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Caribbean

(50 offers included)
11-Day Southern Caribbean: Abc Islands Roundtrip from Fort Lauderdale
Departing on Mar 23, 2027 on the Eurodam
Nights: 11
Dates: Mar 23, 2027 through Apr 03, 2027
Ship: Eurodam
Itinerary:
Fort Lauderdale, Relaxaway Half Moon Cay, Grand Turk, Amber Cove, Cabo Rojo, Curacao, Bonaire, Aruba, Fort Lauderdale
from
$2,164.00
(USD)
Per Person
Inside
$2,164.00
Cat: N
$196.73/Night
Outside
$2,364.00
Cat: HH
$214.91/Night
Balcony
$2,914.00
Cat: VH
$264.91/Night
Suite
$4,014.00
Cat: SZ
$364.91/Night
Departing on Mar 12, 2027 on the Nieuw Amsterdam
Nights: 21
Dates: Mar 12, 2027 through Apr 02, 2027
Itinerary:
Fort Lauderdale, Antigua, St Thomas, Tortola, San Juan, Relaxaway Half Moon Cay, Fort Lauderdale, Relaxaway Half Moon Cay, Aruba, Cartagena, Panama Canal And Gatun Lake, Gatun Lake And Panama Canal, Enter Panama Canal Cristobal, Gatun Lake, Exit Panama Canal Cristobal, Colon, Limon, Grand Cayman, Fort Lauderdale
from
$3,954.00
(USD)
Per Person
Inside
$3,954.00
Cat: N
$188.29/Night
Outside
$4,354.00
Cat: HH
$207.33/Night
Balcony
$5,844.00
Cat: VH
$278.29/Night
Suite
$8,724.00
Cat: SZ
$415.43/Night
Departing on Nov 07, 2026 on the Silver Shadow
Nights: 11
Dates: Nov 07, 2026 through Nov 18, 2026
Itinerary:
Miami, Fl, Day at sea, San Juan, St John, Gustavia, St Barthelemy, Basseterre, St. Kitts, Little Bay, Montserrat, Jost Van Dyke (British Virgin Islands), Day at sea, Miami, Fl
from
$7,150.00
(USD)
Per Person
Suite
$7,150.00
Cat: VI
$650.00/Night
Transoceanic Cruise Miami to Lisbon
Departing on Mar 23, 2027 on the Silver Nova
Nights: 14
Dates: Mar 23, 2027 through Apr 06, 2027
Ship: Silver Nova
Itinerary:
Miami, Fl, Day at sea, Royal Naval Dockyard, Bermuda, Day at sea, Funchal, Madeira, Day at sea, Lisbon
from
$8,200.00
(USD)
Per Person
Suite
$8,200.00
Cat: CV
$585.71/Night
Departing on Mar 24, 2027 on the Oosterdam
Nights: 16
Dates: Mar 24, 2027 through Apr 09, 2027
Ship: Oosterdam
Itinerary:
San Antonio, Coquimbo, General San Martin, Callao (Lima), Trujillo (Salaverry), Manta, Fuerte Amador, Panama Canal (Cruising), Fuerte Amador, Enter Panama Canal Balboa, Exit Panama Canal Cristobal, Grand Cayman, Fort Lauderdale
from
$3,339.00
(USD)
Per Person
Inside
$3,339.00
Cat: N
$208.69/Night
Outside
$3,539.00
Cat: HH
$221.19/Night
Balcony
$5,039.00
Cat: VH
$314.94/Night
Suite
$5,839.00
Cat: SZ
$364.94/Night
15-Day Panama Canal San Diego to Miami
Departing on Jan 30, 2027 on the Zuiderdam
Nights: 15
Dates: Jan 30, 2027 through Feb 14, 2027
Ship: Zuiderdam
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, Cartagena, Relaxaway Half Moon Cay, Miami
from
$2,724.00
(USD)
Per Person
Inside
$2,724.00
Cat: N
$181.60/Night
Outside
$3,024.00
Cat: HH
$201.60/Night
Balcony
$4,974.00
Cat: VH
$331.60/Night
Suite
$6,224.00
Cat: SZ
$414.93/Night
Departing on Nov 28, 2026 on the Zuiderdam
Nights: 7
Dates: Nov 28, 2026 through Dec 05, 2026
Ship: Zuiderdam
Itinerary:
Miami, Relaxaway Half Moon Cay, Amber Cove, Grand Turk, Nassau, Miami
from
$1,084.00
(USD)
Per Person
Inside
$1,084.00
Cat: N
