Deanna Thomson

Deanna Thomson

Deanna Thomson is a passionate traveler, dedicated mother, and seasoned vacation planner from America's hometown-  Plymouth, Massachusetts. A lover of adventure, Deanna’s motto is “I haven’t been everywhere, but it’s on my list.” With a family that includes her three children—Rylynn (10), Raeya (6), and Malcolm (3), along with her husband and their dog Layla—Deanna’s world revolves around family, fun and adventure.

A lover of exploration, Deanna has always prioritized travel. Growing up, her parents instilled a love for vacationing, taking her and her sisters on trips that became some of her most cherished memories. Her travel philosophy is all about creating lasting memories, which she now shares with her own family. Each year, she embarks on a big trip with her extended family of 13, with her little ones in tow. Her travel experiences span across the globe, including destinations like Mexico, Aruba, Disney World, Disneyland, Hawaii, and many cities across the U.S. Deanna has even planned her own destination wedding in Mexico for 80 guests, showcasing her skill in organizing memorable events for large groups.

At home, Deanna enjoys the simple pleasures of life, from beach outings and boating to hiking and hosting friends and family. Deanna’s love for travel is matched by her passion for food. With a gourmet chef father, she grew up savoring diverse cuisines and immersing herself in local cultures while traveling. While coastal destinations are her favorite, Deanna also finds joy in the mountains, whether skiing or hiking and thrilling adventures including Disney and Universal.

Her professional background includes extensive customer service experience, a deep attention to detail, and a natural gift for problem-solving. From her time as a biomedical student to working in the restaurant industry, Deanna’s skills have shaped her approach to vacation planning. Her dream is to help people craft unforgettable vacations, combining her love for travel, food, and family with her dedication to making every trip perfect. Whether you’re planning a family getaway, destination wedding or a romantic escape, Deanna is dedicated to making your vacation perfect.

Deanna’s Favorite Places

Destination wedding Deanna Thomson

  • One of my all-time favorite places to visit is Mexico, and within it, Playa del Carmen and Cabo San Lucas hold a special place in my heart. Playa del Carmen, in particular, feels like a second home to me. From staying at over a dozen resorts to exploring the vibrant downtown area and discovering hidden taco stands where locals gather, every corner of Playa offers something that feels familiar yet always exciting. I first traveled here as a pre-teen with my parents and sisters, and over the years, it has been the backdrop to countless memories — from spring breaks as a college student to romantic getaways with my now-husband, and even my wedding in 2018. The unique Mexican culture, the warmth of the people, and the incredible food make Playa del Carmen a destination that is close to my heart, one that offers something for every age and interest.

    While Playa del Carmen is often my go-to, Cabo San Lucas is another destination that is impossible not to love. Though it’s a bit of a longer flight, the charm of Cabo makes it completely worth it. I’ve visited Cabo several times as a teenager and a child, and each trip left me in awe of its beauty. The dramatic landscapes, with its iconic rock formations and desert-meets-ocean scenery, make it feel like a world of its own. Cabo has a more relaxed, upscale vibe compared to Playa del Carmen, but it has its own unique magic. From the stunning beaches and vibrant nightlife to luxurious resorts and activities like whale watching or sailing, there’s always something exciting to do. The blend of natural beauty, adventure, and relaxation makes Cabo an unforgettable destination that continues to call me back. Whether you’re looking for an adventurous getaway or a place to unwind in style, Cabo San Lucas will always captivate your heart, just as it has captivated mine over the years.

Hawaii

  • One of my favorite trips I’ve ever taken was to Oahu, Hawaii. The moment I arrived, I was greeted by crystal-clear blue waters that stretched out before lush, green mountains. It felt like stepping into a paradise that was almost too beautiful to be real. The hikes through the island’s vibrant trails were breathtaking, offering views that left me speechless, and snorkeling in the warm waters was like discovering a hidden world beneath the surface. The beaches, soft and golden, were the perfect backdrop to moments of pure relaxation.

    What made this trip even more special was sharing it with my 4-year-old and 8-month-old. Oahu turned out to be incredibly family-friendly, with activities that suited every age and energy level. There was something so magical about seeing my kids experiencing such an amazing place. But, at the same time, I couldn’t help but think how perfect this destination would be for a romantic getaway as well. The island has a certain charm and tranquility that could make it an unforgettable experience for couples too. Every moment felt like a dream, and I never wanted to leave, cherishing the memories and the incredible experiences that made Oahu one of my all-time favorite trips.

Disney

  • In this era of my life a new favorite destination of mine is Disney World and Disney Land. This isn't my typical dream destination spot but I have found so much joy and magic as a mom here. While I had the pleasure of visiting as a child, it wasn’t until I returned as a parent that I truly understood the magic of the parks. Watching my children’s faces light up as they meet their favorite characters and experience the rides makes every moment unforgettable. Disney World offers something for everyone, whether it’s the thrills of the roller coasters, the incredible food experiences, or simply strolling through Disney Springs for a night out.

    Having visited Disney four times in recent years, I’ve truly embraced all the features that make the experience so seamless and enjoyable: from FastPasses and Lightning Lanes that help maximize your time, to the convenience of the My Disney Experience app, reservations, and the Memory Maker photo service capturing every precious moment.

    Every time I go, I discover something new—whether it’s an amazing ride I hadn’t yet tried, a hidden gem of a restaurant, or a unique experience in the parks. It’s a place where families, friends, and solo travelers alike can all come together to create memories that will last a lifetime. There’s a certain joy and wonder in Disney that’s hard to replicate, and for me, it will always hold a special place in my heart.

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