Above, the vast sails billow in the wind; below, the fathomless blue, grey, green and black ocean. Between them, a tall ship moving gracefully away from land left behind to land ahoy, accompanied by music and the clink of champagne glasses.
Each time I have taken a cruise on a tall ship – a traditional sailing vessel with multiple masts and large, often square sails – the journey has been imbued with a sense of tradition and romance that most other forms of travel have long since lost. I love the craftsmanship of the build and, of course, the drama and the glamour of the sails unfurling and fluttering in the wind, before they catch it to move gracefully onward.
Though I was born long after the Golden Age of Sail, which was between the mid-19th century and the early 20th century, I still feel a yearning nostalgia for it. Here are six of the best tall ship cruises to book now.
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Best for a relaxed sailing
Summer Breeze Through the Aegean
Sea Cloud Cruises
Key stops: Amorgos, Milos, Nauplio and Poros (Greece)
Departure port: Athens (Greece)
Duration: Seven nights
Ship: Sea Cloud II
Sea Cloud II’s Aegean cruise visits internationally significant sites, including the Monastery of Hozoviotissa, which hangs off a cliff on Amorgos, 300m above sea level, and Klima, on Milos, where the Venus de Milo was discovered.
Life on the ship, one of three immaculate windjammers operated by Sea Cloud Cruises, a specialist in boutique sailings, is gentle. There is no yoga, no tribute bands – just a few lectures and nightly live piano music on the deck. Passengers can also climb the rig and swim off the ship within a cordoned-off area, while island visits allow time to explore and to enjoy local food and swims in secluded bays.
The 23 sails provide their own theatre, drawing passengers to the deck to watch the crew set the sails by hand. Given the ship’s size – 94 guests in 47 cabins – meeting people is easy with friendships made over excellent meals served with wine.
Insider tip
The dress code is relaxed, so you can leave your evening wear at home.
How to do it
A seven-night Summer Breeze Through the Aegean itinerary departing July 24, 2026, costs from £4,146pp for a double cabin. Includes wine with meals, gratuities, port fees and some excursions.
Best for design opulence
Adriatic Gems
Orient Express Sailing Yachts
Key stops: Rovinj and Brijuni Islands (Croatia), Trieste (Italy)
Departure port: Venice (Italy)
Duration: Four nights
Ship: Orient Express Corinthian
Orient Express Corinthian – the largest sailing yacht in the world – launches in 2026, cruising first in the Mediterranean and Adriatic, before crossing the Atlantic to winter in the Caribbean. The Adriatic Gems cruise leaves Venice for Rovinj – with its narrow, cobbled alleys, pastel-coloured houses and car-free historic centre – before visiting the Brijuni Islands, in the north Adriatic and finally Trieste, in Italy. This once-neglected city has a discreet allure that is only recently being recognised.
The yacht’s debut will certainly make waves. Aside from its size – 722ft (220m) long, with three 100m masts – the experience on board is top-tier, as you would expect from Accor Group-owned Orient Express. Its 54 suites are gorgeous: huge windows, art deco styling, terraces in some and a range of five-star hotel experiences, including swimming pools, 13 restaurants and bars, a theatre and a superb spa. Lest that’s not enough, there is a 24-hour butler service to ensure passengers want for nothing.
Insider tip
For true serenity, book one of the yacht’s suites with floor-to-ceiling windows – a rarity at sea.
How to do it
A four-night Adriatic Gems, departing August 30, 2026, costs from £19,415 per suite. Includes drinks, in-suite dining, 24-hour butler service, a VIP truffle hunting and winemaking experience and taxes. (orient-express.com)
Best for a boutique experience
Corsican Shores Under Sail Aboard Le Ponant
Ponant
Key stops: Saint-Florent, Ajaccio, Gulf of Sant’Amanzo, Bonifacio, Roccapina and Calvi (Corsica, France)
Departure port: Nice (France)
Duration: Seven nights
Ship: Le Ponant
Corsica is known as the Island of Beauty, and the included excursions on this round-trip from Nice will show you why. Whether you venture into its mountainous heart, head to its sandy beaches or dive into its cuisine, you’re sure to fall in love with it. In Ajaccio, a hike takes in the coastal path of Sentier des Douaniers, while in gravity-defying Bonifacio, high above a fjord, the views fuel dreams.
Three-masted Le Ponant, part of luxury cruise line Ponant’s fleet, is the first ship to join Relais & Châteaux, a brand with a reputation for gourmet dining and exclusivity. A vital aspect of this is the ratio of 32 passengers to 33 crew, more cabin storage than is usually found on cruise ships, and generous spacing between sunbeds.
There are two restaurants, Le Diamant – all white linen and French sophistication – and Emeraude Lounge, where afternoon tea is served with a dash of ooh la la. Other great features include the seawater pool that can be added to the back deck, watersports, lectures, fitness classes and live music.
Insider tip
Sailing on Le Ponant is much like yachting – great if you love bumping over waves, but less so if you get seasick.
How to do it
A seven-night Corsican Shores under Sail departing September 7, 2027, costs from £7,260pp for a window or porthole cabin. Includes drinks, Wi-Fi, transfers, excursions and port taxes.
