Explore 389 cruise vacations

Showing cruise vacations: All Destinations, November 2025 - December 2025

Quick find:

2 Sailors , 1 Cabin

Insider

Dominican Daze

Miami, Florida
Puerto Plata, Dominican Republic
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$1,490~~$2,220~~

per Cabin

5 nights

Scarlet Lady

+ up to $100 free drinks

80% off second Sailor

Insider cabins from

$1,490~~$2,220~~

per Cabin

Departing on:

Fri, Nov 07 - Wed, Nov 12

from (US$)$1,490

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

$2,856~~$4,432~~

per Cabin

12 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $400 free drinks

80% off second Sailor

Insider cabins from

$2,856~~$4,432~~

per Cabin

Departing on:

Sat, Nov 08 - Thu, Nov 20

from (US$)$2,856

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

$1,386~~$2,112~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,386~~$2,112~~

per Cabin

Departing on:

Sat, Nov 08 - Sat, Nov 15

from (US$)$1,386

Western Caribbean & Bimini Beach Club

Miami, Florida
Costa Maya, Mexico
Roatán, Honduras
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$1,456~~$2,046~~

per Cabin

6 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,456~~$2,046~~

per Cabin

Departing on:

Sun, Nov 09 - Sat, Nov 15

from (US$)$1,456

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

$1,386~~$2,008~~

per Cabin

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,386~~$2,008~~

per Cabin

Departing on:

Sat, Nov 15 - Sat, Nov 22

from (US$)$1,386

Riviera Maya

Miami, Florida
Cozumel, Mexico
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$1,090~~$1,470~~

per Cabin

5 nights

Scarlet Lady

+ up to $100 free drinks

80% off second Sailor

Insider cabins from

$1,090~~$1,470~~

per Cabin

Departing on:

Sun, Nov 16 - Fri, Nov 21

from (US$)$1,090

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

$2,300~~$3,580~~

per Cabin

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$2,300~~$3,580~~

per Cabin

Departing on:

Thu, Nov 20 - Fri, Nov 28

from (US$)$2,300

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

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,386~~$1,998~~

per Cabin

Departing on:

Sat, Nov 22 - Sat, Nov 29

from (US$)$1,386

Sat, Dec 06 - Sat, Dec 13

from (US$)$1,386

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

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,386~~$2,110~~

per Cabin

Departing on:

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

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,962~~$3,000~~

per Cabin

Departing on:

Fri, Nov 28 - Sun, Dec 07

from (US$)$1,962

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

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,386~~$2,022~~

per Cabin

Departing on:

Sat, Nov 29 - Sat, Dec 06

from (US$)$1,386

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

8 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,584~~$2,440~~

per Cabin

Departing on:

Fri, Dec 05 - Sat, Dec 13

from (US$)$1,584

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

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $400 free drinks

80% off second Sailor

Insider cabins from

$2,532~~$3,918~~

per Cabin

Departing on:

Sun, Dec 07 - Thu, Dec 18

from (US$)$2,532

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

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,386~~$1,998~~

per Cabin

Departing on:

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

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,412~~$2,170~~

per Cabin

Departing on:

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

Insider cabins from

$2,064~~$3,192~~

per Cabin

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$2,064~~$3,192~~

per Cabin

Departing on:

Thu, Dec 18 - Fri, Dec 26

from (US$)$2,064

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

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,946~~$2,942~~

per Cabin

Departing on:

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

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,946~~$3,046~~

per Cabin

Departing on:

Sat, Dec 20 - Sat, Dec 27

from (US$)$1,946

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

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$3,942~~$6,340~~

per Cabin

Departing on:

Fri, Dec 26 - Sun, Jan 04

from (US$)$3,942

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

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$3,616~~$5,712~~

per Cabin

Departing on:

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

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$3,346~~$5,406~~

per Cabin

Departing on:

Sat, Dec 27 - Sat, Jan 03

from (US$)$3,346