Price Per Night:$288.57 (USD) (based on double occupancy, for comparison only)
Jan 24, 2026through Jan 31, 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
$2,020.00 Cat:Category 6 288.57 per night
Outside
$2,280.00 Cat:Category 5 325.71 per night
Balcony
N/A
Suite
$4,110.00 Cat:Deluxe Suite with Veranda 587.14 per night
Price Per Night:$793.75 (USD) (based on double occupancy, for comparison only)
Feb 28, 2026through Mar 08, 2026
Itinerary:
Vieux Fort, Portsmouth, Les Saintes, Port Elizabeth, Bequia Island, Mayreau Island, Saint George's, Grenada, Tobago Cays, Bridgetown, Vieux Fort
Price Per Night:$299.93 (USD) (based on double occupancy, for comparison only)
Feb 28, 2026through Mar 14, 2026
Itinerary:
Philipsburg, St. Maarten, Charlestown, Roseau, Pigeon Island, Deshaies, Basseterre, Gustavia, Philipsburg, St. Maarten, Falmouth Harbour, Road Bay...
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:$435.93 (USD) (based on double occupancy, for comparison only)
Mar 07, 2025through Mar 17, 2025
Itinerary:
Fort Lauderdale, Florida, Philipsburg, St. Maarten, Roseau, Dominica, St. George's, Grenada, Bridgetown, Barbados, St. Johns, Antigua, Fort Lauderdale, Florida
Price Per Night:$299.94 (USD) (based on double occupancy, for comparison only)
Jan 14, 2026through Jan 31, 2026
Itinerary:
Philipsburg, St. Maarten, Basseterre, Roseau, Castries, Anse Mitan, Les Saintes, Charlestown, Virgin Gorda / Prickly Pear, British Virgin Islands, Jost Van Dyke, Great Harbour, Gustavia...
Dive, dine, and delight in iconic Caribbean island destinations during a far-ranging Caribbean loop that conveniently begins and ends in Philipsburg on St. Maarten. Cruise a kayak through sapphire waters near Little Bay, Monserrat, and peer at shadowy fruit bats suspended throughout coastal caves. Drift and spin in a floating tube on a rainforest stream outside Roseau on Dominica prior to sipping rum cocktails mixed with tangy tropical juices.
Price Per Night:$280.00 (USD) (based on double occupancy, for comparison only)
Dec 13, 2025through Dec 20, 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:$133.19 (USD) (based on double occupancy, for comparison only)
Nov 19, 2025through Dec 15, 2025
Itinerary:
London (Southampton), England, 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
Escape to the warmth of Caribbean islands on this 26-night voyage. Spend your days ashore however you please, perhaps exploring Bridgetown’s historic Garrison or the Cathedral Basilica in Castries.
Price Per Night:$267.14 (USD) (based on double occupancy, for comparison only)
Feb 08, 2025through Feb 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:$133.40 (USD) (based on double occupancy, for comparison only)
Jan 02, 2027through Jan 09, 2027
Itinerary:
San Juan, Puerto Rico, Charlotte Amalie, St. Thomas, Basseterre, St Kitts & Nevis, Roseau, Dominica, Castries, St. Lucia, Bridgetown, Barbados, San Juan, Puerto Rico
Price Per Night:$133.89 (USD) (based on double occupancy, for comparison only)
Nov 19, 2025through Dec 08, 2025
Itinerary:
London (Southampton), England, 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
Treat yourself to a little Caribbean sunshine on this 19-night voyage. Enjoy days relaxing on sandy beaches or exploring vibrant towns, and indulge in island delicacies like tropical fruits and rum.
Price Per Night:$220.69 (USD) (based on double occupancy, for comparison only)
Dec 06, 2025through Dec 19, 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...
Price Per Night:$328.43 (USD) (based on double occupancy, for comparison only)
Jan 20, 2026through Jan 27, 2026
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:$288.57 (USD) (based on double occupancy, for comparison only)
Mar 07, 2026through Mar 14, 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
$2,020.00 Cat:Category 6 288.57 per night
Outside
$2,280.00 Cat:Category 5 325.71 per night
Balcony
N/A
Suite
$4,110.00 Cat:Deluxe Suite with Veranda 587.14 per night
Price Per Night:$485.64 (USD) (based on double occupancy, for comparison only)
Feb 15, 2025through Mar 01, 2025
Itinerary:
Philipsburg, St. Maarten, Falmouth Harbour, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Soper's Hole, Gustavia, Road Bay, Philipsburg, St. Maarten, Charlestown, 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:$135.13 (USD) (based on double occupancy, for comparison only)
Jan 30, 2027through Feb 06, 2027
Itinerary:
San Juan, Puerto Rico, Tortola, B.V.I., Basseterre, St Kitts & Nevis, Roseau, Dominica, Castries, St. Lucia, Bridgetown, Barbados, San Juan, Puerto Rico
Price Per Night:$136.69 (USD) (based on double occupancy, for comparison only)
Dec 12, 2026through Dec 19, 2026
Itinerary:
San Juan, Puerto Rico, Tortola, B.V.I., Basseterre, St Kitts & Nevis, Roseau, Dominica, Castries, St. Lucia, St. George's, Grenada, San Juan, Puerto Rico
Price Per Night:$280.00 (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:$245.64 (USD) (based on double occupancy, for comparison only)
Nov 08, 2025through Nov 22, 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...
Price Per Night:$292.79 (USD) (based on double occupancy, for comparison only)
Jan 31, 2026through Feb 14, 2026
Itinerary:
Philipsburg, St. Maarten, St. John's, 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, Charlestown...
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:$288.57 (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
$2,020.00 Cat:Category 6 288.57 per night
Outside
$2,280.00 Cat:Category 5 325.71 per night
Balcony
N/A
Suite
$4,110.00 Cat:Deluxe Suite with Veranda 587.14 per night
Price Per Night:$478.50 (USD) (based on double occupancy, for comparison only)
Mar 08, 2025through Mar 22, 2025
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, Charlestown...
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:$139.00 (USD) (based on double occupancy, for comparison only)
Dec 13, 2025through Dec 20, 2025
Itinerary:
San Juan, Basseterre, Castries, Roseau, Bridgetown, Sailing, Philipsburg, San Juan
This 7-night San Juan voyage sails the Caribbean Sea to the best islands of the Lesser Antilles including St. Kitts followed by St. Lucia's tropical city of Castries - home to splendid beaches, lush rainforests, and cascading waterfalls. Next up is Dominica (known for its natural springs), Barbados, and the tiny island of St. Maarten before returning to San Juan.
Price Per Night:$716.25 (USD) (based on double occupancy, for comparison only)
Dec 20, 2025through Dec 28, 2025
Itinerary:
Fort-De-France, Port Elizabeth, Bequia Island, Mayreau Island, Tobago Cays, Union Island, Pigeon Island Beach, Soufrière, Les Saintes, Portsmouth, Fort-De-France
Price Per Night:$221.71 (USD) (based on double occupancy, for comparison only)
Dec 21, 2025through Jan 04, 2026
Itinerary:
Fort Lauderdale, Florida, US, Days At Sea, Cruz Bay, St. John, U.S. Virgin Islands, Days At Sea, Port-of-Spain, Trinidad and Tobago, Saint Georges, Grenada, Roseau, Dominica, Castries, Saint Lucia, Philipsburg, Sint Maarten, St. Johns, Antigua and Barbuda...
Price Per Night:$280.00 (USD) (based on double occupancy, for comparison only)
Feb 07, 2026through Feb 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:$253.17 (USD) (based on double occupancy, for comparison only)
Nov 02, 2026through Dec 19, 2026
Itinerary:
Barcelona, Palma De Mallorca, Alicante, Cartagena, Malaga, Seville (Cadiz), Portimao, Lisbon, Arrecife (Lanzarote), Las Palmas De Gran Canaria...
Price Per Night:$181.46 (USD) (based on double occupancy, for comparison only)
Dec 05, 2026through Dec 18, 2026
Itinerary:
San Juan, Puerto Rico, Virgin Gorda, St. John's, Antigua, St. Pierre, Port Elizabeth, Bequia, Saint George's, Scarborough, Tobago, Bridgetown, Castries, Roseau...
Price Per Night:$288.57 (USD) (based on double occupancy, for comparison only)
Feb 07, 2026through Feb 14, 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
$2,020.00 Cat:Category 6 288.57 per night
Outside
$2,280.00 Cat:Category 5 325.71 per night
Balcony
N/A
Suite
$4,110.00 Cat:Deluxe Suite with Veranda 587.14 per night
Price Per Night:$242.52 (USD) (based on double occupancy, for comparison only)
Dec 24, 2026through Jan 04, 2027
Itinerary:
Fort Lauderdale, Florida, Philipsburg, St. Maarten, St. Johns, Antigua, Castries, St. Lucia, Bridgetown, Barbados, Roseau, Dominica, Basseterre, St Kitts & Nevis, Fort Lauderdale, Florida
Price Per Night:$654.55 (USD) (based on double occupancy, for comparison only)
Feb 16, 2027through Feb 27, 2027
Itinerary:
Bridgetown, Bequia, St George's, Castries, Trois Ilets, Roseau, Les Saintes, Little Bay, Montserrat, Basseterre, St. Kitts, Gustavia, St Barthelemy...
Price Per Night:$136.44 (USD) (based on double occupancy, for comparison only)
Feb 06, 2027through Feb 13, 2027
Itinerary:
San Juan, Puerto Rico, Charlotte Amalie, St. Thomas, St. Johns, Antigua, Roseau, Dominica, Castries, St. Lucia, St. George's, Grenada, San Juan, Puerto Rico
