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(47 offers included)
West Indies Explorer Roundtrip from San Juan
Departing on Jan 05, 2027 on the Viking Sea
Nights: 10
Dates: Jan 05, 2027 through Jan 15, 2027
Ship: Viking Sea
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.
from
$3,799.00
(USD)
Per Person
Inside
N/A
Outside
N/A
Balcony
$3,799.00
Cat: V2
$379.90/Night
Suite
$6,499.00
Cat: PS3
$649.90/Night
Departing on Dec 05, 2025 on the Explora II
Nights: 17
Dates: Dec 05, 2025 through Dec 22, 2025
Ship: Explora II
Itinerary:
Miami, Charlotte Amalie (Saint Thomas), Pointe-à-Pitre, Roseau, Castries, St. George's (Grenada), Kingstown, Bridgetown, Bequia, Port of Spain...
As we glide from Sur de la Florida to the river reeds of Roseau, witness volcanoes snoozing beneath their blankets of thick rainforest. Onwards through Castries’ lush landscapes to the rainbow-flowered gardens of Kingstown and the enchantment of crystalline waters and bright birdlife in Barbados, Trinidad and the British Virgin Islands.
from
$8,200.00
(USD)
Per Person
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$8,200.00
Cat: OT2
$482.35/Night
Caribbean & Central America Cruise Philipsburg to Bridgetown
Departing on Feb 26, 2026 on the Silver Shadow
Nights: 7
Dates: Feb 26, 2026 through Mar 05, 2026
Itinerary:
Philipsburg, St. Maarten, St John, Gustavia, St Barthelemy, Roseau, St George's, Trois Ilets, Kingstown, St. Vincent, Bridgetown
from
$6,100.00
(USD)
Per Person
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$6,100.00
Cat: VI
$871.43/Night
Departing on Dec 21, 2025 on the Volendam
Nights: 14
Dates: Dec 21, 2025 through Jan 04, 2026
Ship: Volendam
Itinerary:
Fort Lauderdale, St. John, Port Of Spain, Grenada, Roseau, St Lucia, St Maarten, Antigua, Grand Turk, Half Moon Cay...
from
$3,109.00
(USD)
Per Person
Inside
$3,109.00
Cat: N
$222.07/Night
Outside
$3,109.00
Cat: HH
$222.07/Night
Balcony
N/A
Suite
$4,699.00
Cat: BC
$335.64/Night
Departing on Feb 28, 2026 on the Wind Spirit
Nights: 15
Dates: Feb 28, 2026 through Mar 15, 2026
Ship: Wind Spirit
Itinerary:
Philipsburg, St. Maarten, Basseterre, Gustavia, St. John's, Les Saintes, Roseau, Mayreau, Bridgetown, Basseterre, St. John's...
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.
from
$3,999.00
(USD)
Per Person
+ $38.00 taxes/fees
Inside
N/A
Outside
$3,999.00
Cat: B
$266.60/Night
Balcony
N/A
Suite
N/A
Departing on Jan 14, 2026 on the Koningsdam
Nights: 21
Dates: Jan 14, 2026 through Feb 04, 2026
Ship: Koningsdam
Itinerary:
Fort Lauderdale, Half Moon Cay, Falmouth, Grand Cayman, Belize City, Mahogany Bay, Cozumel, Fort Lauderdale, St Maarten, Antigua...
from
$3,806.00
(USD)
Per Person
Inside
$3,806.00
Cat: N
$181.24/Night
Outside
$4,886.00
Cat: F
$232.67/Night
Balcony
$4,886.00
Cat: VH
$232.67/Night
Suite
$6,506.00
Cat: BC
$309.81/Night
Departing on Feb 14, 2026 on the Koningsdam
Nights: 11
Dates: Feb 14, 2026 through Feb 25, 2026
Ship: Koningsdam
Itinerary:
Fort Lauderdale, Half Moon Cay, St Thomas, Antigua, Martinique, Roseau, St Kitts, St Maarten, Fort Lauderdale
from
$2,199.00
(USD)
Per Person
Inside
$2,199.00
Cat: N
$199.91/Night
Outside
$2,904.00
Cat: F
$264.00/Night
Balcony
$2,904.00
Cat: VH
$264.00/Night
Suite
$3,749.00
Cat: BC
$340.82/Night
Departing on Jan 31, 2026 on the Wind Spirit
Nights: 14
Dates: Jan 31, 2026 through Feb 14, 2026
Ship: Wind Spirit
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.
