Meet Brittany Madden | Trip Planner for Northern Michigan

We had the good fortune of connecting with Brittany Madden and we’ve shared our conversation below.

Hi Brittany, is there something you can share with us that those outside of the industry might not be aware of?
I actually think many people, especially the younger generation, are unaware trip planners exist and the benefits of using one.

Benefit 1: Personalization – One thing people might not realize about the travel planning industry and trip planners is how much personalization goes into each trip. It’s not just about booking hotels and activities; it’s about deeply understanding the preferences, needs, and desires of each client and crafting their itinerary to fit their occasion and preferences.

Benefit 2: Time savings – Another thing people may not account for is the time commitment it takes to plan a trip—on average, people spend about 16 hours planning vacations, which is equivalent to two full workdays. Many think it’ll be quick and easy, but the reality is it requires a lot of work, time, and attention to detail. Trip planners take the burden off their shoulders and make trips seamless and unforgettable.

Benefit 3 – Unique Experiences – If you’ve never been to a place, you’ll likely only discover the top tourist attractions in your searches. By working with a local expert a travel planner who knows the area, you get access to hidden gems and experiences you may never have found on your own.

Can you give our readers an introduction to your business? Maybe you can share a bit about what you do and what sets you apart from others?
Dashing Departure is all about creating unique, personalized travel experiences in Northern Michigan, with a focus on the Traverse City area. What sets us apart is our deep local knowledge and insider access to hidden gems that most visitors would miss. I don’t just plan trips; I create memorable experiences that truly capture the essence of the region, while helping travelers save time and make trip planning stress-free. With my services, clients can enjoy Northern Michigan without the hassle of figuring out all the details.

I’m most proud of starting my business from the ground up, building meaningful partnerships with local businesses, and being able to help so many visitors enjoy Northern Michigan to the fullest. It’s incredibly rewarding to know that I’ve played a part in creating memorable experiences for people while also supporting the local community.

Getting to where I am today business-wise wasn’t easy. I’ve always wanted to be an entrepreneur and do something around travel but finding the right niche has been journey. My first business was actually a vacation styling service, where I would send clients boxes full of outfits tailored to their destination. However, I ran into challenges with inventory management, and a few years later, I decided to evolve the business to focus on trip planning instead of styling. Like many entrepreneurs, starting a business has been a learning curve with plenty of bumps in the road, but those challenges helped me grow. It’s all about continuously improving and evolving until you find what works best for you and your clients.

One lesson I’ve learned is that collaboration is key. I’ve found so much value in networking, building partnerships and working together with other local businesses to elevate each other. Another important lesson I’ve learned is that you’re not going to be good at everything, and that’s okay. Running a business means wearing many hats—marketer, accountant, salesperson, HR, operations—you name it. You can’t do it all, so it’s essential to ask for help and bring in experts where your weaknesses are. Delegating and getting support in areas where you’re not as strong is crucial to keeping the business running smoothly and allowing you to focus on what you do best.

What I want the world to know about Dashing Departure is that it’s more than just a travel planning service—it’s about creating experiences that leave a lasting impact. I pour my heart into every trip I plan because I believe travel should be exciting, fun, and stress-free. My goal is to help people discover Northern Michigan in a way that feels personal and unique, without all the hassle of planning it themselves.”

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
I’d love nothing more than to answer this question! Let’s say it’s a beautiful summer week in July in Traverse City and they’ve never been here before!

Monday – Wow them with a welcome view and great dinner:
Arrival – 4pm
Welcome Drinks at Blush Rooftop
Dinner at Cooks House
Out to North Bar

Tuesday – Sleeping Bear Dunes – A must visit destination:
Breakfast at the Mill
Pick up to go meal and fun cherry snacks from Cherry Republic
Hike Sleeping Bear Dunes
Beach at Sleeping Bear and picnic at the beach
Putt Putt at River Club
Dinner at Arts Tavern

Wednesday- Winery day!:
Breakfast at Black Star Farms
Winery tour pickup
Winery 1: Mawby
Winery 2: Leelanau Cellars
Lunch at Farm Club
Winery 3: Dune Bird
Cidery 4: Tandem CIder
Dinner at Gilchrist

Thursday- A day in picturesque Leland:
Breakfast at Frenchies Famous
Hike at Whaleback Natural Area
Boat Day on Lake Leelanau
Lunch at The Cove
Shop Leland
Dinner at the Riverside Inn

Friday – Brewery tour by kayak! :
Breakfast Sugar2Salt
Kayak, Bike and Brew – Lunch at Filling Station
Dinner at Loco Boys
Out at Little Fleet

Saturday – A day on the Mission Peninsula:
Breakfast at Mission Proper
Walk the Old Mission Point and see the lighthouse
To go Sammies from Bad Dog Deli
Beach Day at Haserot Beach
Glass of wine at Brys
Dinner at Boathouse
Old Mission General Store for cookies

Sunday:
Breakfast To go Bubbies Bagels
Departure 10am

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
I’d love to dedicate my shoutout to a few key people who have played a significant role in my journey.

First, to my parents, Bruce and Brenda Milnes, for showing me the world and sparking my passion for travel at a young age. Thanks to them, I developed an insatiable love for travel, an obsession with finding unique experiences, and a passion for planning fun trips and events for others. To date, I’ve traveled to 40 states and 17 countries, and I’m always looking for my next adventure.

I also want to thank my dad for inspiring me to start my own business. Watching him successfully run three businesses gave me the confidence to know that entrepreneurship was possible.

My husband deserves huge recognition for always supporting my dreams, encouraging me to take the leap to start my business, and being my biggest champion every step of the way.

I’m incredibly grateful to my amazing partners in Northern Michigan—Alexandra Inn, Black Star Farms, Brys Estate, Two Bay Stay, TC Picnic, TC Decorating, Wander North, Golden Swan, Stocked, Paddle for Pints, and Brew Bus. Their support and willingness to collaborate have been invaluable, and it’s been a joy to cross-promote and grow together.

Lastly, I want to thank my SheEOs group—a powerful group of female entrepreneurs who are all about fostering collaboration, sharing ideas, and supporting one another on this entrepreneurial journey.

Website: https://www.thetraversecityconcierge.com

Instagram: https://www.instagram.com/dashingdeparture/

Linkedin: https://www.linkedin.com/company/dashing-departure/

Facebook: https://www.facebook.com/dashingdeparture

Image Credits
All shot by me or by my clients who gave me approval to use 🙂