Caribbean Cruises Sailing from Southampton

Sailing to the Caribbean from Southampton offers a relaxed, no-fly cruise experience with the convenience of departing directly from the UK. These cruises typically last between 21 and 35 nights, allowing time to explore stunning ports like Antigua, Barbados, St. Lucia, and Grenada. Many itineraries include transatlantic crossings and calls in the Canaries or Madeira en route to the Caribbean. Whether you’re seeking a sunshine escape in winter or an extended voyage through tropical waters, Southampton departures provide a comfortable and well-paced way to reach paradise. With Hello Cruise, you can compare cruise lines, prices, and dates to find your ideal Caribbean cruise from Southampton.

Caribbean cruises from Southampton are available with top cruise lines such as P&O Cruises, Cunard, and Ambassador Cruise Line. These longer sailings often feature round-trip itineraries that combine vibrant Caribbean islands with Atlantic crossings and stops in Europe or the Azores. Perfect for travellers who prefer not to fly, Southampton to Caribbean cruises offer convenience and comfort. Southampton Caribbean cruises are available in the winter months, particularly from November to March.

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19nov2025

Queen Mary 2

Cunard Cruises Logo

Queen Mary 2 is a remarkable flagship, and her style and elegance are legendary. Above all, it‘s the space she offers and the luxury for you to do as little or as much as you wish which set her apart.Welcome to a true icon. Our flagship is a truly astonishing liner and you’ll find an incredible sense of freedom from the space she offers. Whether you’re in the mood for complete relaxation or something more active, you can find it. Immerse yourself in enthralling entertainment, be indulged in the on board spa, or simply relax with a book in her vast library. You’ll discover remarkable craftsmanship in the elegant staterooms and suites and savouring her many sumptuous restaurants and bars is always a pleasure.

  • Mega Ship
  • Timeless
  • Premium

Cruise: Southampton – New York, New York – Sint Maarten – Dominica – Bridgetown – Castries – Saint Kitts – New York, New York

19nov2025

Queen Mary 2

Cunard Cruises Logo

Queen Mary 2 is a remarkable flagship, and her style and elegance are legendary. Above all, it‘s the space she offers and the luxury for you to do as little or as much as you wish which set her apart.Welcome to a true icon. Our flagship is a truly astonishing liner and you’ll find an incredible sense of freedom from the space she offers. Whether you’re in the mood for complete relaxation or something more active, you can find it. Immerse yourself in enthralling entertainment, be indulged in the on board spa, or simply relax with a book in her vast library. You’ll discover remarkable craftsmanship in the elegant staterooms and suites and savouring her many sumptuous restaurants and bars is always a pleasure.

  • Mega Ship
  • Timeless
  • Premium

Cruise: Southampton – New York, New York – Sint Maarten – Dominica – Bridgetown – Castries – Saint Kitts – New York, New York – Southampton

15dec2025

Queen Mary 2

Cunard Cruises Logo

Queen Mary 2 is a remarkable flagship, and her style and elegance are legendary. Above all, it‘s the space she offers and the luxury for you to do as little or as much as you wish which set her apart.Welcome to a true icon. Our flagship is a truly astonishing liner and you’ll find an incredible sense of freedom from the space she offers. Whether you’re in the mood for complete relaxation or something more active, you can find it. Immerse yourself in enthralling entertainment, be indulged in the on board spa, or simply relax with a book in her vast library. You’ll discover remarkable craftsmanship in the elegant staterooms and suites and savouring her many sumptuous restaurants and bars is always a pleasure.

  • Mega Ship
  • Timeless
  • Premium

Cruise: Southampton – New York, New York – Saint Thomas – Saint Kitts – Sint Maarten – Tortola – New York, New York

15dec2025

Queen Mary 2

Cunard Cruises Logo

Queen Mary 2 is a remarkable flagship, and her style and elegance are legendary. Above all, it‘s the space she offers and the luxury for you to do as little or as much as you wish which set her apart.Welcome to a true icon. Our flagship is a truly astonishing liner and you’ll find an incredible sense of freedom from the space she offers. Whether you’re in the mood for complete relaxation or something more active, you can find it. Immerse yourself in enthralling entertainment, be indulged in the on board spa, or simply relax with a book in her vast library. You’ll discover remarkable craftsmanship in the elegant staterooms and suites and savouring her many sumptuous restaurants and bars is always a pleasure.

  • Mega Ship
  • Timeless
  • Premium

Cruise: Southampton – New York, New York – Saint Thomas – Saint Kitts – Sint Maarten – Tortola – New York, New York – Southampton

03jan2026

Ventura

P&O Cruises Logo

The fun all-rounderDiscover the perfect blend of fun, relaxation, and style on Ventura. Designed for guests of all ages, this lively ship invites you to unwind at The Retreat, get creative with hands-on workshops, and enjoy thrilling live shows at the Arena Theatre. With restaurants and bars to please every palate and endless entertainment to keep the kids happy, Ventura offers unforgettable experiences for everyone.There’s always something happening on Ventura, enjoy delicious fine dining, a tranquil spa, many quiet spaces to unwind, great sports facilities and four pools. Evenings are particularly memorable, with the lavish two-deck theatre where you’ll witness elaborate shows and stand-up comedy.

  • Large Ship
  • British
  • Family-Friendly

Cruise: Southampton – Santa Cruz de Tenerife – Bridgetown – Martinique – Castries – Bonaire – Curaçao – Dominica – Guadeloupe – Saint Kitts – Sint Maarten – Saint John's – Tortola – Praia da Vitória – Southampton

03jan2026

Iona

P&O Cruises Logo

Innovation meets explorationYou’ve not cruised until you’ve sailed on Iona, with her cutting-edge design and world-class style. Explore the world in widescreen with the dazzling SkyDome, swim with panoramic views, and indulge in a world of dining and extraordinary entertainment. Get ready for the adventure of a lifetime on Iona.

  • Mid-Size Ship
  • British
  • Family-Friendly

Cruise: Southampton – Santa Cruz de Tenerife – Saint Kitts – Bridgetown – Bridgetown – Saint George's – Castries – Sint Maarten – Tortola – Saint John's – Santa Cruz de Tenerife – La Coruña – Southampton

04jan2026

Queen Victoria

Cunard Cruises Logo

Queen Victoria will delight you with her special appeal, where elegance and unique features combine seamlessly with outstanding hospitality. You’ll discover an extraordinary way to see the world.From the moment you step on board, you’re immersed in an enchanting world of pleasure and escapism. Pass leisurely days soaking up the sunshine or gazing out at the tranquil ocean from her light-filled Winter Garden. Learn something new with our Cunard Insights speakers, or simply unwind with a good read. As evening falls, choose from a delectable array of dining options, and enjoy world-class entertainment in the Royal Court Theatre. On Queen Victoria the freedom to create your perfect trip is all yours.

  • Mega Ship
  • Timeless
  • Premium

Cruise: Southampton – Funchal, Madeira – Bridgetown – Castries – Saint George's – Saint Vincent – Curaçao – Aruba – Aruba – Dominica – Saint John's – Saint Kitts – Sint Maarten – Ponta Delgada, Azores – Southampton

28jan2026

Borealis

Fred.Olsen Cruises Logo

Sister ship of our flagship Bolette, Borealis joined us 2020, and is perfectly suited for enjoying scenic cruising of the world’s lesser-known waterways. From cruising past remarkable landscapes and historical sites to capturing the beauty of the natural world. Redecorated and refurbished when she joined our fleet in order to meet the high standards of the Olsen family, Borealis features a wonderful series of lounges, bars, elegant restaurants and wide-open deck spaces, as well as 702 beautiful cabins and suites; perfectly suited to the Fred. Olsen style of cruising. From January 2026, Borealis will be excusively for adults, so you can relax in the company of other like-minded guests.Enjoy Scenic Discoveries from the perfectly-appointed Observatory, where guests will be able to see outstanding natural scenery and iconic landmarks, accompanied by commentary from our on board teams; or sample delicious Treats of the Region in the Auditorium where our talented chefs will prepare dishes that are local to the exciting destinations you’re visiting. Our friendly crew will be on hand throughout your cruise, providing the personal service they’re known for. 

  • Mid-Size Ship
  • Over 55s+
  • Adults Only
  • Traditional

Cruise: Southampton – La Coruña – Las Palmas de Gran Canaria – Praia, Santiago Island – Salvador de Bahia – Rio de Janeiro – Rio de Janeiro – Ilhabela – Buenos Aires – Buenos Aires – Montevideo – Port Stanley – Cruising by Antarctic Peninsula – Cruising by Antarctic Peninsula – Punta Arenas – Cruising Chilean Fjords – Cruising Chilean Fjords – Valparaiso – Coquimbo – Iquique – Arica – Paracas – Callao – Callao – Amador – Panama Canal – Puerto Limón – Colón – Cartagena – Cartagena – Willemstad – Port Elizabeth, Bequia – Saint John's – Philipsburg – Ponta Delgada, Azores – Southampton

22feb2026

Queen Victoria

Cunard Cruises Logo

Queen Victoria will delight you with her special appeal, where elegance and unique features combine seamlessly with outstanding hospitality. You’ll discover an extraordinary way to see the world.From the moment you step on board, you’re immersed in an enchanting world of pleasure and escapism. Pass leisurely days soaking up the sunshine or gazing out at the tranquil ocean from her light-filled Winter Garden. Learn something new with our Cunard Insights speakers, or simply unwind with a good read. As evening falls, choose from a delectable array of dining options, and enjoy world-class entertainment in the Royal Court Theatre. On Queen Victoria the freedom to create your perfect trip is all yours.

  • Mega Ship
  • Timeless
  • Premium

Cruise: Southampton – Funchal, Madeira – Tortola – Sint Maarten – Saint Kitts – Dominica – Castries – Bridgetown – Bridgetown – Santa Cruz de Tenerife – Southampton

27feb2026

Ventura

P&O Cruises Logo

The fun all-rounderDiscover the perfect blend of fun, relaxation, and style on Ventura. Designed for guests of all ages, this lively ship invites you to unwind at The Retreat, get creative with hands-on workshops, and enjoy thrilling live shows at the Arena Theatre. With restaurants and bars to please every palate and endless entertainment to keep the kids happy, Ventura offers unforgettable experiences for everyone.There’s always something happening on Ventura, enjoy delicious fine dining, a tranquil spa, many quiet spaces to unwind, great sports facilities and four pools. Evenings are particularly memorable, with the lavish two-deck theatre where you’ll witness elaborate shows and stand-up comedy.

  • Large Ship
  • British
  • Family-Friendly

Cruise: Southampton – La Coruña – Hamilton – Hamilton – Freeport, Grand Bahama – Cozumel – Roatán Island – Belize City – New Orleans, Louisiana – New Orleans, Louisiana – Miami, Florida – Port Canaveral, Florida – Praia da Vitória – Southampton

23oct2026

Arvia

P&O Cruises Logo

Arvia is all about luxury. Swim-up bars, infinity pools and the retractable SkyDome. Take some time out in The Retreat, a private deck where you can relax in style. If you’re looking for excitement, Keel and Cow offers a gastropub experience out on the high seas, while The Club House becomes the party centre of the ship at night.

  • Mid-Size Ship
  • British
  • Family-Friendly

Cruise: Southampton – Santa Cruz de Tenerife – Sint Maarten – Saint Kitts – Castries – Bridgetown

23oct2026

Arvia

P&O Cruises Logo

Arvia is all about luxury. Swim-up bars, infinity pools and the retractable SkyDome. Take some time out in The Retreat, a private deck where you can relax in style. If you’re looking for excitement, Keel and Cow offers a gastropub experience out on the high seas, while The Club House becomes the party centre of the ship at night.

  • Mid-Size Ship
  • British
  • Family-Friendly

Cruise: Southampton – Santa Cruz de Tenerife – Sint Maarten – Saint Kitts – Castries – Bridgetown – Bridgetown

23oct2026

Arvia

P&O Cruises Logo

Arvia is all about luxury. Swim-up bars, infinity pools and the retractable SkyDome. Take some time out in The Retreat, a private deck where you can relax in style. If you’re looking for excitement, Keel and Cow offers a gastropub experience out on the high seas, while The Club House becomes the party centre of the ship at night.

  • Mid-Size Ship
  • British
  • Family-Friendly

Cruise: Southampton – Santa Cruz de Tenerife – Sint Maarten – Saint Kitts – Castries – Bridgetown – Bridgetown – Martinique – Saint Kitts – Tortola – Sint Maarten – Saint John's

30oct2026

Britannia

P&O Cruises Logo

Contemporary glamourExplore the world in understated luxury on our stylish, family-friendly flagship, Britannia. Elegant interiors create a boutique hotel ambience at sea, while her stunning three- tier atrium, adorned with a Star Burst sculpture, provides that wow-factor entrance. Whether you want to relax and unwind, indulge yourself or be entertained, you can do it in style on board Britannia.

  • Mid-Size Ship
  • British
  • Family-Friendly

Cruise: Southampton – Santa Cruz de Tenerife – Sint Maarten – Dominica – Castries – Bridgetown

14 nights

30oct2026

Britannia

P&O Cruises Logo

Contemporary glamourExplore the world in understated luxury on our stylish, family-friendly flagship, Britannia. Elegant interiors create a boutique hotel ambience at sea, while her stunning three- tier atrium, adorned with a Star Burst sculpture, provides that wow-factor entrance. Whether you want to relax and unwind, indulge yourself or be entertained, you can do it in style on board Britannia.

  • Mid-Size Ship
  • British
  • Family-Friendly

Cruise: Southampton – Santa Cruz de Tenerife – Sint Maarten – Dominica – Castries – Bridgetown – Bridgetown

01nov2026

Queen Anne

Cunard Cruises Logo

Queen Anne’s breathtaking interiors take inspiration from our past to define a striking new design direction for our future. Come on board to discover a ship that is modern, yet timeless. A ship that offers both exciting, novel experiences, as well as our much-loved signature venues.On a Queen Anne voyage feel inspired by the blend of classic and contemporary. Enjoy the freedom to do as little or as much as you choose and indulge in everything that makes a Cunard ship so special. With luxurious flourishes enhanced by stylish décor, every day on Queen Anne offers a chance to sail the world in unparalleled comfort. Let tension dissipate in the tranquillity that awaits at the Mareel Spa, delight in the ceremony of our signature Afternoon Tea, and enjoy that extra special feeling as you descend into the Grand Lobby in your Gala Evening finery. Above all, rest easy in the knowledge that the finer details have been taken care of. We look forward to welcoming you on board.

  • Mega Ship
  • Timeless
  • Premium

Cruise: Southampton – Ponta Delgada, Azores – Ponta Delgada, Azores – Funchal, Madeira – Lisbon – Vigo – Southampton

03nov2026

Aurora

P&O Cruises Logo

Experience the timeless elegance of Aurora. This adults-only ship exudes classic cruising with a modern twist; with its stunning atrium and refined design, you can indulge in relaxing afternoons, explore destinations, and appreciate the art of leisurely cruising. From relaxing on the sun-drenched Lido deck to enjoying British afternoon tea or exploring extraordinary itineraries, unforgettable adventures await on Aurora.

  • Large Ship
  • British
  • Adults Only

Cruise: Southampton – Santa Cruz de Tenerife – Bridgetown – Saint Vincent – Castries – Dominica – Sint Maarten – Ponta Delgada, Azores – Southampton

10nov2026

Queen Mary 2

Cunard Cruises Logo

Queen Mary 2 is a remarkable flagship, and her style and elegance are legendary. Above all, it‘s the space she offers and the luxury for you to do as little or as much as you wish which set her apart.Welcome to a true icon. Our flagship is a truly astonishing liner and you’ll find an incredible sense of freedom from the space she offers. Whether you’re in the mood for complete relaxation or something more active, you can find it. Immerse yourself in enthralling entertainment, be indulged in the on board spa, or simply relax with a book in her vast library. You’ll discover remarkable craftsmanship in the elegant staterooms and suites and savouring her many sumptuous restaurants and bars is always a pleasure.

  • Mega Ship
  • Timeless
  • Premium

Cruise: Southampton – New York, New York – Saint Thomas – Saint Kitts – English Harbour – Sint Maarten – New York, New York

10nov2026

Queen Mary 2

Cunard Cruises Logo

Queen Mary 2 is a remarkable flagship, and her style and elegance are legendary. Above all, it‘s the space she offers and the luxury for you to do as little or as much as you wish which set her apart.Welcome to a true icon. Our flagship is a truly astonishing liner and you’ll find an incredible sense of freedom from the space she offers. Whether you’re in the mood for complete relaxation or something more active, you can find it. Immerse yourself in enthralling entertainment, be indulged in the on board spa, or simply relax with a book in her vast library. You’ll discover remarkable craftsmanship in the elegant staterooms and suites and savouring her many sumptuous restaurants and bars is always a pleasure.

  • Mega Ship
  • Timeless
  • Premium

Cruise: Southampton – New York, New York – Saint Thomas – Saint Kitts – English Harbour – Sint Maarten – New York, New York – Southampton

12dec2026

Queen Mary 2

Cunard Cruises Logo

Queen Mary 2 is a remarkable flagship, and her style and elegance are legendary. Above all, it‘s the space she offers and the luxury for you to do as little or as much as you wish which set her apart.Welcome to a true icon. Our flagship is a truly astonishing liner and you’ll find an incredible sense of freedom from the space she offers. Whether you’re in the mood for complete relaxation or something more active, you can find it. Immerse yourself in enthralling entertainment, be indulged in the on board spa, or simply relax with a book in her vast library. You’ll discover remarkable craftsmanship in the elegant staterooms and suites and savouring her many sumptuous restaurants and bars is always a pleasure.

  • Mega Ship
  • Timeless
  • Premium

Cruise: Southampton – New York, New York – Tortola – Sint Maarten – Bridgetown – Castries – Dominica – Saint Kitts – New York, New York

12dec2026

Queen Mary 2

Cunard Cruises Logo

Queen Mary 2 is a remarkable flagship, and her style and elegance are legendary. Above all, it‘s the space she offers and the luxury for you to do as little or as much as you wish which set her apart.Welcome to a true icon. Our flagship is a truly astonishing liner and you’ll find an incredible sense of freedom from the space she offers. Whether you’re in the mood for complete relaxation or something more active, you can find it. Immerse yourself in enthralling entertainment, be indulged in the on board spa, or simply relax with a book in her vast library. You’ll discover remarkable craftsmanship in the elegant staterooms and suites and savouring her many sumptuous restaurants and bars is always a pleasure.

  • Mega Ship
  • Timeless
  • Premium

Cruise: Southampton – New York, New York – Tortola – Sint Maarten – Bridgetown – Castries – Dominica – Saint Kitts – New York, New York – Southampton – Southampton

18dec2026

Borealis

Fred.Olsen Cruises Logo

Sister ship of our flagship Bolette, Borealis joined us 2020, and is perfectly suited for enjoying scenic cruising of the world’s lesser-known waterways. From cruising past remarkable landscapes and historical sites to capturing the beauty of the natural world. Redecorated and refurbished when she joined our fleet in order to meet the high standards of the Olsen family, Borealis features a wonderful series of lounges, bars, elegant restaurants and wide-open deck spaces, as well as 702 beautiful cabins and suites; perfectly suited to the Fred. Olsen style of cruising. From January 2026, Borealis will be excusively for adults, so you can relax in the company of other like-minded guests.Enjoy Scenic Discoveries from the perfectly-appointed Observatory, where guests will be able to see outstanding natural scenery and iconic landmarks, accompanied by commentary from our on board teams; or sample delicious Treats of the Region in the Auditorium where our talented chefs will prepare dishes that are local to the exciting destinations you’re visiting. Our friendly crew will be on hand throughout your cruise, providing the personal service they’re known for. 

  • Mid-Size Ship
  • Over 55s+
  • Adults Only
  • Traditional

Cruise: Southampton – Santa Cruz de Tenerife – Saint John's – Saint John's – Philipsburg – Basseterre, Saint Kitts – Castries – Port Elizabeth, Bequia – Saint George's – Bridgetown – Funchal, Madeira – Funchal, Madeira – Southampton

03jan2027

Aurora

P&O Cruises Logo

Experience the timeless elegance of Aurora. This adults-only ship exudes classic cruising with a modern twist; with its stunning atrium and refined design, you can indulge in relaxing afternoons, explore destinations, and appreciate the art of leisurely cruising. From relaxing on the sun-drenched Lido deck to enjoying British afternoon tea or exploring extraordinary itineraries, unforgettable adventures await on Aurora.

  • Large Ship
  • British
  • Adults Only

Cruise: Southampton – Funchal, Madeira – Sint Maarten – Saint John's – Dominica – Saint Vincent – Saint George's – Port-of-Spain – Bonaire – Curaçao – Cartagena – Colón – Cruising by Panama Canal – Puerto Limón – Roatán Island – Costa Maya – Grand Cayman – Cozumel – Progreso – Galveston, Texas – Galveston, Texas – New Orleans, Louisiana – New Orleans, Louisiana – Miami, Florida – Port Canaveral, Florida – Freeport, Grand Bahama – Grand Turk Island – Amber Cove – Ocho Rios – Montego Bay – Tortola – Saint Kitts – Guadeloupe – Martinique – Castries – Scarborough – Bridgetown – Praia da Vitória – Southampton

04jan2027

Iona

P&O Cruises Logo

Innovation meets explorationYou’ve not cruised until you’ve sailed on Iona, with her cutting-edge design and world-class style. Explore the world in widescreen with the dazzling SkyDome, swim with panoramic views, and indulge in a world of dining and extraordinary entertainment. Get ready for the adventure of a lifetime on Iona.

  • Mid-Size Ship
  • British
  • Family-Friendly

Cruise: Southampton – Santa Cruz de Tenerife – Saint Kitts – Bridgetown – Bridgetown – Saint George's – Castries – Sint Maarten – Saint John's – Tortola – Las Palmas de Gran Canaria – La Coruña – Southampton

10jan2027

Queen Anne

Cunard Cruises Logo

Queen Anne’s breathtaking interiors take inspiration from our past to define a striking new design direction for our future. Come on board to discover a ship that is modern, yet timeless. A ship that offers both exciting, novel experiences, as well as our much-loved signature venues.On a Queen Anne voyage feel inspired by the blend of classic and contemporary. Enjoy the freedom to do as little or as much as you choose and indulge in everything that makes a Cunard ship so special. With luxurious flourishes enhanced by stylish décor, every day on Queen Anne offers a chance to sail the world in unparalleled comfort. Let tension dissipate in the tranquillity that awaits at the Mareel Spa, delight in the ceremony of our signature Afternoon Tea, and enjoy that extra special feeling as you descend into the Grand Lobby in your Gala Evening finery. Above all, rest easy in the knowledge that the finer details have been taken care of. We look forward to welcoming you on board.

  • Mega Ship
  • Timeless
  • Premium

Cruise: Southampton – Hamilton – Port Canaveral, Florida – Fort Lauderdale, Florida

12 nights