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Explore 413 cruise vacations

Showing Loading cruise vacations: Transatlantic & Repositioning & Caribbean, September 2025 - November 2027
Showing 76 cruise vacations that match your search
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One-way to SJ: DR, St. Maarten & BVI

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • San Juan, Puerto Rico
Insider cabins from
$1,428$2,018
per Cabin
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6 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$1,428$2,018
per Cabin
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Departing on:
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
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7 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
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EPIC SAVINGS ON ALL VOYAGES THROUGH 2027
70% off 2nd Sailor + up to $600* off
UP TO $600 OFF

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
$1,666$2,318
per Cabin
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7 nights
Resilient Lady & Scarlet Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
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
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7 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
UP TO $600 OFF

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
$2,064$2,972
per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Sea View cabins from
$2,064$2,972
per Cabin
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Departing on:
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
Loading
7 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$1,666$2,400
per Cabin
Loading
Departing on:
UP TO $600 OFF

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
Sea View cabins from
$2,504$3,632
per Cabin
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9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor

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
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6 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Sea View cabins from
$1,548$2,250
per Cabin
Loading
Departing on:
UP TO $600 OFF

San Juan, Samaná & Bimini

  • Miami, Florida
  • San Juan, Puerto Rico
  • Samaná, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$1,668$2,332
per Cabin
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7 nights
Resilient Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
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
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8 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$1,904$2,766
per Cabin
Loading
Departing on:
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
Loading
7 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$1,666$2,416
per Cabin
Loading
Departing on:
UP TO $600 OFF

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
$2,704$3,960
per Cabin
Loading
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Sea View cabins from
$2,704$3,960
per Cabin
Loading
Departing on:
UP TO $600 OFF

Resilient Caribbean Holidays

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,226$3,180
per Cabin
Loading
7 nights
Resilient Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$2,226$3,180
per Cabin
Loading
Departing on:
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
Insider cabins from
$2,226$3,266
per Cabin
Loading
7 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$2,226$3,266
per Cabin
Loading
Departing on:
UP TO $600 OFF

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
$4,304$6,434
per Cabin
Loading
9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$4,304$6,434
per Cabin
Loading
Departing on:
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
Loading
7 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Sea View cabins from
$3,768$5,658
per Cabin
Loading
Departing on:
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
$1,946$2,850
per Cabin
Loading
7 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
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
Loading
7 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Sea View cabins from
$2,086$3,078
per Cabin
Loading
Departing on:
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
Loading
7 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Sea View cabins from
$2,086$3,066
per Cabin
Loading
Departing on:
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
Loading
7 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Sea View cabins from
$2,088$3,062
per Cabin
Loading
Departing on:
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
Loading
7 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Sea View cabins from
$2,226$3,260
per Cabin
Loading
Departing on:
UP TO $600 OFF

San Juan Sunrises & Dominican Dreams

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
$1,948$2,766
per Cabin
Loading
7 nights
Resilient Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
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
Loading
7 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Sea Terrace cabins from
$2,646$3,908
per Cabin
Loading
Departing on:
UP TO $600 OFF

Brilliant Valentine's Voyage

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • St. Croix, U.S. Virgin Islands
  • Miami, Florida
Insider cabins from
$2,544$3,718
per Cabin
Loading
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$2,544$3,718
per Cabin
Loading
Departing on:

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
Loading
7 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Sea View cabins from
$2,226$3,284
per Cabin
Loading
Departing on:
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
Loading
7 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Sea Terrace cabins from
$2,786$4,138
per Cabin
Loading
Departing on:
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
Loading
7 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Sea Terrace cabins from
$2,646$3,932
per Cabin
Loading
Departing on:
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
Loading
7 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
UP TO $600 OFF

Puerto Rican Nights & St. Croix Delights

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • St. Croix, U.S. Virgin Islands
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,960$4,316
per Cabin
Loading
8 nights
Resilient Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$2,960$4,316
per Cabin
Loading
Departing on:

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
Loading
9 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$1,964$2,800
per Cabin
Loading
Departing on:

NY to San Juan: Bermuda & Caribbean

  • New York City, New York
  • Royal Naval Dockyard, Bermuda
  • The Beach Club at Bimini, Bahamas
  • St. Croix, U.S. Virgin Islands
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • San Juan, Puerto Rico
Insider cabins from
$2,856$4,016
per Cabin
Loading
12 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$2,856$4,016
per Cabin
Loading
Departing on:

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
Loading
7 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$1,946$2,844
per Cabin
Loading
Departing on:

November Nights in the Eastern Caribbean

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,384$3,410
per Cabin
Loading
8 nights
Resilient Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$2,384$3,410
per Cabin
Loading
Departing on:

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
Loading
6 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor

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
Loading
8 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$2,384$3,488
per Cabin
Loading
Departing on:

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
Loading
7 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$1,948$2,778
per Cabin
Loading
Departing on:

St. Maarten, Tortola, San Juan & more

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • St. Croix, U.S. Virgin Islands
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,580$3,584
per Cabin
Loading
10 nights
Brilliant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor

Pre-Holiday Caribbean Getaway

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • San Juan, Puerto Rico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,142$3,040
per Cabin
Loading
9 nights
Brilliant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$2,142$3,040
per Cabin
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Departing on:

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
Loading
7 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$2,786$4,136
per Cabin
Loading
Departing on:

Resilient Caribbean Holidays

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,646$3,834
per Cabin
Loading
7 nights
Resilient Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$2,646$3,834
per Cabin
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Departing on:

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
Loading
7 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$3,488$5,198
per Cabin
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Departing on:

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
Loading
8 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$2,226$3,156
per Cabin
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Departing on:

San Juan & St. Isles: Valentine’s Voyage

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • St. Croix, U.S. Virgin Islands
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,780$3,892
per Cabin
Loading
10 nights
Brilliant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$2,780$3,892
per Cabin
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Departing on:

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
Loading
7 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$2,088$2,976
per Cabin
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Departing on:

PR, DR & Bimini: Valentine’s Voyage

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
$2,590$3,676
per Cabin
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7 nights
Resilient Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off second Sailor
Insider cabins from
$2,590$3,676
per Cabin
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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
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7 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
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70% off second Sailor
Insider cabins from
$2,088$2,962
per Cabin
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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
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7 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$2,086$2,950
per Cabin
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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
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8 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$2,386$3,418
per Cabin
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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
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7 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Sea Terrace cabins from
$3,150$4,598
per Cabin
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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
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5 nights
Valiant Lady
+ Instant Savings+ Instant Savings
Instant Savings amount depends on cabin availability and selection at the time of purchase.
Learn more
70% off second Sailor
Insider cabins from
$1,492$2,054
per Cabin
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