from
$4,099.00
(USD)
Per Person
+ $79.00 taxes/fees
Inside
N/A
Outside
$4,099.00
Cat: B
$292.79/Night
Balcony
N/A
Suite
N/A
Iberian Explorer Barcelona to London (Tilbury)
Departing on Jan 13, 2027 on the Viking Vela
Nights: 7
Dates: Jan 13, 2027 through Jan 20, 2027
Ship: Viking Vela
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.
from
$2,299.00
(USD)
Per Person
Inside
N/A
Outside
N/A
Balcony
$2,299.00
Cat: V2
$328.43/Night
Suite
$3,799.00
Cat: PS3
$542.71/Night
Caribbean & Central America Cruise Bridgetown to San Juan
Departing on Feb 16, 2027 on the Silver Shadow
Nights: 11
Dates: Feb 16, 2027 through Feb 27, 2027
Itinerary:
Bridgetown, Bequia, St George's, Castries, Trois Ilets, Roseau, Les Saintes, Little Bay, Montserrat, Basseterre, St. Kitts, Gustavia, St Barthelemy...
from
$7,200.00
(USD)
Per Person
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$7,200.00
Cat: VI
$654.55/Night
Departing on Jan 03, 2026 on the Koningsdam
Nights: 11
Dates: Jan 03, 2026 through Jan 14, 2026
Ship: Koningsdam
Itinerary:
Fort Lauderdale, Half Moon Cay, St Thomas, Antigua, Martinique, Roseau, St Kitts, St Maarten, Fort Lauderdale
from
$2,099.00
(USD)
Per Person
Inside
$2,099.00
Cat: N
$190.82/Night
Outside
$2,799.00
Cat: F
$254.45/Night
Balcony
$2,799.00
Cat: VH
$254.45/Night
Suite
$3,699.00
Cat: BC
$336.27/Night
Departing on Nov 28, 2026 on the Azamara Journey
Nights: 14
Dates: Nov 28, 2026 through Dec 12, 2026
Itinerary:
Bridgetown, Castries, Roseau, Basseterre, St.Kitts, Charlestown, Nevis, Philipsburg, Gustavia, San Juan, Virgin Gorda, St. John's, Antigua...
from
$2,539.00
(USD)
Per Person
Inside
$2,539.00
Cat: 12
$181.36/Night
Outside
$3,129.00
Cat: 08
$223.50/Night
Balcony
$4,169.00
Cat: V3
$297.79/Night
Suite
$6,889.00
Cat: N2
$492.07/Night
21-Day Eastern & Western Caribbean: Mexico Roundtrip from Fort Lauderdale
Departing on Feb 14, 2026 on the Koningsdam
Nights: 21
Dates: Feb 14, 2026 through Mar 07, 2026
Ship: Koningsdam
Itinerary:
Fort Lauderdale, Half Moon Cay, St Thomas, Antigua, Martinique, Roseau, St Kitts, St Maarten, Fort Lauderdale, Half Moon Cay...
from
$3,966.00
(USD)
Per Person
Inside
$3,966.00
Cat: N
$188.86/Night
Outside
$5,050.00
Cat: F
$240.48/Night
Balcony
$5,050.00
Cat: VH
$240.48/Night
Suite
$6,666.00
Cat: BC
$317.43/Night
Departing on Jan 11, 2026 on the Silver Shadow
Nights: 14
Dates: Jan 11, 2026 through Jan 25, 2026
Itinerary:
Philipsburg, St. Maarten, St. John's, St. Thomas, Little Bay, Montserrat, Castries, Mayreau, Les Saintes, Philipsburg, St. Maarten, St John, Gustavia, St Barthelemy...
from
$7,500.00
(USD)
Per Person
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$7,500.00
Cat: VI
$535.71/Night
Departing on Dec 20, 2026 on the Queen Mary 2
Nights: 14
Dates: Dec 20, 2026 through Jan 03, 2027
Ship: Queen Mary 2
Itinerary:
New York, New York, Amber Cove,Dominican Republic, Tortola, B.V.I., Dominica, Dominica, Barbados, Barbados, St Lucia, Saint Lucia, St. Kitts, ST Kitts/Nevis, New York, New York
Enjoy sunny days in Barbados, Dominica, and Saint Lucia, among other tropical islands, on this Christmas voyage to the Caribbean. You’ll also celebrate New Year’s on board – the perfect start to 2024.
from
$3,499.00
(USD)
Per Person
+ $5,904.00 taxes/fees
Inside
$3,499.00
Cat: IF
$249.93/Night
Outside
$4,499.00
Cat: EF
$321.36/Night
Balcony
$4,629.00
Cat: DC
$330.64/Night
Suite
$10,699.00
Cat: P2
$764.21/Night
Caribbean, 21 Nights (Q707A) Roundtrip from Miami, FL, USA
Departing on Feb 25, 2027 on the Queen Elizabeth
Nights: 21
Dates: 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.
from
$2,939.00
(USD)
Per Person
+ $20,768.00 taxes/fees
Inside
$2,939.00
Cat: IE
$139.95/Night
Outside
$3,439.00
Cat: FC
$163.76/Night
Balcony
$4,239.00
Cat: CB
$201.86/Night
Suite
$11,639.00
Cat: P2
$554.24/Night
Caribbean & Central America Cruise Bridgetown to Philipsburg
Departing on Feb 12, 2026 on the Silver Shadow
Nights: 7
Dates: Feb 12, 2026 through Feb 19, 2026
Itinerary:
Bridgetown, Trois Ilets, Kingstown, St. Vincent, Roseau, Gustavia, St Barthelemy, St John, St. John's, Philipsburg, St. Maarten
from
$6,000.00
(USD)
Per Person
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$6,000.00
Cat: VI
$857.14/Night
Southern Caribbean Holiday Roundtrip from San Juan, Puerto Rico
Departing on Dec 19, 2026 on the Radiance of the Seas
Nights: 7
Dates: Dec 19, 2026 through Dec 26, 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
from
$1,101.66
(USD)
Per Person
Inside
$1,101.66
Cat: ZI
$157.38/Night
Outside
$1,251.66
Cat: YO
$178.81/Night
Balcony
$1,558.66
Cat: XB
$222.67/Night
Suite
N/A
7-Day Caribbean Gems Roundtrip from Barbados
Departing on Feb 07, 2026 on the Seabourn Ovation
Nights: 7
Dates: 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.
from
$5,099.00
(USD)
Per Person
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$5,099.00
Cat: V1
$728.43/Night
Departing on Jan 19, 2026 on the Le Bellot
Nights: 10
Dates: Jan 19, 2026 through Jan 29, 2026
Ship: Le Bellot
Itinerary:
Santo Domingo, Jost Van Dyke, Les Saintes, Portsmouth, Pigeon Island Beach, Soufrière, Tobago Cays, Mayreau Island, Port Elizabeth, Bequia Island, Union Island...
from
$6,650.00
(USD)
Per Person
+ $560.00 taxes/fees
Inside
N/A
Outside
N/A
Balcony
$6,650.00
Cat: DEL
$665.00/Night
Suite
$10,870.00
Cat: DS6
$1,087.00/Night
Departing on Mar 07, 2026 on the Wind Spirit
Nights: 14
Dates: Mar 07, 2026 through Mar 21, 2026
Ship: Wind Spirit
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.
from
$4,099.00
(USD)
Per Person
+ $34.00 taxes/fees
Inside
N/A
Outside
$4,099.00
Cat: B
$292.79/Night
Balcony
N/A
Suite
N/A
Departing on Mar 21, 2026 on the Wind Spirit
Nights: 7
Dates: Mar 21, 2026 through Mar 28, 2026
Ship: Wind Spirit
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.
from
$2,599.00
(USD)
Per Person
+ $17.00 taxes/fees
Inside
N/A
Outside
$2,599.00
Cat: B
$371.29/Night
Balcony
N/A
Suite
N/A
Southern Caribbean Cruise Roundtrip from San Juan, Puerto Rico
Departing on Feb 13, 2027 on the Radiance of the Seas
Nights: 7
Dates: Feb 13, 2027 through Feb 20, 2027
Itinerary:
San Juan, Puerto Rico, Charlotte Amalie, St. Thomas, St. Croix, U.S.V.I., Basseterre, St Kitts & Nevis, St. Johns, Antigua, Roseau, Dominica, Cruising, San Juan, Puerto Rico
from
$845.32
(USD)
Per Person
Inside
$845.32
Cat: ZI
$120.76/Night
Outside
$944.82
Cat: YO
$134.97/Night
Balcony
$1,282.82
Cat: XB
$183.26/Night
Suite
N/A
7-Day Caribbean Gems Roundtrip from Barbados
Departing on Mar 14, 2026 on the Seabourn Ovation
Nights: 7
Dates: Mar 14, 2026 through Mar 21, 2026
Itinerary:
Barbados, Carambola Beach, Point-A-Pitre, Trois Ilets, 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.
