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 71)

7 Nights

7-Day Classic Caribbean Yacht Harbors

Departure Date
29 Jan 28
Cruise Line Seabourn
Cruise Type Ocean
Ship Seabourn Ovation
Region Caribbean
Departure Port Bridgetown
Destination Port Sint Maarten
Itinerary
Bridgetown, Castries, Montserrat, Antigua, South Friars Bay, Great Harbour, Jost Van Dyke and Sint Maarten

From £3,598pp

Plus substantial savings from Deluxe Cruises

14 Nights

14-Day Caribbean Yacht Explorer

Featured Cruise
Departure Date
29 Jan 28
Cruise Line Seabourn
Cruise Type Ocean
Ship Seabourn Ovation
Region Caribbean
Departure Port Bridgetown
Destination Port Bridgetown
Itinerary
Bridgetown, Castries, Montserrat, Antigua, South Friars Bay, Great Harbour, Jost Van Dyke, Sint Maarten, Frenchman's Cay, South Friars Bay, Trois-Ilets, Port Elizabeth, Bequia, Saint George's and Bridgetown

From £7,098pp

Plus substantial savings from Deluxe Cruises

7 Nights

Bridgetown to Bridgetown

Departure Date
29 Jan 28
Cruise Line Silversea
Cruise Type Ocean
Ship Silver Spirit
Region Caribbean
Departure Port Bridgetown
Destination Port Bridgetown
Itinerary
Bridgetown, Port Elizabeth, Bequia, Fort-de-France, Gustavia, Roseau, Saint George's, Castries and Bridgetown

From £2,900pp

Plus substantial savings from Deluxe Cruises

7 Nights

A Journey into Dominican Charm & Caribbean Splendour

Departure Date
30 Jan 28
Cruise Line Explora Journeys
Cruise Type Ocean
Ship EXPLORA II
Region Caribbean
Departure Port Miami, Florida
Destination Port San Juan (Puerto Rico)
Itinerary
Miami, Florida, Puerto Plata, Isla Catalana, Charlotte Amalie, Road Bay, Cruz Bay, Saint John and San Juan (Puerto Rico)

From £2,790pp

Plus substantial savings from Deluxe Cruises

14 Nights

Star Collector: Caribbean Explorations

Departure Date
30 Jan 28
Cruise Line Windstar Cruises
Cruise Type Ocean
Ship Wind Surf
Region Caribbean
Departure Port Philipsburg
Destination Port Philipsburg
Itinerary
Philipsburg, Falmouth, Road Bay, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Gustavia, Philipsburg, Roseau, Mayreau Island, Terre-de-Haut, Basseterre, Saint Kitts, Gustavia and Philipsburg

From £4,016pp

Plus substantial savings from Deluxe Cruises

7 Nights

Beach Fun & Sun: A Remote Caribbean Getaway

Departure Date
30 Jan 28
Cruise Line Windstar Cruises
Cruise Type Ocean
Ship Wind Surf
Region Caribbean
Departure Port Philipsburg
Destination Port Philipsburg
Itinerary
Philipsburg, Falmouth, Road Bay, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Great Harbour, Jost Van Dyke, Gustavia and Philipsburg

From £1,683pp

Plus substantial savings from Deluxe Cruises

11 Nights

Miami to Miami

Departure Date
31 Jan 28
Cruise Line Silversea
Cruise Type Ocean
Ship Silver Nova
Region Caribbean
Departure Port Miami, Florida
Destination Port Miami, Florida
Itinerary
Miami, Florida, Saint John Island, Gustavia, Saint John's, Fort-de-France, Basseterre, Saint Kitts, San Juan (Puerto Rico) and Miami, Florida

From £4,800pp

Plus substantial savings from Deluxe Cruises

14 Nights

Star Collector: Lovely Leewards

Departure Date
31 Jan 28
Cruise Line Windstar Cruises
Cruise Type Ocean
Ship Star Legend
Region Caribbean
Departure Port San Juan (Puerto Rico)
Destination Port San Juan (Puerto Rico)
Itinerary
San Juan (Puerto Rico), Gustavia, Philipsburg, Basseterre, Saint Kitts, Great Harbour, Jost Van Dyke, San Juan (Puerto Rico), Saint George's, Port Elizabeth, Bequia, Mayreau Island, Terre-de-Haut, Marigot and San Juan (Puerto Rico)

From £4,134pp

Plus substantial savings from Deluxe Cruises

7 Nights

San Juan & the Virgin Islands

Departure Date
31 Jan 28
Cruise Line Windstar Cruises
Cruise Type Ocean
Ship Star Legend
Region Caribbean
Departure Port San Juan (Puerto Rico)
Destination Port San Juan (Puerto Rico)
Itinerary
San Juan (Puerto Rico), Gustavia, Philipsburg, Basseterre, Saint Kitts, Great Harbour, Jost Van Dyke and San Juan (Puerto Rico)

From £1,756pp

Plus substantial savings from Deluxe Cruises

11 Nights

Leeward & Windward Islands Explorer

Departure Date
02 Feb 28
Cruise Line SeaDream Yacht Club
Cruise Type Ocean
Ship SeaDream I
Region Caribbean
Departure Port Bridgetown
Destination Port Charlotte Amalie
Itinerary
Bridgetown, Bridgetown, Port St Charles, Tobago Cays, Port Elizabeth, Bequia, Port Elizabeth, Bequia, Saint Pierre, Terre-de-Haut, Charlestown, South Friars Bay, Marigot, Gustavia, Gustavia, Spanish Town, Virgin Gorda, Leverick Bay, Virgin Gorda, White Bay, Jost Van Dyke and Charlotte Amalie

From £4,896pp

Plus substantial savings from Deluxe Cruises

10 Nights

Caribbean Splendor

Departure Date
02 Feb 28
Cruise Line Oceania Cruises
Cruise Type Ocean
Ship Oceania Sonata
Region Caribbean
Departure Port Miami, Florida
Destination Port Miami, Florida
Itinerary
Miami, Florida, San Juan (Puerto Rico), Charlotte Amalie, Basseterre, Saint Kitts, Pointe-à-Pitre, Tortola and Miami, Florida

From £3,589pp

Plus substantial savings from Deluxe Cruises

7 Nights

Aruba to San Juan (Puerto Rico)

Departure Date
04 Feb 28
Cruise Line The Ritz-Carlton Yacht Collection
Cruise Type Ocean
Ship Ilma
Region Caribbean
Departure Port Aruba
Destination Port San Juan (Puerto Rico)
Itinerary
Aruba, Willemstad, Kralendijk, Falmouth, Sandy Ground, Virgin Gorda and San Juan (Puerto Rico)

From £7,700pp

Plus substantial savings from Deluxe Cruises