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Explore 385 cruise vacations

Showing Loading cruise vacations: All Destinations, November 2025 - January 2026
Showing 49 cruise vacations that match your search
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Colorful Curaçao to the Charming Caymans

  • Miami, Florida
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Sea View cabins from
A$5,203A$8,159
per Cabin
12 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $400 free drinks
80% off second Sailor
Sea View cabins from
A$5,203A$8,159
per Cabin
Departing on:
2025
Sat, Nov 08 - Thu, Nov 20
from (A$)$5,203Brilliant Lady's Inaugural Season

Saint (Isles) & Seas of the Caribbean

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Bridgetown, Barbados
  • Castries, St. Lucia
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
A$3,031A$4,743
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
A$3,031A$4,743
per Cabin
Departing on:
2025
Sat, Nov 08 - Sat, Nov 15
from (A$)$3,031

Fire & Sunset Soirées

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
A$1,859A$2,695
per Cabin
4 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Sea View cabins from
A$1,859A$2,695
per Cabin
Departing on:
2026Best Rate
Wed, Jan 07 - Sun, Jan 11
from (A$)$1,859
2025
Wed, Nov 12 - Sun, Nov 16
from (A$)$6,723
Only suites remaining
2025
Wed, Nov 26 - Sun, Nov 30
from (A$)$6,225
Only suites remaining

Sunny Miles of Tropical Isles

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Bridgetown, Barbados
  • Castries, St. Lucia
  • Fort-de-France, Martinique
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
Sea Terrace cabins from
A$4,481A$7,179
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Sea Terrace cabins from
A$4,481A$7,179
per Cabin
Departing on:
2025
Sat, Nov 15 - Sat, Nov 22
from (A$)$4,481

Riviera Maya

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
A$1,544A$2,030
per Cabin
5 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Insider cabins from
A$1,544A$2,030
per Cabin
Departing on:
2025Best Rate
Sun, Nov 16 - Fri, Nov 21
from (A$)$1,544
2025
Sun, Dec 14 - Fri, Dec 19
from (A$)$2,168
2026
Sun, Jan 11 - Fri, Jan 16
from (A$)$2,010

Sunny San Juan & Isles of Beach Miles

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • St. Croix, U.S. Virgin Islands
  • Miami, Florida
Insider cabins from
A$3,220A$4,972
per Cabin
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
A$3,220A$4,972
per Cabin
Departing on:
2025
Thu, Nov 20 - Fri, Nov 28
from (A$)$3,220Brilliant Lady's Inaugural Season

Miami, Grand Turk (& back)

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
A$2,480A$3,746
per Cabin
5 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Sea View cabins from
A$2,480A$3,746
per Cabin
Departing on:
2025Best Rate
Sun, Nov 30 - Fri, Dec 05
from (A$)$2,480
2025
Fri, Nov 21 - Wed, Nov 26
from (A$)$7,779
Only suites remaining
2025
Fri, Dec 19 - Wed, Dec 24
from (A$)$2,946

Thanksgiving in the Lesser Antilles

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Basseterre, St. Kitts and Nevis
  • St. John's, Antigua
  • Castries, St. Lucia
  • Charlotte Amalie, St. Thomas
  • San Juan, Puerto Rico
Insider cabins from
A$2,162A$3,290
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
A$2,162A$3,290
per Cabin
Departing on:
2025
Sat, Nov 22 - Sat, Nov 29
from (A$)$2,162

Antigua Waves & Grand Turk Caves

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • St. John's, Antigua
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
  • Miami, Florida
Insider cabins from
A$3,059A$4,677
per Cabin
9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
A$3,059A$4,677
per Cabin
Departing on:
2025
Fri, Nov 28 - Sun, Dec 07
from (A$)$3,059Brilliant Lady's Inaugural Season

Eastern Caribbean & Bimini Beach Club

  • Miami, Florida
  • San Juan, Puerto Rico
  • Samaná, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
A$2,161A$3,153
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
A$2,161A$3,153
per Cabin
Departing on:
2025Best Rate
Sat, Nov 29 - Sat, Dec 06
from (A$)$2,161
2026
Sat, Jan 17 - Sat, Jan 24
from (A$)$2,818

