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Explore 390 cruise vacations

Showing Loading cruise vacations: All Destinations, November 2025 - December 2025
Showing 34 cruise vacations that match your search
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Dominican Daze

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
£1,129£1,681
per Cabin
5 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Insider cabins from
£1,129£1,681
per Cabin
Departing on:
2025Best Rate
Fri, Nov 07 - Wed, Nov 12
from £1,129
2025
Fri, Dec 05 - Wed, Dec 10
from £1,129

Colorful Curaçao to the Charming Caymans

  • Miami, Florida
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Insider cabins from
£2,164£3,356
per Cabin
12 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $400 free drinks
80% off second Sailor
Insider cabins from
£2,164£3,356
per Cabin
Departing on:
2025
Sat, Nov 08 - Thu, Nov 20
from £2,164Brilliant 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
£1,052£1,600
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
£1,052£1,600
per Cabin
Departing on:
2025
Sat, Nov 08 - Sat, Nov 15
from £1,052

Western Caribbean & Bimini Beach Club

  • Miami, Florida
  • Costa Maya, Mexico
  • Roatán, Honduras
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
£1,102£1,548
per Cabin
6 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
£1,102£1,548
per Cabin
Departing on:
2025
Sun, Nov 09 - Sat, Nov 15
from £1,102

Fire & Sunset Soirées

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
£1,026£1,498
per Cabin
4 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Sea View cabins from
£1,026£1,498
per Cabin
Departing on:
2025Best Rate
Wed, Dec 10 - Sun, Dec 14
from £1,026
2025
Wed, Nov 12 - Sun, Nov 16
from £1,086
2025
Wed, Nov 26 - Sun, Nov 30
from £3,024
Only suites remaining

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£1,519
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
£1,049£1,519
per Cabin
Departing on:
2025
Sat, Nov 15 - Sat, Nov 22
from £1,049

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
£2,176£3,486
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Sea Terrace cabins from
£2,176£3,486
per Cabin
Departing on:
2025
Sat, Nov 15 - Sat, Nov 22
from £2,176

Riviera Maya

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
£828£1,114
per Cabin
5 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Insider cabins from
£828£1,114
per Cabin
Departing on:
2025Best Rate
Sun, Nov 16 - Fri, Nov 21
from £828
2025
Sun, Dec 14 - Fri, Dec 19
from £1,054

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£2,616
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
£1,684£2,616
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
Sea View cabins from
£1,206£1,820
per Cabin
5 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Sea View cabins from
£1,206£1,820
per Cabin
Departing on:
2025Best Rate
Sun, Nov 30 - Fri, Dec 05
from £1,206
2025
Fri, Nov 21 - Wed, Nov 26
from £1,595
2025
Fri, Dec 19 - Wed, Dec 24
from £1,432

Cayman Coves & Jamaican Waterfalls

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
£1,051£1,513
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
£1,051£1,513
per Cabin
Departing on:
2025Best Rate
Sat, Nov 22 - Sat, Nov 29
from £1,051
2025
Sat, Dec 06 - Sat, Dec 13
from £1,051

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
£1,051£1,599
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
£1,051£1,599
per Cabin
Departing on:
2025
Sat, Nov 22 - Sat, Nov 29
from £1,051

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
£1,487£2,271
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
£1,487£2,271
per Cabin
Departing on:
2025
Fri, Nov 28 - Sun, Dec 07
from £1,487Brilliant 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
£1,050£1,532
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
£1,050£1,532
per Cabin
Departing on:
2025
Sat, Nov 29 - Sat, Dec 06
from £1,050

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
RockStar Quarters suites from
£3,360
per Cabin
6 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
RockStar Quarters suites from
£3,360
per Cabin
Departing on:
2025
Sat, Nov 29 - Fri, Dec 05
from £3,360
Only suites remaining

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£1,847
per Cabin
8 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
£1,201£1,847
per Cabin
Departing on:
2025
Fri, Dec 05 - Sat, Dec 13
from £1,201

Aruban Sunsets & Calm Cayman Days

  • Miami, Florida
  • Oranjestad, Aruba
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Insider cabins from
£1,918£2,966
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
£1,918£2,966
per Cabin
Departing on:
2025
Sun, Dec 07 - Thu, Dec 18
from £1,918Brilliant 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
£1,051£1,513
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
£1,051£1,513
per Cabin
Departing on:
2025
Sat, Dec 13 - Sat, Dec 20
from £1,051

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
£1,067£1,641
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
£1,067£1,641
per Cabin
Departing on:
2025
Sat, Dec 13 - Sat, Dec 20
from £1,067

Brilliant Caribbean Holidays

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Samaná, Dominican Republic
  • Miami, Florida
Insider cabins from
£1,563£2,417
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
£1,563£2,417
per Cabin
Departing on:
2025
Thu, Dec 18 - Fri, Dec 26
from £1,563Brilliant 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
£1,475£2,227
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
£1,475£2,227
per Cabin
Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from £1,475

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
£1,474£2,306
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
£1,474£2,306
per Cabin
Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from £1,474

Scarlet Caribbean Holidays

  • Miami, Florida
  • Nassau, Bahamas
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
£1,657£2,565
per Cabin
4 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Sea Terrace cabins from
£1,657£2,565
per Cabin
Departing on:
2025
Wed, Dec 24 - Sun, Dec 28
from £1,657

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
£2,986£4,800
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
£2,986£4,800
per Cabin
Departing on:
2025
Fri, Dec 26 - Sun, Jan 04
from £2,986Brilliant 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
£2,737£4,323
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
£2,737£4,323
per Cabin
Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from £2,737

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
£2,533£4,091
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
£2,533£4,091
per Cabin
Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from £2,533

Scarlet New Year's Ahoy!

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
£2,492£3,888
per Cabin
5 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Sea View cabins from
£2,492£3,888
per Cabin
Departing on:
2025
Sun, Dec 28 - Fri, Jan 02
from £2,492
Average starting price per cabin (incl. taxes & fees)