You’ll kick things off from the Eternal City, where you’ll enjoy lunch with the scenic countryside passing by as you head toward Venice. You’ll arrive there by the early evening, where a private water taxi will cruise toward the city center, giving you the chance to explore its winding canals, stop for a tipple or two, or opt for one of the company’s curated adventures to see Venice in a new light. After you climb back onboard, the Bar Cart will come alive with live entertainment and musicians to cap off your night.

From there, you’re off to Matera, an ancient city known for its Sassi, cave dwellings craved right into the cliffs. You can explore the winding streets here before climbing on the train once more to set out for Sicily, with dinner whipped up by Michelin three-star chef Heinz Beck. The next morning, with olive groves and cliffs in the distance, you’ll begin the journey to Sicily, where the train is dismantled and then transported by ferry across the Strait of Messina with the shining Mediterranean Sea beyond. To wrap up the adventure, you’ll make stops in the stunning cities of Taormina and Palermo before heading back to Rome to wrap up the scenic journey—a grand tour, indeed.

You’ll find plenty of wonders aboard the train, too. La Dolce Vita Orient Express, which debuted back in 2025, is chock full of 1960s-style Italian glamour and modern touches: Think suites covered in gold, rich red, and wooden tones and menus from Beck that are customised to each locale. Plus, there’s only space for 62 passengers on this train, making for an even more intimate experience on the rails.

The Grand Tour journey will embark for the first time on 21 May 2026, with pricing starting from 15,760 euros per passenger. To hop onboard, head to Orient Express’s website.

This story was first published on Robb Report USA. Featured photo by La Dolce Vita Orient Express