Explore 387 cruise vacations

Showing cruise vacations: All Destinations, November 2025 - April 2027

Quick find:

Departs San Juan, Puerto Rico

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

Sat, Mar 21 - Sat, Mar 28

from (US$)$2,410

Sat, Jan 02 - Sat, Jan 09

from (US$)$1,946

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

$1,806~~$2,838~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,806~~$2,838~~

per Cabin

Departing on:

Sat, Feb 28 - Sat, Mar 07

from (US$)$1,806

Sat, Nov 15 - Sat, Nov 22

from (US$)$2,876

Sat, Nov 07 - Sat, Nov 14

from (US$)$1,806

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

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

$4,440

per Cabin

6 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

RockStar Quarters suites from

$4,440

per Cabin

Departing on:

Sat, Nov 29 - Fri, Dec 05

from (US$)$4,440

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

$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

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

$1,386~~$2,128~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,386~~$2,128~~

per Cabin

Departing on:

Sat, Dec 13 - Sat, Dec 20

from (US$)$1,386

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

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

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

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,806~~$2,834~~

per Cabin

Departing on:

Sat, Jan 03 - Sat, Jan 10

from (US$)$1,806

Sat, Feb 06 - Sat, Feb 13

from (US$)$2,086

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

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,526~~$2,382~~

per Cabin

Departing on:

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

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,526~~$2,366~~

per Cabin

Departing on:

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

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,666~~$2,594~~

per Cabin

Departing on:

Sat, Jan 24 - Sat, Jan 31

from (US$)$1,666

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

$1,746~~$2,704~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,746~~$2,704~~

per Cabin

Departing on:

Sat, Jan 31 - Sat, Feb 07

from (US$)$1,746

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

$1,666~~$2,576~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,666~~$2,576~~

per Cabin

Departing on:

Sat, Feb 07 - Sat, Feb 14

from (US$)$1,666

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

$1,666~~$2,602~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,666~~$2,602~~

per Cabin

Departing on:

Sat, Feb 14 - Sat, Feb 21

from (US$)$1,666

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

$1,806~~$2,826~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,806~~$2,826~~

per Cabin

Departing on:

Sat, Feb 21 - Sat, Feb 28

from (US$)$1,806

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

$1,944~~$3,066~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,944~~$3,066~~

per Cabin

Departing on:

Sat, Mar 07 - Sat, Mar 14

from (US$)$1,944

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~~$2,824~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,806~~$2,824~~

per Cabin

Departing on:

Sat, Dec 05 - Sat, Dec 12

from (US$)$1,806

Sat, Mar 14 - Sat, Mar 21

from (US$)$2,340

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

$1,784~~$2,700~~

per Cabin

9 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,784~~$2,700~~

per Cabin

Departing on:

Sat, Mar 28 - Mon, Apr 06

from (US$)$1,784

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

Sea Terrace cabins from

$2,876~~$4,604~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Sea Terrace cabins from

$2,876~~$4,604~~

per Cabin

Departing on:

Sat, Oct 31 - Sat, Nov 07

from (US$)$2,876

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

$1,668~~$2,388~~

per Cabin

6 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,668~~$2,388~~

per Cabin

Departing on:

Sat, Jan 23 - Fri, Jan 29

from (US$)$1,668

Sat, Nov 14 - Fri, Nov 20

from (US$)$1,730

Sat, Mar 13 - Fri, Mar 19

from (US$)$1,788

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

$2,224~~$3,484~~

per Cabin

8 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$2,224~~$3,484~~

per Cabin

Departing on:

Fri, Nov 20 - Sat, Nov 28

from (US$)$2,224

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

$1,946~~$2,974~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,946~~$2,974~~

per Cabin

Departing on:

Sat, Nov 28 - Sat, Dec 05

from (US$)$1,946

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

$2,646~~$4,224~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$2,646~~$4,224~~

per Cabin

Departing on:

Sat, Dec 19 - Sat, Dec 26

from (US$)$2,646

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

$3,486~~$5,604~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$3,486~~$5,604~~

per Cabin

Departing on:

Sat, Dec 26 - Sat, Jan 02

from (US$)$3,486

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

$2,224~~$3,376~~

per Cabin

8 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$2,224~~$3,376~~

per Cabin

Departing on:

Fri, Jan 29 - Sat, Feb 06

from (US$)$2,224

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

$2,086~~$3,186~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$2,086~~$3,186~~

per Cabin

Departing on:

Sat, Feb 13 - Sat, Feb 20

from (US$)$2,086

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

$2,086~~$3,170~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$2,086~~$3,170~~

per Cabin

Departing on:

Sat, Feb 20 - Sat, Feb 27

from (US$)$2,086

★

UP TO $700 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~~$3,156~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$2,086~~$3,156~~

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

$2,384~~$3,664~~

per Cabin

8 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$2,384~~$3,664~~

per Cabin

Departing on:

Fri, Mar 19 - Sat, Mar 27

from (US$)$2,384

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

$3,016~~$4,718~~

per Cabin

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Sea Terrace cabins from

$3,016~~$4,718~~

per Cabin

Departing on:

Sat, Mar 27 - Sat, Apr 03

from (US$)$3,016

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

$1,490~~$2,186~~

per Cabin

5 nights

Valiant Lady

+ up to $100 free drinks

80% off second Sailor

Insider cabins from

$1,490~~$2,186~~

per Cabin

Departing on:

Sat, Apr 10 - Thu, Apr 15

from (US$)$1,490