Price Per Night:$228.55 (USD) (based on double occupancy, for comparison only)
Dec 23, 2025through Jan 03, 2026
Itinerary:
Miami, 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...
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:$142.28 (USD) (based on double occupancy, for comparison only)
Feb 13, 2027through Feb 20, 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
Unwind during this pleasant 22-day transatlantic crossing that includes Caribbean islands before you head to Portugal. This vacation offers the perfect opportunity to reconnect and spend quality time with the people who matter most to you or enjoy time by yourself, as you find true relaxation. In Basseterre, go for a safari zipline adventure through the rainforest or join a snorkel safari taking you to reefs teeming with tropical fish and coral life.
Price Per Night:$357.00 (USD) (based on double occupancy, for comparison only)
Feb 28, 2026through Mar 07, 2026
Itinerary:
Philipsburg, St. Maarten, Basseterre, Gustavia, St. John's, Les Saintes, Roseau, Mayreau, Bridgetown
Enjoy the perfect mix of must-see Caribbean towns and harbors off the beaten path as you cruise and sail the royal beauties of the Lesser Antilles islands. Explore colonial history in pastel waterfronts, weathered forts and former sugar plantations. See the Caribbean at its most wild and beautiful on Dominica, St. Lucia and St. Kitts. Join the jetsetters on St. Barts, and everywhere you go, find delicious white beaches that turn rose and orange under Caribbean sunsets.
Price Per Night:$198.36 (USD) (based on double occupancy, for comparison only)
Nov 21, 2025through Dec 01, 2025
Itinerary:
Fort Lauderdale, Florida, Philipsburg, St. Maarten, Castries, St. Lucia, Roseau, Dominica, Bridgetown, Barbados, St. Johns, Antigua, Fort Lauderdale, Florida
Price Per Night:$730.00 (USD) (based on double occupancy, for comparison only)
Nov 12, 2025through Nov 27, 2025
Itinerary:
Miami, Saint John/Cruz Bay, Deshaies, Bridgetown, Roseau, St. Maarten/Philipsburg, San Juan, Road Bay, St. John's (Antigua), Gustavia...
With your soul full of Miami energy, sway through the Greater and Lesser Antilles to relax in Cruz Bay's cool vibe and Deshaies' natural tranquillity. Sip rum cocktails at sunset in Bridgetown and capture the drama of Roseau's waterfalls and volcanic hot springs. Savour the azure hues of Phillipsburg and the serene sands of Road Bay and St John's. Dine and dance under the stars on Gustavia's stunning beaches, admire the lagoons of Tortola, then indulge in a haven of pampered delights at sea on your way back to Miami.
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:$113.97 (USD) (based on double occupancy, for comparison only)
Jan 31, 2027through Feb 07, 2027
Itinerary:
San Juan, Puerto Rico, Tortola, B.V.I., St. Johns, Antigua, Roseau, Dominica, St. Croix, U.S.V.I., Basseterre, St Kitts & Nevis, Cruising, San Juan, Puerto Rico
Price Per Night:$135.13 (USD) (based on double occupancy, for comparison only)
Jan 16, 2027through Jan 23, 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:$201.62 (USD) (based on double occupancy, for comparison only)
Oct 31, 2026through Nov 21, 2026
Itinerary:
Fort Lauderdale, Relaxaway Half Moon Cay, Falmouth, Grand Cayman, Mahogany Bay, Belize City, Cozumel, Fort Lauderdale, St Maarten, Antigua...
Price Per Night:$156.50 (USD) (based on double occupancy, for comparison only)
Nov 29, 2025through Dec 05, 2025
Itinerary:
San Juan, St. Maarten, St. Kitts, Roseau, Barbados, San Juan
This 6-night San Juan sojourn first arrives at the crystalline lagoons of lush landscapes of St. Maarten. Next, you'll dock in St. Kitt's for a beautiful blend of simple relaxation and beach adventures before heading to Roseau, Dominica - followed by the bright colors, welcoming beaches, and exciting food scene of Barbados. Finally, spend a day of self-care on board returning to sunny San Juan.