Best for visiting remote destinations
SeaTrek The Jewels of Raja Ampat
SeaTrek Sailing Adventures
Key stops: Misool, Batanta and Central Raja Ampat (Indonesia)
Departure port: Sorong (Indonesia)
Duration: Nine nights
Ship: Ombak Putih
This trip is for anyone wishing to substitute normal life for a total immersion into a paradise only nature can provide. Sailing around the least developed and easternmost islands of Raja Ampat in Indonesia, SeaTrek Sailing Adventures – a specialist in responsible, exploration cruises to this remote region – takes guests to reefs and forests that other parts of the world struggle to match.
While there are no guarantees where nature is concerned, there is a good chance of seeing Red and Wilson’s bird-of-paradise – two of nearly 500 indigenous bird species – and corals that are found nowhere else.
Life on the Ombak Putih, which means “white waves”, is an adventure. You won’t find a spa or theatre, but you will have kayaks, paddle boards, snorkelling equipment, beautiful cabins (12 of them for 24 passengers), excellent meals and excursions that are led by experts. The ship itself is a beauty: built by the seafaring Sulawesi people, it’s a traditional, two-masted ironwood vessel – called a pinisi – that sails gracefully, as guests enjoy time in the spacious salon, in the rooftop lounge or in the covered area.
Insider tip
This is responsible tourism at its best. As such, nature rules and itineraries might change to accommodate wildlife, so be prepared to go with the flow.
How to do it
A nine-night SeaTrek The Jewels of Raja Ampat round-trip from Sorong, departing January 10, 2027, costs from £6,142pp for a standard cabin. Includes soft drinks, water sports activities, lectures from experts and nature expeditions. (seatrekbali.com)
Best for laid-back luxury
The Colourful Canary Islands
Windstar Cruises
Key stops: Las Palmas, San Sebastián de La Gomera and Santa Cruz de La Palma (Canary Islands), Cadiz (Spain), Funchal (Madeira)
Departure port: Santa Cruz de Tenerife (Tenerife)
Duration: 10 nights
Ship: Wind Spirit
The Canary Islands have such a versatility of mood, appearance and personality that they introduce visitors to different eras, cultures and even planets – some say that La Palma’s black lava landscapes resemble the surface of the moon.
Windstar Cruises is known for luxury sailing on small ships. Its fleet includes three windjammers, one of which is four-masted, four-decked, Wind Spirit. Sleek and refined, it takes its 148 passengers from port to port in a manner that feels more like yachting than cruising. The vibe on board is relaxing and relaxed, with open seating both in the gourmet restaurant, Amphora, and in Veranda, where breakfast and lunch are served. Guests can also dine beneath the stars at reservation-only Candles, which specialises in steak and seafood.
Entertainment includes lectures, live music and cookery demonstrations, with highlights being the open-bridge policy and the sail-away. It’s automated, but no less impressive for that, and is accompanied by Vangelis’ rousing 1492: Conquest of Paradise.
Insider tip
If you love to watch the waves crashing against your porthole, book a deck one cabin on the lower level.
How to do it
A 10-night Colourful Canary Islands, departing January 26, 2027, costs from £2,699pp for a standard cabin. Includes a one-night pre-cruise hotel stay and 10 nights on board with soft drinks.
Best for hands-on sailing
Leeward Islands 7 Nights
Star Clippers
Key stops: Charlestown (Nevis), Cabrits (Dominica), Terre-de Haut (Îles des Saintes), Deshaies (Guadeloupe), Falmouth Harbour (Antigua), Gustavia (St Barts)
Departure port: Phillipsburg (St Maarten)
Duration: Seven nights
Ship: Star Flyer
The very sound of the Leeward Islands in the Lesser Antilles suggests calm, hints at relaxation and calls to mind languid days spent looking for whales or wandering through lush, magical forests. While that’s largely true, there are a few surprises. St Maarten, for instance, draws crowds with its designer shopping. Then there are Dominica’s orchid-festooned rainforests, its lakes and the twin waterfalls at Trafalgar Falls, which are known as the Mother and Father Falls.
Star Flyer, part of the Star Clippers fleet, carries 166 passengers on this round-trip from St Maarten in great style. Though the ship’s build replicates vessels from the grand age of sail, the luxurious interiors are wholly 21st century. Passengers enjoy a hands-on sailing experience that includes steering the ship, visiting the bridge and climbing up to the crow’s nests for spirit-lifting views. Equally exhilarating is resting on the nets at the front of the ship. The experience on board is informal yet sophisticated, with a relaxed dress code, open-seat dining and light entertainment (think lectures and live music).
Insider tip
The best views are to be had from bow-facing staterooms with balconies, or from the crow’s nest. Ask the crew to arrange the latter for you.
How to do it
A seven-night Leeward Islands sailing, departing January 30, 2027, costs from £1,835pp for an inside cabin. Includes watersports, lectures and entertainment. Excludes port charges.
About our expert
Xenia Taliotis
Xenia was born and raised in London, but yearns to live by the sea. Until she can make that dream a reality, she spends her time on the water, putting in the nautical miles to meet some of the planet’s most remarkable creatures.