from
$4,674.00
(USD)
Per Person
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$4,674.00
Cat: V1
$667.71/Night
Dates: Mar 02, 2025 through Mar 02, 2027
Avoid the mobs while taking in the beauty of the Emerald Pool, Trafalgar Falls, and local gardens on this perfect Eco tour.
from
$115.00
(USD)
Per Person
Departing on Jan 03, 2026 on the Zuiderdam
Nights: 28
Dates: Jan 03, 2026 through Jan 31, 2026
Ship: Zuiderdam
Itinerary:
Miami, Half Moon Cay, Amber Cove, San Juan, Tortola, St Maarten, Antigua, Roseau, Martinique, Barbados...
from
$5,284.00
(USD)
Per Person
Inside
$5,284.00
Cat: N
$188.71/Night
Outside
$6,284.00
Cat: HH
$224.43/Night
Balcony
$7,334.00
Cat: VH
$261.93/Night
Suite
$10,934.00
Cat: SZ
$390.50/Night
Southern Caribbean Cruise Roundtrip from San Juan, Puerto Rico
Departing on Apr 13, 2025 on the Rhapsody of The Seas
Nights: 8
Dates: Apr 13, 2025 through Apr 21, 2025
Itinerary:
San Juan, Puerto Rico, St. Croix, U.S.V.I., Charlotte Amalie, St. Thomas, Philipsburg, St. Maarten, Basseterre, St Kitts & Nevis, Bridgetown, Barbados, Roseau, Dominica, Cruising, San Juan, Puerto Rico
from
$1,568.13
(USD)
Per Person
Non-Refundable
Inside
$1,568.13
Cat: ZI
$196.02/Night
Outside
N/A
Balcony
N/A
Suite
$3,527.13
Cat: J4
$440.89/Night
Departing on Nov 29, 2025 on the Azamara Quest
Nights: 7
Dates: Nov 29, 2025 through Dec 06, 2025
Itinerary:
Bridgetown, Castries, Roseau, Basseterre, Charlestown, Philipsburg, Road Town, Tortola, San Juan, Puerto Rico
from
$1,729.00
(USD)
Per Person
Inside
$1,729.00
Cat: 12
$247.00/Night
Outside
$1,879.00
Cat: 08
$268.43/Night
Balcony
$2,199.00
Cat: V3
$314.14/Night
Suite
$2,739.00
Cat: N2
$391.29/Night
Caribbean & Central America Cruise Bridgetown to Bridgetown
Departing on Dec 08, 2025 on the Silver Spirit
Nights: 7
Dates: Dec 08, 2025 through Dec 15, 2025
Itinerary:
Bridgetown, Castries, Fort-De-France, Gustavia, St Barthelemy, Roseau, St George's, Bequia, Bridgetown
from
$6,400.00
(USD)
Per Person
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$6,400.00
Cat: VI
$914.29/Night
Departing on Dec 24, 2026 on the Celebrity Ascent
Nights: 11
Dates: Dec 24, 2026 through 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
from
$2,667.76
(USD)
Per Person
Non-Refundable
Inside
$3,042.76
Cat: I2
$276.61/Night
Outside
$3,387.76
Cat: O2
$307.98/Night
Balcony
$3,894.26
Cat: P2
$354.02/Night
Suite
$10,975.76
Cat: MS
$997.80/Night
Southern Caribbean Cruise Roundtrip from San Juan, Puerto Rico
Departing on Jan 30, 2027 on the Radiance of the Seas
Nights: 7
Dates: Jan 30, 2027 through Feb 06, 2027
Itinerary:
San Juan, Puerto Rico, Charlotte Amalie, St. Thomas, Philipsburg, St. Maarten, St. Croix, U.S.V.I., St. Johns, Antigua, Roseau, Dominica, Cruising, San Juan, Puerto Rico
from
$854.93
(USD)
Per Person
Inside
$854.93
Cat: ZI
$122.13/Night
Outside
$954.43
Cat: YO
$136.35/Night
Balcony
$1,292.43
Cat: XB
$184.63/Night
Suite
N/A
Departing on Dec 09, 2025 on the Koningsdam
Nights: 18
Dates: Dec 09, 2025 through Dec 27, 2025
Ship: Koningsdam
Itinerary:
Fort Lauderdale, St Maarten, Antigua, St Lucia, Roseau, St Kitts, St Thomas, Half Moon Cay, Fort Lauderdale, Half Moon Cay...
from
$2,992.00
(USD)
Per Person
Inside
$2,992.00
Cat: N
$166.22/Night
Outside
$3,842.00
Cat: F
$213.44/Night
Balcony
$3,842.00
Cat: VH
$213.44/Night
Suite
$5,032.00
Cat: BC
$279.56/Night
Dates: Mar 02, 2025 through Mar 02, 2027
This truly scenic and private tour offers visitors a chance to experience the lush and green rainforest, waterfalls and scenic Botanical Gardens while providing many picture photo opportunities.
from
$129.00
(USD)
Per Person
Around the World in 180 Days Roundtrip from Miami
Departing on Jan 06, 2026 on the Vista
Nights: 180
Dates: Jan 06, 2026 through Jul 05, 2026
Ship: Vista
Itinerary:
Miami, Gustavia, Roseau, Bridgetown, Devil's Island, Belem (Icoaraci), Fortaleza, Salvador, Buzios, Rio De Janeiro...
from
$68,199.00
(USD)
Per Person
Inside
N/A
Outside
N/A
Balcony
$68,199.00
Cat: B3
$378.88/Night
Suite
N/A
Caribbean & Central America Cruise Fort Lauderdale to Fort Lauderdale
Departing on Dec 22, 2025 on the Silver Dawn
Nights: 14
Dates: Dec 22, 2025 through Jan 05, 2026
Ship: Silver Dawn
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...
from
$9,600.00
(USD)
Per Person
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$9,600.00
Cat: VI
$685.71/Night
Southern Caribbean Cruise Roundtrip from San Juan, Puerto Rico
Departing on Jan 31, 2027 on the Brilliance of the Seas
Nights: 7
Dates: Jan 31, 2027 through 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
from
$797.82
(USD)
Per Person
Inside
$797.82
Cat: ZI
$113.97/Night
Outside
$897.82
Cat: YO
$128.26/Night
Balcony
$1,235.32
Cat: XB
$176.47/Night
Suite
N/A
Departing on Apr 19, 2027 on the Celebrity Ascent
Nights: 11
Dates: Apr 19, 2027 through Apr 30, 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
from
$1,768.97
(USD)
Per Person
Non-Refundable
Inside
$2,008.97
Cat: I2
$182.63/Night
Outside
$2,353.97
Cat: O2
$214.00/Night
Balcony
$2,975.47
Cat: P2
$270.50/Night
Suite
$7,136.97
Cat: MS
$648.82/Night
Southern Caribbean Cruise Roundtrip from San Juan, Puerto Rico
Departing on May 02, 2026 on the Radiance of the Seas
Nights: 7
Dates: May 02, 2026 through May 09, 2026
Itinerary:
San Juan, Puerto Rico, Charlotte Amalie, St. Thomas, St. Croix, U.S.V.I., St. Johns, Antigua, Philipsburg, St. Maarten, Roseau, Dominica, Cruising, San Juan, Puerto Rico
from
$940.05
(USD)
Per Person
Inside
$940.05
Cat: ZI
$134.29/Night
Outside
$1,026.05
Cat: YO
$146.58/Night
Balcony
$1,334.05
Cat: XB
$190.58/Night
Suite
N/A
Departing on Jan 14, 2026 on the Wind Spirit
Nights: 17
Dates: Jan 14, 2026 through Jan 31, 2026
Ship: Wind Spirit
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.
