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Cruises from Southampton to the Caribbean

Find the best cruise to the Caribbean from Southampton for you in 2026, 2027 and 2028 with Stewart Travel below. Call one of our Cruise Experts on 0800 019 0063 to book your dream cruise holiday today!

Caribbean Cruises from Southampton

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    Caribbean Discovery

    P&O Cruises

    Small Ship Experience

    Aurora 03 November 2026 24 nights

    Itinerary: Southampton - Teneriffa - Barbados - Kingstown - Castries - Dominica - Philipsburg - Ponta Delgada - Southampton

    • Adult Only
    • New P&O All Inclusive Upgrade Package - Drinks, WiFi & Dining Credit from only £49pp per day
    • FREE Extra On Board Spend When Booking Select Fare Pricing
    • No Tipping Required

    Sail From UK from

    • Interior £2,269pp
    • Ocean View £3,859pp
    • Balcony £5,639pp

    Includes extra savings of up to £57pp

    more details

    Transatlantic Crossing And Eastern Caribbean

    Cunard

    Queen Mary 2 10 November 2026 18 nights

    Itinerary: Southampton - New York - St. Thomas (US Virgin Islands) - St. Kitts - Englischer Hafen - Philipsburg - New York

    • FREE up to $600 On Board Spend per couple On Balcony & Above Cabins - When Booking Cunard Fare
    • Upgrade to Include Beverage Collection, WiFi & Dining Credit from £60pp per day
    • Book Today with a Low £100pp Deposit
    • Elevate your Experience - Upgrade to Grill Suites - Ask for full details

    Sail From UK from

    • Interior £1,759pp
    • Ocean View Call Us
    • Balcony £2,449pp
    • Suite Call Us

    Includes extra savings of up to £50pp

    more details

    Transatlantic Crossing And Eastern Caribbean

    Cunard

    Queen Mary 2 10 November 2026 25 nights

    Itinerary: Southampton - New York - St. Thomas (US Virgin Islands) - St. Kitts - Englischer Hafen - Philipsburg - New York - Southampton

    • FREE up to $600 On Board Spend per couple On Balcony & Above Cabins - When Booking Cunard Fare
    • Upgrade to Include Beverage Collection, WiFi & Dining Credit from £60pp per day
    • Elevate your Experience - Upgrade to Grill Suites - Ask for full details

    Sail From UK from

    • Interior £2,789pp
    • Ocean View £3,619pp
    • Balcony £3,719pp
    • Suite £8,519pp

    Includes extra savings of up to £174pp

    more details

    Transatlantic Crossing And Caribbean Celebration

    Cunard

    Queen Mary 2 12 December 2026 21 nights

    Itinerary: Southampton - New York - Roadtown - Philipsburg - Barbados - Castries - Roseau - St. Kitts - New York

    • FREE up to $600 On Board Spend per couple On Balcony & Above Cabins - When Booking Cunard Fare
    • Upgrade to Include Beverage Collection, WiFi & Dining Credit from £60pp per day
    • Book Today with a Low £100pp Deposit
    • Elevate your Experience - Upgrade to Grill Suites - Ask for full details

    Sail From UK from

    • Interior £2,689pp
    • Ocean View Call Us
    • Balcony Call Us
    • Suite £10,579pp

    Includes extra savings of up to £216pp

    more details

    Transatlantic Crossing And Caribbean Celebration

    Cunard

    Queen Mary 2 12 December 2026 30 nights

    Itinerary: Southampton - New York - Roadtown - Philipsburg - Barbados - Castries - Roseau - St. Kitts - New York - Southampton

    • FREE up to $600 On Board Spend per couple On Balcony & Above Cabins - When Booking Cunard Fare
    • Upgrade to Include Beverage Collection, WiFi & Dining Credit from £60pp per day
    • Elevate your Experience - Upgrade to Grill Suites - Ask for full details

    Sail From UK from

    • Interior £3,279pp
    • Ocean View £4,159pp
    • Balcony £4,259pp
    • Suite Call Us

    Includes extra savings of up to £87pp

    more details

    Caribbean Christmas Island-Hopping

    Fred Olsen Cruise Lines

    Small Ship Experience

    Borealis 18 December 2026 31 nights

    Itinerary: Southampton - Tenerife - St John's - Philipsburg - Basse-Terre - Castries - Port Elizabeth (Grenadines) - St Georges - Barbados - Funchal...

