️

If traveling more for less is on your 2027 vision board, start doing two things now:

1. Figure out WHEN you can travel and give yourself as much flexibility as possible.
2. Make a list of WHERE you’d actually want to go.

Because once Black Friday, Cyber Week and Travel Tuesday deals start rolling in, it gets overwhelming FAST.

And this year, we’re doing the searching for you. 👀

The Travel Tuesday Hub is coming back with flight deals, hotel deals, cruises, experiences and more, organized by deal type AND destination so you can skip the endless scrolling and go straight to the deals that actually make sense for you.

Comment “Hub” and I’ll send you the link!

Between now and Travel Tuesday, I’ll also be sharing everything I know about finding the best travel deals, planning your 2027 travel calendar and making your travel budget go further.

Send this to your travel group chat because we are NOT waiting until Travel Tuesday to decide we want to go to Europe 😂

10/12/2026

The only no-show at this Florida wedding was the hurricane 🥂🤠

Spent the weekend with my handsome guy and Nashville friends celebrating dear friends Carol-Ann Remillard & Pat 🤍

The hurricane in the forecast didn’t find its way to our little patch of paradise, and we had a ball!

10/09/2026

You had to be there. An evening celebrating the second year of Modern Luxury Nashville ✨

Hosted at The Manning Luxury Residences , the perfect backdrop for an all white party (I felt like I was at the gossip girl white party in the Hamptons eek!)

Some highlights from the evening included:

✨Welcome ch*****ne with a luxury travel tag…which is immediately going on my suitcase for my trip to Florida this weekend.
✨ An opportunity to make your own custom fragrance
✨ Wonderful company and conversations centered around hospitality and luxury
✨ One too many delicious spritzes from Bebemos Tequila

As we’ve built Sarollé it’s been my intention to connect more with the Nashville hospitality community. This event was so enriching and aligned.

10/04/2026

Choosing Texas this weekend 🤠⭐️👍🏻

My mom is an Aggie alum, I was raised on Aggie football. College Station has always carried a little piece of our family history (including the announcement of me at a midnight yell in 1998😂🕺) . And getting to be there together during Texas A&M’s 150th celebration made this weekend feel extra special.

We did College Station the way you’re supposed to…plenty of time at the Dixie Chicken, soaking up all the traditions, and just enjoying being together rain or shine. An Aggie win was the cherry on top 🍒

The next day we traded maroon for Cowboys blue and headed to Houston for Texans vs. Cowboys, during Houston’s celebration of the 25th anniversary season.

Two Texas football games. Two milestone seasons. Two wins for the teams we came to see. 🏈

There’s just something about fall that always brings me back to the same things: football, family, tradition, and making memories in places that already hold so many.

This weekend had all of it.

🏈

10/02/2026

A few things worth knowing if you’re booking Thanksgiving or Christmas flights for 2026:

• Thanksgiving airfare has historically hit a low around 5 weeks before the holiday, with prices climbing more sharply within 2 weeks of departure.
• If your plans are flexible, flying on Thanksgiving Day itself can be significantly cheaper than leaving during the peak travel days.
• For Christmas travel, fares have historically dipped about 4–6 weeks before departure, roughly mid-November through early December.
• Don’t automatically default to the Friday, Saturday or Sunday everyone else wants to fly. Search the surrounding dates and compare the total trip price before booking.
• Set a Google Flights price alert now, even if you’re not ready to purchase today. That gives you a baseline for your route and makes it much easier to recognize a genuinely good fare.
• And remember, the cheapest base fare isn’t always the cheapest trip. Compare bags, seat selection and change policies before choosing an airline.

The biggest takeaway: if you already know where you’re spending the holidays, now is the time to start actively watching and booking your 2026 holiday flights, not the week before Thanksgiving.

Save this for when you’re booking Thanksgiving and Christmas travel, and follow for more ways to travel smarter and more like an industry insider.

