Crowded airports and airplanes, hour-long queues for theme park rides, and endless work messages on your beach day can make just about any person yearn for a time when travel embraced a slower, less connected pace of life. If you’re feeling nostalgic for a bygone era of transport, several cruise lines are leaning into that throwback energy. After all, sailing a ship across the sea is one of the original modes of exploration.
If you like the idea of cruising on a historic yacht, climbing the mast of an authentic sailing ship, or taking the slow route to Europe on a grand ocean liner, these retro-inspired cruises are perfectly poised to transport you back in time.
The forthcoming Orient Express Sailing Yacts will have sleek, sustainable exteriors (L); and vintage-inspired interiors (R).
Courtesy of Orient Express (L); photo by Alixe Lay (R)
An Orient Express ship that evokes the golden age of rail travel
Orient Express set the standard for luxurious train travel in the 1930s, and now travelers can experience the brand’s renowned style at sea. Orient Express is launching two modern sailing yachts, the 110-passenger Orient Express Corinthian and Orient Express Olympian, in 2026 and 2027, respectively, with a focus on the brand’s original slow travel ethos. Guests can step back in time in the Roaring ‘20s–themed speakeasy bar or watch a classic movie from a plush armchair in the cinema. The highlights of every sailing include evening soirees ashore in small, intimate ports of the Caribbean and the Mediterranean that are havens for yachts. Guests can channel James Bond at a spy-themed affair on Moskito Island or watch the sunset from Porto Cervo’s exclusive Phi Beach club in Sardinia. The ship may exude early-20th-century French elegance, but its hybrid engines powered by wind and liquefied natural gas, as well as its rigid fiberglass sails, offer modern sustainability innovations.
Get reacquainted with the original fuel source of ships—wind power—on Sea Cloud Spirit.
Courtesy of Sea Cloud Cruises
A traditional sailing ship in the Caribbean and Mediterranean
Fans of historic ships and nautical novels might dream of climbing the rigging and setting the sails of a masted sailing vessel, and Sea Cloud Cruises’ trio of multimasted windjammers will indulge that fantasy. On the line’s newest ship, the 136-passenger Sea Cloud Spirit, guests enjoy modern luxury amenities, like a spa and fine dining. Nautically inspired cabins mix classic touches like porthole windows and teak deck chairs with today’s comforts (on-demand movies, coffee makers, and 25 rooms with private verandas). Guests have time for leisurely activities such as sunbathing on the deck or snorkeling from the ship’s water sports marina, and they can also help the crew prepare the ship to sail or get a bird’s-eye view from a 46-foot-high platform on one of the ship’s masts.
There’s nothing quite like rollin’ on down the river, powered by a big red paddle wheel.
Courtesy of American Cruise Lines
A classic paddle wheeler on the Mississippi River
Literature lovers can dig deeper into the life and stories of Mark Twain with a Mississippi River cruise on one of American Cruise Line’s replica paddle wheelers, the 150-passenger American Heritage and the 180-guest American Splendor. The ships look like classic white steamboats with gingerbread trim, patriotic bunting, and the signature red paddle wheel in the back, but they have modern accommodations and comfortable cabins within. Onboard programming focuses on Americana, including regional history and music performances. Nostalgia levels are high on shore as well, with excursions including a walk with a Mark Train impersonator in Hannibal, Missouri, and a Grand Ole Opry show in Nashville, Tennessee.
Get a taste of early 20th century travel but with all the modern comforts on Holland America Line’s Pan Am 100th anniversary sailing abour the classic Zuiderdam ship.
Photo by Michel Verdure/Courtesy of Holland America Line
A Pan Am–inspired cruise on Holland America
Pan Am’s Clipper service flew from the U.S. throughout the Caribbean in the 1930s and ‘40s. Its fleet of Sikorsky S-40s and S-42 planes emulated the grand ocean liners of the day with nautical theming and a boatlike design that allowed the planes to land on water. It’s fitting, then, that Holland America Line, a classic cruise line with its own 150-year history, is paying homage to these “flying boats” with a 28-night “Pan Am 100th Anniversary Legendary Voyage.” The 1,964-passenger Zuiderdam departs October 30, 2027, from Pan Am’s former home base of Miami. Half of the 18 Caribbean ports on the itinerary are original Pan Am destinations (including Nassau, San Juan, and Port of Spain, Trinidad). The line has not finalized the onboard programming for this special sailing but promises dinners, decor, and guest lectures celebrating the heyday of the iconic airline.
See the world in throwback style aboard Cunard’s Queen Mary 2.
Courtesy of Cunard
A transatlantic crossing on a classic ocean liner
In the 19th and early 20th centuries, Americans heading to Europe for a cultural tour had to begin with a trip across the Atlantic on an ocean liner. Today’s travelers can still enjoy the slow route from New York to Southampton, England, by crossing the pond on Cunard’s 2,691-passenger Queen Mary 2. The QM2, as it’s known, was built in 2004 to offer a smooth ride across the high seas year-round. It carries on Cunard’s historic legacy of transatlantic travel, dating back to 1840. Enjoy onboard pursuits like deck quoits (a ring-toss game) and fencing lessons, and pack your tux or ball gown for formal evenings of fine dining and ballroom dancing.
The hottest accommodations on board are the kennels, where a select few dogs and cats can get pampered by uniformed kennel masters during their sea journey. Humans can choose from QM2’s three tiers of service. The Princess and Queens Grill suites, with their exclusive restaurants and lounges, may evoke yesteryear’s first and second class, but the base Britannia Class offers modern cruise comforts and doesn’t in the least resemble steerage.
Make like royalty and book onto the 16-passenger Grace yacht for an intimate sailing into more secluded ports.
Courtesy of Quasar Expeditions
A historic yacht formerly owned by a Hollywood princess
Wish you could honeymoon in the suite where Grace Kelly spent hers? You’ll want to book a cruise on Quasar Expeditions’ 16-passenger Grace, the yacht that Aristotle Onassis gave to Grace Kelly and Prince Rainier of Monaco for their wedding in 1956. While the Hollywood star and her royal husband cruised around Corsica and Sardinia on their honeymoon, travelers today can sail the renovated yacht around the Galapagos Islands. Grace’s design pays homage to the archipelago with its abundant outdoor spaces and use of materials such as faux tortoiseshell and slate rock. The interiors are modern, but you’ll still get the thrill of sailing a historic vessel that once carried celebrities, royalty, heads of state, and wealthy businessmen.