    • Adult Only Ship
    • Wine, Beer & Soft Drinks Included with Lunch & Dinner - When Booking Freedom Fare
    • Gratuities Included
    • Upgrade to Premium Drinks from £40pp per day
    • Features Fred. Olsen Signature Experiences - Scenic Discoveries, Itinerary Insights & Destination Inspired Menus

    Sail From UK from

    • Interior £4,359pp
    • Ocean View £4,829pp
    • Balcony £7,099pp

    Includes extra savings of up to £170pp

    more details

    America And Caribbean Discovery

    P&O Cruises

    Small Ship Experience

    Aurora 03 January 2027 75 nights

    Itinerary: Southampton - Madeira - Philipsburg - Antigua - Dominica - St Vincent - Grenadinen - Port of Spain - Bonaire - Willemstad...

    • Adult Only
    • New P&O All Inclusive Upgrade Package - Drinks, WiFi & Dining Credit from only £49pp per day
    • FREE Extra On Board Spend When Booking Select Fare Pricing
    • No Tipping Required

    Sail From UK from

    • Interior £7,959pp
    • Ocean View £7,719pp
    • Balcony £9,989pp

    Includes extra savings of up to £160pp

    more details

    Caribbean Winter Warmth

    P&O Cruises

    Iona 04 January 2027 35 nights

    Itinerary: Southampton - Teneriffa - St. Kitts - Barbados - Grenadinen - St. Lucia - Philipsburg - Antigua - Gran Canaria - La Coruna...

    • New P&O All Inclusive Upgrade Package - Drinks, WiFi & Dining Credit from only £49pp per day
    • Ask About Reduced Kids Places from £49pp
    • FREE Extra On Board Spend When Booking Select Fare Pricing
    • No Tipping Required

    Sail From UK from

    • Interior £3,259pp
    • Ocean View £4,849pp
    • Balcony £5,639pp

    Includes extra savings of up to £69pp

    more details

    World Cruise - Southampton to Sydney

    P&O Cruises

    Arcadia 06 January 2027 44 nights

    Itinerary: Southampton - Madeira - Barbados - Willemstad - Panama Canal - Manzanillo - San Francisco - Kona - Honolulu - Apia...

    • Adult Only
    • New P&O All Inclusive Upgrade Package - Drinks, WiFi & Dining Credit from only £49pp per day
    • FREE Extra On Board Spend When Booking Select Fare Pricing
    • No Tipping Required

    Sail From UK from

    • Interior Call Us
    • Ocean View £6,969pp
    • Balcony £7,519pp

    Includes extra savings of up to £76pp

    more details

    World Cruise - Southampton to Brisbane

    P&O Cruises

    Arcadia 06 January 2027 49 nights

    Itinerary: Southampton - Madeira - Barbados - Willemstad - Panama Canal - Manzanillo - San Francisco - Hilo - Honolulu - Apia...

    • Adult Only
    • New P&O All Inclusive Upgrade Package - Drinks, WiFi & Dining Credit from only £49pp per day
    • FREE Extra On Board Spend When Booking Select Fare Pricing
    • No Tipping Required

    Sail From UK from

    • Interior Call Us
    • Ocean View £7,779pp
    • Balcony £8,909pp

    Includes extra savings of up to £90pp

    more details

    World Cruise - Southampton To San Francisco

    P&O Cruises

    Arcadia 06 January 2027 23 nights

    Itinerary: Southampton - Madeira - Barbados - Willemstad - Panama Canal - Manzanillo - San Francisco - Hilo - Honolulu - Apia...

    • Adult Only
    • New P&O All Inclusive Upgrade Package - Drinks, WiFi & Dining Credit from only £49pp per day
    • Book today from 5% Deposit
    • FREE Extra On Board Spend When Booking Select Fare Pricing
    • Additional Savings of up to £400 per couple For Past Guests
    • No Tipping Required

    Sail From UK from

    Call us now on 0800 019 0063

    more details

    Caribbean

    Cunard

    Queen Mary 2 11 January 2027 34 nights

    Itinerary: Southampton - Funchal - St. Kitts - Barbados - Castries - St Georges - Roseau - Englischer Hafen - Amber Cove - Philipsburg...

