Madison Rolley

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

08/21/2026

National Cheap Flights Day is August 23 ✈️ and if you’re planning fall travel, this is your sign to start watching airfare NOW.

National Cheap Flights Day isn’t necessarily a one-day sale. It’s more of a marker for the end of the summer travel season, when airlines start lowering fares to fill seats for fall and winter travel.

My strategy for finding cheap flights:
✈️ Start tracking prices before you’re ready to book
✈️ Watch for airfare drops as summer travel winds down
✈️ Be flexible with your travel dates and routes
✈️ Compare multiple airlines and booking options
✈️ When you find the right fare, book directly with the airline

I’m already seeing more cheap flight deals come through, and I’ll be keeping an eye out 👀

What route are you looking for? Drop it in the comments and I’ll keep an eye out for a deal.

08/19/2026

✈️ Comment “Thrifty” for 30% off for National Cheap Flight Day.

If you want cheap flight deals sent directly to your inbox instead of constantly searching for them yourself, this is the tool I recommend.

I personally use Thrifty Traveler Premium to get personalized flight deal alerts, and it catches way more deals than I’m able to find on my own. It’s also one of the ways I find the deals I share with you here.

The 30% off deal is live now, so if you’ve been wanting to try it, this is a good time.

Get Thrifty Traveler Premium through the link in my bio ✈️

08/08/2026

A 2PM–2AM workday in Nashville as a content agency founder, speaker & influencer👀

One thing I’ve learned about running a creative agency: no two workdays look the same.

This day started with a large-scale content production in Nashville for two of our Sarollé hospitality clients photographers, videographers, models, food + beverage content, and plenty of behind-the-scenes footage.

Then it was time to shift from agency owner to speaker and creator for Blogger Exchange Expo, including a private dinner at STK Nashville with the event’s speakers and promoters.

And because apparently that wasn’t enough for one day… I wrapped the night by meeting back up with my co-founder and friends to see The Black Keys at Pinnacle in Nashville.

This is the part of entrepreneurship I love: getting to move between content strategy, hospitality marketing, creative production, networking, speaking, and actually experiencing the city I work in.

A very Nashville workday. 🤍

08/05/2026

If Europe has been sitting on your bucket list, this flight deal is worth acting on. ✈️

First follow Madison Rolley if you want more travel deals and insider strategies.

Roundtrip flights to Finland, Norway, and Sweden are starting as low as $384, with availability from August 2026 through June 2027 including some rare summer 2027 dates.

In this video, I break down:
• Which U.S. departure cities have the cheapest fares
• How to find these prices on Google Flights
• Which dates have the best availability
• How to use positioning flights if your airport isn’t listed

If you’re dreaming of visiting Helsinki, Stockholm, Oslo, Bergen, or Gothenburg, save this post for later and send it to your travel buddy. I share cheap flight deals like this all the time so you can travel smarter and like an industry insider.

08/04/2026

National Cheap Flights Day is Sunday, August 23, 2026. Here’s what you need to know before booking your next trip.

Despite the name, National Cheap Flights Day is not a day when airlines suddenly release huge sales. Instead, it marks the point in the year when airfare often starts becoming more competitive as peak summer travel comes to an end.

If you’re planning fall or winter travel, Sunday, August 23, 2026, is a great reminder to start tracking flights instead of rushing to book. Search your route in Google Flights, turn on Price Tracking, and let the price alerts do the work for you. You’ll get notified if fares change, making it easier to book at the right time.

There is never a guarantee that prices will drop, but monitoring airfare around National Cheap Flights Day 2026 is one of the smartest ways to save money on flights.

Where are you hoping to travel this fall or winter? Leave your destination in the comments, and I’ll tell you when I would start watching for deals.

08/03/2026

A weekend in Nashville as a local 🌻

One of my favorite things about living in Nashville is that there’s always something new to experience.

As a local, weekends look a little different than the Broadway itenerary…

I spent an afternoon wandering the grounds at Belle Meade Historic Site, learning about the estate’s history before ending the visit with a wine tasting.

I celebrated the grand reopening of the MAKEUP BY MARIO at the Green Hills put together by one of my friends (and celebrity makeup artist) Lesley Sanchez .

I finally finished two contemporary paintings that are headed straight to my dining room walls.

Grayson and I tried SHO Pizza Sho Pizza Bar for the first time, where watching our pizza being made and cutting it with scissors was just as memorable as the flavors themselves. Naturally, we couldn’t resist ending the night with a warm cobbler from The Tennessee Cobbler Co. just across the street in East Nashville.

To wrap up the weekend, we caught a Nashville Sounds game before enjoying dinner at the bar at Henrietta Red in Germantown.

It’s weekends like these that remind me why I love calling Nashville home.

Yes, Broadway and country music are iconic, but they’re only one chapter of the city’s story. There are historic neighborhoods to explore, incredible local restaurants to discover, art to create, sporting events to cheer at, and new experiences waiting around every corner.

That’s what keeps Nashville feeling exciting, no matter how long you’ve lived here.

07/31/2026

I wasn’t convinced a robot could give a good massage… but then I tried it…🤖✨

If you’ve been searching for an Aescape massage review or wondering whether a robot massage is actually worth it, here’s my honest experience.

I booked my session at Paddle Haus, one of only a couple places in Nashville offering the Aescape experience.

Here’s what surprised me most:
✔️ The table scans your body before your session to map your muscles.
✔️ You can customize the pressure, focus areas, and massage length.
✔️ The massage arms are heated, which made it feel surprisingly similar to a hot stone massage.

I chose the Upper + Mid Back massage because between constant flights, editing videos, and working from my laptop, that’s where I carry almost all of my tension.

What impressed me most wasn’t the technology it was how well it found the tight spots in my back and adjusted throughout the session. It felt much more personalized than I expected.

If you’re visiting Nashville or you’re a local looking for a different wellness experience, I’d definitely add this to your list.

Now I’m curious… would you trust a robot for your next massage, or are you staying loyal to a human massage therapist? 👀

SG

07/30/2026

Most people think traveling more is about making more money. It’s actually about building better habits.

These are the 10 habits that consistently save me thousands of dollars on flights every year from using Google Flights the right way to setting flight alerts, searching by region instead of city, booking positioning flights, using the multi-city tool, and letting cheap airfare decide where I travel next.

Most people search for flights after they’ve already picked a destination.

I do the opposite.

If you want to travel more without doubling your budget, these are the exact flight booking strategies I use to find cheaper airfare over and over again.

Which habit surprised you the most?

✈️ Save this for your next trip, and follow for more budget travel tips, cheap flight hacks, Google Flights tutorials, airfare deals, travel planning strategies, and insider travel advice.

07/25/2026

This brunch may ruin all future brunches 👀🍹🍳

Between the live DJ, skyline views, and the energy, Sun Up at Dusk at Kane Brown’s Bar is giving Saturday plans a serious upgrade.

We tried the:
🍸 What Happened in the Group Chat
🦑 Crispy Mango Chili Calamari
🥦 Honey Sriracha Brussels
🌮 Breakfast Tacos
🍗🧇 Nashville Hot Chicken & Waffle Sandwich

If you’re looking for one of the most fun brunches on Broadway, this one’s worth adding to your Nashville list.

📍Sun Up at Dusk at Kane Brown’s Bar
312 Broadway, Nashville, TN
🗓️ Every Saturday | 10 AM–2 PM

Address

Washington D.C., DC

Website

https://madisonrolley.com/

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