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Showing Loading cruise vacations: All Destinations, October 2025 - December 2025
Showing 42 cruise vacations that match your search
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★
UP TO $700 OFF

Brilliant Lady Miami MerMaiden

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
£2,659£3,913
per Cabin
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea Terrace cabins from
£2,659£3,913
per Cabin
Departing on:
2025
Fri, Oct 17 - Sat, Oct 25
from £2,659Brilliant Lady's Inaugural Season

Riviera Maya: Halloween Edition

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
£902£1,174
per Cabin
5 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
£902£1,174
per Cabin
Departing on:
2025
Sun, Oct 19 - Fri, Oct 24
from £902
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EPIC SAVINGS ON ALL VOYAGES THROUGH 2027
70% off 2nd Sailor + up to $700* off
BOOK NOW

Dominican Daze: Halloween Edition

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
£1,165£1,631
per Cabin
5 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
£1,165£1,631
per Cabin
Departing on:
2025
Fri, Oct 24 - Wed, Oct 29
from £1,165

Resilient's Haunted Halloween Soirée

  • Barcelona
  • Valencia, Spain
  • Casablanca, Morocco
  • Las Palmas de Gran Canaria, Spain
  • Miami, Florida
Sea View cabins from
£2,098£3,112
per Cabin
14 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
£2,098£3,112
per Cabin
Departing on:
2025
Sun, Oct 26 - Sun, Nov 09
from £2,098

Valiant's Haunted Halloween Soirée

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
£1,024£1,406
per Cabin
4 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
£1,024£1,406
per Cabin
Departing on:
2025
Wed, Oct 29 - Sun, Nov 02
from £1,024
★
UP TO $700 OFF

Scarlet's Haunted Halloween Soirée

  • Miami, Florida
  • Roatán, Honduras
  • Costa Maya, Mexico
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
£1,049£1,361
per Cabin
7 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
£1,049£1,361
per Cabin
Departing on:
2025
Fri, Oct 31 - Fri, Nov 07
from £1,049
★
UP TO $700 OFF

Western Caribbean: From Miami to Bimini

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
£1,579£2,237
per Cabin
7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
£1,579£2,237
per Cabin
Departing on:
2025
Sat, Nov 01 - Sat, Nov 08
from £1,579Brilliant Lady's Inaugural Season

One-way to SJ: DR, St. Maarten & BVI

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • San Juan, Puerto Rico
Insider cabins from
£901£1,249
per Cabin
6 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
£901£1,249
per Cabin
Departing on:
2025
Sun, Nov 02 - Sat, Nov 08
from £901

Dominican Daze

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
£901£1,225
per Cabin
5 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
£901£1,225
per Cabin
Departing on:
2025Best Rate
Fri, Dec 05 - Wed, Dec 10
from £901
2025
Fri, Nov 07 - Wed, Nov 12
from £1,205
★
UP TO $700 OFF

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
£2,526£3,684
per Cabin
12 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
£2,526£3,684
per Cabin
Departing on:
2025
Sat, Nov 08 - Thu, Nov 20
from £2,526Brilliant Lady's Inaugural Season
★
UP TO $700 OFF

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
£1,368£1,982
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
£1,368£1,982
per Cabin
Departing on:
2025
Sat, Nov 08 - Sat, Nov 15
from £1,368

Western Caribbean Charm

  • Miami, Florida
  • Costa Maya, Mexico
  • Roatán, Honduras
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
£900£1,152
per Cabin
6 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
£900£1,152
per Cabin
Departing on:
2025
Sun, Nov 09 - Sat, Nov 15
from £900

Fire & Sunset Soirées

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
£966£1,314
per Cabin
4 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
£966£1,314
per Cabin
Departing on:
2025Best Rate
Wed, Nov 12 - Sun, Nov 16
from £966
2025
Wed, Nov 26 - Sun, Nov 30
from £1,340
2025
Wed, Dec 10 - Sun, Dec 14
from £966
★
UP TO $700 OFF

San Juan Sunrises & Dominican Dreams

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
£1,049£1,429
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
£1,049£1,429
per Cabin
Departing on:
2025
Sat, Nov 15 - Sat, Nov 22
from £1,049
★
UP TO $700 OFF

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 View cabins from
£1,722£2,534
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
£1,722£2,534
per Cabin
Departing on:
2025
Sat, Nov 15 - Sat, Nov 22
from £1,722

Riviera Maya

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
£902£1,174
per Cabin
5 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
£902£1,174
per Cabin
Departing on:
2025Best Rate
Sun, Nov 16 - Fri, Nov 21
from £902
2025
Sun, Dec 14 - Fri, Dec 19
from £902
★
UP TO $700 OFF

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
Sea View cabins from
£1,684£2,436
per Cabin
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
£1,684£2,436
per Cabin
Departing on:
2025
Thu, Nov 20 - Fri, Nov 28
from £1,684Brilliant Lady's Inaugural Season

Miami, Grand Turk (& back)

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
£1,058£1,474
per Cabin
5 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
£1,058£1,474
per Cabin
Departing on:
2025Best Rate
Sun, Nov 30 - Fri, Dec 05
from £1,058
2025
Fri, Nov 21 - Wed, Nov 26
from £1,203
2025
Fri, Dec 19 - Wed, Dec 24
from £1,956
★
UP TO $700 OFF

Cayman Coves & Jamaican Waterfalls

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
£1,049£1,423
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
£1,049£1,423
per Cabin
Departing on:
2025Best Rate
Sat, Nov 22 - Sat, Nov 29
from £1,049
2025
Sat, Dec 06 - Sat, Dec 13
from £1,049
★
UP TO $700 OFF

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
£1,119£1,597
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
£1,119£1,597
per Cabin
Departing on:
2025
Sat, Nov 22 - Sat, Nov 29
from £1,119
★
UP TO $700 OFF

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
Sea View cabins from
£1,893£2,747
per Cabin
9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
£1,893£2,747
per Cabin
Departing on:
2025
Fri, Nov 28 - Sun, Dec 07
from £1,893Brilliant Lady's Inaugural Season

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
Insider cabins from
£1,130£1,638
per Cabin
6 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
£1,130£1,638
per Cabin
Departing on:
2025
Sat, Nov 29 - Fri, Dec 05
from £1,130
★
UP TO $700 OFF

San Juan, Samaná & Bimini

  • Miami, Florida
  • San Juan, Puerto Rico
  • Samaná, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
£1,052£1,440
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
£1,052£1,440
per Cabin
Departing on:
2025
Sat, Nov 29 - Sat, Dec 06
from £1,052
★
UP TO $700 OFF

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
£1,201£1,723
per Cabin
8 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
£1,201£1,723
per Cabin
Departing on:
2025
Fri, Dec 05 - Sat, Dec 13
from £1,201
★
UP TO $700 OFF

Aruban Sunsets & Calm Cayman Days

  • Miami, Florida
  • Oranjestad, Aruba
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Insider cabins from
£1,982£2,864
per Cabin
11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
£1,982£2,864
per Cabin
Departing on:
2025
Sun, Dec 07 - Thu, Dec 18
from £1,982Brilliant Lady's Inaugural Season
★
UP TO $700 OFF

Cayman Coves & Jamaican Waterfalls

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
£1,367£1,911
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea Terrace cabins from
£1,367£1,911
per Cabin
Departing on:
2025
Sat, Dec 13 - Sat, Dec 20
from £1,367
★
UP TO $700 OFF

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
Sea View cabins from
£1,155£1,665
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
£1,155£1,665
per Cabin
Departing on:
2025
Sat, Dec 13 - Sat, Dec 20
from £1,155
★
UP TO $700 OFF

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
£1,927£2,811
per Cabin
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
£1,927£2,811
per Cabin
Departing on:
2025
Thu, Dec 18 - Fri, Dec 26
from £1,927Brilliant Lady's Inaugural Season
★
UP TO $700 OFF

Resilient Caribbean Holidays

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
£1,685£2,407
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
£1,685£2,407
per Cabin
Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from £1,685
★
UP TO $700 OFF

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
Sea View cabins from
£1,686£2,472
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
£1,686£2,472
per Cabin
Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from £1,686

Scarlet Caribbean Holidays

  • Miami, Florida
  • Nassau, Bahamas
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
£1,207£1,699
per Cabin
4 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
£1,207£1,699
per Cabin
Departing on:
2025
Wed, Dec 24 - Sun, Dec 28
from £1,207
★
UP TO $700 OFF

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
£3,378£5,056
per Cabin
9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
£3,378£5,056
per Cabin
Departing on:
2025
Fri, Dec 26 - Sun, Jan 04
from £3,378Brilliant Lady's Inaugural Season
★
UP TO $700 OFF

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
£2,735£4,015
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Insider cabins from
£2,735£4,015
per Cabin
Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from £2,735
★
UP TO $700 OFF

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
Sea View cabins from
£2,977£4,477
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
£2,977£4,477
per Cabin
Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from £2,977

Scarlet New Year's Ahoy!

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
£2,492£3,620
per Cabin
5 nights
Scarlet Lady
BOOK NOW
+ Instant Savings
70% off second Sailor
Sea View cabins from
£2,492£3,620
per Cabin
Departing on:
2025
Sun, Dec 28 - Fri, Jan 02
from £2,492
Average starting price per cabin (incl. taxes & fees)