Sunset over the Pitons and Soufrière, St Lucia

Tall ship cruises in the Caribbean

Sail the Grenadines, the Windward and Leeward Islands and the British Virgin Islands aboard Royal Clipper, Star Flyer or Sea Cloud II, with a different island to explore almost every day.

Caribbean · Small ship sailing cruises

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  • ATOL protectedFlight-inclusive holidays
  • ABTOT memberHolidays without flights
  • Independent since 1995A family company
  • Avg. passengersper vessel
Cruising the Caribbean

Why choose a tall ship cruise in the Caribbean

A tall ship is one of the most memorable ways to see the Caribbean: the sails go up as you leave port, and each morning brings a new island, from the Grenadines in the south to the British Virgin Islands in the north.

Every Caribbean cruise we offer can be booked as a complete holiday, with return flights from the UK, transfers, a seven-night cruise and hotel nights in Barbados or St Maarten, from two nights to a full week.

Royal Clipper sails from Barbados to the Grenadines and the Windward Islands, Star Flyer from St Maarten to the Leeward and British Virgin Islands, and the elegant Sea Cloud II sails from both.

4Caribbean tall ship holidays
7Nights on board on every cruise
30+Years of specialist expertise
98%Would book with us again
Itineraries

Our Caribbean cruises

Four tall ship holidays, from the Grenadines in the south to the British Virgin Islands in the north.

  • A palm-fringed beach in the Tobago Cays, St Vincent and the Grenadines

    Tall shipRoyal Clipper

    Caribbean Royal Clipper

    A week at the Hilton Barbados Resort followed by seven nights aboard Royal Clipper, sailing the Grenadines or the Windward Islands from Barbados.

    14 days · December to March

    From £3,945 ppFlights & hotel included
  • Yachts at anchor off Jost Van Dyke in the British Virgin Islands

    Tall shipStar Flyer

    Caribbean Star Flyer

    Two nights at La Playa Orient Bay, then seven nights aboard Star Flyer from St Maarten to the Leeward Islands or the British Virgin Islands.

    10 days · November to March

    From £3,240 ppFlights & hotel included
  • Gustavia harbour on St Barthélemy

    Tall shipSea Cloud II

    Lesser Antilles & Grenadines

    Seven nights aboard the three-masted Sea Cloud II from St Maarten to St Barths, Dominica, the Îles des Saintes and Martinique, with two nights at La Playa Orient Bay.

    10 days · February to March

    Prices TBAFlights & hotel included
  • Admiralty Bay on Bequia, St Vincent and the Grenadines

    Tall shipSea Cloud II

    Sea Cloud Caribbean

    A round trip from Barbados aboard Sea Cloud II to Bequia, Canouan, Grenada, Martinique and St Lucia, followed by three nights at the Hilton Barbados Resort.

    11 days · Dates TBA

    Prices TBAFlights & hotel included
Your holiday, your way

Four ways to book your Caribbean cruise

Take a complete holiday with flights and hotels, book the cruise on its own where available, or let us shape the trip around your dates.

  1. Cruise & Stay

    Return flights from the UK, transfers, the cruise and hotel nights before or after you sail, all arranged together and ATOL protected.

  2. Cruise Only

    On the Royal Clipper, Star Flyer and Lesser Antilles voyages you can book the seven-night cruise on its own and make your own travel plans.

  3. Tailor-Made

    Add extra nights, upgrade your flights or combine your cruise with a stay elsewhere: the holiday is shaped around you.

  4. Expert Advice

    We know these ships and itineraries well, and can help you choose the right cruise, cabin and dates.

The ships

Tall ships for your Caribbean cruise

Three genuine sailing ships, each with its own character, and each small enough to anchor off quiet bays and small harbours.

Royal Clipper under full sail
Star Clippers · Tall ship

Royal Clipper

The largest five-masted clipper ship in the world, combining the elegance of a classic sailing vessel with two swimming pools and generous teak decks. Sails from Barbados.

  • Five masts
  • Two pools
  • From Barbados
Star Flyer under full sail in the Caribbean
Star Clippers · Tall ship

Star Flyer

A four-masted clipper with polished brass, teak decks, two swimming pools and an open-seating restaurant. Sails from St Maarten.

  • Four masts
  • Two pools
  • From St Maarten
The three-masted tall ship Sea Cloud II at sea
Sea Cloud Cruises · Tall ship

Sea Cloud II

An elegant three-masted sailing ship with a refined, intimate atmosphere. Sails the Lesser Antilles from St Maarten and the Sea Cloud Caribbean voyage from Barbados.

