Tall ship cruise lines: the real sailing ships you can book, and a tall ship cruise in the Caribbean

A tall ship cruise is a week on a ship that really sails: square sails on tall masts, a crew who set them, and engines kept for calm days. Only a handful of cruise lines run ships like this, and they’re quite different from each other. Below: the tall ship cruise lines you can book, the rig words that tell you how much a ship really sails, where to take a tall ship cruise in the Caribbean, what a week costs, and the history, books and films behind it all, for anyone who wants to turn up knowing what a topgallant is. We sail the Royal Clipper in January 2028. I haven’t sailed any of these ships yet, so the facts below come from the lines’ published specifications and the sources at the bottom.

What counts as a tall ship?

There’s no single definition. In practice “tall ship” means a traditionally rigged sailing ship, usually with square sails: rectangular sails hung from horizontal spars called yards. The rig names tell you which masts carry square sails:

Rig	What it means	Cruise example
Full-rigged ship	Square sails on every mast	Royal Clipper (5 masts), Sea Cloud Spirit (3 masts)
Barque	Square sails on all masts but the last	Sea Cloud (4 masts)
Barquentine	Square sails on the front mast only	Star Flyer, Star Clipper (4 masts)
Motor-sail ship	Fore-and-aft sails set by computer from the bridge	Wind Star, Wind Spirit, Wind Surf

A full-rigged ship takes the most crew work and looks the most like the old cargo clippers. Fore-and-aft sails, the triangular kind on a yacht, are easier to handle, and they’re what many modern sailing cruise ships use. (If you only learn one word before you go, make it “full-rigged.” It’s the one that tells you you’re getting the real thing.)

Tall ship cruise lines compared

Line	Ships	Rig	Guests per ship	How the sails are set
Star Clippers	Royal Clipper (2000)	Full-rigged ship, 5 masts, 42 sails	227	Crew, with powered controls
Star Clippers	Star Flyer (1991), Star Clipper (1992)	Barquentine, 4 masts, 16 sails	170	Crew
Sea Cloud Cruises	Sea Cloud (1931)	Barque, 4 masts	64	Crew
Sea Cloud Cruises	Sea Cloud Spirit (2021)	Full-rigged ship, 3 masts	136	Crew, by hand
Windstar	Wind Star, Wind Spirit	4 masts, fore-and-aft sails	148	Computer, from the bridge
Windstar	Wind Surf	5 masts, fore-and-aft sails	Larger	Computer, from the bridge

Star Clippers

Star Clippers runs three sailing ships, all registered in Malta. The Royal Clipper is its flagship: a five-masted full-rigger modeled on the German ship Preussen of 1902, and listed by Guinness World Records as the largest fully rigged ship in the world. Star Flyer and Star Clipper are smaller four-masted barquentines that each carry 170 guests. The style is relaxed: one open seating at dinner, casual dress, included water sports from a stern platform, and a crew that sets and trims the sails while you watch, lie in the bowsprit net or climb the mast on a supervised climb.

Sea Cloud Cruises

Sea Cloud Cruises, based in Hamburg, runs the oldest ship on this page. Sea Cloud was launched in Kiel, Germany, in 1931 as Hussar V, a private yacht for Marjorie Merriweather Post and E.F. Hutton. She served as a weather ship for the US Coast Guard and Navy in the Second World War, and today she carries 64 guests. The line added Sea Cloud II in 2001 and Sea Cloud Spirit in 2021. Sea Cloud Spirit is a three-masted full-rigged ship for up to 136 guests, and every sheet and halyard on board is worked by hand. All three are smaller than the Royal Clipper.

Windstar’s sailing ships

Windstar’s three “sailing yachts” are a different idea. Wind Star and Wind Spirit carry four masts and up to 148 guests, and Wind Surf, the largest, carries five. Their sails are fore-and-aft, raised and trimmed by computer from the bridge, with engines working alongside. They’re comfortable small cruise ships with real sails, not square-riggers with a working deck crew. If watching the sail handling matters to you, that’s the key difference. If it doesn’t, they’re a perfectly good choice for a small-ship week.

