Real Italy Anniversary Vacation: Rome, Florence, and Tuscany

I’m so excited to share another real DWD vacation with you! Italy is a dream destination for many. And for this couple, their trip to Rome, Florence, and the Tuscan countryside was the adventure of a lifetime. With DWD Travel taking care of every detail, Alison & Todd were able to fully immerse themselves in Italy’s rich culture, stunning landscapes, and incredible food and wine. From exploring historic cities to enjoying wine tastings in Tuscany, every moment was carefully curated for an unforgettable experience just for them. Read to hear about this couple’s anniversary vacation to Italy!

About the Destination: Rome, Florence, & San Gimignano

Ali & Todd explored 2 cities in Italy and a small Tuscan village. Their trip began in the Eternal City! Rome, with its ancient history and vibrant streets, was their first stop. They took in iconic landmarks on a tuk tuk ride, enjoyed a food tour filled with local delicacies, and soaked up the energy of this bustling city. Of course they had a private tour of the Vatican as well! Florence, their favorite stop, offered a more intimate experience as they wandered through picturesque streets, discovered hidden gems like a wine window, and spent their evenings at the hotel’s cozy “Book Bar.” I’ve got to throw in that they did one of my favorite activities as well—a pizza making class! Finally, they departed Florence for the rolling hills of Tuscany. They had a private driver who stopped at vineyards for wine tastings along the way to their last “home” of the trip. The medieval town of San Gimignano provided the perfect backdrop for private wine tastings and relaxation. The blend of history, culture, and charm in each destination gave them a well-rounded taste of Italy’s diverse beauty.

How DWD Helped Plan Their Experience

As a travel planner, I specialize in making dream trips a reality by handling every detail of their journey. Whether it’s arranging flights, booking trains, or securing private drivers for exclusive tours, I take care of all the logistics. From coordinating travel to organizing experiences like food tours, wine tastings, and, like for Alison & Todd, even last-minute photoshoots, my goal is to ensure your trip is as stress-free as possible. With DWD Travel, you can relax and focus on creating memories, knowing that every aspect is expertly managed from start to finish.

Q&A with the Couple

What was the highlight of your experience? The highlight of our experience was being able to experience a different culture in the best way possible. The tours we went on really taught us about the history of Italy, especially in Rome. Also, the food and wine (and gelato) were amazing and always top of mind when people ask how our trip was. On our way to the Tuscany countryside and being able to do the wine tastings with a private driver was elite. That is something I never would’ve planned on my own and I’m so grateful you were able to plan into our trip! The photoshoot (Thank you PixAround!) on our last day was something we can cherish forever! 🙂

What was the biggest surprise about your trip? I can’t really think of a big surprise, but finding out how big the city of Rome is caught me off guard. It was a lot to take in and very touristy. Don’t forget about the scammers! Just have to be aware of your surroundings, but we knew that before! Ah, the lack of central air and it being SO HOT was not something we planned for!

What was your favorite spot to visit and why? Our favorite spot was Florence! We loved being able to just walk around. Each street had something different to offer, and the wine window was adorable. Our hotel had a “Book Bar” that opened at night. The bartender was so friendly and made the best drinks, especially Aperol Spritz.

What was your favorite meal of the trip? I still think about that food tour our first night in Rome. We almost missed it because the bus was late and I’m so glad we made it! The fried pasta and fried artichokes, the carbonara pasta and cacio e pepe – YUM!

Alison, I dream about those artichokes too! You can try them on this tour.

Unforgettable Italy Anniversary Vacation Memories and Seamless Travel with DWD

How would you describe your overall experience with working with DWD? We couldn’t ask for a better experience! DWD takes care of every last detail. Dana works around the clock to make sure customers are taken care of and is quick to solve any issues that may arise. We had a tour cancellation on our last day and she quickly thought to turn the day into a photoshoot with an amazing photographer! I love traveling with DWD’s itineraries because we are able to relax and know it’s all taken care of. DWD is the best!

For this couple, Italy exceeded every expectation, from the history to the charm and everything in between. Thanks to DWD Travel, every detail of their trip was expertly planned, allowing them to relax and enjoy every moment. Whether you’re dreaming of an Italy or another destination, DWD Travel will create a seamless experience tailored just for you! Schedule a call with DWD to plan your own adventure across Italy.