Price Per Night:$328.50 (USD) (based on double occupancy, for comparison only)
Jan 04, 2025through Jan 18, 2025
Itinerary:
Philipsburg, St. Maarten, Roseau, Pigeon Island, Les Saintes, Gustavia, Basseterre, Philipsburg, St. Maarten, Falmouth Harbour, Gustavia, Jost Van Dyke, Great Harbour...
Skip the usual Caribbean cruise stops and discover the small harbors, overlooked havens and most remote secrets among the Leeward Islands. Whether you’re looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of Les Saintes, Anse Mitan, Pigeon Island and much more.
Price Per Night:$271.43 (USD) (based on double occupancy, for comparison only)
Dec 28, 2024through Jan 04, 2025
Itinerary:
Bridgetown, Barbados, Rodney Bay, St. Lucia, Sail with Star Flyer to Cabrits, Cabrits, Dominica, Falmouth Harbour, Antigua, Basseterre, St. Kitts (morning), South Friar's Bay (beach), St. Kitts (PM), Terre de Haut, Iles des Saintes, Beach, Martinique, Bridgetown, Barbados
Other Categories Starting At:
Inside
$1,900.00 Cat:Category 6 271.43 per night
Outside
$2,140.00 Cat:Category 5 305.71 per night
Balcony
N/A
Suite
$3,720.00 Cat:Deluxe Suite with Veranda 531.43 per night
Price Per Night:$285.64 (USD) (based on double occupancy, for comparison only)
Jan 11, 2026through Jan 25, 2026
Itinerary:
Philipsburg, St. Maarten, Basseterre, Little Bay, Gustavia, Deshaies, Roseau, Pigeon Island, Bridgetown, Anse Mitan, Pigeon Island...
Discover less-traveled roads and concealed refuges throughout the Caribbean on this 14-day cruise that blends iconic destinations and little-known shorelines like a favorite beachside cocktail. Search for green sea turtles and watch iridescent fish flit among sunken freighter wreckage from the dry side of a porthole in a Gustavia-based, semi-submersible. Sail past St. Kitts uncrowded southeast shores before slipping silently beneath the surface to snorkel among exotic fish and colorful coral.
Price Per Night:$144.68 (USD) (based on double occupancy, for comparison only)
Nov 26, 2025through Dec 15, 2025
Itinerary:
New York, New York, St. Maarten, Netherlands Antilles, Dominica, Dominica, Barbados, Barbados, St Lucia, Saint Lucia, St. Kitts, ST Kitts/Nevis, New York, New York, London (Southampton), England
Enjoy days waking up to blue skies and sparkling seas on this 19-night voyage. On shore, explore historic Garrisons in Bridgetown and indulge in some retail therapy at Old Roseau market.
Price Per Night:$292.79 (USD) (based on double occupancy, for comparison only)
Dec 07, 2024through Dec 21, 2024
Itinerary:
Bridgetown, Pigeon Island, Castries, Kingstown, Mayreau, St. George's, Bequia, Bridgetown, Basseterre, Les Saintes...
Indulge in exquisite white-sand delights and delicious regional cuisine during this voyage to the Lesser Antilles’ Windward Islands, a journey rich in exclusive excursions seldom experienced by others. Trek through a private nature reserve inhabited by lyrical thrushes, curious macaws, and radiant tropical birds to Mount Pimard’s summit views above Pigeon Island. Sample local St. Lucian bites and Trinidadian culinary delights during a walking food tour at Rodney Bay.
Price Per Night:$255.71 (USD) (based on double occupancy, for comparison only)
Feb 21, 2026through Feb 28, 2026
Itinerary:
Bridgetown, Barbados, Rodney Bay, St. Lucia, Sail with Star Flyer to Cabrits, Cabrits, Dominica, Falmouth Harbour, Antigua, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon), Terre de Haut, Iles des Saintes, Beach, Martinique, Bridgetown, Barbados
Other Categories Starting At:
Inside
$1,790.00 Cat:Category 6 255.71 per night
Outside
$2,040.00 Cat:Category 5 291.43 per night
Balcony
N/A
Suite
$3,880.00 Cat:Deluxe Suite with Veranda 554.29 per night
Price Per Night:$409.99 (USD) (based on double occupancy, for comparison only)
Jan 08, 2025through Apr 08, 2025
Itinerary:
Miami, Cruising The Straits Of Florida, George Town, Cruising The Caribbean Sea, Cartagena, Panama Canal Daylight Transit, Cruising The Pacific Ocean, Puntarenas, Corinto, Puerto Quetzal...