Tall ship cruise in the Caribbean

Winter is tall ship season in the Caribbean: it’s the dry season, and it falls outside the June-to-November hurricane season. For winter 2027–28, Star Clippers’ rate file shows all three of its ships in the region:

Ship	Base port	Typical sailing	Islands
Royal Clipper	Bridgetown, Barbados	7 nights, Saturday to Saturday	Grenadines route: Grenada, Tobago Cays, St Vincent, Bequia, Martinique, St Lucia. Windward route: St Lucia, Dominica, Antigua, St Kitts, Îles des Saintes, Martinique
Star Flyer	Philipsburg, St Maarten	7 nights	Leeward and “Treasure Islands” routes in the northern Caribbean
Star Clipper	St John’s, Antigua	7 nights (Nov to early Jan), then Panama and Costa Rica	Round trips from Antigua, then Central America

On the Royal Clipper’s Windward route the Royal Clipper and Star Flyer meet and sail alongside each other on the way to Dominica. Our Royal Clipper guide has that route port by port, and the Royal Clipper cost guide has Star Clippers’ published fares. Sea Cloud has also sailed the Caribbean in winter; check its current schedule.

What is the best time of year for a Caribbean sailing cruise?

Winter, roughly December to March. Three reasons: it’s the dry season, it’s outside the Atlantic hurricane season, which NOAA defines as 1 June to 30 November, and it’s when the sailing ships are actually there. Star Clippers’ Caribbean season runs from late November to March; by April the Royal Clipper is crossing to the Mediterranean. Christmas and New Year weeks cost more; in 2027–28 the early-December weeks are the cheapest.

How much does a 7-day Caribbean sailing cruise cost?

On Star Clippers’ ships, winter 2027–28, advance-purchase fares per person, sharing, as of November 2026:

Ship (7 nights)	Cheapest cabin	Standard outside	Top cabin
Royal Clipper, from Barbados, Jan 2028	$2,620	$3,090	$6,070
Star Flyer, from St Maarten, Jan 2028	$2,060	$2,570	$4,370
Star Clipper, from Antigua, Dec 2027	$2,020	$2,520	$4,280

Add flights, drinks, gratuities and port charges. Sea Cloud and Windstar price their own sailings; we haven’t priced those, so check with them. The full breakdown, cabin by cabin, is in our Royal Clipper cost guide.

Choosing the best small ship Caribbean cruise for sailing

Ask yourself four questions:

1. Do you want square sails and a working crew? Then Star Clippers or Sea Cloud.
2. How many people do you want on board? 64 on Sea Cloud, 136 on Sea Cloud Spirit, 170 on Star Flyer or Star Clipper, 227 on the Royal Clipper.
3. How much of the sailing do you want to see? Square-riggers with deck crews (Star Clippers, Sea Cloud) or computer-set sails (Windstar).
4. Where do you want to start? Star Clippers’ Caribbean ships start from Barbados, Antigua or St Maarten.

Cabin choice matters more on a sailing ship than on a big one, because the cabins are small. Our Royal Clipper cabins guide explains the trade-offs.

Tall ship vs a regular cruise ship: which is better for you?

Neither is better. They’re different holidays. Here’s the honest trade:

	Tall ship (e.g. Royal Clipper)	Big cruise ship
Guests	64 to 227	Thousands
Getting ashore	Mostly by tender, at small anchorages	Mostly docked at big ports
On board	The sailing, a bar on deck, water sports off the stern	Shows, many restaurants, pools, casinos
Dining	One dining room, open seating	Many choices
Dress	Casual, no formal nights (Star Clippers)	Varies by line
Motion	You’ll feel the sea more	Bigger ships move less
Cabins	Small	Wider range, many with balconies

Pick the tall ship if the sailing is the point, you like a small crowd and you’d rather anchor off a little island than dock beside four other ships. Pick the big ship if you want lots of choice on board, a balcony as standard, or the steadiest ride you can get.

Crewed sailing cruise vs bareboat charter

These come up together in searches, but they’re very different trips.

• Bareboat charter. You rent a yacht with no crew and sail it yourself: navigation, anchoring, docking, food. The Moorings says it doesn’t require a certificate in the British Virgin Islands, but you do need real boat-handling and navigation skills, and many companies ask for a sailing résumé.
• Crewed charter. You rent a yacht with a captain, and often a cook. They sail; you’re on holiday. Usually just your group on board.
• Sailing cruise ship. What this page is about. You buy a cabin, not the boat. A professional crew does everything, you share the ship with up to a couple of hundred other guests, and you need no sailing skills at all.

If you’ve never sailed, bareboat isn’t where you start. (Ask anyone who’s tried to anchor a catamaran in a crowded bay on day one.)

Are there adults-only sailing cruises in the Caribbean?

Not on Star Clippers. Its FAQ says it accepts children from six months old, though it has no children’s club or babysitting, so parents are in charge of keeping them busy. If adults-only matters to you, ask each line about its age policy for your exact sailing.

What to pack for a week on a sailing ship

Cabins are small and the dress code is casual, so pack less than you think.

