Explore 389 cruise vacations

Fri, Jan 02 - Wed, Jan 07

+ up to $100 free drinks

80% off second Sailor

Sea View cabins from

CA$2,119~~CA$3,167~~

per Cabin

Departing on:

2026Best Rate

from (CA$)$2,119

Fri, Nov 07 - Wed, Nov 12

from (CA$)$3,950

Fri, Dec 05 - Wed, Dec 10

from (CA$)$2,122

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

CA$4,066~~CA$6,308~~

per Cabin

12 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $400 free drinks

80% off second Sailor

Insider cabins from

CA$4,066~~CA$6,308~~

per Cabin

Departing on:

Sat, Nov 08 - Thu, Nov 20

from (CA$)$4,066

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

CA$1,972~~CA$3,004~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$1,972~~CA$3,004~~

per Cabin

Departing on:

Sat, Nov 08 - Sat, Nov 15

from (CA$)$1,972

Western Caribbean & Bimini Beach Club

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

Insider cabins from

CA$2,069~~CA$2,909~~

per Cabin

6 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$2,069~~CA$2,909~~

per Cabin

Departing on:

Sun, Nov 09 - Sat, Nov 15

from (CA$)$2,069

Fire & Sunset Soirées

Miami, Florida
Key West, Florida
The Beach Club at Bimini, Bahamas
Miami, Florida

Sea View cabins from

CA$1,696~~CA$2,458~~

per Cabin

4 nights

Scarlet Lady

Wed, Jan 07 - Sun, Jan 11

+ up to $100 free drinks

80% off second Sailor

Sea View cabins from

CA$1,696~~CA$2,458~~

per Cabin

Departing on:

2026Best Rate

from (CA$)$1,696

Wed, Nov 12 - Sun, Nov 16

from (CA$)$2,038

Wed, Nov 26 - Sun, Nov 30

from (CA$)$5,680

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

CA$1,974~~CA$2,858~~

per Cabin

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$1,974~~CA$2,858~~

per Cabin

Departing on:

Sat, Nov 15 - Sat, Nov 22

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

CA$4,091~~CA$6,553~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Sea Terrace cabins from

CA$4,091~~CA$6,553~~

per Cabin

Departing on:

Sat, Nov 15 - Sat, Nov 22

from (CA$)$4,091

Riviera Maya

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

Insider cabins from

CA$1,551~~CA$2,091~~

per Cabin

5 nights

Scarlet Lady

+ up to $100 free drinks

80% off second Sailor

Insider cabins from

CA$1,551~~CA$2,091~~

per Cabin

Departing on:

Sun, Nov 16 - Fri, Nov 21

from (CA$)$1,551

Sun, Dec 14 - Fri, Dec 19

from (CA$)$1,979

Sun, Jan 11 - Fri, Jan 16

from (CA$)$1,793

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

CA$3,167~~CA$4,919~~

per Cabin

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $300 free drinks

80% off second Sailor

Sea View cabins from

CA$3,167~~CA$4,919~~

per Cabin

Departing on:

Thu, Nov 20 - Fri, Nov 28

from (CA$)$3,167

Miami, Grand Turk (& back)

Miami, Florida
Grand Turk, Turks and Caicos
The Beach Club at Bimini, Bahamas
Miami, Florida

Sea View cabins from

CA$2,261~~CA$3,417~~

per Cabin

5 nights

Scarlet Lady

+ up to $100 free drinks

80% off second Sailor

Sea View cabins from

CA$2,261~~CA$3,417~~

per Cabin

Departing on:

Sun, Nov 30 - Fri, Dec 05

from (CA$)$2,261

Fri, Nov 21 - Wed, Nov 26

from (CA$)$3,003

Fri, Dec 19 - Wed, Dec 24

from (CA$)$2,689

Cayman Coves & Jamaican Waterfalls

Miami, Florida
Ocho Rios, Jamaica
George Town, Grand Cayman
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

CA$1,974~~CA$2,844~~

per Cabin

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$1,974~~CA$2,844~~

per Cabin

Departing on:

Sat, Nov 22 - Sat, Nov 29

Sat, Dec 06 - Sat, Dec 13

Sat, Jan 24 - Sat, Jan 31

from (CA$)$2,371

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

CA$1,971~~CA$3,001~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$1,971~~CA$3,001~~

per Cabin

Departing on:

Sat, Nov 22 - Sat, Nov 29

from (CA$)$1,971

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

CA$2,793~~CA$4,269~~

per Cabin

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$2,793~~CA$4,269~~

per Cabin

Departing on:

Fri, Nov 28 - Sun, Dec 07

from (CA$)$2,793

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

CA$1,971~~CA$2,877~~

per Cabin

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$1,971~~CA$2,877~~

per Cabin

Departing on:

Sat, Nov 29 - Sat, Dec 06

from (CA$)$1,971

Sat, Jan 17 - Sat, Jan 24

from (CA$)$1,975

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

CA$6,317

per Cabin

6 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

RockStar Quarters suites from

CA$6,317

per Cabin

Departing on:

Sat, Nov 29 - Fri, Dec 05

from (CA$)$6,317

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

CA$2,256~~CA$3,472~~

per Cabin

8 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$2,256~~CA$3,472~~

per Cabin

Departing on:

Fri, Dec 05 - Sat, Dec 13

from (CA$)$2,256

Aruban Sunsets & Calm Cayman Days

Miami, Florida
Oranjestad, Aruba
Cartagena, Colombia
Ocho Rios, Jamaica
George Town, Grand Cayman
Miami, Florida

