Jan 08, 2025
through Jan 25, 2025
through Jan 25, 2025
Nights:
17
Ship:
Seven Seas Mariner
Jan 08, 2025
through Jan 25, 2025
Itinerary:
Miami, Cruising The Atlantic Ocean, Roseau, Bridgetown, Cruising The Atlantic Ocean, Devil's Island, Cruising The Atlantic Ocean, Belem (Icoaraci), Cruising The Atlantic Ocean, Recife...
Mar 22, 2025
through Apr 02, 2025
through Apr 02, 2025
Nights:
11
Ship:
Eurodam
Mar 22, 2025
through Apr 02, 2025
Itinerary:
Fort Lauderdale, Florida, US, Days At Sea, Philipsburg, Sint Maarten, St. Johns, Antigua and Barbuda, Castries, Saint Lucia, Roseau, Dominica, Basseterre, St Kitts and Nevis, St. Thomas, U.S.V.I., Days At Sea, Half Moon Cay, Bahamas...
Feb 06, 2025
through Feb 16, 2025
through Feb 16, 2025
Nights:
10
Ship:
Explorer of the Seas
Feb 06, 2025
through Feb 16, 2025
Itinerary:
Miami, Florida, Cruising, Puerto Plata, Dominican Rep, San Juan, Puerto Rico, Philipsburg, St. Maarten, Roseau, Dominica, St. Johns, Antigua, Basseterre, St Kitts & Nevis, Cruising, Miami, Florida
Feb 08, 2025
through Feb 15, 2025
through Feb 15, 2025
Nights:
7
Ship:
Royal Clipper
Feb 08, 2025
through Feb 15, 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
Feb 25, 2027
through Mar 18, 2027
through Mar 18, 2027
Nights:
21
Ship:
Queen Elizabeth
Feb 25, 2027
through Mar 18, 2027
Itinerary:
Miami, FL, USA, San Juan, Puerto Rico, Antigua, Dominica, Dominica, Barbados, Barbados, St. Maarten, Netherlands Antilles, Tortola, B.V.I., Miami, FL, USA, Grand Cayman, Cayman Islands, Montego Bay, Jamaica...
Soak up the atmosphere in bustling harbors in Antigua and Barbados, before exploring Miami’s fusion food scene and Maya ruins in Cozumel, on this 21-night Caribbean adventure on Queen Elizabeth.
Feb 07, 2026
through Feb 14, 2026
through Feb 14, 2026
Nights:
7
Ship:
Star Flyer
Feb 07, 2026
through 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
Nov 22, 2025
through Dec 06, 2025
through Dec 06, 2025
Nights:
14
Ship:
Azamara Quest
Nov 22, 2025
through 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...
Feb 25, 2027
through Mar 09, 2027
through Mar 09, 2027
Nights:
12
Ship:
Queen Elizabeth
Feb 25, 2027
through Mar 09, 2027
Itinerary:
Miami, FL, USA, San Juan, Puerto Rico, Antigua, Dominica, Dominica, Barbados, Barbados, St. Maarten, Netherlands Antilles, Tortola, B.V.I., Miami, FL, USA
Twelve nights on Queen Elizabeth bring a chance to enjoy life on board when you’re not exploring colonial architecture and colorful, vibrant streets in places like Puerto Rico, Antigua, and Barbados.
Jan 05, 2026
through Jan 16, 2026
through Jan 16, 2026
Nights:
11
Ship:
Silver Spirit
Jan 05, 2026
through Jan 16, 2026
Itinerary:
Bridgetown, Bequia, Soufrière, St. Lucia, Roseau, Deshaies, Charlestown (Nevis), St. John's, St John, Road Town, Tortola, Day at sea...
Feb 06, 2027
through Feb 13, 2027
through Feb 13, 2027
Nights:
7
Ship:
Celebrity Constellation
Feb 06, 2027
through 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
Feb 06, 2027
through Feb 16, 2027
through Feb 16, 2027
Nights:
10
Ship:
Silver Shadow
Feb 06, 2027
through Feb 16, 2027
Itinerary:
San Juan, Jost Van Dyke (British Virgin Islands), Gustavia, St Barthelemy, Basseterre, St. Kitts, Little Bay, Montserrat, Les Saintes, Roseau, Trois Ilets, Castries, St George's...
Dec 13, 2025
through Dec 20, 2025
through Dec 20, 2025
Nights:
7
Ship:
Star Flyer
Dec 13, 2025
through 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
Apr 18, 2027
through Apr 25, 2027
through Apr 25, 2027
Nights:
7
Ship:
Brilliance of the Seas
Apr 18, 2027
through Apr 25, 2027
Itinerary:
San Juan, Puerto Rico, Charlotte Amalie, St. Thomas, St. Croix, U.S.V.I., Philipsburg, St. Maarten, St. Johns, Antigua, Roseau, Dominica, Cruising, San Juan, Puerto Rico
Jan 26, 2026
through Feb 12, 2026
through Feb 12, 2026
Nights:
17
Ship:
Silver Spirit
Jan 26, 2026
through Feb 12, 2026
Itinerary:
Bridgetown, Castries, Fort-De-France, Gustavia, St Barthelemy, Roseau, St George's, Bequia, Bridgetown, Bequia, Soufrière, St. Lucia...
Feb 09, 2026
through Feb 19, 2026
through Feb 19, 2026
Nights:
10
Ship:
Allura
Feb 09, 2026
through Feb 19, 2026
Itinerary:
Miami, San Juan, Basseterre, Castries, Roseau, Charlotte Amalie, Miami
Dec 19, 2026
through Dec 26, 2026
through Dec 26, 2026
Nights:
7
Ship:
Celebrity Constellation
Dec 19, 2026
through Dec 26, 2026
Itinerary:
San Juan, Puerto Rico, Tortola, B.V.I., Basseterre, St Kitts & Nevis, Roseau, Dominica, Castries, St. Lucia, Bridgetown, Barbados, San Juan, Puerto Rico
Nov 29, 2025
through Dec 06, 2025
through Dec 06, 2025
Nights:
7
Ship:
Azamara Quest
Nov 29, 2025
through Dec 06, 2025
Itinerary:
Bridgetown, Castries, Roseau, Basseterre, Charlestown, Philipsburg, Road Town, Tortola, San Juan, Puerto Rico
21-Day Eastern & Western Caribbean: Leeward Islands & Mexico
Roundtrip from Fort Lauderdale, Florida, US
Roundtrip from Fort Lauderdale, Florida, US
Jan 03, 2026
through Jan 24, 2026
through Jan 24, 2026
Nights:
21
Ship:
Koningsdam
Jan 03, 2026
through Jan 24, 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...
Feb 14, 2025
through Feb 28, 2025
through Feb 28, 2025
Nights:
14
Ship:
Explora II
Feb 14, 2025
through Feb 28, 2025
Itinerary:
Miami, Road Bay, Roseau, Basse-Terre, Marigot, San Juan, Oranjestad, Willemstad, Kralendijk, Tobago/Scarborough...
Mar 01, 2025
through Mar 12, 2025
through Mar 12, 2025
Nights:
11
Ship:
Eurodam
Mar 01, 2025
through Mar 12, 2025
Itinerary:
Fort Lauderdale, Half Moon Cay, St Thomas, Antigua, Point-A-Pitre, Roseau, St Kitts, St Maarten, Fort Lauderdale
Jan 11, 2027
through Feb 14, 2027
through Feb 14, 2027
Nights:
34
Ship:
Queen Mary 2
Jan 11, 2027
through Feb 14, 2027
Itinerary:
London (Southampton), England, Madeira, Portugal, St. Kitts, ST Kitts/Nevis, Barbados, Barbados, St Lucia, Saint Lucia, Grenada, Grenada, Dominica, Dominica, English Harbour, Antigua, Amber Cove,Dominican Republic, St. Maarten, Netherlands Antilles...
Start 2027 in style on this 34-night Caribbean cruise. Sip rum overnight in Barbados, explore lush rainforest in St. Lucia, and banish your January blues with sun-filled days on white sand beaches.
Dec 05, 2025
through Dec 14, 2025
through Dec 14, 2025
Nights:
9
Ship:
Explora II
Dec 05, 2025
through Dec 14, 2025
Itinerary:
Miami, Charlotte Amalie (Saint Thomas), Pointe-Ã -Pitre, Roseau, Castries, St. George's (Grenada), Kingstown, Bridgetown
Mar 15, 2025
through Mar 22, 2025
through Mar 22, 2025
Nights:
7
Ship:
Wind Surf
Mar 15, 2025
through Mar 22, 2025
Itinerary:
Philipsburg, St. Maarten, Charlestown, Roseau, Pigeon Island, Les Saintes, Basseterre, Gustavia, 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.