$154.86/Night
Outside
$1,114.00
Cat: HH
$159.14/Night
Balcony
$1,254.00
Cat: VH
$179.14/Night
Suite
$1,654.00
Cat: SZ
$236.29/Night
Tropical Sparkle & Holiday Cheer 17 nights on board Seven Seas Splendor
Departing on Dec 11, 2026 on the Seven Seas Splendor
Nights: 17
Dates: Dec 11, 2026 through Dec 28, 2026
Itinerary:
Houston (Galveston), Cruising The Gulf, Cruising The Caribbean Sea, Montego Bay, Ocho Rios, Cruising The Caribbean Sea, Punta Cana, San Juan, Tortola, Philipsburg, Gustavia, St. John's, Cruising The Caribbean Sea, George Town, Cruising The Gulf, Houston (Galveston)
from
$12,799.00
(USD)
Per Person
Suite
$12,799.00
Cat: F1
$752.88/Night
Departing on Feb 07, 2027 on the Silver Ray
Nights: 12
Dates: Feb 07, 2027 through Feb 19, 2027
Ship: Silver Ray
Itinerary:
Miami, Fl, Day at sea, San Juan, St John, Basseterre, St. Kitts, Gustavia, St Barthelemy, St. John's, Deshaies, Roseau, Fort-De-France, Bequia, Bridgetown
from
$9,200.00
(USD)
Per Person
Suite
$9,200.00
Cat: CV
$766.67/Night
No Image Available
Nights: 11
Dates: Dec 22, 2026 through Jan 02, 2027
Itinerary:
Fort Lauderdale, St Maarten, St Kitts, Roseau, St Lucia, Antigua, St Thomas, Relaxaway Half Moon Cay, Fort Lauderdale
from
$2,764.00
(USD)
Per Person
Inside
$2,764.00
Cat: N
$251.27/Night
Outside
$3,414.00
Cat: F
$310.36/Night
Balcony
$3,714.00
Cat: VH
$337.64/Night
Suite
$5,614.00
Cat: BC
$510.36/Night
Caribbean & Central America Cruise Bridgetown to San Juan
Departing on Jan 20, 2027 on the Silver Shadow
Nights: 10
Dates: Jan 20, 2027 through Jan 30, 2027
Itinerary:
Bridgetown, Canouan, Castries, Trois Ilets, Roseau, Les Saintes, Little Bay, Montserrat, Basseterre, St. Kitts, Gustavia, St Barthelemy, St John, San Juan
from
$7,150.00
(USD)
Per Person
Suite
$7,150.00
Cat: VI
$715.00/Night
New World Passage 14 nights on board Seven Seas Grandeur
Departing on Nov 08, 2026 on the Seven Seas Grandeur
Nights: 14
Dates: Nov 08, 2026 through Nov 22, 2026
Itinerary:
Rome (Civitavecchia), Cruising The Mediterranean Sea, Palma De Mallorca, Cruising The Gibraltar Straight, Cruising The Atlantic Ocean, Funchal (Madeira), Cruising The Atlantic Ocean, Royal Naval Dockyard, Cruising The Atlantic Ocean, Miami
from
$11,049.00
(USD)
Per Person
Suite
$11,049.00
Cat: E
$789.21/Night
Departing on Jan 05, 2027 on the Silver Ray
Nights: 11
Dates: Jan 05, 2027 through Jan 16, 2027
Ship: Silver Ray
Itinerary:
Miami, Fl, Day at sea, San Juan, St John, Basseterre, St. Kitts, Deshaies, St. John's, Road Town, Tortola, Day at sea, Miami, Fl
from
$8,750.00
(USD)
Per Person
Suite
$8,750.00
Cat: CV
$795.45/Night
Departing on Dec 05, 2026 on the Zuiderdam
Nights: 7
Dates: Dec 05, 2026 through Dec 12, 2026
Ship: Zuiderdam
Itinerary:
Miami, Grand Turk, San Juan, St Thomas, Relaxaway Half Moon Cay, Miami
from
$1,204.00
(USD)
Per Person
Inside
$1,204.00
Cat: N
$172.00/Night
Outside
$1,254.00
Cat: HH
$179.14/Night
Balcony
$1,354.00
Cat: VH
$193.43/Night
Suite
$1,854.00
Cat: SZ
$264.86/Night
Departing on Dec 27, 2026 on the Nieuw Statendam
Nights: 7
Dates: Dec 27, 2026 through Jan 03, 2027
Itinerary:
Fort Lauderdale, Nassau, Grand Turk, Amber Cove, Relaxaway Half Moon Cay, Fort Lauderdale
from
$1,704.00
(USD)
Per Person
Inside
$1,704.00
Cat: N
$243.43/Night
Outside
$1,854.00
Cat: F
$264.86/Night
Balcony
$2,104.00
Cat: VH
$300.57/Night
Suite
$3,054.00
Cat: BC
$436.29/Night
Departing on Jan 06, 2027 on the Silver Nova
Nights: 12
Dates: Jan 06, 2027 through Jan 18, 2027
Ship: Silver Nova
Itinerary:
Miami, Fl, Day at sea, San Juan, St John, Gustavia, St Barthelemy, Basseterre, St. Kitts, Day at sea, Oranjestad, Aruba, Willemstad, Curaçao, Kralendijk, Bonaire, Day at sea, Bridgetown
from
$5,850.00
(USD)
Per Person
Suite
$5,850.00
Cat: CV
$487.50/Night
17-Day Panama Canal Fort Lauderdale to San Diego
Departing on Apr 11, 2027 on the Nieuw Amsterdam
Nights: 17
Dates: Apr 11, 2027 through Apr 28, 2027
Itinerary:
Fort Lauderdale, Aruba, Panama Canal (Cruising), Enter Panama Canal Cristobal, Exit Panama Canal Balboa, Puntarenas, Acajutla, Puerto Quetzal, Acapulco, Puerto Vallarta, Cabo San Lucas, San Diego
from
$2,929.00
(USD)
Per Person
Inside
$2,929.00
Cat: N
$172.29/Night
Outside
$3,089.00
Cat: HH
$181.71/Night
Balcony
$4,179.00
Cat: VH
$245.82/Night
Suite
$7,429.00
Cat: SZ
$437.00/Night
Departing on Nov 18, 2026 on the Oosterdam
Nights: 16
Dates: Nov 18, 2026 through Dec 04, 2026
Ship: Oosterdam
Itinerary:
Fort Lauderdale, Grand Cayman, Panama Canal (Cruising), Enter Panama Canal Cristobal, Exit Panama Canal Balboa, Fuerte Amador, Cross Equator, Manta, Trujillo (Salaverry), Callao (Lima), General San Martin, Coquimbo, San Antonio
from
$1,749.00
(USD)
Per Person
Non-Refundable
Inside
$1,749.00
Cat: N
$109.31/Night
Suite
$3,499.00
Cat: SZ
$218.69/Night
Caribbean & Central America Cruise Bridgetown to Bridgetown
Departing on Jan 15, 2027 on the Silver Spirit
Nights: 10
Dates: Jan 15, 2027 through Jan 25, 2027
Itinerary:
Bridgetown, Bequia, Castries, St George's, Canouan, Day at sea, Kralendijk, Bonaire, Oranjestad, Aruba, Willemstad, Curaçao, Day at sea, Bridgetown
from
$5,150.00
(USD)
Per Person
Suite
$5,150.00
Cat: PA
$515.00/Night
Departing on Dec 26, 2026 on the Zuiderdam
Nights: 7
Dates: Dec 26, 2026 through Jan 02, 2027
Ship: Zuiderdam
Itinerary:
Miami, Grand Turk, San Juan, St Thomas, Relaxaway Half Moon Cay, Miami
from
$1,554.00
(USD)
Per Person
Inside
$1,554.00
Cat: N
$222.00/Night
Outside
$1,604.00
Cat: HH
$229.14/Night
Balcony
$1,854.00
Cat: VH
$264.86/Night
Suite
$2,354.00
Cat: SZ
$336.29/Night
Departing on Feb 26, 2027 on the Silver Ray
Nights: 12
Dates: Feb 26, 2027 through Mar 10, 2027
Ship: Silver Ray
Itinerary:
Bridgetown, Bequia, St George's, Fort-De-France, Deshaies, Soufrière, St. Lucia, Basseterre, St. Kitts, Philipsburg, St. Maarten, Gustavia, St Barthelemy, Anguilla, Day at sea, Miami, Fl
from
$8,900.00
(USD)
Per Person
Suite
$8,900.00
Cat: CV
$741.67/Night
No Image Available
Nights: 10
Dates: Nov 21, 2026 through Dec 01, 2026
Itinerary:
Fort Lauderdale, Relaxaway Half Moon Cay, Falmouth, Mahogany Bay, Belize City, Costa Maya, Cozumel, Fort Lauderdale
from
$799.00
(USD)
Per Person
Non-Refundable
Inside
$799.00
Cat: N
$79.90/Night
Caribbean & Central America Cruise Bridgetown to Bridgetown
Departing on Dec 05, 2026 on the Silver Spirit
Nights: 7
Dates: Dec 05, 2026 through Dec 12, 2026
Itinerary:
Bridgetown, Bequia, Fort-De-France, Deshaies, Gustavia, St Barthelemy, St. John's, Castries, Bridgetown
from
$4,550.00
(USD)
Per Person
Suite
$4,550.00
Cat: VI
$650.00/Night
Departing on Jan 29, 2027 on the Nieuw Amsterdam
Nights: 9
Dates: Jan 29, 2027 through Feb 07, 2027
Itinerary:
Fort Lauderdale, Antigua, St Thomas, Tortola, San Juan, Relaxaway Half Moon Cay, Fort Lauderdale
from
$1,734.00
(USD)
Per Person
Inside
$1,734.00
Cat: N
$192.67/Night
Outside
$1,834.00
Cat: HH
$203.78/Night
Balcony
$2,184.00
Cat: VH
$242.67/Night
Suite
$3,734.00
Cat: SZ
$414.89/Night
Departing on Feb 06, 2027 on the Silver Spirit
Nights: 12
Dates: Feb 06, 2027 through Feb 18, 2027
Itinerary:
Miami, Fl, Day at sea, San Juan, St John, Day at sea, Oranjestad, Aruba, Willemstad, Curaçao, Kralendijk, Bonaire, Day at sea, St George's, Castries, Bridgetown
from
$7,700.00
(USD)
Per Person
Suite
$7,700.00
Cat: PA
$641.67/Night
Transoceanic Cruise Lisbon to Bridgetown
Departing on Dec 09, 2026 on the Silver Nova
Nights: 12
Dates: Dec 09, 2026 through Dec 21, 2026
Ship: Silver Nova
Itinerary:
Lisbon, Day at sea, Las Palmas, Canary Islands, Day at sea, Mindelo, Day at sea, Bridgetown
from
$3,950.00
(USD)
Per Person
Suite
$3,950.00
Cat: CV
$329.17/Night
Departing on Nov 30, 2026 on the Silver Shadow
Nights: 10
Dates: Nov 30, 2026 through Dec 10, 2026
Itinerary:
Miami, Fl, Day at sea, San Juan, St John, Gustavia, St Barthelemy, Basseterre, St. Kitts, Jost Van Dyke (British Virgin Islands), Day at sea, Miami, Fl
from
$6,450.00
(USD)
Per Person
Suite
$6,450.00
Cat: VI
$645.00/Night
Departing on Oct 18, 2026 on the Nieuw Amsterdam
Nights: 12
Dates: Oct 18, 2026 through Oct 30, 2026
Itinerary:
Fort Lauderdale, Relaxaway Half Moon Cay, Aruba, Cartagena, Panama Canal And Gatun Lake, Gatun Lake And Panama Canal, Enter Panama Canal Cristobal, Gatun Lake, Exit Panama Canal Cristobal, Colon, Limon, Grand Cayman, Fort Lauderdale
from
$2,179.00
(USD)
Per Person
Inside
$2,179.00
Cat: N
$181.58/Night
Outside
$2,329.00
Cat: F
$194.08/Night
14-Day Cultural Crossing With Andalusia Barcelona to Fort Lauderdale
Departing on Nov 04, 2026 on the Oosterdam
Nights: 14
Dates: Nov 04, 2026 through Nov 18, 2026
Ship: Oosterdam
Itinerary:
Barcelona, Cartagena, Malaga, Gibraltar, Kings Wharf, Fort Lauderdale
from
$2,059.00
(USD)
Per Person
Inside
$2,059.00
Cat: MM
$147.07/Night
Outside
$2,149.00
Cat: F
$153.50/Night
Balcony
$2,349.00
Cat: VH
$167.79/Night
Suite
$3,499.00
Cat: SZ
$249.93/Night
Departing on Mar 07, 2027 on the Silver Spirit
Nights: 12
Dates: Mar 07, 2027 through Mar 19, 2027
Itinerary:
Bridgetown, Bequia, St George's, Day at sea, Willemstad, Curaçao, Oranjestad, Aruba, Kralendijk, Bonaire, Day at sea, Spanish Town, San Juan, Day at sea, Miami, Fl
from
$8,100.00
(USD)
Per Person
Suite
$8,100.00
Cat: SV
$675.00/Night
Departing on Mar 19, 2027 on the Silver Spirit
Nights: 12
Dates: Mar 19, 2027 through Mar 31, 2027
Itinerary:
Miami, Fl, Day at sea, San Juan, St John, Gustavia, St Barthelemy, Day at sea, Willemstad, Curaçao, Kralendijk, Bonaire, Day at sea, St George's, Canouan, Bridgetown
from
$6,800.00
(USD)
Per Person
Suite
$6,800.00
Cat: VI
$566.67/Night
7-Day Eastern Caribbean: Amber Cove & Bahamas Roundtrip from Fort Lauderdale
Departing on Jan 17, 2027 on the Nieuw Statendam
Nights: 7
Dates: Jan 17, 2027 through Jan 24, 2027
Itinerary:
Fort Lauderdale, Nassau, Relaxaway Half Moon Cay, Grand Turk, Amber Cove, Fort Lauderdale
from
$1,254.00
(USD)
Per Person
Inside
$1,254.00
Cat: N
$179.14/Night
Outside
$1,404.00
Cat: F
$200.57/Night
Balcony
$1,654.00
Cat: VH
$236.29/Night
Suite
$2,104.00
Cat: BC
$300.57/Night
Caribbean Celebration, 12 Nights (Q634) Roundtrip from Miami, FL, USA
Departing on Dec 17, 2026 on the Queen Elizabeth
Nights: 12
Dates: Dec 17, 2026 through Dec 29, 2026
Itinerary:
Miami, FL, USA, San Juan, Puerto Rico, Antigua, St Lucia, Saint Lucia, Barbados, Barbados, St. Maarten, Netherlands Antilles, Miami, FL, USA
The jungles of St. Lucia and St. Maarten’s unique border are among the memorable experiences in store on this 12-night Caribbean sailing on Queen Elizabeth, not to mention a Cunard Christmas on board.
from
$1,299.00
(USD)
Per Person
Inside
$1,299.00
Cat: GA
$108.25/Night
Outside
$1,299.00
Cat: FB
$108.25/Night
Balcony
$1,399.00
Cat: BF
$116.58/Night
Suite
$3,199.00
Cat: P2
$266.58/Night
New York To Los Angeles, 17 Nights (V704) New York, New York to Los Angeles, California
Departing on Jan 19, 2027 on the Queen Victoria
Nights: 17
Dates: Jan 19, 2027 through Feb 05, 2027
Itinerary:
New York, New York, Aruba, Aruba, Panama Canal, Panama, Acajutla, El Salvador, Puerto Vallarta, Mexico, Los Angeles, California
Calls in Aruba’s capital, Oranjestad, and Puerto Vallarta await on this 17-night Queen Victoria voyage. You’ll also dock overnight in Los Angeles, home of Hollywood and the star-studded Walk of Fame.
from
$2,559.00
(USD)
Per Person
Inside
$2,559.00
Cat: IA
$150.53/Night
Outside
$2,559.00
Cat: FC
$150.53/Night
Balcony
$4,059.00
Cat: BF
$238.76/Night
Departing on Nov 01, 2026 on the Resilient Lady
Nights: 7
Dates: Nov 01, 2026 through Nov 08, 2026
Itinerary:
Miami, Florida, Sailing, George Town, Sailing, Ocho Rios, Sailing, Beach Club at Bimini, Miami, Florida
This 7-night Eastern Caribbean getaway departs from Miami and spends a day sailing to your first stop, George Town, Grand Cayman. Spend the day here swimming with stingrays, soaking up the culture (and the sun), and witnessing ocean wildlife through a glass bottom boat.
from
$693.00
(USD)
Per Person
Inside
$693.00
Cat: IZ
$99.00/Night
Outside
$763.00
Cat: VZ
$109.00/Night
Balcony
$833.00
Cat: TZ
$119.00/Night
Suite
$3,003.00
Cat: RZ
$429.00/Night
Departing on Oct 03, 2026 on the Resilient Lady
Nights: 5
Dates: Oct 03, 2026 through Oct 08, 2026
Itinerary:
Miami, Sailing, Grand Turk, Sailing, Beach Club at Bimini, Miami
Miami, Grand Turk (& back) sails to the snow-white shores of the Grand Turk for plenty of time to lay by the beach and explore the city streets. Add a full day spent at the exclusive Beach Club in Bimini, Bahamas.