Insider cabins from

CA$3,601~~CA$5,573~~

per Cabin

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $400 free drinks

80% off second Sailor

Insider cabins from

CA$3,601~~CA$5,573~~

per Cabin

Departing on:

Sun, Dec 07 - Thu, Dec 18

from (CA$)$3,601

Cayman Coves & Jamaican Waterfalls

Miami, Florida
Ocho Rios, Jamaica
George Town, Grand Cayman
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

CA$1,974~~CA$2,844~~

per Cabin

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$1,974~~CA$2,844~~

per Cabin

Departing on:

Sat, Dec 13 - Sat, Dec 20

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

CA$2,008~~CA$3,086~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$2,008~~CA$3,086~~

per Cabin

Departing on:

Sat, Dec 13 - Sat, Dec 20

from (CA$)$2,008

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

CA$3,620~~CA$5,680~~

per Cabin

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $300 free drinks

80% off second Sailor

Sea View cabins from

CA$3,620~~CA$5,680~~

per Cabin

Departing on:

Thu, Dec 18 - Fri, Dec 26

from (CA$)$3,620

Resilient Caribbean Holidays

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

Insider cabins from

CA$2,770~~CA$4,186~~

per Cabin

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$2,770~~CA$4,186~~

per Cabin

Departing on:

Sat, Dec 20 - Sat, Dec 27

from (CA$)$2,770

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

CA$2,768~~CA$4,334~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$2,768~~CA$4,334~~

per Cabin

Departing on:

Sat, Dec 20 - Sat, Dec 27

from (CA$)$2,768

Scarlet Caribbean Holidays

Miami, Florida
Nassau, Bahamas
The Beach Club at Bimini, Bahamas
Miami, Florida

Sea Terrace cabins from

CA$3,109~~CA$4,817~~

per Cabin

4 nights

Scarlet Lady

+ up to $100 free drinks

80% off second Sailor

Sea Terrace cabins from

CA$3,109~~CA$4,817~~

per Cabin

Departing on:

Wed, Dec 24 - Sun, Dec 28

from (CA$)$3,109

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

CA$5,610~~CA$9,022~~

per Cabin

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$5,610~~CA$9,022~~

per Cabin

Departing on:

Fri, Dec 26 - Sun, Jan 04

from (CA$)$5,610

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

CA$5,144~~CA$8,128~~

per Cabin

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$5,144~~CA$8,128~~

per Cabin

Departing on:

Sat, Dec 27 - Sat, Jan 03

from (CA$)$5,144

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

CA$4,762~~CA$7,694~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$4,762~~CA$7,694~~

per Cabin

Departing on:

Sat, Dec 27 - Sat, Jan 03

from (CA$)$4,762

Scarlet New Year's Ahoy!

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

Sea View cabins from

CA$4,683~~CA$7,309~~

per Cabin

5 nights

Scarlet Lady

+ up to $100 free drinks

80% off second Sailor

Sea View cabins from

CA$4,683~~CA$7,309~~

per Cabin

Departing on:

Sun, Dec 28 - Fri, Jan 02

from (CA$)$4,683

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

CA$2,570~~CA$4,032~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$2,570~~CA$4,032~~

per Cabin

Departing on:

Sat, Jan 03 - Sat, Jan 10

from (CA$)$2,570

Cozumel, Grand Cayman & Bimini

Miami, Florida
George Town, Grand Cayman
Cozumel, Mexico
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

CA$1,973~~CA$2,747~~

per Cabin

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$1,973~~CA$2,747~~

per Cabin

Departing on:

Sat, Jan 03 - Sat, Jan 10

from (CA$)$1,973

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

CA$5,685~~CA$9,031~~

per Cabin

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $400 free drinks

80% off second Sailor

Sea View cabins from

CA$5,685~~CA$9,031~~

per Cabin

Departing on:

Sun, Jan 04 - Thu, Jan 15

from (CA$)$5,685

Cayman Isles & Jamaican Miles

Miami, Florida
George Town, Grand Cayman
Ocho Rios, Jamaica
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

CA$1,971~~CA$2,853~~

per Cabin

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$1,971~~CA$2,853~~

per Cabin

Departing on:

Sat, Jan 10 - Sat, Jan 17

from (CA$)$1,971

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

CA$2,174~~CA$3,390~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$2,174~~CA$3,390~~

per Cabin

Departing on:

Sat, Jan 10 - Sat, Jan 17

from (CA$)$2,174

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

Sea View cabins from

CA$2,570~~CA$4,030~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Sea View cabins from

CA$2,570~~CA$4,030~~

per Cabin

Departing on:

Sat, Jan 17 - Sat, Jan 24

from (CA$)$2,570

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

CA$2,372~~CA$3,692~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$2,372~~CA$3,692~~

per Cabin

Departing on:

Sat, Jan 24 - Sat, Jan 31

from (CA$)$2,372

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

CA$3,399~~CA$5,265~~

per Cabin

6 nights

Brilliant Lady

+ up to $300 free drinks

80% off second Sailor

Sea View cabins from

CA$3,399~~CA$5,265~~

per Cabin

Departing on:

Mon, Jan 26 - Sun, Feb 01

from (CA$)$3,399

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

CA$2,173~~CA$3,331~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$2,173~~CA$3,331~~

per Cabin

Departing on:

Sat, Jan 31 - Sat, Feb 07

from (CA$)$2,173

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

CA$1,973~~CA$2,883~~

per Cabin

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$1,973~~CA$2,883~~

per Cabin

Departing on: