Currency, current value
$USD

Explore 385 cruise vacations

Showing Loading cruise vacations: All Destinations, November 2025 - January 2026
Showing 49 cruise vacations that match your search
LoadingLoadingLoading
Loading
Loading

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
$3,336$5,232
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
$3,336$5,232
per Cabin
Departing on:
2025
Sat, Nov 08 - Thu, Nov 20
from (US$)$3,336Brilliant 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
$1,944$3,042
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,944$3,042
per Cabin
Departing on:
2025
Sat, Nov 08 - Sat, Nov 15
from (US$)$1,944

Fire & Sunset Soirées

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$1,192$1,728
per Cabin
Loading
4 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Sea View cabins from
$1,192$1,728
per Cabin
Loading
Departing on:
2026Best Rate
Wed, Jan 07 - Sun, Jan 11
from (US$)$1,192
2025
Wed, Nov 12 - Sun, Nov 16
from (US$)$4,312
Only suites remaining
2025
Wed, Nov 26 - Sun, Nov 30
from (US$)$3,992
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
$2,876$4,606
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Sea Terrace cabins from
$2,876$4,606
per Cabin
Loading
Departing on:
2025
Sat, Nov 15 - Sat, Nov 22
from (US$)$2,876

Riviera Maya

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$990$1,302
per Cabin
Loading
5 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Insider cabins from
$990$1,302
per Cabin
Loading
Departing on:
2025Best Rate
Sun, Nov 16 - Fri, Nov 21
from (US$)$990
2025
Sun, Dec 14 - Fri, Dec 19
from (US$)$1,390
2026
Sun, Jan 11 - Fri, Jan 16
from (US$)$1,290

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
$2,064$3,188
per Cabin
Loading
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$2,064$3,188
per Cabin
Loading
Departing on:
2025
Thu, Nov 20 - Fri, Nov 28
from (US$)$2,064Brilliant 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
$1,590$2,402
per Cabin
Loading
5 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Sea View cabins from
$1,590$2,402
per Cabin
Loading
Departing on:
2025Best Rate
Sun, Nov 30 - Fri, Dec 05
from (US$)$1,590
2025
Fri, Nov 21 - Wed, Nov 26
from (US$)$4,990
Only suites remaining
2025
Fri, Dec 19 - Wed, Dec 24
from (US$)$1,890

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
$1,386$2,110
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,386$2,110
per Cabin
Loading
Departing on:
2025
Sat, Nov 22 - Sat, Nov 29
from (US$)$1,386

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
$1,962$3,000
per Cabin
Loading
9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,962$3,000
per Cabin
Loading
Departing on:
2025
Fri, Nov 28 - Sun, Dec 07
from (US$)$1,962Brilliant 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
$1,386$2,022
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,386$2,022
per Cabin
Loading
Departing on:
2025Best Rate
Sat, Nov 29 - Sat, Dec 06
from (US$)$1,386
2026
Sat, Jan 17 - Sat, Jan 24
from (US$)$1,806

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
$2,008$3,184
per Cabin
Loading
6 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Sea Terrace cabins from
$2,008$3,184
per Cabin
Loading
Departing on:
2025
Sat, Nov 29 - Fri, Dec 05
from (US$)$2,008

Dominican Daze

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$1,490$2,220
per Cabin
Loading
5 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Sea View cabins from
$1,490$2,220
per Cabin
Loading
Departing on:
2025Best Rate
Fri, Dec 05 - Wed, Dec 10
from (US$)$1,490
2026
Fri, Jan 02 - Wed, Jan 07
from (US$)$1,490
2026
Fri, Jan 30 - Wed, Feb 04
from (US$)$1,590

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
$1,584$2,440
per Cabin
Loading
8 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,584$2,440
per Cabin
Loading
Departing on:
2025
Fri, Dec 05 - Sat, Dec 13
from (US$)$1,584

Cayman Coves & Jamaican Waterfalls

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,386$1,998
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,386$1,998
per Cabin
Loading
Departing on:
2025Best Rate
Sat, Dec 06 - Sat, Dec 13
from (US$)$1,386
2026
Sat, Jan 24 - Sat, Jan 31
from (US$)$1,666

Aruban Sunsets & Calm Cayman Days

  • Miami, Florida
  • Oranjestad, Aruba
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Insider cabins from
$2,532$3,918
per Cabin
Loading
11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $400 free drinks
80% off second Sailor
Insider cabins from
$2,532$3,918
per Cabin
Loading
Departing on:
2025
Sun, Dec 07 - Thu, Dec 18
from (US$)$2,532Brilliant 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
$1,386$1,998
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,386$1,998
per Cabin
Loading
Departing on:
2025
Sat, Dec 13 - Sat, Dec 20
from (US$)$1,386

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
$1,412$2,170
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,412$2,170
per Cabin
Loading
Departing on:
2025
Sat, Dec 13 - Sat, Dec 20
from (US$)$1,412

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
$2,544$3,992
per Cabin
Loading
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Sea View cabins from
$2,544$3,992
per Cabin
Loading
Departing on:
2025
Thu, Dec 18 - Fri, Dec 26
from (US$)$2,544Brilliant 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
$1,946$2,942
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,946$2,942
per Cabin
Loading
Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from (US$)$1,946

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
$1,946$3,046
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,946$3,046
per Cabin
Loading
Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from (US$)$1,946

Scarlet Caribbean Holidays

  • Miami, Florida
  • Nassau, Bahamas
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
$1,912$2,930
per Cabin
Loading
4 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Sea Terrace cabins from
$1,912$2,930
per Cabin
Loading
Departing on:
2025
Wed, Dec 24 - Sun, Dec 28
from (US$)$1,912

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
$3,942$6,340
per Cabin
Loading
9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$3,942$6,340
per Cabin
Loading
Departing on:
2025
Fri, Dec 26 - Sun, Jan 04
from (US$)$3,942Brilliant 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
$3,616$5,712
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$3,616$5,712
per Cabin
Loading
Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from (US$)$3,616

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
$3,346$5,406
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$3,346$5,406
per Cabin
Loading
Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from (US$)$3,346

Scarlet New Year's Ahoy!

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$3,290$5,136
per Cabin
Loading
5 nights
Scarlet Lady
BOOK NOW
+ up to $100 free drinks
80% off second Sailor
Sea View cabins from
$3,290$5,136
per Cabin
Loading
Departing on:
2025
Sun, Dec 28 - Fri, Jan 02
from (US$)$3,290

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
$1,806$2,834
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,806$2,834
per Cabin
Loading
Departing on:
2026
Sat, Jan 03 - Sat, Jan 10
from (US$)$1,806

Cozumel, Grand Cayman & Bimini

  • Miami, Florida
  • George Town, Grand Cayman
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,386$1,930
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,386$1,930
per Cabin
Loading
Departing on:
2026
Sat, Jan 03 - Sat, Jan 10
from (US$)$1,386

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
$3,996$6,348
per Cabin
Loading
11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ up to $400 free drinks
80% off second Sailor
Sea View cabins from
$3,996$6,348
per Cabin
Loading
Departing on:
2026
Sun, Jan 04 - Thu, Jan 15
from (US$)$3,996Brilliant 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
$1,386$2,006
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,386$2,006
per Cabin
Loading
Departing on:
2026
Sat, Jan 10 - Sat, Jan 17
from (US$)$1,386

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
$1,526$2,382
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,526$2,382
per Cabin
Loading
Departing on:
2026
Sat, Jan 10 - Sat, Jan 17
from (US$)$1,526

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
$1,526$2,366
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,526$2,366
per Cabin
Loading
Departing on:
2026
Sat, Jan 17 - Sat, Jan 24
from (US$)$1,526

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
$1,666$2,594
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,666$2,594
per Cabin
Loading
Departing on:
2026
Sat, Jan 24 - Sat, Jan 31
from (US$)$1,666

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
$2,388$3,700
per Cabin
Loading
6 nights
Brilliant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Sea View cabins from
$2,388$3,700
per Cabin
Loading
Departing on:
2026
Mon, Jan 26 - Sun, Feb 01
from (US$)$2,388

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
$1,526$2,340
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,526$2,340
per Cabin
Loading
Departing on:
2026
Sat, Jan 31 - Sat, Feb 07
from (US$)$1,526

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
$1,386$2,026
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ up to $300 free drinks
80% off second Sailor
Insider cabins from
$1,386$2,026
per Cabin
Loading
Departing on:
2026
Sat, Jan 31 - Sat, Feb 07
from (US$)$1,386
Average starting price per cabin (incl. taxes & fees)