Jan 11, 2025
through Jan 18, 2025
through Jan 18, 2025
Nights:
7
Ship:
Star Flyer
Jan 11, 2025
through Jan 18, 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
Jan 11, 2025
through Jan 25, 2025
through Jan 25, 2025
Nights:
14
Ship:
Wind Surf
Jan 11, 2025
through Jan 25, 2025
Itinerary:
Philipsburg, St. Maarten, Falmouth Harbour, Gustavia, Jost Van Dyke, Great Harbour, Soper's Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Road Bay, 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.
Nov 15, 2025
through Nov 22, 2025
through Nov 22, 2025
Nights:
7
Ship:
Azamara Quest
Nov 15, 2025
through Nov 22, 2025
Itinerary:
Bridgetown, Castries, Roseau, Basseterre, Charlestown, Philipsburg, Road Town, Tortola, San Juan, Puerto Rico
Dec 28, 2025
through Jan 04, 2026
through Jan 04, 2026
Nights:
7
Ship:
Wind Spirit
Dec 28, 2025
through Jan 04, 2026
Itinerary:
Bridgetown, Basseterre, Les Saintes, Roseau, Mayreau, Anse Mitan, Bridgetown
This is the Caribbean of days gone by – deep blue waters, quiet coves and tropical islands dotted with powdery beaches and lush green hillsides. Sail from the rugged natural beauty of St. Lucia to little-known isles that are off the tourist radar. From colorful Bequia and Mayreau in St. Vincent & the Grenadines to the open-air markets of exotic St. George’s, you’ll discover a part of the Caribbean that remains authentic and unspoiled.
Mar 08, 2025
through Mar 22, 2025
through Mar 22, 2025
Nights:
14
Ship:
Wind Surf
Mar 08, 2025
through 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.
Apr 08, 2025
through Apr 19, 2025
through Apr 19, 2025
Nights:
11
Ship:
Vista
Apr 08, 2025
through Apr 19, 2025
Itinerary:
Miami, Cruising The Atlantic Ocean, St. John's, Castries, St. George's, Bridgetown, Roseau, Gustavia, Cruising The Atlantic Ocean, Miami
Mar 21, 2025
through Mar 30, 2025
through Mar 30, 2025
Nights:
9
Ship:
Grandeur of the Seas
Mar 21, 2025
through Mar 30, 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
Dec 22, 2025
through Jan 05, 2026
through Jan 05, 2026
Nights:
14
Ship:
Silver Dawn
Dec 22, 2025
through 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...
Feb 27, 2026
through Mar 25, 2026
through Mar 25, 2026
Nights:
26
Ship:
Zuiderdam
Feb 27, 2026
through Mar 25, 2026
Itinerary:
San Diego, Puerto Vallarta, Huatulco, Puerto Chiapas, Puerto Quetzal, Fuerte Amador, Panama Canal (Cruising), Fuerte Amador, Enter Panama Canal Balboa, Exit Panama Canal Cristobal...
Jan 04, 2025
through Jan 18, 2025
through Jan 18, 2025
Nights:
14
Ship:
Wind Surf
Jan 04, 2025
through Jan 18, 2025
Itinerary:
Philipsburg, St. Maarten, Charlestown, Roseau, Pigeon Island, Les Saintes, Gustavia, Basseterre, Philipsburg, St. Maarten, Falmouth Harbour, Gustavia...
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.
Dec 20, 2026
through Dec 27, 2026
through Dec 27, 2026
Nights:
7
Ship:
Brilliance of the Seas
Dec 20, 2026
through Dec 27, 2026
Itinerary:
San Juan, Puerto Rico, Tortola, B.V.I., St. Johns, Antigua, Roseau, Dominica, St. Croix, U.S.V.I., Cruising, Basseterre, St Kitts & Nevis, San Juan, Puerto Rico
Mar 07, 2026
through Mar 14, 2026
through Mar 14, 2026
Nights:
7
Ship:
Star Flyer
Mar 07, 2026
through 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
Feb 16, 2027
through Mar 09, 2027
through Mar 09, 2027
Nights:
21
Ship:
Queen Elizabeth
Feb 16, 2027
through Mar 09, 2027
Itinerary:
Miami, FL, USA, Grand Cayman, Cayman Islands, Montego Bay, Jamaica, Roatan, Honduras, Costa Maya, Mexico, Cozumel, Mexico, Miami, FL, USA, San Juan, Puerto Rico, Antigua, Dominica, Dominica...
Take each day as slowly as you like on this 21-night sailing in the Caribbean that includes captivating ports like Montego Bay in Jamaica, San Juan in Puerto Rico, and Philipsburg in St. Maarten.