San Juan to Barbados & the St. Isles

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • Roseau, Dominica
  • Bridgetown, Barbados
  • San Juan, Puerto Rico
Sea Terrace cabins from
A$3,128A$4,962
per Cabin
6 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Sea Terrace cabins from
A$3,128A$4,962
per Cabin
Departing on:
2025
Sat, Nov 29 - Fri, Dec 05
from (A$)$3,128

Dominican Daze

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
A$2,322A$3,470
per Cabin
5 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Sea View cabins from
A$2,322A$3,470
per Cabin
Departing on:
2026Best Rate
Fri, Jan 02 - Wed, Jan 07
from (A$)$2,322
2025
Fri, Dec 05 - Wed, Dec 10
from (A$)$2,323
2026
Fri, Jan 30 - Wed, Feb 04
from (A$)$2,478

Nicky Jam x Virgin Voyages

  • San Juan, Puerto Rico
  • Willemstad, Curaçao
  • Oranjestad, Aruba
  • Roseau, Dominica
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
A$2,472A$3,806
per Cabin
8 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
A$2,472A$3,806
per Cabin
Departing on:
2025
Fri, Dec 05 - Sat, Dec 13
from (A$)$2,472

Cayman Coves & Jamaican Waterfalls

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
A$2,161A$3,115
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
A$2,161A$3,115
per Cabin
Departing on:
2025Best Rate
Sat, Dec 06 - Sat, Dec 13
from (A$)$2,161
2026
Sat, Jan 24 - Sat, Jan 31
from (A$)$2,598

Aruban Sunsets & Calm Cayman Days

  • Miami, Florida
  • Oranjestad, Aruba
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Insider cabins from
A$3,947A$6,109
per Cabin
11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $400 free drinks
80% off second Sailor
Insider cabins from
A$3,947A$6,109
per Cabin
Departing on:
2025
Sun, Dec 07 - Thu, Dec 18
from (A$)$3,947Brilliant Lady's Inaugural Season

Cayman Coves & Jamaican Waterfalls

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
A$2,161A$3,115
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
A$2,161A$3,115
per Cabin
Departing on:
2025
Sat, Dec 13 - Sat, Dec 20
from (A$)$2,161

St. Lucia, St. Maarten, Barbados & More

  • San Juan, Puerto Rico
  • Basseterre, St. Kitts and Nevis
  • Castries, St. Lucia
  • Roseau, Dominica
  • Bridgetown, Barbados
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
A$2,200A$3,382
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
A$2,200A$3,382
per Cabin
Departing on:
2025
Sat, Dec 13 - Sat, Dec 20
from (A$)$2,200

Brilliant Caribbean Holidays

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Samaná, Dominican Republic
  • Miami, Florida
Sea View cabins from
A$3,967A$6,225
per Cabin
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Sea View cabins from
A$3,967A$6,225
per Cabin
Departing on:
2025
Thu, Dec 18 - Fri, Dec 26
from (A$)$3,967Brilliant Lady's Inaugural Season

Resilient Caribbean Holidays

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
A$3,036A$4,588
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
A$3,036A$4,588
per Cabin
Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from (A$)$3,036

Valiant Caribbean Holidays

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • St. John's, Antigua
  • Castries, St. Lucia
  • Tortola, British Virgin Islands
  • San Juan, Puerto Rico
Insider cabins from
A$3,034A$4,750
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
A$3,034A$4,750
per Cabin
Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from (A$)$3,034

Scarlet Caribbean Holidays

  • Miami, Florida
  • Nassau, Bahamas
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
A$3,408A$5,280
per Cabin
4 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Sea Terrace cabins from
A$3,408A$5,280
per Cabin
Departing on:
2025
Wed, Dec 24 - Sun, Dec 28
from (A$)$3,408

Brilliant New Year's Ahoy!

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
  • Miami, Florida
Insider cabins from
A$6,148A$9,886
per Cabin
9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
A$6,148A$9,886
per Cabin
Departing on:
2025
Fri, Dec 26 - Sun, Jan 04
from (A$)$6,148Brilliant Lady's Inaugural Season

Resilient New Year's Ahoy!

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
A$5,635A$8,905
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
A$5,635A$8,905
per Cabin
Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from (A$)$5,635

Valiant New Year’s Ahoy!

