In this Midweek Mini, we take you to the cobblestone streets and Spanish moss of Savannah, Georgia—submitted by Wendy. It is an amazing spot for a charming, walkable weekend escape. We chat about the best times to visit (spring and fall are ideal!), where to stay for easy access to the city’s highlights, and the can’t-miss food and experiences that make Savannah so memorable.

We share our love for the historic district and accommodations like the Andaz, which even includes bike rentals to help you explore. From iconic Southern dining at The Grey and The Old Pink House to strolling through Forsyth Park or along the river walk, Savannah offers something for everyone. We also touch on the city’s vibrant culture, including its lively nightlife and, of course, the wildly entertaining Savannah Bananas baseball team.

Whether you’re into history, food, or just soaking in the charm of the South, Savannah is a weekend destination worth adding to your list.

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In this episode, we’re joined by financial educator and profit strategist Jamie Trull for a conversation that bridges travel, family, and finance. Jamie shares how her background as a CPA led her to help families and small business owners make smarter financial decisions—and how those choices can open the door to more meaningful (and affordable) travel.

We dig into how points and miles fit into a bigger financial strategy, the importance of separating personal and business expenses, and when it might make sense to form an LLC or S-Corp. Jamie also breaks down the often-overlooked tax implications of credit card rewards and offers tips for keeping finances organized to maximize benefits.

One highlight? Our chat about teaching kids financial literacy—whether by adding them as authorized users, paying them through a family business, or simply involving them in travel budgeting. Jamie encourages families to create “fun funds” by setting aside a percentage of profits, making room for joy and connection without financial guilt.

This episode is packed with practical advice and empowering insights for anyone looking to make their money—and their miles—go further.

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The above link includes referrals for almost all travel cards (AMEX, CapitalOne, co-branded cards)

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We receive a small commission when you use our links. This is an amazing way to show your support for the show at no cost to you ❤️

In this Midweek Mini, we’re heading to the sugar-white sands and emerald waters of Destin, Florida thanks to our listener Katie—but it just so happens, this is one of our favorite beach destinations for our families as well. We share our own experiences exploring this stretch of the Emerald Coast and offer tips for making the most of your trip, from the best times to visit to our favorite spots for outdoor adventures.

We talk about quieter, family-friendly beach options like Henderson Beach State Park, fun outings to Crab Island, and activities like parasailing and snorkeling that add a little thrill to your beach days. And of course, we couldn’t leave out the food—whether it’s kid-friendly spots like Fudd Pucker’s or the food trucks in Seaside, Destin is full of delicious finds.

If you’re dreaming of a beach trip that’s easy, fun, and packed with things to do, this episode will help you plan your perfect getaway to Florida’s Emerald Coast.

Submit Your Summer Road Trip Series Story HERE

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Mary Ellen | Jo

Affiliate Links

Credit Card Affiliate Links

The above link includes referrals for almost all travel cards (AMEX, CapitalOne, co-branded cards)

If you need Chase links please reach out! We would be happy to send you our personal referral links or the Daily Drop newsletter link that will allow you to access our affiliate links.

We receive a small commission when you use our links. This is an amazing way to show your support for the show at no cost to you ❤️