    • FREE up to $600 On Board Spend per couple On Balcony & Above Cabins - When Booking Cunard Fare
    • Upgrade to Include Beverage Collection, WiFi & Dining Credit from £60pp per day
    • Elevate your Experience - Upgrade to Grill Suites - Ask for full details

    Sail From UK from

    • Interior £2,989pp
    • Ocean View £4,319pp
    • Balcony £4,579pp
    • Suite £13,719pp

    Includes extra savings of up to £280pp

    more details

    13 Night Spain & Bermuda Transatlantic

    Celebrity Cruises

    Luxury

    Celebrity Apex 17 October 2027 13 nights

    Itinerary: Southampton - La Coruna - Vigo - Ponta Delgada - Royal Naval Dockyard - Port Canaveral

    • Includes savings of up to 60% Off Second Guest
    • Additional Savings of up to £500 per couple
    • Ask about adding Drinks & WiFi
    • Big Balcony Sale - Upgrade for Less

    Sail From UK from

    • Interior £1,139pp
    • Ocean View £1,289pp
    • Balcony £1,449pp
    • Suite £3,929pp

    Includes extra savings of up to £122pp

    more details

    17 Night Spain & Portugal Transatlantic

    Royal Caribbean

    Mariner of the Seas 18 October 2027 17 nights

    Itinerary: Southampton - La Coruna - Vigo - Lisbon - Madeira - Nassau - New Orleans

    • Ask About Reduced Kids Fares from £99pp
    • Limited Time Savings of up to £750 per couple - Call Our Cruise Experts Today

    Sail From UK from

    • Interior £889pp
    • Ocean View £939pp
    • Balcony £1,339pp

    Includes extra savings of up to £42pp

    more details

    Caribbean Transatlantic

    P&O Cruises

    Arvia 22 October 2027 14 nights

    Itinerary: Southampton - Teneriffa - Philipsburg - St. Kitts - St. Lucia - Barbados

    • New P&O All Inclusive Upgrade Package - Drinks, WiFi & Dining Credit from only £49pp per day
    • Book today from £60pp Deposit
    • Additional Savings of up to £400 per couple For Past Guests
    • No Tipping Required
    • Big Balcony Sale - Upgrade for Less

    Sail From UK from

    • Interior £1,179pp
    • Ocean View £1,379pp
    • Balcony £1,479pp

    Includes extra savings of up to £20pp

    more details

    Caribbean Transatlantic

    P&O Cruises

    Arvia 22 October 2027 15 nights

    Itinerary: Southampton - Teneriffa - Philipsburg - St. Kitts - St. Lucia - Barbados

    • New P&O All Inclusive Upgrade Package - Drinks, WiFi & Dining Credit from only £49pp per day
    • Book today from £65pp Deposit
    • Additional Savings of up to £400 per couple For Past Guests
    • No Tipping Required
    • Big Balcony Sale - Upgrade for Less

    Sail From UK from

    • Interior £1,279pp
    • Ocean View £1,509pp
    • Balcony £1,529pp

    Includes extra savings of up to £24pp

    more details

    Caribbean Transatlantic

    P&O Cruises

    Arvia 22 October 2027 17 nights

    Itinerary: Southampton - Teneriffa - Philipsburg - St. Kitts - St. Lucia - Barbados - St. Kitts

    • New P&O All Inclusive Upgrade Package - Drinks, WiFi & Dining Credit from only £49pp per day
    • Book today from £71pp Deposit
    • Additional Savings of up to £400 per couple For Past Guests
    • No Tipping Required
    • Big Balcony Sale - Upgrade for Less

    Sail From UK from

    • Interior £1,409pp
    • Ocean View £1,709pp
    • Balcony £1,729pp

    Includes extra savings of up to £25pp

    more details

    Caribbean Transatlantic

    P&O Cruises

    Arvia 22 October 2027 22 nights

    Itinerary: Southampton - Teneriffa - Philipsburg - St. Kitts - St. Lucia - Barbados - St. Kitts - Tortola - Philipsburg - Dominica...

    • New P&O All Inclusive Upgrade Package - Drinks, WiFi & Dining Credit from only £49pp per day
    • Book today from £92pp Deposit
    • Additional Savings of up to £400 per couple For Past Guests
    • No Tipping Required

    Sail From UK from

    • Interior £1,829pp
    • Ocean View £2,199pp
    • Balcony £2,249pp

    Includes extra savings of up to £33pp

    more details

    Caribbean Transatlantic

    P&O Cruises

    Iona 30 October 2027 13 nights

    Itinerary: Southampton - Teneriffa - Philipsburg - Dominica - Barbados

    • New P&O All Inclusive Upgrade Package - Drinks, WiFi & Dining Credit from only £49pp per day
    • Book today from £57pp Deposit
    • Additional Savings of up to £400 per couple For Past Guests
    • No Tipping Required
    • Big Balcony Sale - Upgrade for Less