10/01/2026

Comment “Hub” and I’ll send you a link to my 2026 Travel Tuesday Hub ✨( The organized source for hundreds of Travel Tuesday Deals)

Travel Tuesday ✈️ is often called the Black Friday 🛍️ of travel deals for a reason. 💡

It’s one of the biggest opportunities of the year to find standout savings on flights, hotels, cruises, and vacation packages.

But the best deals aren’t always about finding the lowest price. They’re about knowing what you’re looking for before the deals start dropping.

For 2026, that means having flexible dates, a few destinations in mind, and knowing how to filter through the noise so you can quickly spot the deals that actually fit your schedule, budget, and travel style.

Last year, travelers found hundreds of dollars in savings on everything from roundtrip flights to Europe and domestic getaways to cruises and hotels. And with Travel Tuesday deals often overlapping with Black Friday and Cyber Monday promotions, the savings can stretch well beyond a single day.

The key? Timing, flexibility, and knowing where to look.

That’s why I’m keeping a close eye on the best 2026 Travel Tuesday deals so you don’t have to.

09/29/2026

Comment “TRAVEL” and I’ll send you a link to the Travel Tuesday Hub for 2026

Ready to travel in 2027?!

Here’s what you need to know in order to get the best deals

✈️

👉 Travel Tueaday is the Tuesday AFTER Black Friday and Cyber Monday weekend.

It’s a pretty recent expansion of cyber week that covers travel.

🚨The more flexible you can be about deals and locations the better deals you will find!

09/22/2026

just rolled out 3 AI travel features that could make planning your next trip a whole lot easier ✈️

Here’s the TLDR:

1️⃣ Track flights with AI Mode
Tell Google the route you’re watching and when you want to travel, then let AI Mode keep an eye on it for you instead of constantly checking Google Flights.

2️⃣ Find and book hotels based on what you actually want
You can describe what you’re looking for, like a family-friendly hotel, specific amenities or certain preferences, and AI Mode can help you find options and book with the hotel.

3️⃣ Use points and miles in the search ⭐️
You can tell AI Mode which airline or credit card points you have and how many, then use that information when looking at flight options and redemption values.

The third feature is my favorite because it means less jumping between airline programs, credit card portals and points calculators just to figure out how to use your miles.

Google is clearly leaning further into AI for travel planning, and these are the kinds of tools I’ll actually use.

Save this for your next trip and follow for more ways to travel smarter and more like an insider.

09/21/2026

Travel Tuesday is often called the Black Friday of travel deals for a reason. ✨

It’s the one day when airlines, hotels, and travel companies release some of their steepest discounts of the year.

And if you’re hoping to travel more in 2026 or start planning 2027 trips, this is a day worth paying attention to.

The key is preparation. Have your destination ideas ready, know your flexible dates, set a budget, and know what kind of deal is actually worth jumping on.

I’ll be tracking Travel Tuesday 2026 deals and looking ahead at 2027 travel opportunities so you can find the good stuff without sorting through hundreds of offers yourself.

Save this for Travel Tuesday and follow along for the deals. ✈️

09/18/2026

There are some parts of travel you never think about until you suddenly have to navigate them.

Going through this made me realize how little most of us know about bereavement policies, and how different they can be from one company to the next.

A few positive shoutouts from my experience:

✈️ Southwest Airlines was incredibly helpful. The representative I spoke with took the time to understand the situation and ultimately helped me receive a voucher for the full value of the flight.

✈️ Allegiant Air surprised me in the best way. Their bereavement policy allowed me to receive a full refund for a flight that was otherwise nonrefundable.

For hotels, I learned that asking about a bereavement rate was a bit of a waste of time, and probably won’t be the lowest rate available.

I’m sharing this because these are the kinds of things you don’t want to have to figure out for the first time when you’re already navigating a difficult season.

If you’ve had an experience with an airline or hotel during a time of loss, share it below. I’d love to build a resource people can actually use. 🤍

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