Best Tall Ship Cruise Lines for Sailing Voyages

There is a feeling on the deck of a sailing ship that no engine can match. The sails fill, the ship leans into the wind, and the only sound is the water and the rigging. The tall ship cruise lines that still carry guests are a small, rare group. This guide covers the kinds of voyage, the finest vessels, where they sail, and the itineraries we book.

The Kinds of Tall Ship Cruise

The sailing-ship fleet falls into a few clear groups. At the top sit the classic square-rigged yachts, ships with tall masts and a cloud of canvas, sailed in much the way ships were a century ago. Below them are the modern sailing yachts, sleek vessels with computer-assisted sails that combine the feel of sail with up-to-date comfort. There are also larger and more affordable sail-cruise ships for travelers who want the romance of canvas without the luxury price.

All of them share the moment when the engines go quiet and the sails take over.

The Finest Ships

The Sea Cloud is the most beautiful sailing ship still carrying guests. She was built in 1931 for the American heiress Marjorie Merriweather Post, with around 30 sails across four masts and original cabins whose 1930s grandeur belongs to a vanished world. She carries about 64 guests with a crew nearly as large, and she is among the largest private sailing yachts ever built. Her younger sister, the Sea Cloud II, brings the same square-rigged romance with a touch more modern comfort and sails the Caribbean and the Mediterranean.

Le Ponant is the modern counterpart. A three-masted yacht carrying just a few dozen guests, she pairs genuine sail with the polish travelers expect today, and she sails some of the loveliest coasts in the Caribbean and the Mediterranean.

When and Where They Sail

The sailing-ship season follows the sun. The ships cross to the Caribbean for the winter, where steady trade winds and short hops between islands make ideal sailing, and return to the Mediterranean for the summer, calling at the smaller harbors that larger ships cannot enter. Most voyages run about a week, which is long enough to settle into the rhythm of sail and short enough to suit the high fares. Spring and autumn bring repositioning voyages across the Atlantic for travelers who want days of pure open-water sailing.

Recommended Sailing Voyages

Each fare is a starting per-person price, and live dates sit on the itinerary page.

• Classic square-rigger: the Sailing the Caribbean Aboard Sea Cloud II with National Geographic and Lindblad, from around $10,500.
• The Mediterranean under sail: the Ancient Shores of Sicily and Malta Aboard Sea Cloud II, from around $11,421.
• A modern yacht: the Reverie Under Sail in the Lesser Antilles on Le Ponant, from around $8,220.
• The Adriatic: the Croatia, Under Sail Aboard Le Ponant, from around $10,020.

Why Book Your Sailing Voyage with Us

A tall ship is a special trip, and the ships are very different from one another. The grandeur of a classic square-rigger is a world apart from the easy modern feel of a sailing yacht, and the right choice depends on what you are after. We book these voyages and can match you to the ship, the route, and the season that suit.

Booking through us, you can also join the Small Ship Travel Loyalty Program, a four-tier program that pays members 2 to 5 percent back per booking, plus perks like cabin upgrades and concierge access. The credit builds across every cruise line we book.

Related Reading

• Best Luxury River Cruises 2026: the top end of the river fleet.
• Small Ship Cruise Cabin Selection Guide: how to pick a cabin on a small vessel.
• River Cruising vs Ocean Cruising: how the formats compare.
• All-Inclusive Small Ship Cruises: What Is Included: how luxury fares work.

Sources

Ship history and specifications come from the operators' published material and our own bookings.

• Sea Cloud Cruises.