Price Per Night:$375.88 (USD) (based on double occupancy, for comparison only)
Dec 20, 2025through Jul 05, 2026
Itinerary:
Los Angeles, Cabo San Lucas, Puerto Vallarta, Manzanillo, Acapulco, Puerto Quetzal, Corinto, Puntarenas, Panama Canal Daylight Transit, Cartagena...
Price Per Night:$176.38 (USD) (based on double occupancy, for comparison only)
Feb 14, 2026through Mar 07, 2026
Itinerary:
Fort Lauderdale, Florida, US, Days At Sea, Philipsburg, Sint Maarten, St. Johns, Antigua and Barbuda, Fort-De-France, Martinique, Roseau, Dominica, Basseterre, St Kitts and Nevis, St. Thomas, U.S.V.I., Days At Sea, Half Moon Cay, Bahamas...
Price Per Night:$255.71 (USD) (based on double occupancy, for comparison only)
Mar 21, 2026through Mar 28, 2026
Itinerary:
Bridgetown, Barbados, Rodney Bay, St. Lucia, Sail with Star Flyer to Cabrits, Cabrits, Dominica, Falmouth Harbour, Antigua, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon), Terre de Haut, Iles des Saintes, Beach, Martinique, Bridgetown, Barbados
Other Categories Starting At:
Inside
$1,790.00 Cat:Category 6 255.71 per night
Outside
$2,040.00 Cat:Category 5 291.43 per night
Balcony
N/A
Suite
$3,880.00 Cat:Deluxe Suite with Veranda 554.29 per night
Price Per Night:$399.86 (USD) (based on double occupancy, for comparison only)
Jan 03, 2025through Jan 10, 2025
Itinerary:
Barcelona, Murcia (Cartagena), Granada (Málaga), Sail the Strait of Gibraltar, Vigo, Sail the Atlantic Ocean, Portsmouth, London (Tilbury)
Circumnavigate the Iberian Peninsula and uncover the historic treasures of Spain. Explore the Roman past and tranquil beauty of Cartagena and its Murcia province. Visit Málaga, the city of Picasso’s birth, and Granada’s Alhambra palace. Cruise through the Strait of Gibraltar and into the scenic bay of Vigo, gateway to Santiago de Compostela. This enlightening itinerary is complemented by a call on England’s maritime city of Portsmouth.
Price Per Night:$236.34 (USD) (based on double occupancy, for comparison only)
Nov 09, 2024through Dec 23, 2024
Itinerary:
Miami, Cruising The Atlantic Ocean, St. John's, Castries, St. George's, Port Of Spain, Cruising The Atlantic Ocean, Macapa, Santarem (Amazon River), Boca Da Valeria (Amazon River)...
Price Per Night:$371.29 (USD) (based on double occupancy, for comparison only)
Feb 07, 2026through Feb 14, 2026
Itinerary:
Philipsburg, St. Maarten, Roseau, Pigeon Island, Les Saintes, Gustavia, Basseterre, Philipsburg, St. Maarten
From the stunning drama of the Pitons to the captivating charm of Les Saintes. From hidden coves and secret beaches to exotic markets and lively cafés. Discover the best of this region with one single Caribbean cruise. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre unique to the Caribbean life.
Price Per Night:$428.43 (USD) (based on double occupancy, for comparison only)
Oct 01, 2025through Oct 08, 2025
Itinerary:
London (Tilbury), Portsmouth, Sail the Atlantic Ocean, Vigo, Sail the Strait of Gibraltar, Granada (Málaga), Murcia (Cartagena), Barcelona
Circumnavigate the Iberian Peninsula and uncover the historic treasures of Spain. Explore the Roman past and tranquil beauty of Cartagena and its Murcia province. Visit Málaga, the city of Picasso’s birth, and Granada’s Alhambra palace. Cruise through the Strait of Gibraltar and into the scenic bay of Vigo, gateway to Santiago de Compostela. This enlightening itinerary is complemented by a call on England’s maritime city of Portsmouth.
Price Per Night:$122.83 (USD) (based on double occupancy, for comparison only)
Jan 04, 2026through Feb 08, 2026
Itinerary:
London (Southampton), England, Madeira, Portugal, Barbados, Barbados, St Lucia, Saint Lucia, Grenada, Grenada, St. Vincent, St. Vincent/Grenadines, Curacao, Antilles, Aruba, Aruba, Dominica, Dominica, Antigua...
This roundtrip Caribbean voyage from Southampton is the perfect way to escape the January blues. Enjoy an enviable start to 2026, soaking up the sun on some of the world’s best white-sand beaches.
Price Per Night:$196.36 (USD) (based on double occupancy, for comparison only)
Dec 21, 2025through Jan 04, 2026
Itinerary:
Fort Lauderdale, Florida, US, Half Moon Cay, Bahamas, Days At Sea, Cruz Bay, St. John, U.S. Virgin Islands, Days At Sea, Port-of-Spain, Trinidad and Tobago, Saint Georges, Grenada, Bridgetown, Barbados, Castries, Saint Lucia, Roseau, Dominica...
Price Per Night:$399.90 (USD) (based on double occupancy, for comparison only)
Nov 09, 2024through Nov 19, 2024
Itinerary:
San Juan, Tortola (Road Town), St. Kitts (Basseterre), Castries, Bridgetown, Roseau, Antigua (St. John’s), Philipsburg, St. Thomas (Charlotte Amalie), San Juan
Set sail on a roundtrip voyage from San Juan to explore the colorful Caribbean. Start deep in the heart of this tropical paradise and avoid the long sea days associated with most Caribbean cruises-allowing you to visit more ports and spend more time discovering rich island cultures. Immerse yourself in the British, French and Dutch cultures of the Lesser Antilles as you cruise azure waters from Tortola and St. Lucia to Dominica, St. Martin and St. Thomas.
Price Per Night:$234.29 (USD) (based on double occupancy, for comparison only)
Mar 08, 2025through Mar 15, 2025
Itinerary:
Philipsburg, St. Maarten, River Bay, Barbuda, Sail with Royal Clipper South of Iles des Saintes, Cabrits, Dominica, Terre-de-Haut, Iles des Saintes, Deshaies, Guadeloupe, Falmouth Harbour, Antigua, Gustavia, St. Barts, Philipsburg, St. Maarten
Price Per Night:$285.64 (USD) (based on double occupancy, for comparison only)
Feb 28, 2026through Mar 14, 2026
Itinerary:
Philipsburg, St. Maarten, Basseterre, Gustavia, Little Bay, Les Saintes, Roseau, Pigeon Island, Bridgetown, Little Bay, Les Saintes...
Discover less-traveled roads and concealed refuges throughout the Caribbean on this 14-day cruise that blends iconic destinations and little-known shorelines like a favorite beachside cocktail. Search for green sea turtles and watch iridescent fish flit among sunken freighter wreckage from the dry side of a porthole in a Gustavia-based, semi-submersible. Sail past St. Kitts uncrowded southeast shores before slipping silently beneath the surface to snorkel among exotic fish and colorful coral.
Price Per Night:$247.14 (USD) (based on double occupancy, for comparison only)
Mar 07, 2026through Mar 14, 2026
Itinerary:
Philipsburg, St. Maarten, River Bay, Barbuda, Sail with Royal Clipper South of Iles des Saintes, Cabrits, Dominica, Terre-de-Haut, Iles des Saintes, Deshaies, Guadeloupe, Falmouth Harbour, Antigua, Gustavia, St. Barts, Philipsburg, St. Maarten
Price Per Night:$428.43 (USD) (based on double occupancy, for comparison only)
Oct 02, 2025through Oct 09, 2025
Itinerary:
London (Tilbury), Portsmouth, Sail the Atlantic Ocean, Vigo, Sail the Strait of Gibraltar, Granada (Málaga), Murcia (Cartagena), Barcelona
Circumnavigate the Iberian Peninsula and uncover the historic treasures of Spain. Explore the Roman past and tranquil beauty of Cartagena and its Murcia province. Visit Málaga, the city of Picasso’s birth, and Granada’s Alhambra palace. Cruise through the Strait of Gibraltar and into the scenic bay of Vigo, gateway to Santiago de Compostela. This enlightening itinerary is complemented by a call on England’s maritime city of Portsmouth.
Price Per Night:$657.14 (USD) (based on double occupancy, for comparison only)
Dec 22, 2025through Jan 05, 2026
Itinerary:
Fort Lauderdale, Florida, Day at sea, Grand Turk, Day at sea, St. Thomas, Basseterre, St. Kitts, Roseau, Bequia, Fort-De-France, St. John's...