Price Per Night:$384.11 (USD) (based on double occupancy, for comparison only)
Jan 13, 2027through Feb 01, 2027
Itinerary:
Barcelona, Murcia (Cartagena), Granada (Málaga), Scenic Sailing: Strait of Gibraltar, Vigo, Sail the Atlantic Ocean, Portsmouth, London (Tilbury), Sail the North Sea, Edinburgh (Rosyth)...
Trace the Iberian Peninsula during quiet season and revel in the relaxed atmosphere of Spain’s mild winter climate. Explore the legacy of Moorish culture at the magnificent Alhambra Palace, indulge in delectable cuisine and explore Roman history in Cartagena. Call at iconic London and travel through the pristine landscapes of Norway, marveling at snowcapped peaks and icy fjords as you search for the north’s mesmerizing phenomenon, the aurora borealis.
Price Per Night:$280.00 (USD) (based on double occupancy, for comparison only)
Feb 21, 2026through Feb 28, 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:$342.79 (USD) (based on double occupancy, for comparison only)
Feb 07, 2026through Feb 21, 2026
Itinerary:
Philipsburg, St. Maarten, Charlestown, Roseau, Mayreau, Anse Mitan, Basseterre, Gustavia, Philipsburg, St. Maarten, St. John's, 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:$65.57 (USD) (based on double occupancy, for comparison only)
Nov 19, 2025through Dec 06, 2025
Itinerary:
Rotterdam (Amsterdam) Netherlands, Southampton (London) United Kingdom, Le Havre (Paris) France, Ponta Delgada (Azores) Portugal, Bridgetown Barbados, Basseterre St Kitts & Nevis, St. John's Antigua And Barbuda, Roseau Dominica, Fort De France Martinique
Price Per Night:$230.90 (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:$155.00 (USD) (based on double occupancy, for comparison only)
Dec 05, 2025through Dec 13, 2025
Itinerary:
San Juan, Curacao, Aruba, Roseau, Antigua, Philipsburg, San Juan
This 8-night getaway provides a day of on-board relaxation while sailing to the sprawling coral reefs and ocean blues as bright as the drink it's famous for, Curaçao. Dock the next day on the white sand beaches of Aruba, followed by a self-care day at sea before arriving in Dominica. Next, wake up in St. John's, Antigua then at the lush landscapes of St. Maarten before returning to San Juan.
Price Per Night:$371.29 (USD) (based on double occupancy, for comparison only)
Jan 03, 2026through Jan 17, 2026
Itinerary:
Rome (Civitavecchia), Florence/Pisa (Livorno), Monte Carlo, Marseille, Sète, Barcelona, Murcia (Cartagena), Granada (Málaga), Sail the Atlantic Ocean, Vigo...
Delve into Roman history, delight in the Tuscan countryside and stroll the upscale coast of Monte Carlo. Sail to Spain and call at iconic cities and charismatic towns. Visit the ancient city of Cartagena, discover southern Spain’s Andalusian gems and journey through the storied Strait of Gibraltar to Vigo, gateway to the UNESCO city of Santiago de Compostela, famed for its stunning cathedral—the final stop on the epic Camino de Santiago pilgrim route.
Price Per Night:$223.05 (USD) (based on double occupancy, for comparison only)
Mar 06, 2027through Mar 27, 2027
Itinerary:
Fort Lauderdale, Relaxaway Half Moon Cay, Falmouth, Grand Cayman, Mahogany Bay, Belize City, Cozumel, Fort Lauderdale, St Maarten, Antigua...
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:$280.00 (USD) (based on double occupancy, for comparison only)
Nov 29, 2025through Dec 06, 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:$118.31 (USD) (based on double occupancy, for comparison only)
Oct 17, 2026through Oct 24, 2026
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
Price Per Night:$671.29 (USD) (based on double occupancy, for comparison only)
Oct 14, 2026through Oct 21, 2026
Itinerary:
Philipsburg, Gustavia, Carambola Beach, Pointe-á-Pitre, Cabrits (Portsmouth), Dominica, Fort-de-France, Port Elizabeth (Bequia), Bridgetown
Get swept away by the colorful scenes of the Caribbean. Departing late from Gustavia, take the time for a snorkeling adventure amid the island's underwater wonders. Carambola Beach begins your adventure to Canada Hill, where a natural guide can take you on an off-road hike through a former bustling sugar plantation. From Pointe-á-Pitre, an extended evening in port gives you time to venture out to Deshaies for a delectable encounter with French gastronomy enlivened by the unique zest of local flavors.
Price Per Night:$216.06 (USD) (based on double occupancy, for comparison only)
Dec 19, 2025through Jan 06, 2026
Itinerary:
San Juan, Charlotte Amalie, St. Thomas, Virgin Gorda, St. John's, Antigua, Saint- Pierre, Port Elizabeth, Bequia, Scarborough, Tobago, Bridgetown, Mayreau, Grenadines, Castries...
Price Per Night:$811.67 (USD) (based on double occupancy, for comparison only)
Dec 28, 2025through Jan 09, 2026
Itinerary:
Fort-De-France, Antigua, Marigot, Jost Van Dyke, South Friars Bay, Saint-Kitts, Les Saintes, Portsmouth, Pigeon Island Beach, Soufrière, Tobago Cays...
Price Per Night:$606.67 (USD) (based on double occupancy, for comparison only)
Feb 05, 2026through Feb 20, 2026
Itinerary:
San Juan, Tortola/Road Town, St. John's (Antigua), Gustavia, Road Bay, Miami, Puerto Plata, Dominican Republic, Roseau, Bridgetown, Deshaies...
Sail from San Juan to roam among charming coves and linger by crystal-glass waters in Tortola and Antigua. Gustavia offers French-Caribbean chic before you relax in Anguilla's Road Bay. Pausing in lively Miami, cross the azure waves to Puerto Plata's golden sands, then discover Roseau's tropical rainforests, Bridgetown's rich culture and the scenic coastline of Les Trois-Îlets. The vibrant markets and verdant hills of Basseterre welcome you before we return to the colourful streets of San Juan.
Price Per Night:$182.07 (USD) (based on double occupancy, for comparison only)
Nov 07, 2026through Nov 21, 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:$132.81 (USD) (based on double occupancy, for comparison only)
Feb 16, 2027through 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.
Price Per Night:$621.43 (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:$540.00 (USD) (based on double occupancy, for comparison only)
Jan 20, 2027through 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)...
Price Per Night:$162.19 (USD) (based on double occupancy, for comparison only)
Dec 27, 2026through Jan 03, 2027
Itinerary:
San Juan, Puerto Rico, Charlotte Amalie, St. Thomas, St. Croix, U.S.V.I., St. Johns, Antigua, Roseau, Dominica, Cruising, Philipsburg, St. Maarten, San Juan, Puerto Rico
Price Per Night:$687.50 (USD) (based on double occupancy, for comparison only)
Feb 03, 2026through Feb 19, 2026
Itinerary:
Cartagena, Santa Marta, Oranjestad, Aruba, Kralendijk, Bonaire, Willemstad, Curaçao, Day at sea, Soufrière, St. Lucia, Bequia, Bridgetown, Trois Ilets...
Price Per Night:$472.00 (USD) (based on double occupancy, for comparison only)
Nov 17, 2025through Dec 02, 2025
Itinerary:
Bridgetown, Roseau, St. Maarten/Philipsburg, San Juan, Road Bay, St. John's (Antigua), Gustavia, Tortola/Road Town, Miami, Charlotte Amalie (Saint Thomas)...