    Sail From UK from

    • Interior £1,129pp
    • Ocean View £1,279pp
    • Balcony £1,379pp

    Includes extra savings of up to £19pp

    more details

    Caribbean Transatlantic

    P&O Cruises

    Iona 30 October 2027 14 nights

    Itinerary: Southampton - Teneriffa - Philipsburg - Dominica - Barbados

    • New P&O All Inclusive Upgrade Package - Drinks, WiFi & Dining Credit from only £49pp per day
    • Book today from £60pp Deposit
    • Additional Savings of up to £400 per couple For Past Guests
    • No Tipping Required
    • Big Balcony Sale - Upgrade for Less

    Sail From UK from

    • Interior £1,179pp
    • Ocean View £1,379pp
    • Balcony £1,379pp

    Includes extra savings of up to £20pp

    more details

    Caribbean Transatlantic

    P&O Cruises

    Iona 30 October 2027 16 nights

    Itinerary: Southampton - Teneriffa - Philipsburg - Dominica - Barbados - St. Kitts

    • New P&O All Inclusive Upgrade Package - Drinks, WiFi & Dining Credit from only £49pp per day
    • Book today from £65pp Deposit
    • Additional Savings of up to £400 per couple For Past Guests
    • No Tipping Required
    • Big Balcony Sale - Upgrade for Less

    Sail From UK from

    • Interior £1,279pp
    • Ocean View £1,479pp
    • Balcony £1,579pp

    Includes extra savings of up to £23pp

    more details

    Caribbean Transatlantic

    P&O Cruises

    Iona 30 October 2027 21 nights

    Itinerary: Southampton - Teneriffa - Philipsburg - Dominica - Barbados - St. Kitts - Tortola - Philipsburg - Martinique - Antigua

    • New P&O All Inclusive Upgrade Package - Drinks, WiFi & Dining Credit from only £49pp per day
    • Book today from £82pp Deposit
    • Additional Savings of up to £400 per couple For Past Guests
    • No Tipping Required

    Sail From UK from

    • Interior £1,629pp
    • Ocean View £1,999pp
    • Balcony £2,049pp

    Includes extra savings of up to £31pp

    more details

    MSC Grand Voyages from Southampton (London)

    MSC Cruises

    MSC Meraviglia 06 November 2027 13 nights

    Itinerary: Southampton - Paris - Ponta Delgada - St John's - Kingstown - Barbados

    • Elevate your Experience - Upgrade to Yacht Club - Ask for full details
    • Great family prices - children up to 17 years
    • Upgrade to All Inclusive from £26pppd
    • Gratuities Included
    • Big Balcony Sale - Upgrade for Less

    Sail From UK from

    • Interior £699pp
    • Ocean View £829pp
    • Balcony £979pp
    • Suite £3,719pp

    Includes extra savings of up to £196pp

    more details

    MSC Grand Voyages from Southampton (London)

    MSC Cruises

    MSC Meraviglia 06 November 2027 14 nights

    Itinerary: Southampton - Paris - Ponta Delgada - St John's - Kingstown - Barbados - Fort de France

    • Elevate your Experience - Upgrade to Yacht Club - Ask for full details
    • Great family prices - children up to 17 years
    • Upgrade to All Inclusive from £26pppd
    • Gratuities Included
    • Big Balcony Sale - Upgrade for Less

    Sail From UK from

    • Interior £769pp
    • Ocean View £909pp
    • Balcony £1,059pp
    • Suite Call Us

    Includes extra savings of up to £56pp

    more details

    MSC Grand Voyages from Southampton (London)

    MSC Cruises

    MSC Meraviglia 06 November 2027 24 nights

    Itinerary: Southampton - Paris - Ponta Delgada - St John's - Kingstown - Barbados - Fort de France - Point-a-Pitre - St John's - Philipsburg...

    • Elevate your Experience - Upgrade to Yacht Club - Ask for full details
    • Great family prices - children up to 17 years
    • Upgrade to All Inclusive from £26pppd
    • Gratuities Included

    Sail From UK from

    Call us now on 0800 019 0063

    more details

    • Next

    See more cruise destinations from Southampton

    See more Transatlantic and Repositioning Cruises

    What our clients say

    Platinum Service Award Winners

    Average Customer Rating: 5/5

    2 Holidays booked ????

    Staff are always friendly and very helpful. Always leave with a great holiday to look forward to.

    Mrs Grant / February 2026

    Excellent service

    Excellent service from start to finish from Lisa at the parkhead forge Glasgow got us a fantastic holiday 5 ⭐ service would definitely recommend Stewart travel

    Trusted Customer / February 2026

    Excellent Service

    Excellent service as always

    Trusted Customer / February 2026

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