• A soft bag, not a big hard case. It squashes under the bed.
• One smart-casual outfit for dinner, maybe two. No formal wear. On Star Clippers, skip shorts and swimwear in the dining room at dinner.
• Swimwear, a cover-up and sandals you can get wet getting in and out of tenders.
• Sun protection: hat, sunglasses, high-SPF sunscreen. It’s the tropics, and you’ll be on deck a lot.
• A light layer for the deck at night and the air conditioning.
• Seasickness remedies if you need them. You’ll feel the sea more than on a big ship.
• A plug adapter. The Royal Clipper runs on 220 volts; single-voltage gadgets need a converter.
• Some euros. Martinique and the Îles des Saintes are French.
• Your passport, and a copy stored somewhere else.

A short history of the age of sail

The cargo sailing ships these cruise ships copy had their last great era from the 1840s to the 1920s. Here are the milestones:

• 1840s to 1860s: the clipper ships. Fast, narrow square-riggers built to carry tea, wool and passengers quickly. The best-known survivor is the Cutty Sark, launched at Dumbarton, Scotland, on 22 November 1869. She carried tea from China and later wool from Australia, and she’s now a museum ship in dry dock at Greenwich, London. Her name comes from the witch in Robert Burns’s poem “Tam o’ Shanter.”
• 1869: the Suez Canal opens. Steamships using the canal take most of the tea trade within a few years. (The Cutty Sark was launched five days after it opened. Rotten timing.)
• 1890s to 1920s: the windjammers. Big steel square-riggers carry bulk cargo such as nitrate and grain on long ocean routes. The Hamburg firm F. Laeisz names its ships with a P, and they become the Flying P-Liners. Its Preussen, launched in 1902, is the only five-masted full-rigged ship ever built until the Royal Clipper. She sank after a collision near Dover in 1910.
• 1949: Pamir, another Flying P-Liner, becomes the last commercial sailing ship to round Cape Horn. She sank in a hurricane in the Atlantic in September 1957 with 80 of the 86 people on board.
• 1931 to today: sail for pleasure. Sea Cloud is built as a private yacht in 1931. Later, cruise lines start building sailing ships again: Windstar’s motor-sail ships, then Star Clippers’ Star Flyer (1991), Star Clipper (1992) and Royal Clipper (2000).

The Caribbean routes run through older sea history too. The Royal Clipper’s Windward route passes Rodney Bay in St Lucia, where Admiral Rodney’s fleet waited in 1782, and the Îles des Saintes, where he beat the French that April. It also stops at Nelson’s Dockyard in Antigua, where Horatio Nelson served from 1784 to 1787.

Photo: Star Clippers

Books about tall ships

A reading list for before you sail. The older books are out of copyright and free online.

Book	Year	What it is
Two Years Before the Mast, Richard Henry Dana Jr.	1840	A young Bostonian signs on as a common sailor in 1834 and sails from Boston around Cape Horn to California. The plainest account of life before the mast. Free on Project Gutenberg.
Moby-Dick, Herman Melville	1851	The whaling novel, with long chapters on how a whaling ship and her crew work.
Treasure Island, Robert Louis Stevenson	1883	Pirates, a map, and the schooner Hispaniola.
Captain Blood, Rafael Sabatini	1922	A doctor is shipped to Barbados as a convict, escapes and turns pirate captain. On our trip’s reading list.
Master and Commander, Patrick O’Brian	1969	The first of the Aubrey–Maturin novels about a Royal Navy captain and his ship’s surgeon in the Napoleonic wars. Twenty books, and the deepest fiction there is about life on a square-rigged warship.

Films about tall ships

• Captain Blood (1935). Errol Flynn and Olivia de Havilland in the film of Sabatini’s novel; the story starts in Barbados.
• Two Years Before the Mast (1946). The film of Dana’s book.
• Pirates of the Caribbean: Dead Man’s Chest (2006). Shot partly in Dominica, which the Royal Clipper visits. See our guide to the Pirates of the Caribbean filming locations.
• Master and Commander: The Far Side of the World (2003). Peter Weir’s film with Russell Crowe, from O’Brian’s novels. The ship playing HMS Surprise was a replica of the 18th-century frigate HMS Rose, now at the Maritime Museum of San Diego. It won two Oscars, for cinematography and sound editing.

Our tall ship trip

Our hosted week, Mermaids, Pirates and Poets (Caribbean Sail), sails the Royal Clipper’s Windward Islands route from Barbados, 15 to 22 January 2028, for up to 20 guests, and I’m on board all week. Before the trip the group reads Captain Blood and Caribbean novels together and watches the films. The books are on our Royal Clipper reading list.