from
$795.00
(USD)
Per Person
Inside
$895.00
Cat: IZ
$179.00/Night
Outside
$795.00
Cat: VZ
$159.00/Night
Balcony
$995.00
Cat: TZ
$199.00/Night
Suite
$2,395.00
Cat: RZ
$479.00/Night
Departing on Oct 31, 2026 on the Scarlet Lady
Nights: 5
Dates: Oct 31, 2026 through Nov 05, 2026
Ship: Scarlet Lady
Itinerary:
Miami, Florida, Sailing, Cozumel (Playa del Carmen), Sailing, Beach Club at Bimini, Miami, Florida
This 5-night excursion departs Miami and allows for a day of self-care, spooky surprises and on-board luxury while sailing to one of the most popular destinations for beach-goers and water-adventurer's alike: Cozumel. From there spend a day recuperating with a cocktail on the sun deck headed to our private beach club on the picturesque island of Bimini before returning the following day to Miami.
from
$545.00
(USD)
Per Person
Inside
$545.00
Cat: IZ
$109.00/Night
Outside
$595.00
Cat: VZ
$119.00/Night
Balcony
$645.00
Cat: TZ
$129.00/Night
Suite
$2,295.00
Cat: RZ
$459.00/Night
Departing on Dec 03, 2026 on the Scarlet Lady
Nights: 4
Dates: Dec 03, 2026 through Dec 07, 2026
Ship: Scarlet Lady
Itinerary:
Miami, Key West, Bimini Islands, Miami
Cruise from vibrant Miami to Key West for a day spent splashing around in the cerulean waters or exploring the lively downtown scene. Afterwards, you’ll head to our private Beach Club experience in Bimini, Bahamas.
from
$516.00
(USD)
Per Person
Inside
$556.00
Cat: IZ
$139.00/Night
Outside
$516.00
Cat: VZ
$129.00/Night
Balcony
$636.00
Cat: TZ
$159.00/Night
Suite
$1,756.00
Cat: RZ
$439.00/Night
Departing on Oct 25, 2026 on the Scarlet Lady
Nights: 6
Dates: Oct 25, 2026 through Oct 31, 2026
Ship: Scarlet Lady
Itinerary:
Miami, Florida, Sailing, Grand Turk, Puerto Plata, Sailing, Beach Club at Bimini, Miami, Florida
This 6-night sojourn starts in Miami and spends a day sailing to the beach-ladened city of Grand Turk, followed by a day of outdoor adventure, self-care, or utter relaxation on the beaches of Puerto Plata. Spend one more day at sea sailing to Bimini, home of our famous Beach Club at Bimini, where you can sunbathe, swim in the enormous pool, and sip perfect cocktails before returning to Miami.
from
$1,134.00
(USD)
Per Person
Inside
$1,134.00
Cat: IZ
$189.00/Night
Outside
$1,194.00
Cat: VZ
$199.00/Night
Balcony
$1,314.00
Cat: TZ
$219.00/Night
Suite
$2,775.00
Cat: RZ
$462.50/Night
Departing on Nov 14, 2026 on the Valiant Lady
Nights: 6
Dates: Nov 14, 2026 through Nov 20, 2026
Ship: Valiant Lady
Itinerary:
San Juan, Tortola Island, St. Kitts, Antigua, St. Lucia, San Juan
This 6-night voyage departs from San Juan, arriving the next day in Tortola, British Virgin Islands. Next, sail to Basseterre, St. Kitts and Nevis, where the beauty of their beaches match the vibe of the local landscape.
from
$594.00
(USD)
Per Person
Inside
$594.00
Cat: IZ
$99.00/Night
Outside
$654.00
Cat: VZ
$109.00/Night
Balcony
$714.00
Cat: TZ
$119.00/Night
Suite
$2,994.00
Cat: RZ
$499.00/Night
Departing on Nov 20, 2026 on the Valiant Lady
Nights: 8
Dates: Nov 20, 2026 through Nov 28, 2026
Ship: Valiant Lady
Itinerary:
San Juan, St. Thomas, Sailing, Willemstad, Oranjestad, Sailing, Basseterre, Philipsburg, St. Maarten, San Juan
This 8-night Thanksgiving sailing departs from San Juan, first docking at the stunning St. Thomas, U.S. Virgin Islands. After a day at sea, arrive in Willemstad, Curaçao's capital that combines European influences with Caribbean cultures (and vibrant architecture). Next, wake up in Aruba, followed by sailing to St. Kitts and Nevis, then on to St. Maarten, before returning to San Juan.
