The 2026 season highlights high-touch personalization, such as "Marina Days" where guests can kayak or paddleboard directly from the ship's stern. Onboard, the Caribbean experience is refined through regional farm-to-table dining, featuring fresh snapper and lobster, while shore excursions lean into private access - think guided hikes to Dominica’s thermal pools or helicopter tours over the turquoise reefs of the Bahamas.

Barbados

Caribbean Itineraries (Page 7)

11 Nights

Azure Antilles

Departure Date
26 Feb 26
Cruise Line Oceania Cruises
Cruise Type Ocean
Ship Oceania Allura
Region Caribbean
Departure Port Miami, Florida
Destination Port Miami, Florida
Itinerary
Miami, Florida, San Juan (Puerto Rico), San Juan (Puerto Rico), Basseterre, Saint Kitts, Gustavia, Philipsburg, Tortola and Miami, Florida

From £4,679pp

Plus substantial savings from Deluxe Cruises

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12 Nights

Tropical Island Rhythms

Departure Date
26 Feb 26
Cruise Line Oceania Cruises
Cruise Type Ocean
Ship Oceania Nautica
Region Caribbean
Departure Port Miami, Florida
Destination Port Miami, Florida
Itinerary
Miami, Florida, Oranjestad, Willemstad, Saint George's, Castries, Basseterre, Saint Kitts, San Juan (Puerto Rico), Grand Turk Island and Miami, Florida

From £2,329pp

Plus substantial savings from Deluxe Cruises

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4 Nights

A Journey through Azure Waters & Island Marvels

Departure Date
26 Feb 26
Cruise Line Explora Journeys
Cruise Type Ocean
Ship EXPLORA I
Region Caribbean
Departure Port Bridgetown
Destination Port San Juan (Puerto Rico)
Itinerary
Bridgetown, Terre-de-Haut, Philipsburg, Great Harbour, Jost Van Dyke and San Juan (Puerto Rico)

From £1,835pp

Plus substantial savings from Deluxe Cruises

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4 Nights

San Juan (Puerto Rico) Roundtrip

Departure Date
26 Feb 26
Cruise Line The Ritz-Carlton Yacht Collection
Cruise Type Ocean
Ship Evrima
Region Caribbean
Departure Port San Juan (Puerto Rico)
Destination Port San Juan (Puerto Rico)
Itinerary
San Juan (Puerto Rico), Virgin Gorda, Marigot, Saint John Island and San Juan (Puerto Rico)

From £3,800pp

Plus substantial savings from Deluxe Cruises

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7 Nights

Philipsburg to Bridgetown

Departure Date
26 Feb 26
Cruise Line Silversea
Cruise Type Ocean
Ship Silver Shadow
Region Caribbean
Departure Port Philipsburg
Destination Port Bridgetown
Itinerary
Philipsburg, Saint John Island, Gustavia, Roseau, Saint George's, Trois-Ilets, Kingstown and Bridgetown

From Please Call

Plus substantial savings from Deluxe Cruises

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10 Nights

West Indies Explorer

Departure Date
27 Feb 26
Cruise Line Viking Ocean Cruises
Cruise Type Ocean
Ship Viking Sea
Region Caribbean
Departure Port San Juan (Puerto Rico)
Destination Port San Juan (Puerto Rico)
Itinerary
San Juan (Puerto Rico), San Juan (Puerto Rico), Charlotte Amalie, Basseterre, Saint Kitts, Castries, Bridgetown, Roseau, Saint John's, Philipsburg, Frederiksted, Saint Croix and San Juan (Puerto Rico)

From £4,590pp

Plus substantial savings from Deluxe Cruises

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11 Nights

Fort Lauderdale to Fort Lauderdale

Departure Date
27 Feb 26
Cruise Line Silversea
Cruise Type Ocean
Ship Silver Ray
Region Caribbean
Departure Port Fort Lauderdale, Florida
Destination Port Fort Lauderdale, Florida
Itinerary
Fort Lauderdale, Florida, Grand Turk Island, Saint Thomas, Basseterre, Saint Kitts, Saint John's, Philipsburg, San Juan (Puerto Rico) and Fort Lauderdale, Florida

From £6,900pp

Plus substantial savings from Deluxe Cruises

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7 Nights

Windward Islands Surf & Sunsets

Departure Date
27 Feb 26
Cruise Line Windstar Cruises
Cruise Type Ocean
Ship Star Seeker
Region Caribbean
Departure Port San Juan (Puerto Rico)
Destination Port San Juan (Puerto Rico)
Itinerary
San Juan (Puerto Rico), Philipsburg, Terre-de-Haut, Mayreau Island, Port Elizabeth, Bequia, Mayreau Island and San Juan (Puerto Rico)

From £2,792pp

Plus substantial savings from Deluxe Cruises

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14 Nights

Star Collector: Lovely Leewards

Departure Date
27 Feb 26
Cruise Line Windstar Cruises
Cruise Type Ocean
Ship Star Seeker
Region Caribbean
Departure Port San Juan
Destination Port San Juan
Itinerary
San Juan, Philipsburg, Terre-de-Haut, Mayreau Island, Port Elizabeth, Bequia, Mayreau Island, San Juan, Basseterre, Saint Kitts, Gustavia, Philipsburg, Great Harbour, Jost Van Dyke and San Juan

From £11,950pp

Plus substantial savings from Deluxe Cruises

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7 Nights

Windward Islands Surf & Sunsets

Departure Date
27 Feb 26
Cruise Line Windstar Cruises
Cruise Type Ocean
Ship Star Seeker
Region Caribbean
Departure Port San Juan (Puerto Rico)
Destination Port San Juan (Puerto Rico)
Itinerary
San Juan (Puerto Rico), Philipsburg, Terre-de-Haut, Mayreau Island, Port Elizabeth, Bequia, Soufrière and San Juan (Puerto Rico)

From Please Call

Plus substantial savings from Deluxe Cruises

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14 Nights

Star Collector: Lovely Leewards

Departure Date
27 Feb 26
Cruise Line Windstar Cruises
Cruise Type Ocean
Ship Star Seeker
Region Caribbean
Departure Port San Juan (Puerto Rico)
Destination Port San Juan (Puerto Rico)
Itinerary
San Juan (Puerto Rico), Philipsburg, Terre-de-Haut, Mayreau Island, Port Elizabeth, Bequia, Soufrière, San Juan (Puerto Rico), Basseterre, Saint Kitts, Gustavia, Philipsburg, Great Harbour, Jost Van Dyke and San Juan (Puerto Rico)

From Please Call

Plus substantial savings from Deluxe Cruises

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14 Nights

Discover the yachting islands of the Caribbean

Departure Date
28 Feb 26
Cruise Line Emerald Cruises
Cruise Type Ocean
Ship Emerald Azzurra
Region Caribbean
Departure Port San Juan (Puerto Rico)
Destination Port Saint Thomas
Itinerary
San Juan (Puerto Rico), Culebra Island, Saint John Island, Great Harbour, Jost Van Dyke, Philipsburg, Gustavia, Little Bay, Saint John's, Gustavia, Îles des Saintes, Deshaies, Barbuda, Virgin Gorda, Norman Island and Saint Thomas

From Please Call

Plus substantial savings from Deluxe Cruises

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