Maddie Jackson
Based in Maryland
English
Maddie Jackson
Ask me about
My Story
As your travel advisor, my goal is to help you stop waiting for your bucket list and start living it. Outside of travel, I pursue roles that fuel my creativity and love for meaningful connection, like my work in higher education and wedding photography. I married my high school sweetheart, and together we’ve built a life filled with adventure, laughter, and shared experiences. That same passion for creating lasting memories inspires the way I plan every trip, helping my clients turn their travel dreams into unforgettable moments.
Travel Style
I bring a creative eye and a passion for authentic, one-of-a-kind experiences to every itinerary I design. Rooted in Maryland, I love sharing East Coast favorites while also curating travel across the US and around the globe. My goal is to craft personalized, value-driven journeys that reflect who you are, whether it’s a romantic escape, a once-in-a-lifetime adventure, or a peaceful getaway. Every detail is planned with care and attention, because your journey deserves to be as unique and memorable as you are.
Stay connected
Travel ideas (2)
Pet-Friendly Activities & Spots in Washington, DC
Discover the best pet-friendly spots and activities in Washington, DC, from luxurious dog-welcoming hotels like The LINE DC and The Ritz-Carlton Georgetown, to local favorites such as Baked & Wired, Yards Park, and historic Rock Creek Park. Enjoy dog-friendly events, outdoor spaces, and dining experiences that make exploring the city with your furry companion easy and fun.
Pet-Friendly Activities & Spots in Washington, DC
Discover the best pet-friendly spots and activities in Washington, DC, from luxurious dog-welcoming hotels like The LINE DC and The Ritz-Carlton Georgetown, to local favorites such as Baked & Wired, Yards Park, and historic Rock Creek Park. Enjoy dog-friendly events, outdoor spaces, and dining experiences that make exploring the city with your furry companion easy and fun.
5 Reasons You Should Plan a Weekend Trip to Plymouth, MA in the Fall
Plymouth, Massachusetts is a charming fall destination full of history, cozy spots, and seasonal treats. From historic sites and peaceful gardens to local shops, taverns, and delicious comfort food, it’s a must-visit town in New England. Nothing screams “fall” quite like New England. One day you’re soaking up the sun on a beach in a charming coastal town, and the next it’s a crisp 65℉, the trees have turned the color of a sunset, and pumpkins are lining the steps of your favorite small-town coffee shop. New England is full of picture-perfect towns worth visiting, but there’s one in particular you absolutely can’t miss in the fall.
5 Reasons You Should Plan a Weekend Trip to Plymouth, MA in the Fall
Plymouth, Massachusetts is a charming fall destination full of history, cozy spots, and seasonal treats. From historic sites and peaceful gardens to local shops, taverns, and delicious comfort food, it’s a must-visit town in New England. Nothing screams “fall” quite like New England. One day you’re soaking up the sun on a beach in a charming coastal town, and the next it’s a crisp 65℉, the trees have turned the color of a sunset, and pumpkins are lining the steps of your favorite small-town coffee shop. New England is full of picture-perfect towns worth visiting, but there’s one in particular you absolutely can’t miss in the fall.
Pet-Friendly Activities & Spots in Washington, DC
Discover the best pet-friendly spots and activities in Washington, DC, from luxurious dog-welcoming hotels like The LINE DC and The Ritz-Carlton Georgetown, to local favorites such as Baked & Wired, Yards Park, and historic Rock Creek Park. Enjoy dog-friendly events, outdoor spaces, and dining experiences that make exploring the city with your furry companion easy and fun.
Pet-Friendly Activities & Spots in Washington, DC
Discover the best pet-friendly spots and activities in Washington, DC, from luxurious dog-welcoming hotels like The LINE DC and The Ritz-Carlton Georgetown, to local favorites such as Baked & Wired, Yards Park, and historic Rock Creek Park. Enjoy dog-friendly events, outdoor spaces, and dining experiences that make exploring the city with your furry companion easy and fun.
5 Reasons You Should Plan a Weekend Trip to Plymouth, MA in the Fall
Plymouth, Massachusetts is a charming fall destination full of history, cozy spots, and seasonal treats. From historic sites and peaceful gardens to local shops, taverns, and delicious comfort food, it’s a must-visit town in New England. Nothing screams “fall” quite like New England. One day you’re soaking up the sun on a beach in a charming coastal town, and the next it’s a crisp 65℉, the trees have turned the color of a sunset, and pumpkins are lining the steps of your favorite small-town coffee shop. New England is full of picture-perfect towns worth visiting, but there’s one in particular you absolutely can’t miss in the fall.
5 Reasons You Should Plan a Weekend Trip to Plymouth, MA in the Fall
Plymouth, Massachusetts is a charming fall destination full of history, cozy spots, and seasonal treats. From historic sites and peaceful gardens to local shops, taverns, and delicious comfort food, it’s a must-visit town in New England. Nothing screams “fall” quite like New England. One day you’re soaking up the sun on a beach in a charming coastal town, and the next it’s a crisp 65℉, the trees have turned the color of a sunset, and pumpkins are lining the steps of your favorite small-town coffee shop. New England is full of picture-perfect towns worth visiting, but there’s one in particular you absolutely can’t miss in the fall.
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