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • Castries, St. Lucia
  • Bridgetown, Barbados
  • St. Croix, U.S. Virgin Islands
  • San Juan, Puerto Rico
Insider cabins from
A$5,217A$8,429
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
A$5,217A$8,429
per Cabin
Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from (A$)$5,217

Scarlet New Year's Ahoy!

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
A$5,130A$8,008
per Cabin
5 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Sea View cabins from
A$5,130A$8,008
per Cabin
Departing on:
2025
Sun, Dec 28 - Fri, Jan 02
from (A$)$5,130

Aruban Sights & Antiguan Nights

  • San Juan, Puerto Rico
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
A$2,816A$4,418
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
A$2,816A$4,418
per Cabin
Departing on:
2026
Sat, Jan 03 - Sat, Jan 10
from (A$)$2,816

Cozumel, Grand Cayman & Bimini

  • Miami, Florida
  • George Town, Grand Cayman
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
A$2,162A$3,010
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
A$2,162A$3,010
per Cabin
Departing on:
2026
Sat, Jan 03 - Sat, Jan 10
from (A$)$2,162

Aruba, Bonaire, Colombia, Jamaica & More

  • Miami, Florida
  • Oranjestad, Aruba
  • Kralendijk, Bonaire
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Sea View cabins from
A$6,229A$9,895
per Cabin
11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $400 free drinks
80% off second Sailor
Sea View cabins from
A$6,229A$9,895
per Cabin
Departing on:
2026
Sun, Jan 04 - Thu, Jan 15
from (A$)$6,229Brilliant Lady's Inaugural Season

Cayman Isles & Jamaican Miles

  • Miami, Florida
  • George Town, Grand Cayman
  • Ocho Rios, Jamaica
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
A$2,162A$3,128
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
A$2,162A$3,128
per Cabin
Departing on:
2026
Sat, Jan 10 - Sat, Jan 17
from (A$)$2,162

Virgin Island Views & Saint Isle Blues

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Bridgetown, Barbados
  • Kingstown, St. Vincent
  • Basseterre, St. Kitts and Nevis
  • St. Croix, U.S. Virgin Islands
  • San Juan, Puerto Rico
Insider cabins from
A$2,381A$3,715
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
A$2,381A$3,715
per Cabin
Departing on:
2026
Sat, Jan 10 - Sat, Jan 17
from (A$)$2,381

St. Kitts, Barbados, Martinique & More

  • San Juan, Puerto Rico
  • Basseterre, St. Kitts and Nevis
  • Bridgetown, Barbados
  • Fort-de-France, Martinique
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
A$2,382A$3,690
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
A$2,382A$3,690
per Cabin
Departing on:
2026
Sat, Jan 17 - Sat, Jan 24
from (A$)$2,382

Barbados, Antigua, BVI & More

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Bridgetown, Barbados
  • Fort-de-France, Martinique
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
A$2,598A$4,044
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
A$2,598A$4,044
per Cabin
Departing on:
2026
Sat, Jan 24 - Sat, Jan 31
from (A$)$2,598

Grand Turk, Puerto Plata & Bimini

  • Miami, Florida
  • The Beach Club at Bimini, Bahamas
  • Puerto Plata, Dominican Republic
  • Grand Turk, Turks and Caicos
  • Miami, Florida
Sea View cabins from
A$3,724A$5,770
per Cabin
6 nights
Brilliant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Sea View cabins from
A$3,724A$5,770
per Cabin
Departing on:
2026
Mon, Jan 26 - Sun, Feb 01
from (A$)$3,724

Antigua & the St. Isles

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • St. John's, Antigua
  • Castries, St. Lucia
  • Charlotte Amalie, St. Thomas
  • San Juan, Puerto Rico
Insider cabins from
A$2,382A$3,650
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
A$2,382A$3,650
per Cabin
Departing on:
2026
Sat, Jan 31 - Sat, Feb 07
from (A$)$2,382

San Juan Sunrises & Dominican Dreams

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
A$2,160A$3,158
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
A$2,160A$3,158
per Cabin
Departing on:
2026
Sat, Jan 31 - Sat, Feb 07
from (A$)$2,160
Average starting price per cabin (incl. taxes & fees)