  • Three masts
  • From St Maarten
  • From Barbados
Why the Caribbean

What makes a Caribbean tall ship cruise special

  • Star Flyer and Royal Clipper sailing together south of the Îles des Saintes
    Îles des Saintes

    Life Under Sail

    Watch the crew raise the sails as you leave port, then relax on deck as the ship heels gently in the trade winds.

  • Saint-Pierre and Mount Pelée above the bay, Martinique
    Martinique

    Island Variety

    French, British and Dutch heritage, rainforest, volcanoes and colonial towns, with several islands in a single week.

  • Yachts anchored in clear turquoise water off a beach in the Grenadines
    Grenadines

    Beaches & Snorkelling

    Days anchored off white-sand beaches such as the Tobago Cays and Jost Van Dyke, with clear, warm water for swimming.

  • A white-sand beach with a small catamaran on Barbados
    Barbados

    Winter Sun

    The cruises sail between November and March, when the Caribbean is warm and sunny and the UK is not.

Why book with Seafarer

Small ship cruise specialists since 1995

For three decades we have arranged small ship cruises and the flights, hotels and transfers that go with them.

  • Three Decades of Experience

    Trading since 1995, with first-hand knowledge of our ships, itineraries and destinations.

  • Complete Holiday Packages

    Cruise, flights, hotels and transfers arranged together, around your dates.

  • Small Ships, Closer Access

    Islands, bays and harbours that large cruise ships cannot reach.

  • Independent & Family-Run

    A family company, independent since 1995.

  • UK Agent for Variety Cruises

    Official UK General Sales Agent for Variety Cruises boutique yacht cruises.

  • ATOL & ABTOT Protected

    Full financial protection on every booking, with or without flights.

Good to know

Caribbean cruises: FAQs

When is the best time for a Caribbean cruise?

Our Caribbean tall ship cruises sail between November and March, the most popular time to visit. The dry season runs from December to May, with warm, sunny days of around 22–30°C.

Which islands will I visit?

Royal Clipper sails from Barbados to the Grenadines, including the Tobago Cays and Bequia, or to the Windward Islands, including St Lucia, Dominica and Antigua. Star Flyer sails from St Maarten to the Leeward Islands or the British Virgin Islands. Sea Cloud II sails from St Maarten to St Barths, Dominica and Martinique, or from Barbados to Bequia, Grenada and St Lucia.

Are flights and hotels included?

Yes. Each holiday includes return flights from the UK, transfers and hotel nights: a week at the Hilton Barbados Resort with Royal Clipper, three nights there with Sea Cloud Caribbean, and two nights at La Playa Orient Bay with the St Maarten departures.

Can I book the cruise only?

Yes. On Royal Clipper, Star Flyer and the Lesser Antilles & Grenadines voyage aboard Sea Cloud II you can book the seven-night cruise on its own. The Sea Cloud Caribbean holiday is sold as a complete package.

How much does a Caribbean tall ship cruise cost?

As a guide, our Caribbean cruise packages start from about £3,250 per person sharing for 10 days on Star Flyer, or about £3,950 for 14 days on Royal Clipper with a week in Barbados Flights & hotel included, and 8-day cruise-only fares from about £1,950 per person. Sea Cloud II prices are available on request. The price depends on the ship, cabin and departure date, and special offers change through the season, so each cruise page shows its live prices.

What is life on board like?

Relaxed. Days are spent exploring ashore, swimming or simply watching the sails from the deck, and evenings over dinner with fellow guests. Each ship has its own character, so ask us which would suit you best.

Do I need sailing experience?

No. The professional crew sails the ship, and you are free to simply relax and enjoy the voyage.

Speak to a specialist

Plan your Caribbean cruise

Tell us when you would like to travel and which cruise appeals, and we will check availability and put your holiday together.

Our sister brand

Prefer to sail yourself?

Seafarer Cruises is the small ship cruise brand of Seafarer Cruising & Sailing Holidays.

If you would rather take the helm, our sister brand Seafarer Sailing offers flotilla holidays, bareboat and skippered yacht charter and RYA sailing courses in Greece and Croatia.

Visit Seafarer Sailing

Other cruise destinations
Peace of mind

Book your Caribbean cruise with confidence

Seafarer is licensed by the Civil Aviation Authority (ATOL 9511) and all air holidays we operate are ATOL protected. We are also members of ABTOT (Membership No. 5660), providing additional protection for bookings without flights.

We have been trading since 1995 — all your deposits and balance payments to us are fully financially secure.

ATOL protected
ATOL protected: licence 9511All flight-inclusive holidays are fully ATOL protected
ABTOT member 5660
ABTOT member: No. 5660Financial protection for bookings without flights
Guest reviews

98% of our customers say they’d book with us again

Independent reviews of Seafarer, collected by Feefo.

Excellent

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Based on 643 guest reviews of our service on Feefo

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