Explore 399 cruise vacations

Sat, Jan 02 - Sat, Jan 09

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

2027Best Rate

Sat, Nov 08 - Sat, Nov 15

Sat, Mar 21 - Sat, Mar 28

DEAL

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

Insider cabins from

per Cabin

7 nights

Valiant Lady

Sat, Feb 28 - Sat, Mar 07

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

2026Best Rate

Sat, Nov 15 - Sat, Nov 22

Sat, Nov 07 - Sat, Nov 14

DEAL

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

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Nov 22 - Sat, Nov 29

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

per Cabin

6 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Nov 29 - Fri, Dec 05

DEAL

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

per Cabin

8 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Fri, Dec 05 - Sat, Dec 13

DEAL

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

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

per Cabin

Departing on:

Sat, Dec 13 - Sat, Dec 20

DEAL

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

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

per Cabin

Departing on:

Sat, Dec 20 - Sat, Dec 27

DEAL

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

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Dec 27 - Sat, Jan 03

DEAL

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

per Cabin

7 nights

Valiant Lady

Sat, Feb 06 - Sat, Feb 13

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

2027Best Rate

Sat, Jan 03 - Sat, Jan 10

DEAL

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

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Jan 10 - Sat, Jan 17

DEAL

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

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

per Cabin

Departing on:

Sat, Jan 17 - Sat, Jan 24

DEAL

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

Sea View cabins from

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

per Cabin

Departing on:

Sat, Jan 24 - Sat, Jan 31

DEAL

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

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Jan 31 - Sat, Feb 07

DEAL

St. Lucia, Barbados & More

San Juan, Puerto Rico
Philipsburg, St. Maarten
Basseterre, St. Kitts and Nevis
Castries, St. Lucia
Bridgetown, Barbados
Charlotte Amalie, St. Thomas
San Juan, Puerto Rico

Insider cabins from

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Feb 07 - Sat, Feb 14

Valiant Valentine's Voyage

San Juan, Puerto Rico
Oranjestad, Aruba
Willemstad, Curaçao
St. Croix, U.S. Virgin Islands
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Feb 14 - Sat, Feb 21

DEAL

Antigua, Martinique, & Barbados & More

San Juan, Puerto Rico
Philipsburg, St. Maarten
Bridgetown, Barbados
Fort-de-France, Martinique
St. John's, Antigua
Tortola, British Virgin Islands
San Juan, Puerto Rico

Insider cabins from

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Feb 21 - Sat, Feb 28

DEAL

Quaint Castries to Elegant Antigua

San Juan, Puerto Rico
Basseterre, St. Kitts and Nevis
Castries, St. Lucia
Fort-de-France, Martinique
St. John's, Antigua
Tortola, British Virgin Islands
San Juan, Puerto Rico

Insider cabins from

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Mar 07 - Sat, Mar 14

DEAL

Sunsets in the Lesser Antilles

San Juan, Puerto Rico
Oranjestad, Aruba
Willemstad, Curaçao
Fort-de-France, Martinique
Basseterre, St. Kitts and Nevis
San Juan, Puerto Rico

Insider cabins from

per Cabin

7 nights

Valiant Lady

Sat, Dec 05 - Sat, Dec 12

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

2026Best Rate

Sat, Mar 14 - Sat, Mar 21

Sat, Jan 09 - Sat, Jan 16

Tortola, Charleston, Newport & More

San Juan, Puerto Rico
Tortola, British Virgin Islands
Puerto Plata, Dominican Republic
Charleston, South Carolina
Newport, Rhode Island
New York City, New York

Insider cabins from

per Cabin

9 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Mar 28 - Mon, Apr 06

DEAL

Valiant's Haunted Halloween Soirée

San Juan, Puerto Rico
Willemstad, Curaçao
Oranjestad, Aruba
Fort-de-France, Martinique
Basseterre, St. Kitts and Nevis
San Juan, Puerto Rico

Insider cabins from

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Oct 31 - Sat, Nov 07

Caribbean East: Virgin & Saint Isles

San Juan, Puerto Rico
Tortola, British Virgin Islands
Basseterre, St. Kitts and Nevis
St. John's, Antigua
Castries, St. Lucia
San Juan, Puerto Rico

Insider cabins from

per Cabin

6 nights

Valiant Lady

Sat, Jan 23 - Fri, Jan 29

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

2027Best Rate

Sat, Nov 14 - Fri, Nov 20

Sat, Mar 13 - Fri, Mar 19

DEAL

Thanksgiving: St. Isles, Aruba & Curaçao

San Juan, Puerto Rico
Charlotte Amalie, St. Thomas
Willemstad, Curaçao
Oranjestad, Aruba
Basseterre, St. Kitts and Nevis
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

per Cabin

8 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Fri, Nov 20 - Sat, Nov 28

DEAL

Antiguan Elegance & Sunny St. Isles

San Juan, Puerto Rico
Charlotte Amalie, St. Thomas
Tortola, British Virgin Islands
Basseterre, St. Kitts and Nevis
St. John's, Antigua
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Nov 28 - Sat, Dec 05

DEAL

Valiant Caribbean Holidays

San Juan, Puerto Rico
Basseterre, St. Kitts and Nevis
Fort-de-France, Martinique
Oranjestad, Aruba
Willemstad, Curaçao
San Juan, Puerto Rico

Insider cabins from

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Dec 19 - Sat, Dec 26

DEAL

Valiant New Year's Ahoy!

San Juan, Puerto Rico
Philipsburg, St. Maarten
Fort-de-France, Martinique
Bridgetown, Barbados
Castries, St. Lucia
St. John's, Antigua
San Juan, Puerto Rico

Insider cabins from

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Dec 26 - Sat, Jan 02

DEAL

Puerto Rico to Aruba, Bonaire & More

San Juan, Puerto Rico
Oranjestad, Aruba
Willemstad, Curaçao
Kralendijk, Bonaire
Fort-de-France, Martinique
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

per Cabin

8 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Fri, Jan 29 - Sat, Feb 06

DEAL

Lesser Antilles: Valentine's Day

San Juan, Puerto Rico
Oranjestad, Aruba
Willemstad, Curaçao
Fort-de-France, Martinique
Basseterre, St. Kitts and Nevis
San Juan, Puerto Rico

Insider cabins from

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Feb 13 - Sat, Feb 20

DEAL

Saint Isles & The Greater Antilles

San Juan, Puerto Rico
Tortola, British Virgin Islands
Castries, St. Lucia
Bridgetown, Barbados
Roseau, Dominica
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Feb 20 - Sat, Feb 27

DEAL

Saint (Isles) & Seas of the Caribbean

San Juan, Puerto Rico
Philipsburg, St. Maarten
Bridgetown, Barbados
Castries, St. Lucia
St. John's, Antigua
Tortola, British Virgin Islands
San Juan, Puerto Rico

Insider cabins from

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Mar 06 - Sat, Mar 13

DEAL

Barbados, Dominica & St. Isle Spring

San Juan, Puerto Rico
Charlotte Amalie, St. Thomas
Bridgetown, Barbados
Kingstown, St. Vincent
Roseau, Dominica
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

per Cabin

8 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Fri, Mar 19 - Sat, Mar 27

DEAL

Colorful Curaçao, Aruba & Antigua

San Juan, Puerto Rico
Willemstad, Curaçao
Oranjestad, Aruba
St. John's, Antigua
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Mar 27 - Sat, Apr 03

San Juan to Miami: Dominican Daze

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

Insider cabins from

per Cabin

5 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Apr 10 - Thu, Apr 15