Explore 414 cruise vacations

Showing cruise vacations: All Destinations, September 2025 - October 2027

Departs San Juan, Puerto Rico

LIMITED-TIME ONLY:

70% off 2nd Sailor + up to $600* instant savings

Extra savings on 7+ night Caribbean winter cruises.

★

UP TO $600 OFF

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

$1,948~~$2,736~~

per Cabin

7 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Insider cabins from

$1,948~~$2,736~~

per Cabin

Departing on:

Sat, Jan 02 - Sat, Jan 09

from (US$)$1,948

Sat, Nov 08 - Sat, Nov 15

from (US$)$2,366

Sat, Mar 21 - Sat, Mar 28

from (US$)$3,360

★

UP TO $600 OFF

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 View cabins from

$1,806~~$2,628~~

per Cabin

7 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Sea View cabins from

$1,806~~$2,628~~

per Cabin

Departing on:

Sat, Nov 15 - Sat, Nov 22

from (US$)$1,806

Sat, Feb 28 - Sat, Mar 07

from (US$)$2,226

Sat, Nov 07 - Sat, Nov 14

from (US$)$1,806

EPIC SAVINGS ON ALL VOYAGES THROUGH 2027

70% off 2nd Sailor + up to $600* off

★

UP TO $600 OFF

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

$1,666~~$2,400~~

per Cabin

7 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Insider cabins from

$1,666~~$2,400~~

per Cabin

Departing on:

Sat, Nov 22 - Sat, Nov 29

from (US$)$1,666

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 View cabins from

$1,548~~$2,250~~

per Cabin

6 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Sea View cabins from

$1,548~~$2,250~~

per Cabin

Departing on:

Sat, Nov 29 - Fri, Dec 05

from (US$)$1,548

★

UP TO $600 OFF

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

$1,904~~$2,766~~

per Cabin

8 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Insider cabins from

$1,904~~$2,766~~

per Cabin

Departing on:

Fri, Dec 05 - Sat, Dec 13

from (US$)$1,904

★

UP TO $600 OFF

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

$1,666~~$2,416~~

per Cabin

7 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Insider cabins from

$1,666~~$2,416~~

per Cabin

Departing on:

Sat, Dec 13 - Sat, Dec 20

from (US$)$1,666

★

UP TO $600 OFF

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

$2,508~~$3,698~~

per Cabin

7 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Sea View cabins from

$2,508~~$3,698~~

per Cabin

Departing on:

Sat, Dec 20 - Sat, Dec 27

from (US$)$2,508

★

UP TO $600 OFF

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

Sea View cabins from

$3,768~~$5,658~~

per Cabin

7 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Sea View cabins from

$3,768~~$5,658~~

per Cabin

Departing on:

Sat, Dec 27 - Sat, Jan 03

from (US$)$3,768

★

UP TO $600 OFF

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

$2,088~~$2,962~~

per Cabin

7 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Insider cabins from

$2,088~~$2,962~~

per Cabin

Departing on:

Sat, Feb 06 - Sat, Feb 13

from (US$)$2,088

Sat, Jan 03 - Sat, Jan 10

from (US$)$2,366

★

UP TO $600 OFF

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

Sea View cabins from

$2,086~~$3,078~~

per Cabin

7 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Sea View cabins from

$2,086~~$3,078~~

per Cabin

Departing on:

Sat, Jan 10 - Sat, Jan 17

from (US$)$2,086

★

UP TO $600 OFF

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

$2,086~~$3,066~~

per Cabin

7 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Sea View cabins from

$2,086~~$3,066~~

per Cabin

Departing on:

Sat, Jan 17 - Sat, Jan 24

from (US$)$2,086

★

UP TO $600 OFF

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

$2,088~~$3,062~~

per Cabin

7 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Sea View cabins from

$2,088~~$3,062~~

per Cabin

Departing on:

Sat, Jan 24 - Sat, Jan 31

from (US$)$2,088

★

UP TO $600 OFF

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

Sea View cabins from

$2,226~~$3,260~~

per Cabin

7 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Sea View cabins from

$2,226~~$3,260~~

per Cabin

Departing on:

Sat, Jan 31 - Sat, Feb 07

from (US$)$2,226

★

UP TO $600 OFF

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

Sea Terrace cabins from

$2,646~~$3,908~~

per Cabin

7 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Sea Terrace cabins from

$2,646~~$3,908~~

per Cabin

Departing on:

Sat, Feb 07 - Sat, Feb 14

from (US$)$2,646

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

Sea View cabins from

$2,226~~$3,284~~

per Cabin

7 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Sea View cabins from

$2,226~~$3,284~~

per Cabin

Departing on:

Sat, Feb 14 - Sat, Feb 21

from (US$)$2,226

★

UP TO $600 OFF

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

Sea Terrace cabins from

$2,786~~$4,138~~

per Cabin

7 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Sea Terrace cabins from

$2,786~~$4,138~~

per Cabin

Departing on:

Sat, Feb 21 - Sat, Feb 28

from (US$)$2,786

★

UP TO $600 OFF

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

Sea Terrace cabins from

$2,646~~$3,932~~

per Cabin

7 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Sea Terrace cabins from

$2,646~~$3,932~~

per Cabin

Departing on:

Sat, Mar 07 - Sat, Mar 14

from (US$)$2,646

★

UP TO $600 OFF

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

$1,806~~$2,628~~

per Cabin

7 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Insider cabins from

$1,806~~$2,628~~

per Cabin

Departing on:

Sat, Dec 05 - Sat, Dec 12

from (US$)$1,806

Sat, Mar 14 - Sat, Mar 21

from (US$)$3,066

Sat, Jan 09 - Sat, Jan 16

from (US$)$1,946

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

$1,964~~$2,800~~

per Cabin

9 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Insider cabins from

$1,964~~$2,800~~

per Cabin

Departing on:

Sat, Mar 28 - Mon, Apr 06

from (US$)$1,964

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

$1,946~~$2,844~~

per Cabin

7 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Insider cabins from

$1,946~~$2,844~~

per Cabin

Departing on:

Sat, Oct 31 - Sat, Nov 07

from (US$)$1,946

Caribbean East: Virgin & Saint Isles

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

Insider cabins from

$1,550~~$2,182~~

per Cabin

6 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Insider cabins from

$1,550~~$2,182~~

per Cabin

Departing on:

Sat, Nov 14 - Fri, Nov 20

from (US$)$1,550

Sat, Jan 23 - Fri, Jan 29

from (US$)$1,668

Sat, Mar 13 - Fri, Mar 19

from (US$)$1,790

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

$2,384~~$3,488~~

per Cabin

8 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Insider cabins from

$2,384~~$3,488~~

per Cabin

Departing on:

Fri, Nov 20 - Sat, Nov 28

from (US$)$2,384

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

$1,948~~$2,778~~

per Cabin

7 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Insider cabins from

$1,948~~$2,778~~

per Cabin

Departing on:

Sat, Nov 28 - Sat, Dec 05

from (US$)$1,948

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

$2,786~~$4,136~~

per Cabin

7 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Insider cabins from

$2,786~~$4,136~~

per Cabin

Departing on:

Sat, Dec 19 - Sat, Dec 26

from (US$)$2,786

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

$3,488~~$5,198~~

per Cabin

7 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Insider cabins from

$3,488~~$5,198~~

per Cabin

Departing on:

Sat, Dec 26 - Sat, Jan 02

from (US$)$3,488

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

$2,226~~$3,156~~

per Cabin

8 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Insider cabins from

$2,226~~$3,156~~

per Cabin

Departing on:

Fri, Jan 29 - Sat, Feb 06

from (US$)$2,226

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

$2,088~~$2,976~~

per Cabin

7 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Insider cabins from

$2,088~~$2,976~~

per Cabin

Departing on:

Sat, Feb 13 - Sat, Feb 20

from (US$)$2,088

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

$2,088~~$2,962~~

per Cabin

7 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Insider cabins from

$2,088~~$2,962~~

per Cabin

Departing on:

Sat, Feb 20 - Sat, Feb 27

from (US$)$2,088

★

UP TO $600 OFF

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

$2,086~~$2,950~~

per Cabin

7 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Insider cabins from

$2,086~~$2,950~~

per Cabin

Departing on:

Sat, Mar 06 - Sat, Mar 13

from (US$)$2,086

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

$2,386~~$3,418~~

per Cabin

8 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Insider cabins from

$2,386~~$3,418~~

per Cabin

Departing on:

Fri, Mar 19 - Sat, Mar 27

from (US$)$2,386

Colorful Curaçao, Aruba & Antigua

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

Sea Terrace cabins from

$3,150~~$4,598~~

per Cabin

7 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Sea Terrace cabins from

$3,150~~$4,598~~

per Cabin

Departing on:

Sat, Mar 27 - Sat, Apr 03

from (US$)$3,150

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

$1,492~~$2,054~~

per Cabin

5 nights

Valiant Lady

+ Instant Savings

70% off second Sailor

Insider cabins from

$1,492~~$2,054~~

per Cabin

Departing on:

Sat, Apr 10 - Thu, Apr 15

from (US$)$1,492