Oct 31, 2025
through Nov 08, 2025
through Nov 08, 2025
Nights:
8
Ship:
Jewel of the Seas
Oct 31, 2025
through Nov 08, 2025
Itinerary:
Fort Lauderdale, Florida, Cruising, Labadee, Haiti, Cruising, Basseterre, St Kitts & Nevis, Castries, St. Lucia, Roseau, Dominica, Philipsburg, St. Maarten, San Juan, Puerto Rico
Jan 07, 2025
through Jun 24, 2025
through Jun 24, 2025
Nights:
168
Ship:
Seven Seas Mariner
Jan 07, 2025
through Jun 24, 2025
Itinerary:
Miami, Cruising The Atlantic Ocean, Roseau, Bridgetown, Cruising The Atlantic Ocean, Devil's Island, Cruising The Atlantic Ocean, Belem (Icoaraci), Cruising The Atlantic Ocean, Recife...
Jan 18, 2025
through Feb 01, 2025
through Feb 01, 2025
Nights:
14
Ship:
Wind Surf
Jan 18, 2025
through Feb 01, 2025
Itinerary:
Philipsburg, St. Maarten, Charlestown, Roseau, Pigeon Island, Les Saintes, Gustavia, Basseterre, 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.
Oct 23, 2026
through Dec 19, 2026
through Dec 19, 2026
Nights:
57
Ship:
Insignia
Oct 23, 2026
through Dec 19, 2026
Itinerary:
Venice, Rijeka, Split, Kotor, Igoumenitsa, Gallipoli, Catania (Sicily), Naples/Pompeii, Rome (Civitavecchia), Barcelona...
Feb 28, 2026
through Mar 07, 2026
through Mar 07, 2026
Nights:
7
Ship:
Wind Surf
Feb 28, 2026
through Mar 07, 2026
Itinerary:
Philipsburg, St. Maarten, Charlestown, Roseau, Pigeon Island, Deshaies, Basseterre, Gustavia, 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.
Jan 02, 2027
through Jan 09, 2027
through Jan 09, 2027
Nights:
7
Ship:
Celebrity Constellation
Jan 02, 2027
through 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
Feb 04, 2026
through Feb 25, 2026
through Feb 25, 2026
Nights:
21
Ship:
Koningsdam
Feb 04, 2026
through Feb 25, 2026
Itinerary:
Fort Lauderdale, Florida, US, Half Moon Cay, Bahamas, Days At Sea, St. Thomas, U.S.V.I., St. Johns, Antigua and Barbuda, Basseterre, St Kitts and Nevis, Frederiksted, St. Croix, U.S. Virgin Islands, San Juan, Puerto Rico, Days At Sea, Fort Lauderdale, Florida, US...
Jan 20, 2027
through Jan 30, 2027
through Jan 30, 2027
Nights:
10
Ship:
Silver Shadow
Jan 20, 2027
through Jan 30, 2027
Itinerary:
Bridgetown, Bequia, Castries, Trois Ilets, Roseau, Les Saintes, Little Bay, Montserrat, Basseterre, St. Kitts, Gustavia, St Barthelemy, Jost Van Dyke (British Virgin Islands)...
Nov 12, 2025
through Dec 07, 2025
through Dec 07, 2025
Nights:
25
Ship:
Insignia
Nov 12, 2025
through Dec 07, 2025
Itinerary:
Miami, St. John's, Castries, St. George's, Scarborough, Santarem (Amazon River), Boca Da Valeria (Amazon River), Manaus (Amazon River), Parintins (Amazon River), Alter Do Chao (Amazon River)...
Mar 12, 2025
through Apr 02, 2025
through Apr 02, 2025
Nights:
21
Ship:
Eurodam
Mar 12, 2025
through Apr 02, 2025
Itinerary:
Fort Lauderdale, Florida, US, Half Moon Cay, Bahamas, Days At Sea, Falmouth, Jamaica, Georgetown, Cayman Islands, Days At Sea, Belize City, Belize, Cozumel, Mexico, Days At Sea, Nassau, Bahamas...
Jan 18, 2025
through Feb 01, 2025
through Feb 01, 2025
Nights:
14
Ship:
Wind Spirit
Jan 18, 2025
through Feb 01, 2025
Itinerary:
Bridgetown, Pigeon Island, The Pitons, Castries, Kingstown, Mayreau, St. George's, Bequia, Bridgetown, St. John's...
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.
