Explore 379 cruise vacations

Sat, Mar 21 - Sat, Mar 28

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$160

per Sailor per night

Departing on:

2026Best Rate

from (US$)$160

Sat, Nov 08 - Sat, Nov 15

from (US$)$235

Sunny Miles of Tropical Isles

San Juan, Puerto Rico • Philipsburg • Bridgetown • Castries • Fort-de-France • Basseterre • San Juan, Puerto Rico

Insider cabins from

$139

per Sailor per night

7 nights

Valiant Lady

Sat, Nov 15 - Sat, Nov 22

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$139

per Sailor per night

Departing on:

2025Best Rate

from (US$)$139

Sat, Feb 28 - Sat, Mar 07

from (US$)$149

Thanksgiving in the Lesser Antilles

San Juan, Puerto Rico • Tortola • Basseterre • St. John's • Castries • St. Thomas • San Juan, Puerto Rico

Insider cabins from

$150

per Sailor per night

7 nights

Valiant Lady

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$150

per Sailor per night

Departing on:

Sat, Nov 22 - Sat, Nov 29

from (US$)$150

San Juan to Barbados & the St. Isles

San Juan, Puerto Rico • Philipsburg • Basseterre • Roseau • Bridgetown • San Juan, Puerto Rico

Insider cabins from

$130

per Sailor per night

6 nights

Valiant Lady

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$130

per Sailor per night

Departing on:

Sat, Nov 29 - Fri, Dec 05

from (US$)$130

Aruba, Curaçao and the Lesser Antilles

San Juan, Puerto Rico • Willemstad • Oranjestad • Roseau • St. John's • Philipsburg • San Juan, Puerto Rico

Insider cabins from

$155

per Sailor per night

8 nights

Valiant Lady

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$155

per Sailor per night

Departing on:

Fri, Dec 05 - Sat, Dec 13

from (US$)$155

St. Lucia, St. Maarten, Barbados & More

San Juan, Puerto Rico • Basseterre • Castries • Roseau • Bridgetown • Philipsburg • San Juan, Puerto Rico

Insider cabins from

$149

per Sailor per night

7 nights

Valiant Lady

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$149

per Sailor per night

Departing on:

Sat, Dec 13 - Sat, Dec 20

from (US$)$149

Valiant Caribbean Holidays

San Juan, Puerto Rico • Philipsburg • Basseterre • St. John's • Castries • Tortola • San Juan, Puerto Rico

Insider cabins from

$170

per Sailor per night

7 nights

Valiant Lady

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$170

per Sailor per night

Departing on:

Sat, Dec 20 - Sat, Dec 27

from (US$)$170

Valiant New Year’s Ahoy!

San Juan, Puerto Rico • Philipsburg • Basseterre • Castries • Bridgetown • St. Croix • San Juan, Puerto Rico

Insider cabins from

$270

per Sailor per night

7 nights

Valiant Lady

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$270

per Sailor per night

Departing on:

Sat, Dec 27 - Sat, Jan 03

from (US$)$270

Aruban Sights & Antiguan Nights

San Juan, Puerto Rico • Oranjestad • Willemstad • St. John's • Philipsburg • San Juan, Puerto Rico

Insider cabins from

$150

per Sailor per night

7 nights

Valiant Lady

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$150

per Sailor per night

Departing on:

Sat, Jan 03 - Sat, Jan 10

from (US$)$150

Virgin Island Views & Saint Isle Blues

San Juan, Puerto Rico • Tortola • Bridgetown • Kingstown • Basseterre • St. Croix • San Juan, Puerto Rico

Insider cabins from

$139

per Sailor per night

7 nights

Valiant Lady

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$139

per Sailor per night

Departing on:

Sat, Jan 10 - Sat, Jan 17

from (US$)$139

St. Kitts, Barbados, Martinique & More

San Juan, Puerto Rico • Basseterre • Bridgetown • Fort-de-France • St. John's • Philipsburg • San Juan, Puerto Rico

Insider cabins from

$139

per Sailor per night

7 nights

Valiant Lady

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$139

per Sailor per night

Departing on:

Sat, Jan 17 - Sat, Jan 24

from (US$)$139

Barbados, Antigua, BVI & More

San Juan, Puerto Rico • Tortola • Bridgetown • Fort-de-France • St. John's • Philipsburg • San Juan, Puerto Rico

Insider cabins from

$140

per Sailor per night

7 nights

Valiant Lady

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$140

per Sailor per night

Departing on:

Sat, Jan 24 - Sat, Jan 31

from (US$)$140

Antigua & the St. Isles

San Juan, Puerto Rico • Philipsburg • Basseterre • St. John's • Castries • St. Thomas • San Juan, Puerto Rico

Insider cabins from

$130

per Sailor per night

7 nights

Valiant Lady

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$130

per Sailor per night

Departing on:

Sat, Jan 31 - Sat, Feb 07

from (US$)$130

St. Lucia, Barbados & More

San Juan, Puerto Rico • Philipsburg • Basseterre • Castries • Bridgetown • St. Thomas • San Juan, Puerto Rico

Insider cabins from

$140

per Sailor per night

7 nights

Valiant Lady

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$140

per Sailor per night

Departing on:

Sat, Feb 07 - Sat, Feb 14

from (US$)$140

Aruba, Curaçao and the St. Isles

San Juan, Puerto Rico • Oranjestad • Willemstad • St. Croix • Philipsburg • San Juan, Puerto Rico

Insider cabins from

$140

per Sailor per night

7 nights

Valiant Lady

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$140

per Sailor per night

Departing on:

Sat, Feb 14 - Sat, Feb 21

from (US$)$140

Antigua, Martinique, & Barbados & More

San Juan, Puerto Rico • Philipsburg • Bridgetown • Fort-de-France • St. John's • Tortola • San Juan, Puerto Rico

Insider cabins from

$175

per Sailor per night

7 nights

Valiant Lady

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$175

per Sailor per night

Departing on:

Sat, Feb 21 - Sat, Feb 28

from (US$)$175

Quaint Castries to Elegant Antigua

San Juan, Puerto Rico • Basseterre • Castries • Fort-de-France • St. John's • Tortola • San Juan, Puerto Rico

Insider cabins from

$159

per Sailor per night

7 nights

Valiant Lady

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$159

per Sailor per night

Departing on:

Sat, Mar 07 - Sat, Mar 14

from (US$)$159

Sunsets in the Lesser Antilles

San Juan, Puerto Rico • Oranjestad • Willemstad • Fort-de-France • Basseterre • San Juan, Puerto Rico

Insider cabins from

$160

per Sailor per night

7 nights

Valiant Lady

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$160

per Sailor per night

Departing on:

Sat, Mar 14 - Sat, Mar 21

from (US$)$160

Tortola, Charleston, Newport & More

San Juan, Puerto Rico • Tortola • Puerto Plata • Charleston, South Carolina • Newport, Rhode Island • New York City, New York

Insider cabins from

$120

per Sailor per night

9 nights

Valiant Lady

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$120

per Sailor per night

Departing on:

Sat, Mar 28 - Mon, Apr 06

from (US$)$120

Valiant's Haunted Halloween Soirée

San Juan, Puerto Rico • Willemstad • Oranjestad • Fort-de-France • Basseterre • San Juan, Puerto Rico

Insider cabins from

$170

per Sailor per night

7 nights

Valiant Lady

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$170

per Sailor per night

Departing on: