Tall-ship cruises that take you back in time

Greg Keraghosian

star clippers
star clippers

Ever dreamed of sailing off into the horizon under billowing white sails? Gulls soaring overhead, sea spray misting your face, sun glistening on the ocean surface, hair blowing in the wind . . . fuel the fantasies of your inner seafarer aboard one of these four leading tall-ship cruise lines.

Star Clippers

For more than 20 years, Star Clippers has offered mega-yacht sailings with an informal slant. Their three-masted vessels—recreations of 19th-century clipper ships—include the 170-passenger Star Flyer, 170-passenger Star Clipper, and 227-passenger Royal Clipper (the latter comes with 42 spellbinding sails). Onboard, partake in basic nautical training (learn to tie a knot, raise the sails, navigate by the stars, or climb the rigs), or take directly to the seas with water-sports activities like kayaking, sailing, and snorkeling (all included in the rates).

Where They Sail: The line focuses on flexible itineraries to off-the-track ports in Europe, the Caribbean, and Costa Rica.

Book It: Rates from $1,511/person for seven-night sailings, including water sports.

Windstar Cruises

Casually elegant Windstar Cruises has outfitted three recently refurbished sailing yachts—the 148-passenger Wind Spirit, 148-passenger Wind Star, and 310-passenger Wind Surf—with teak decks, computer-run sails, and water-sports platforms (featuring complimentary water sports for guests). Onboard atmosphere is laid back, with plenty of big-ship amenities matched by top-notch service; plus, an open-bridge policy that allows guests to chat up officers about the vessel’s navigational systems, charts, and functionality of the sails.

Where They Sail: The cruise line sails to some 100 ports throughout Europe, the South Pacific, the Caribbean, and Central America.

Book It: Rates from $1,799/person for seven-night sailings, including non-alcoholic beverages and water sports.

Sea Cloud Cruises

This upscale German cruise line operates two five-star windjammers (plus, a river yacht), including the 94-passenger Sea Cloud II and grand-dame 64-passenger Sea Cloud, a legendary 82-year-old vessel. Onboard atmosphere is refined, with plush appointments, polished service, decadent cuisine, and formal evenings fueled by cocktails and piano music. Expect easy camaraderie between guests (mostly Americans and Germans), and plenty of outdoor spaces to enjoy meals, sunbathing, and the overall nautical scene.

Where They Sail: Sea Cloud’s vessels sail in summer to Europe and in winter to the Caribbean and Central America.

Book It: Rates from $3,995/person for seven-night sailings, including beverages (with wine and beer) and excursions on select itineraries.

Island Windjammers

This four-year-old company (formed on the foundations of former Windjammers Barefoot Cruises) offers two intimate schooners, the 12-passenger Diamant and the 24-passenger Sagitta. Each ply Caribbean waters on relaxed, intimate sailings, with some specialized “Solo Sojourns” and “Rum Cruises,” geared towards even more sociable onboard environments. Expect a wood-paneled saloon, alfresco dining areas, well-appointed cabins, and a laid-back “barefoot” onboard philosophy—plus, guests are welcome to help hoist the sails or taking a turn at the helm.

Where They Sail: Island Windjammers sails the Caribbean from St. Maarten, Grenada, or St. Lucia.

Book It: Rates from $1,299/person for six-night sailings, including beverages (with beer and wine) and use of snorkeling gear.