Price Per Night:$139.50 (USD) (based on double occupancy, for comparison only)
Dec 27, 2025through Jan 03, 2026
Itinerary:
San Juan, Puerto Rico, Charlotte Amalie, St. Thomas, Philipsburg, St. Maarten, St. Croix, U.S.V.I., Roseau, Dominica, Bridgetown, Barbados, Cruising, San Juan, Puerto Rico
Price Per Night:$84.44 (USD) (based on double occupancy, for comparison only)
Oct 04, 2024through Oct 12, 2024
Itinerary:
Fort Lauderdale, Florida, Labadee, Haiti, St. Johns, Antigua, Roseau, Dominica, Castries, St. Lucia, Basseterre, St Kitts & Nevis, San Juan, Puerto Rico
Price Per Night:$98.00 (USD) (based on double occupancy, for comparison only)
Oct 18, 2025through Oct 29, 2025
Itinerary:
Fort Lauderdale, Florida, Philipsburg, St. Maarten, Fort- De- France, Martinique, Castries, St. Lucia, Bridgetown, Barbados, Roseau, Dominica, St. Johns, Antigua, Fort Lauderdale, Florida
Price Per Night:$255.71 (USD) (based on double occupancy, for comparison only)
Jan 10, 2026through Jan 17, 2026
Itinerary:
Bridgetown, Barbados, Rodney Bay, St. Lucia, Sail with Star Flyer to Cabrits, Cabrits, Dominica, Falmouth Harbour, Antigua, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon), Terre de Haut, Iles des Saintes, Beach, Martinique, Bridgetown, Barbados
Other Categories Starting At:
Inside
$1,790.00 Cat:Category 6 255.71 per night
Outside
$2,040.00 Cat:Category 5 291.43 per night
Balcony
N/A
Suite
$3,880.00 Cat:Deluxe Suite with Veranda 554.29 per night
Price Per Night:$234.29 (USD) (based on double occupancy, for comparison only)
Mar 22, 2025through Mar 29, 2025
Itinerary:
Philipsburg, St. Maarten, River Bay, Barbuda, Sail with Royal Clipper South of Iles des Saintes, Cabrits, Dominica, Terre-de-Haut, Iles des Saintes, Deshaies, Guadeloupe, Falmouth Harbour, Antigua, Gustavia, St. Barts, Philipsburg, St. Maarten
Price Per Night:$675.00 (USD) (based on double occupancy, for comparison only)
Nov 25, 2025through Dec 15, 2025
Itinerary:
Lisbon, Day at sea, Funchal, Madeira, Santa Cruz De La Palma (Canary Islands), Day at sea, Mindelo, Day at sea, Bridgetown, Bequia, Fort-De-France...
Price Per Night:$118.96 (USD) (based on double occupancy, for comparison only)
Dec 19, 2025through Jan 06, 2026
Itinerary:
San Juan, Puerto Rico, Charlotte Amalie, St. Thomas, Virgin Gorda, St. John's, Antigua, St. Pierre, Port Elizabeth, Bequia, Scarborough, Tobago, Bridgetown, Mayreau, Grenadines, Castries...
Price Per Night:$58.72 (USD) (based on double occupancy, for comparison only)
Jan 24, 2025through Feb 02, 2025
Itinerary:
Fort Lauderdale, Florida, Cruising, Philipsburg, St. Maarten, Roseau, Dominica, Basseterre, St Kitts & Nevis, San Juan, Puerto Rico, Puerto Plata, Dominican Rep, Cruising, Fort Lauderdale, Florida
Price Per Night:$113.25 (USD) (based on double occupancy, for comparison only)
Nov 26, 2025through Dec 08, 2025
Itinerary:
New York, New York, St. Maarten, Netherlands Antilles, Dominica, Dominica, Barbados, Barbados, St Lucia, Saint Lucia, St. Kitts, ST Kitts/Nevis, New York, New York
The chance to spend time in five Caribbean islands is a highlight of this 12-night voyage. Sink your toes into white sands and warm shallows as you escape New York’s winter for tropical sunshine.
Price Per Night:$264.21 (USD) (based on double occupancy, for comparison only)
Mar 14, 2026through Mar 28, 2026
Itinerary:
Philipsburg, St. Maarten, Falmouth Harbour, Road Bay, Jost Van Dyke, Great Harbour, Soper's Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St. Maarten, Roseau...
Skip the usual Caribbean cruise stops and discover the small harbors, overlooked havens and most remote secrets among the Leeward Islands. Whether you’re looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of Les Saintes, Anse Mitan, Pigeon Island and much more.
Price Per Night:$266.63 (USD) (based on double occupancy, for comparison only)
Nov 09, 2024through Dec 03, 2024
Itinerary:
Miami, Cruising The Atlantic Ocean, St. John's, Castries, St. George's, Port Of Spain, Cruising The Atlantic Ocean, Macapa, Santarem (Amazon River), Boca Da Valeria (Amazon River)...
Price Per Night:$110.80 (USD) (based on double occupancy, for comparison only)
Nov 22, 2025through Dec 06, 2025
Itinerary:
San Juan, Puerto Rico, Virgin Gorda, St. John's, Antigua, St. Pierre, Port Elizabeth, Bequia, Saint George's, Scarborough, Tobago, Bridgetown, Castries, Roseau...