from
$792.00
(USD)
Per Person
Inside
$792.00
Cat: IZ
$99.00/Night
Outside
$872.00
Cat: VZ
$109.00/Night
Balcony
$952.00
Cat: TZ
$119.00/Night
Suite
$4,312.00
Cat: RZ
$539.00/Night
Departing on Nov 28, 2026 on the Valiant Lady
Nights: 7
Dates: Nov 28, 2026 through Dec 05, 2026
Ship: Valiant Lady
Itinerary:
San Juan, St. Thomas, Sailing, Tortola, Basseterre, St. John's, Philipsburg, St. Maarten, San Juan
This 7-night pre-holiday sailing departs San Juan, docking the next day on the colorful shores with picturesque waters of St. Thomas, US Virgin Islands. Next sail over to Tortola, followed by the bustling beach town of Basseterre, St. Kitts and Nevis. Next arrive in the epicenter of paradise, St. John's, Antigua, then over to St. Maarten, before returning to San Juan.
from
$693.00
(USD)
Per Person
Inside
$693.00
Cat: IZ
$99.00/Night
Outside
$763.00
Cat: VZ
$109.00/Night
Balcony
$833.00
Cat: TZ
$119.00/Night
Suite
$2,703.00
Cat: RZ
$386.14/Night
Departing on Nov 16, 2026 on the Resilient Lady
Nights: 6
Dates: Nov 16, 2026 through Nov 22, 2026
Itinerary:
Miami, Sailing, Costa Maya, Cozumel (Playa Del Carmen), Sailing, Beach Club at Bimini, Miami, Florida
This idyllic Caribbean getaway departs from Miami and spends a day sailing to the heart of the Yucatan Peninsula, Costa Maya, Mexico, where turquoise blue lagoons and dreamy cenotes await. The next day you'll arrive in charming Cozumel before spending a day of self-care at sea headed to the oasis of relaxation that is our private Beach Club at Bimini. The next day you'll return to majestic Miami.
from
$534.00
(USD)
Per Person
Inside
$534.00
Cat: IZ
$89.00/Night
Outside
$594.00
Cat: VZ
$99.00/Night
Balcony
$714.00
Cat: TZ
$119.00/Night
Suite
$2,394.00
Cat: RZ
$399.00/Night
Departing on Dec 05, 2026 on the Valiant Lady
Nights: 7
Dates: Dec 05, 2026 through Dec 12, 2026
Ship: Valiant Lady
Itinerary:
San Juan, Sailing, Oranjestad, Willemstad, Sailing, Fort-de-France, Basseterre, San Juan
Cruise from San Juan to the dreamiest islands in the southeast Caribbean - sailing to Aruba, Curaçao, Martinique, and St. Kitts & Nevis. With a very late-stay in Aruba, you can start your day beach-lounging and end it with a cocktail aboard a catamaran under the stars.
from
$903.00
(USD)
Per Person
Inside
$903.00
Cat: IZ
$129.00/Night
Outside
$1,043.00
Cat: VZ
$149.00/Night
Balcony
$1,113.00
Cat: TZ
$159.00/Night
Suite
$3,703.00
Cat: RZ
$529.00/Night
Departing on Dec 12, 2026 on the Valiant Lady
Nights: 7
Dates: Dec 12, 2026 through Dec 19, 2026
Ship: Valiant Lady
Itinerary:
San Juan, Philipsburg, Sailing, Bridgetown, Castries, Fort-de-France, Basseterre, San Juan
This dreamy 7-night Caribbean adventure begins in San Juan and docks the following day in St. Maarten. After spending a day of self-care at sea you'll land in Barbados, followed by St. Lucia, and stylish Martinique before arriving in Basseterre, St. Kitts - a bustling beach town known for its sprawling white sand beaches and quaint Caribbean vibes before returning to San Juan.
from
$973.00
(USD)
Per Person
Inside
$973.00
Cat: IZ
$139.00/Night
Outside
$1,043.00
Cat: VZ
$149.00/Night
Balcony
$1,183.00
Cat: TZ
$169.00/Night
Suite
$2,711.00
Cat: RZ
$387.29/Night
Departing on Nov 08, 2026 on the Resilient Lady
Nights: 8
Dates: Nov 08, 2026 through Nov 16, 2026
Itinerary:
Miami, Florida, Sailing, Puerto Plata, San Juan, Tortola, Sailing, Beach Club at Bimini, Miami, Florida
This stunning sojourn leaves Miami and sails a day to the picturesque silvers coasts, crystalline cenotes and lush jungles of Puerto Plata, Dominican Republic. Next, awake to the blissful sound of crashing waves in San Juan before arriving the next day in magical Tortola, nestled into the British Virgin Islands. Then sail two days to our private Beach Club at Bimini before returning to Miami.