from
$5,099.00
(USD)
Per Person
+ $95.00 taxes/fees
Inside
N/A
Outside
$5,099.00
Cat: B
$299.94/Night
Balcony
N/A
Suite
N/A
Southern Caribbean Cruise Roundtrip from San Juan, Puerto Rico
Departing on Nov 07, 2026 on the Radiance of the Seas
Nights: 7
Dates: Nov 07, 2026 through Nov 14, 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
from
$793.73
(USD)
Per Person
Inside
$793.73
Cat: ZI
$113.39/Night
Outside
$872.73
Cat: YO
$124.68/Night
Balcony
$1,230.23
Cat: XB
$175.75/Night
Suite
N/A
Departing on Feb 05, 2026 on the Explora I
Nights: 15
Dates: Feb 05, 2026 through Feb 20, 2026
Ship: Explora I
Itinerary:
San Juan, Tortola/Road Town, St. John's (Antigua), Gustavia, Road Bay, Miami, Puerto Plata, Dominican Republic, Roseau, Bridgetown, Saint-Pierre...
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.
from
$7,535.00
(USD)
Per Person
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$7,535.00
Cat: OT2
$502.33/Night
Departing on Feb 03, 2026 on the Silver Shadow
Nights: 16
Dates: Feb 03, 2026 through Feb 19, 2026
Itinerary:
Cartagena, Santa Marta, Oranjestad, Aruba, Kralendijk, Bonaire, Willemstad, Curaçao, Day at sea, Soufrière, St. Lucia, Bequia, Bridgetown, Trois Ilets...
from
$8,100.00
(USD)
Per Person
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$8,100.00
Cat: VI
$506.25/Night
Departing on Dec 07, 2025 on the Wind Surf
Nights: 14
Dates: Dec 07, 2025 through Dec 21, 2025
Ship: Wind Surf
Itinerary:
Philipsburg, St. Maarten, Charlestown, Roseau, Mayreau, Les Saintes, 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.
from
$3,699.00
(USD)
Per Person
+ $120.00 taxes/fees
Inside
N/A
Outside
$3,699.00
Cat: B
$264.21/Night
Balcony
N/A
Suite
$9,799.00
Cat: OS
$699.93/Night
Leeward Isles Serenade Roundtrip from Tampa
Departing on Mar 03, 2026 on the Insignia
Nights: 15
Dates: Mar 03, 2026 through Mar 18, 2026
Ship: Insignia
Itinerary:
Tampa, San Juan, Charlotte Amalie, Philipsburg, St. John's, Roseau, Basseterre, Frederiksted, Tortola, Tampa
from
$4,799.00
(USD)
Per Person
Inside
$4,799.00
Cat: G
$319.93/Night
Outside
$5,399.00
Cat: D
$359.93/Night
Balcony
$7,099.00
Cat: B2
$473.27/Night
Suite
$9,199.00
Cat: PH3
$613.27/Night
Caribbean Illumination Roundtrip from Miami
Departing on Feb 09, 2026 on the Allura
Nights: 10
Dates: Feb 09, 2026 through Feb 19, 2026
Ship: Allura
Itinerary:
Miami, San Juan, Basseterre, Castries, Roseau, Charlotte Amalie, Miami
from
$3,999.00
(USD)
Per Person
Inside
N/A
Outside
N/A
Balcony
$3,999.00
Cat: B5
$399.90/Night
Suite
$6,599.00
Cat: PH3
$659.90/Night
Departing on Nov 08, 2025 on the Azamara Quest
Nights: 14
Dates: Nov 08, 2025 through Nov 22, 2025
Itinerary:
San Juan, Virgin Gorda, St. John's, Antigua, Saint- Pierre, Port Elizabeth, Bequia, Saint George's, Scarborough, Tobago, Bridgetown, Castries, Roseau...
from
$3,299.00
(USD)
Per Person
Inside
$3,299.00
Cat: 12
$235.64/Night
Outside
$3,809.00
Cat: 08
$272.07/Night
Balcony
N/A
Suite
N/A
Departing on Nov 26, 2025 on the Queen Mary 2
Nights: 19
Dates: Nov 26, 2025 through Dec 15, 2025
Ship: Queen Mary 2
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.
from
$2,646.00
(USD)
Per Person
+ $7,229.00 taxes/fees
Inside
$2,646.00
Cat: IE
$139.26/Night
Outside
N/A
Balcony
$3,715.00
Cat: DF
$195.53/Night
Suite
$10,221.00
Cat: P2
$537.95/Night