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Fly Cruises to the Caribbean

Find the best fly cruise to the Caribbean for you in 2027, 2028 and 2029 with Stewart Travel below. From Jamaica and Cuba to Mexico, call one of our Cruise Experts on 0800 917 5742 to book your dream fly cruise holiday today!

Caribbean Fly Cruise Deals

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    5-Day Bahamas Round-Trip Jacksonville

    Norwegian Cruise Line

    Norwegian Dawn 25 November 2026 5 nights

    Itinerary: Jacksonville - Bahama Islands - Nassau - Great Stirrup Cay - Jacksonville

    • Upgrade for £199pp & get: Premium Drinks, Speciality Dining, WiFi & Excursion Discounts

    Cruise Only from

    • Interior £419pp
    • Ocean View £429pp
    • Balcony £759pp

    Includes extra savings of up to £40pp

    more details

    Barcelona To Miami

    Oceania Cruises

    Luxury

    Marina 25 November 2026 15 nights

    Itinerary: Barcelona - Valencia - Alicante - Malaga - Funchal - San Juan - Puerto Plata/Dominican Republic - Miami

    • Gratuities
    • Unlimited WiFi
    • Gourmet Speciality Dining
    • Soft Drinks, Bottled Water, Speciality Tea & Coffee
    • In Suite & Stateroom Dining

    Cruise Only from

    • Interior £2,719pp
    • Ocean View £3,579pp
    • Balcony £3,719pp
    • Suite £5,369pp

    Includes extra savings of up to £328pp

    more details

    Miami To Miami

    Oceania Cruises

    Luxury

    Vista 25 November 2026 12 nights

    Itinerary: Miami - Charlotte Amalie - Philipsburg - Gustavia - Fort de France - Point-a-Pitre - St John's - Tortola - Miami

    • Gratuities
    • Unlimited WiFi
    • Gourmet Speciality Dining
    • Soft Drinks, Bottled Water, Speciality Tea & Coffee
    • In Suite & Stateroom Dining

    Cruise Only from

    • Balcony £3,649pp
    • Suite Call Us

    Includes extra savings of up to £264pp

    more details

    San Juan to San Juan

    Viking

    Viking Sea 25 November 2026 10 nights

    Itinerary: San Juan - St. Thomas - Basseterre - Castries - Barbados - Roseau - St John's - Philipsburg - Frederiksted - San Juan

    Fly Cruise from

    • Ocean View Call Us
    • Balcony £4,989pp

    more details

    Very Merrytime Bahamian Cruise from Fort Lauderdale

    Disney Cruise Line

    Disney Destiny 25 November 2026 5 nights

    Itinerary: Port Everglades - Nassau - Castaway Cay - Port Everglades

    Cruise Only from

    • Interior £1,339pp
    • Ocean View Call Us
    • Balcony £2,109pp

    more details

    Grand Turk & Bimini Beach Club

    Virgin Voyages

    Brilliant Lady 25 November 2026 5 nights

    Itinerary: Miami - Grand Turk - Bimini - Miami

    • Black Friday Sale - Includes Savings of up to 80% off 2nd Guest
    • Black Friday Sale - FREE up to $600 Bar Tab
    • Adult Only
    • Filtered water, non-pressed juices, sodas, teas & coffee
    • WiFi

    Cruise Only from

    • Interior £939pp
    • Ocean View £1,009pp
    • Balcony £1,029pp

    more details

    A Journey of Caribbean Charm & Spectacular Natural Beauty

    Explora Journeys

    EXPLORA I 25 November 2026 10 nights

    Itinerary: Miami - Willemstad - Oranjestad - Santa Marta - Cartagena - George Town - Miami

    • Unlimited Fine Beverages
    • Choice of 8 Culinary Experiences
    • All on board gratuities
    • High-speed WiFi
    • In-suite welcome bottle of champagne & sweet treats

    Cruise Only from

    • Suite £5,549pp

    Includes extra savings of up to £293pp

    more details

    An Extended Journey of Historic Echoes & Ocean Breezes

    Explora Journeys

    EXPLORA I 25 November 2026 18 nights

    Itinerary: Miami - Willemstad - Oranjestad - Santa Marta - Cartagena - George Town - Miami - Cozumel - Puerto Costa Maya - Santo Tomas De Castilla...

    • Unlimited Fine Beverages
    • Choice of 8 Culinary Experiences
    • All on board gratuities
    • High-speed WiFi
    • In-suite welcome bottle of champagne & sweet treats

    Cruise Only from

    • Suite £9,339pp

    Includes extra savings of up to £492pp

    more details

    Caribbean Getaway with Grand Turk

    Princess Cruises

    Small Ship Experience

    Island Princess 25 November 2026 5 nights

    Itinerary: Fort Lauderdale - Grand Turk - Amber Cove - Fort Lauderdale

    • Upgrade for only £53pp per day & get: All Inclusive Drinks, WiFi, Four Casual Dining Meals & Gratuities

    Call us now on 0800 917 5742

    more details

    27-Day Legendary Amazon Explorer

    Holland America Line

    Volendam 25 November 2026 27 nights

    Itinerary: Fort Lauderdale - Philipsburg - Fort de France - Barbados - Macapa - Santarem - Boca De Valeira - Manaus - Parintins - Alter Do Chao...

    • Have It All - Beverage Package, Speciality Dining, Shore Excursion Credit, WiFi, Gratuities

    Call us now on 0800 917 5742

    more details

    Eastern Caribbean

    Cunard

    Queen Elizabeth 26 November 2026 12 nights

    Itinerary: Miami - San Juan - St John's - Castries - Barbados - Philipsburg - Road Town - Miami

    • Upgrade to Include Beverage Collection, WiFi & Dining Credit from £60pp per day
    • Elevate your Experience - Upgrade to Grill Suites - Ask for full details

    Fly Cruise from

    • Interior £1,759pp
    • Ocean View £1,959pp
    • Balcony £2,419pp
    • Suite £3,669pp

    more details

    Caribbean

    Cunard

    Queen Elizabeth 26 November 2026 21 nights

    Itinerary: Miami - San Juan - St John's - Castries - Barbados - Philipsburg - Road Town - Miami - Grand Cayman - Montego Bay...

    • Upgrade to Include Beverage Collection, WiFi & Dining Credit from £60pp per day
    • Elevate your Experience - Upgrade to Grill Suites - Ask for full details

    Fly Cruise from

    • Interior £2,689pp
    • Ocean View £2,939pp
    • Balcony £3,789pp
    • Suite £7,149pp

    more details

    Transatlantic Combination Cruise: Malta, Malaga & Miami

    Azamara

    Luxury

    Azamara Quest 26 November 2026 21 nights

    Itinerary: Athens - Olympia (Katakolon) - Syracuse - Malta - Sicily - La Goulette - Cartagena - Malaga - Tangier - San Juan...

    • FREE up to $750 On Board Spend
    • More Inclusive Drinks
    • Gratuities Included
    • Boutique Small-Ship Experience

    Cruise Only from

    • Interior Call Us
    • Ocean View Call Us
    • Balcony £4,589pp
    • Suite Call Us

    more details

    Exotic Islands

    Marella Cruises

    Marella Explorer 2 26 November 2026 7 nights

    Itinerary: Barbados - Castries - St Georges - Oranjestad - Willemstad - Barbados

    • Adult Only
    • Drinks & Tips Included

    Fly Cruise from

    • Interior £1,329pp
    • Ocean View £1,389pp
    • Balcony £1,549pp

    more details

    Exotic Islands followed by Cocktails and Coconuts

    Marella Cruises

    Marella Explorer 2 26 November 2026 14 nights

    Itinerary: Barbados - Castries - St Georges - Oranjestad - Willemstad - Barbados - Road Town - Philipsburg - Basseterre - St John's...

    • Adult Only
    • Drinks & Tips Included

    Call us now on 0800 917 5742

    more details

    Caribbean Islands Fly-Cruise

    P&O Cruises

    Britannia 27 November 2026 14 nights

    Itinerary: Barbados - Grenadine Islands - Willemstad - Ocho Rios - Amber Cove - Grand Turk - Philipsburg - Dominica - Barbados

    • Upgrade to the New All Inclusive Package - Drinks, WiFi & Dining Credit from only £49pp per day
    • FREE Extra On Board Spend When Booking Select Fare Pricing
    • Direct Flights available from London, Birmingham & Manchester
    • No Tipping Required

    Fly Cruise from

    • Interior £1,279pp
    • Balcony £1,679pp

    more details

    3 Night Bahamas & Perfect Day Cruise

    Royal Caribbean

    Utopia of the Seas 27 November 2026 3 nights

    Itinerary: Port Canaveral - Nassau - Perfect Day CocoCay - Port Canaveral

    • Experience 'Perfect Day CocoCay'
    • Black Friday Sale - FREE On Board Spend
    • Black Friday Sale - Save up to 50% Off Onboard Favourites
    • Black Friday Sale - Includes Limited Time Savings

    Cruise Only from

    • Interior Call Us
    • Ocean View £699pp
    • Balcony £679pp

    more details

    5 Night Eastern Caribbean Cruise

    Royal Caribbean

    Explorer of the Seas 27 November 2026 5 nights

    Itinerary: Port Canaveral - Grand Turk - Puerto Plata/Dominican Republic - Port Canaveral

    • Black Friday Sale - FREE On Board Spend
    • Black Friday Sale - Save up to 50% Off Onboard Favourites
    • Black Friday Sale - Includes Limited Time Savings

    Cruise Only from

    • Interior Call Us
    • Ocean View Call Us
    • Balcony Call Us

    more details

    7-Day Caribbean Round-Trip Orlando: Great Stirrup Cay & Dominican Republic

    Norwegian Cruise Line

    Norwegian Escape 27 November 2026 7 nights

    Itinerary: Orlando - Puerto Plata/Dominican Republic - St. Thomas (US Virgin Islands) - Tortola - Great Stirrup Cay - Orlando

    • Upgrade for £249pp & get: Premium Drinks, Speciality Dining, WiFi & Excursion Discounts
    • Big Balcony Sale - Upgrade for Less

    Cruise Only from

    • Interior £429pp
    • Ocean View £489pp
    • Balcony £609pp

    more details

    San Juan to Cartagena

    Crystal Cruises

    Luxury

    Crystal Serenity 27 November 2026 5 nights

    Itinerary: San Juan - Jost Van Dyke - Oranjestad - Cartagena

    • Unlimited Beverages
    • Specialty Dining
    • Unlimited WiFi
    • Gratuities

    Cruise Only from

    • Ocean View £2,399pp
    • Balcony £2,699pp
    • Suite £2,899pp

    more details

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    See More Caribbean Cruises

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    What our clients say

    Platinum Service Award Winners

    Average Customer Rating: 4.9/5

    Stress free booking

    As always we were welcomed and in a relaxing atmosphere given advice and recommendation for our holiday next April. All aspects of our holiday was successfully booked, seats on the plane and parking. Best value was explored , different dates and carriers were explored, nothing was too much trouble and the tress of booking was taken care for us.

    Mrs Walker / November 2026

    40th anniversary holiday cruise.

    Very efficient and easy to deal with, passed our requirements to Justine who put together several options and emailed them to us the next day, brilliant service.

    Trusted Customer / November 2026

    Experts in travel

    Very professional. Customer centred service and great value

    Trusted Customer / November 2026

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