from
$2,599.00
(USD)
Per Person
+ $52.00 taxes/fees
Feb 28, 2026
through Mar 07, 2026
through Mar 07, 2026
Nights:
7
Ship:
Wind Surf
Price Per Night:$371.29 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 28, 2026
through Mar 07, 2026
Itinerary:
Philipsburg, St. Maarten, Charlestown, Roseau, Mayreau, 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.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,419.00
(USD)
Per Person
Dec 13, 2025
through Dec 27, 2025
through Dec 27, 2025
Nights:
14
Ship:
Azamara Quest
Price Per Night:$172.79 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 13, 2025
through Dec 27, 2025
Itinerary:
Bridgetown, Castries, Roseau, Basseterre, St.Kitts, Charlestown, Nevis, Philipsburg, San Juan, Charlotte Amalie, St. Thomas, Virgin Gorda, St. John's, Antigua...
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,599.00
(USD)
Per Person
+ $8,887.00 taxes/fees
Feb 25, 2027
through Mar 09, 2027
through Mar 09, 2027
Nights:
12
Ship:
Queen Elizabeth
Price Per Night:$133.25 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
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.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,030.00
(USD)
Per Person
Mar 07, 2026
through Mar 14, 2026
through Mar 14, 2026
Nights:
7
Ship:
Royal Clipper
Price Per Night:$290.00 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 07, 2026
through 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
Outside
Balcony
Suite
from
$2,030.00
(USD)
Per Person
Mar 21, 2026
through Mar 28, 2026
through Mar 28, 2026
Nights:
7
Ship:
Royal Clipper
Price Per Night:$290.00 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 21, 2026
through 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
Outside
Balcony
Suite
from
$11,899.00
(USD)
Per Person
Nov 02, 2026
through Dec 19, 2026
through Dec 19, 2026
Nights:
47
Ship:
Insignia
Price Per Night:$253.17 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Nov 02, 2026
through Dec 19, 2026
Itinerary:
Barcelona, Palma De Mallorca, Alicante, Cartagena, Malaga, Seville (Cadiz), Portimao, Lisbon, Arrecife (Lanzarote), Las Palmas De Gran Canaria...
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$9,899.00
(USD)
Per Person
Nov 09, 2026
through Dec 19, 2026
through Dec 19, 2026
Nights:
40
Ship:
Insignia
Price Per Night:$247.48 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Nov 09, 2026
through Dec 19, 2026
Itinerary:
Lisbon, Arrecife (Lanzarote), Las Palmas De Gran Canaria, Santa Cruz De La Palma, San Juan, Nassau, Miami, Tortola, St. John's, Castries...
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,970.00
(USD)
Per Person
Feb 21, 2026
through Feb 28, 2026
through Feb 28, 2026
Nights:
7
Ship:
Star Flyer
Price Per Night:$281.43 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 21, 2026
through 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
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$8,999.00
(USD)
Per Person
Mar 07, 2026
through Mar 21, 2026
through Mar 21, 2026
Nights:
14
Ship:
Seabourn Ovation
Price Per Night:$642.79 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 07, 2026
through Mar 21, 2026
Itinerary:
St Maarten, Frenchman's Cay, Carambola Beach, Saint Pierre, Port Elizabeth, Grenada, Barbados, Carambola Beach, Point-A-Pitre, Trois Ilets...
Aboard The Yachts of Seabourn, the world is more intimate and more enchanting. Here, you’ll explore ports rarely visited by larger ships and meet people who are happy to show you around their hidden corner of the globe. With their unmatched sense of style, elegance and grace, The Yachts of Seabourn beckon you to travel beyond the bounds of the imagination. Aboard Seabourn, every desire is met promptly and with a welcoming smile. Whether it's a warm blanket and a cup of gourmet hot chocolate as you drift along the Norwegian Fjords or a relaxing neck massage poolside, you'll feel that you're a member of a very exclusive club.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$3,099.00
(USD)
Per Person
+ $17.00 taxes/fees
Dec 28, 2025
through Jan 04, 2026
through Jan 04, 2026
Nights:
7
Ship:
Wind Spirit
Price Per Night:$442.71 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
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.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$8,999.00
(USD)
Per Person
Jan 31, 2026
through Feb 14, 2026
through Feb 14, 2026
Nights:
14
Ship:
Seabourn Ovation
Price Per Night:$642.79 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 31, 2026
through Feb 14, 2026
Itinerary:
St Maarten, Frenchman's Cay, Carambola Beach, Saint Pierre, Port Elizabeth, Grenada, Barbados, Carambola Beach, Trois Ilets, Point-A-Pitre...
Aboard The Yachts of Seabourn, the world is more intimate and more enchanting. Here, you’ll explore ports rarely visited by larger ships and meet people who are happy to show you around their hidden corner of the globe. With their unmatched sense of style, elegance and grace, The Yachts of Seabourn beckon you to travel beyond the bounds of the imagination. Aboard Seabourn, every desire is met promptly and with a welcoming smile. Whether it's a warm blanket and a cup of gourmet hot chocolate as you drift along the Norwegian Fjords or a relaxing neck massage poolside, you'll feel that you're a member of a very exclusive club.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$8,999.00
(USD)
Per Person
Feb 07, 2026
through Feb 21, 2026
through Feb 21, 2026
Nights:
14
Ship:
Seabourn Ovation
Price Per Night:$642.79 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 07, 2026
through Feb 21, 2026
Itinerary:
Barbados, Carambola Beach, Trois Ilets, Point-A-Pitre, Roseau, Rodney Bay, Barbados, St Lucia, Montserrat, Antigua...
Aboard The Yachts of Seabourn, the world is more intimate and more enchanting. Here, you’ll explore ports rarely visited by larger ships and meet people who are happy to show you around their hidden corner of the globe. With their unmatched sense of style, elegance and grace, The Yachts of Seabourn beckon you to travel beyond the bounds of the imagination. Aboard Seabourn, every desire is met promptly and with a welcoming smile. Whether it's a warm blanket and a cup of gourmet hot chocolate as you drift along the Norwegian Fjords or a relaxing neck massage poolside, you'll feel that you're a member of a very exclusive club.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$9,899.00
(USD)
Per Person
Nov 18, 2025
through Dec 14, 2025
through Dec 14, 2025
Nights:
26
Ship:
Seabourn Ovation
Price Per Night:$380.73 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Nov 18, 2025
through Dec 14, 2025
Itinerary:
Barcelona, Tangier, Carambola Beach, Tortola, San Juan, Aruba, Curacao, Bonaire, Trois Ilets, Roseau...
Aboard The Yachts of Seabourn, the world is more intimate and more enchanting. Here, you’ll explore ports rarely visited by larger ships and meet people who are happy to show you around their hidden corner of the globe. With their unmatched sense of style, elegance and grace, The Yachts of Seabourn beckon you to travel beyond the bounds of the imagination. Aboard Seabourn, every desire is met promptly and with a welcoming smile. Whether it's a warm blanket and a cup of gourmet hot chocolate as you drift along the Norwegian Fjords or a relaxing neck massage poolside, you'll feel that you're a member of a very exclusive club.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,599.00
(USD)
Per Person
+ $17.00 taxes/fees
Mar 21, 2026
through Mar 28, 2026
through Mar 28, 2026
Nights:
7
Ship:
Wind Spirit
Price Per Night:$371.29 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 21, 2026
through Mar 28, 2026
Itinerary:
Bridgetown, Basseterre, Les Saintes, Roseau, Anse Mitan, Mayreau, 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.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$4,499.00
(USD)
Per Person
+ $120.00 taxes/fees
Feb 28, 2026
through Mar 14, 2026
through Mar 14, 2026
Nights:
14
Ship:
Wind Surf
Price Per Night:$321.36 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 28, 2026
through Mar 14, 2026
Itinerary:
Philipsburg, St. Maarten, Charlestown, Roseau, Mayreau, 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.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,970.00
(USD)
Per Person
Nov 29, 2025
through Dec 06, 2025
through Dec 06, 2025
Nights:
7
Ship:
Star Flyer
Price Per Night:$281.43 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Nov 29, 2025
through 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
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,639.00
(USD)
Per Person
Nov 15, 2025
through Nov 29, 2025
through Nov 29, 2025
Nights:
14
Ship:
Azamara Quest
Price Per Night:$188.50 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Nov 15, 2025
through Nov 29, 2025
Itinerary:
Bridgetown, Castries, Roseau, Basseterre, St.Kitts, Charlestown, Nevis, Philipsburg, Road Town, Tortola, San Juan, Virgin Gorda, St. John's, Antigua...
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,170.00
(USD)
Per Person
Dec 27, 2025
through Jan 03, 2026
through Jan 03, 2026
Nights:
7
Ship:
Star Flyer
Price Per Night:$310.00 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 27, 2025
through Jan 03, 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
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,709.00
(USD)
Per Person
Dec 21, 2025
through Jan 04, 2026
through Jan 04, 2026
Nights:
14
Ship:
Volendam
Price Per Night:$193.50 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 21, 2025
through Jan 04, 2026
Itinerary:
Fort Lauderdale, St. John, Port Of Spain, Grenada, Roseau, St Lucia, St Maarten, Antigua, Grand Turk, Half Moon Cay...
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$3,899.00
(USD)
Per Person
Apr 04, 2026
through Apr 14, 2026
through Apr 14, 2026
Nights:
10
Ship:
Allura
Price Per Night:$389.90 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Apr 04, 2026
through Apr 14, 2026
Itinerary:
Miami, San Juan, Basseterre, Castries, Roseau, Charlotte Amalie, Miami
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$3,559.00
(USD)
Per Person
+ $450.00 taxes/fees
Feb 22, 2026
through Mar 22, 2026
through Mar 22, 2026
Nights:
28
Ship:
Queen Victoria
Price Per Night:$127.11 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 22, 2026
through Mar 22, 2026
Itinerary:
London (Southampton), England, Madeira, Portugal, Tortola, B.V.I., St. Maarten, Netherlands Antilles, St. Kitts, ST Kitts/Nevis, Dominica, Dominica, St Lucia, Saint Lucia, Barbados, Barbados, Tenerife, Canary Islands, London (Southampton), England
Fulfill the ultimate holiday fantasy, sinking your toes into the white sands of Caribbean beaches on this 28-night voyage. On board, make use of Queen Victoria’s sun decks, as you sail between islands.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,016.06
(USD)
Per Person
Jan 18, 2026
through Jan 25, 2026
through Jan 25, 2026
Nights:
7
Ship:
Brilliance of the Seas
Price Per Night:$145.15 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 18, 2026
through Jan 25, 2026
Itinerary:
San Juan, Puerto Rico, Tortola, B.V.I., St. Johns, Antigua, St. George's, Grenada, Kingstown, St. Vincent, Roseau, Dominica, Cruising, San Juan, Puerto Rico
Other Categories Starting At:
Inside
Outside
Balcony
Suite
Transatlantic Crossing And Caribbean Celebration, 21 Nights (M634A)
London (Southampton), England to New York, New York
London (Southampton), England to New York, New York
from
$4,259.00
(USD)
Per Person
+ $5,904.00 taxes/fees
Dec 12, 2026
through Jan 02, 2027
through Jan 02, 2027
Nights:
21
Ship:
Queen Mary 2
Price Per Night:$202.81 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 12, 2026
through Jan 02, 2027
Itinerary:
London (Southampton), England, New York, New York, Tortola, B.V.I., St. Maarten, Netherlands Antilles, Barbados, Barbados, St Lucia, Saint Lucia, Dominica, Dominica, St. Kitts, ST Kitts/Nevis, New York, New York
What could be better than Christmas spent in the Caribbean sunshine? This festive voyage offers days ashore to explore the likes of Dominica and Barbados, with plenty of festive cheer on board.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,999.00
(USD)
Per Person
Feb 06, 2026
through Feb 16, 2026
through Feb 16, 2026
Nights:
10
Ship:
Nautica
Price Per Night:$299.90 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 06, 2026
through Feb 16, 2026
Itinerary:
Miami, Tortola, Basseterre, Roseau, St. John's, Philipsburg, Miami
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,399.00
(USD)
Per Person
+ $7,229.00 taxes/fees
Nov 26, 2025
through Dec 08, 2025
through Dec 08, 2025
Nights:
12
Ship:
Queen Mary 2
Price Per Night:$116.58 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Nov 26, 2025
through 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.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,677.28
(USD)
Per Person
Dec 27, 2025
through Jan 03, 2026
through Jan 03, 2026
Nights:
7
Ship:
Jewel of the Seas
Price Per Night:$239.61 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 27, 2025
through 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
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$739.00
(USD)
Per Person
Jan 17, 2027
through Jan 24, 2027
through Jan 24, 2027
Nights:
7
Ship:
MSC Seaview
Price Per Night:$105.57 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 17, 2027
through Jan 24, 2027
Itinerary:
Pointe-A-Pitre Guadeloupe, Philipsburg St. Maarten, St. John's Antigua And Barbuda, Basseterre St Kitts & Nevis, Roseau Dominica, Fort De France Martinique, Pointe-A-Pitre Guadeloupe
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,969.00
(USD)
Per Person
Dec 27, 2025
through Jan 06, 2026
through Jan 06, 2026
Nights:
10
Ship:
Azamara Quest
Price Per Night:$196.90 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Dec 27, 2025
through Jan 06, 2026
Itinerary:
Bridgetown, Mayreau, Grenadines, Castries, Roseau, Basseterre, Philipsburg, Road Town, Tortola, Miami, Florida
Other Categories Starting At:
Inside
Outside
Balcony
Suite
Feb 05, 2027
through Feb 15, 2027
through Feb 15, 2027
Nights:
10
Ship:
Celebrity Ascent
Price Per Night:$174.93 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 05, 2027
through Feb 15, 2027
Itinerary:
Fort Lauderdale, Florida, Philipsburg, St. Maarten, Castries, St. Lucia, St. George's, Grenada, Roseau, Dominica, St. Johns, Antigua, Fort Lauderdale, Florida
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$6,000.00
(USD)
Per Person
Jan 18, 2026
through Jan 25, 2026
through Jan 25, 2026
Nights:
7
Ship:
Silver Shadow
Price Per Night:$857.14 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 18, 2026
through Jan 25, 2026
Itinerary:
Philipsburg, St. Maarten, St John, Gustavia, St Barthelemy, Roseau, St George's, Trois Ilets, Kingstown, St. Vincent, Bridgetown
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$7,298.00
(USD)
Per Person
Jan 13, 2027
through Feb 01, 2027
through Feb 01, 2027
Nights:
19
Ship:
Viking Vela
Price Per Night:$384.11 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 13, 2027
through 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.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$4,699.00
(USD)
Per Person
Feb 09, 2026
through Feb 19, 2026
through Feb 19, 2026
Nights:
10
Ship:
Allura
Price Per Night:$469.90 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 09, 2026
through Feb 19, 2026
Itinerary:
Miami, San Juan, Basseterre, Castries, Roseau, Charlotte Amalie, Miami
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$3,939.00
(USD)
Per Person
Mar 14, 2026
through Apr 04, 2026
through Apr 04, 2026
Nights:
21
Ship:
Zuiderdam
Price Per Night:$187.57 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 14, 2026
through Apr 04, 2026
Itinerary:
Miami, 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...
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,999.00
(USD)
Per Person
Nov 15, 2025
through Nov 22, 2025
through Nov 22, 2025
Nights:
7
Ship:
Azamara Quest
Price Per Night:$285.57 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Nov 15, 2025
through Nov 22, 2025
Itinerary:
Bridgetown, Castries, Roseau, Basseterre, St.Kitts, Charlestown, Nevis, Philipsburg, Road Town, Tortola, San Juan
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$8,499.00
(USD)
Per Person
Jan 15, 2026
through Feb 15, 2026
through Feb 15, 2026
Nights:
31
Ship:
Insignia
Price Per Night:$274.16 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 15, 2026
through Feb 15, 2026
Itinerary:
Miami, Oranjestad, Willemstad, Port Of Spain, St. George's, Castries, Kingstown, Roseau, Fort-De-France, Bridgetown...
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Inside
Outside
Balcony
Suite
from
$3,499.00
(USD)
Per Person
Nov 15, 2026
through Nov 25, 2026
through Nov 25, 2026
Nights:
10
Ship:
Viking Sea
Price Per Night:$349.90 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Nov 15, 2026
through Nov 25, 2026
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.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$4,999.00
(USD)
Per Person
Feb 07, 2026
through Feb 14, 2026
through Feb 14, 2026
Nights:
7
Ship:
Seabourn Ovation
Price Per Night:$714.14 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Feb 07, 2026
through Feb 14, 2026
Itinerary:
Barbados, Carambola Beach, Trois Ilets, Point-A-Pitre, Roseau, Rodney Bay, Barbados
Aboard The Yachts of Seabourn, the world is more intimate and more enchanting. Here, you’ll explore ports rarely visited by larger ships and meet people who are happy to show you around their hidden corner of the globe. With their unmatched sense of style, elegance and grace, The Yachts of Seabourn beckon you to travel beyond the bounds of the imagination. Aboard Seabourn, every desire is met promptly and with a welcoming smile. Whether it's a warm blanket and a cup of gourmet hot chocolate as you drift along the Norwegian Fjords or a relaxing neck massage poolside, you'll feel that you're a member of a very exclusive club.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$4,099.00
(USD)
Per Person
+ $34.00 taxes/fees
Mar 07, 2026
through Mar 21, 2026
through Mar 21, 2026
Nights:
14
Ship:
Wind Spirit
Price Per Night:$292.79 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 07, 2026
through Mar 21, 2026
Itinerary:
Bridgetown, Basseterre, St. John's, Les Saintes, Roseau, Mayreau, Anse Mitan, Bridgetown, Tobago Cays, Pigeon Island...
The Windward Islands will enchant you with their natural beauty – dense rainforests, lush green peaks, cascading waterfalls, stunning black sand beaches. And on this two-week voyage you’ll visit the best of them, from islands so small they have only one village, to villages so small they have only one road. See nature’s artistry in the lush green volcanic pitons of St.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$2,789.00
(USD)
Per Person
+ $20,768.00 taxes/fees
Feb 16, 2027
through Mar 09, 2027
through Mar 09, 2027
Nights:
21
Ship:
Queen Elizabeth
Price Per Night:$132.81 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
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.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$4,099.00
(USD)
Per Person
+ $43.00 taxes/fees
Mar 21, 2026
through Apr 12, 2026
through Apr 12, 2026
Nights:
22
Ship:
Wind Spirit
Price Per Night:$186.32 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 21, 2026
through Apr 12, 2026
Itinerary:
Bridgetown, Basseterre, Les Saintes, Roseau, Anse Mitan, Mayreau, Bridgetown, Lisbon
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.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
Jan 08, 2027
through Jan 17, 2027
through Jan 17, 2027
Nights:
9
Ship:
Celebrity Eclipse
Price Per Night:$166.39 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Jan 08, 2027
through Jan 17, 2027
Itinerary:
Fort Lauderdale, Florida, St. Johns, Antigua, Roseau, Dominica, Fort- De- France, Martinique, Philipsburg, St. Maarten, Fort Lauderdale, Florida
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$3,699.00
(USD)
Per Person
+ $120.00 taxes/fees
Mar 21, 2026
through Apr 04, 2026
through Apr 04, 2026
Nights:
14
Ship:
Wind Surf
Price Per Night:$264.21 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Mar 21, 2026
through Apr 04, 2026
Itinerary:
Philipsburg, St. Maarten, Charlestown, Roseau, Mayreau, Les Saintes, 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.
Other Categories Starting At:
Inside
Outside
Balcony
Suite
from
$1,399.00
(USD)
Per Person
Nov 14, 2026
through Nov 21, 2026
through Nov 21, 2026
Nights:
7
Ship:
Azamara Journey
Price Per Night:$199.86 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Nov 14, 2026
through Nov 21, 2026
Itinerary:
Bridgetown, Castries, Roseau, Basseterre, Charlestown, Philipsburg, Road Town, Tortola, San Juan, Puerto Rico
Other Categories Starting At:
Inside
Outside
Balcony
Suite