from
$792.00
(USD)
Per Person
Inside
$792.00
Cat: IZ
$99.00/Night
Outside
$872.00
Cat: VZ
$109.00/Night
Balcony
$952.00
Cat: TZ
$119.00/Night
Suite
$3,512.00
Cat: RZ
$439.00/Night
Departing on Dec 26, 2026 on the Valiant Lady
Nights: 7
Dates: Dec 26, 2026 through Jan 02, 2027
Ship: Valiant Lady
Itinerary:
San Juan, Philipsburg, St. Maarten, Basseterre, Castries, Bridgetown, Sailing, St. Croix, San Juan
This 7-night sunny adventure departs from San Juan before docking the next day in Phillipsburg, St. Maarten followed by Basseterre, St. Kitts - home to some of the world's best beaches and dreamiest vacay-vibes. The next day you'll hit Castries, St. Lucia before Bridgetown, Barbados. Then spend a day relaxing on board headed to Frederiksted, St. Croix before returning to San Juan.
from
$1,533.00
(USD)
Per Person
Inside
$1,533.00
Cat: IZ
$219.00/Night
Outside
$1,603.00
Cat: VZ
$229.00/Night
Balcony
$1,743.00
Cat: TZ
$249.00/Night
Suite
$4,823.00
Cat: RZ
$689.00/Night
Departing on Jan 23, 2027 on the Valiant Lady
Nights: 6
Dates: Jan 23, 2027 through Jan 29, 2027
Ship: Valiant Lady
Itinerary:
San Juan, Tortola, Basseterre, St. John's, Castries, Sailing, San Juan
This 6-night voyage departs from San Juan, arriving the next day in Tortola, British Virgin Islands. Next, sail to Basseterre, St. Kitts and Nevis, where the beauty of their beaches match the vibe of the local landscape. Next, wake up in St. John's, a true vacationer's paradise on the island of Antigua, followed by Castries, St. Lucia, and a relaxing day at sea before returning to San Juan.
from
$894.00
(USD)
Per Person
Inside
$894.00
Cat: IZ
$149.00/Night
Outside
$894.00
Cat: VZ
$149.00/Night
Balcony
$1,014.00
Cat: TZ
$169.00/Night
Suite
$3,294.00
Cat: RZ
$549.00/Night
Departing on Oct 31, 2026 on the Valiant Lady
Nights: 7
Dates: Oct 31, 2026 through Nov 07, 2026
Ship: Valiant Lady
Itinerary:
San Juan, Willemstad, Oranjestad, Fort-de-France, Basseterre, San Juan
This spooky season sailing spends a day sailing from San Juan to Willemstad, nestled onto the picturesque shores of Curaçao, followed by the iridescent turquoise waters of nearby Oranjestad, Aruba. From there, you'll sail another day to Fort-de-France, Martinique followed by Basseterre, St. Kitts and Nevis, where you'll be greeted by warm locals & white sand beaches before returning to San Juan.
from
$693.00
(USD)
Per Person
Inside
$693.00
Cat: IZ
$99.00/Night
Outside
$763.00
Cat: VZ
$109.00/Night
Balcony
$833.00
Cat: TZ
$119.00/Night
Suite
$3,703.00
Cat: RZ
$529.00/Night
Departing on Mar 06, 2027 on the Valiant Lady
Nights: 7
Dates: Mar 06, 2027 through Mar 13, 2027
Ship: Valiant Lady
Itinerary:
San Juan, Tortola, Sailing, Bridgetown, Castries, St. John's, Philipsburg, St. Maarten, San Juan
This 7-night voyage from San Juan sails to some of the Caribbean's most stunning islands, including Barbados, St. Lucia, and Tortola. You'll also visit St. John's, Antigua - a dream destination for paradise seekers - and Philipsburg, St. Maarten. Though spanning just four city streets, each less than a mile long, Philipsburg perfectly captures the charm of a "small town with a big-city vibe."
from
$1,043.00
(USD)
Per Person
Inside
$1,043.00
Cat: IZ
$149.00/Night
Outside
$1,183.00
Cat: VZ
$169.00/Night
Balcony
$1,253.00
Cat: TZ
$179.00/Night
Suite
$3,983.00
Cat: RZ
$569.00/Night