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Explore 404 cruise vacations

Showing Loading cruise vacations: North America & Caribbean, July 2025 - October 2026
6-8 & 9-12 nights
Showing 49 cruise vacations that match your search
Showing 49 cruise vacations that match your search
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Grand Cayman, Costa Maya & More

  • Miami, Florida
  • George Town, Grand Cayman
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Sea Terrace cabins from
per Cabin
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Departing on:
2025
Sun, Jul 13 - Sun, Jul 20
from (US$)

Grand Turk, Puerto Plata & More

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • Grand Turk, Turks and Caicos
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Sea Terrace cabins from
per Cabin
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Departing on:
2025
Sun, Jul 20 - Sun, Jul 27
from (US$)

Brilliant Lady Miami MerMaiden

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2025
Fri, Oct 17 - Sat, Oct 25
from (US$) Brilliant Lady's Inaugural Season

Honduras, Mexico & Bahamas

  • Miami, Florida
  • Roatán, Honduras
  • Costa Maya, Mexico
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
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per Cabin
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7 nights
Scarlet Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2025
Fri, Oct 31 - Fri, Nov 07
from (US$)

Western Caribbean: From Miami to Bimini

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
per Cabin
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7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Sea View cabins from
per Cabin
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Departing on:
2025
Sat, Nov 01 - Sat, Nov 08
from (US$) Brilliant Lady's Inaugural Season

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
per Cabin
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6 nights
Valiant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2025
Sun, Nov 02 - Sat, Nov 08
from (US$)

Colorful Curaçao to the Charming Caymans

  • Miami, Florida
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Insider cabins from
per Cabin
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12 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2025
Sat, Nov 08 - Thu, Nov 20
from (US$) Brilliant Lady's Inaugural Season

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
Sea View cabins from
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Sea View cabins from
per Cabin
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Departing on:
2026Best Rate
Sat, Mar 21 - Sat, Mar 28
from (US$)
2025
Sat, Nov 08 - Sat, Nov 15
from (US$)

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
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026Best Rate
Sat, Mar 28 - Sat, Apr 04
from (US$)
2025
Sat, Nov 15 - Sat, Nov 22
from (US$)
2026
Sat, Apr 18 - Sat, Apr 25
from (US$)

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
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7 nights
Valiant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026Best Rate
Sat, Feb 28 - Sat, Mar 07
from (US$)
2025
Sat, Nov 15 - Sat, Nov 22
from (US$)

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
Insider cabins from
per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2025
Thu, Nov 20 - Fri, Nov 28
from (US$) Brilliant Lady's Inaugural Season

Cayman Coves & Jamaican Waterfalls

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026Best Rate
Sat, Jan 24 - Sat, Jan 31
from (US$)
2025
Sat, Nov 22 - Sat, Nov 29
from (US$)
2025
Sat, Dec 06 - Sat, Dec 13
from (US$)

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
Insider cabins from
per Cabin
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9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2025Best Rate
Fri, Nov 28 - Sun, Dec 07
from (US$) Brilliant Lady's Inaugural Season
2026
Fri, Feb 20 - Sun, Mar 01
from (US$) Brilliant Lady's Inaugural Season

San Juan, Samaná & Bimini

  • Miami, Florida
  • San Juan, Puerto Rico
  • Samaná, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2025Best Rate
Sat, Nov 29 - Sat, Dec 06
from (US$)
2026
Sat, Jan 17 - Sat, Jan 24
from (US$)

Aruban Sunsets & Calm Cayman Days

  • Miami, Florida
  • Oranjestad, Aruba
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Insider cabins from
per Cabin
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11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
Loading
Departing on:
2026Best Rate
Sun, Mar 01 - Thu, Mar 12
from (US$) Brilliant Lady's Inaugural Season
2025
Sun, Dec 07 - Thu, Dec 18
from (US$) Brilliant Lady's Inaugural Season

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
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7 nights
Valiant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Sea View cabins from
per Cabin
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Departing on:
2025
Sat, Dec 13 - Sat, Dec 20
from (US$)

Brilliant Caribbean Holidays

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Samaná, Dominican Republic
  • Miami, Florida
Insider cabins from
per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2025
Thu, Dec 18 - Fri, Dec 26
from (US$) Brilliant Lady's Inaugural Season

Brilliant New Year's Ahoy!

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • St. John's, Antigua
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
  • Miami, Florida
Insider cabins from
per Cabin
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9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2025
Fri, Dec 26 - Sun, Jan 04
from (US$) Brilliant Lady's Inaugural Season

Resilient New Year's Ahoy!

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from (US$)

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
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7 nights
Valiant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from (US$)

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
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7 nights
Valiant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Sat, Jan 03 - Sat, Jan 10
from (US$)

Cozumel, Grand Cayman & Bimini

  • Miami, Florida
  • George Town, Grand Cayman
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Sat, Jan 03 - Sat, Jan 10
from (US$)

Aruba, Bonaire, Colombia, Jamaica & More

  • Miami, Florida
  • Oranjestad, Aruba
  • Kralendijk, Bonaire
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Insider cabins from
per Cabin
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11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Sun, Jan 04 - Thu, Jan 15
from (US$) Brilliant Lady's Inaugural Season

Cayman Isles & Jamaican Miles

  • Miami, Florida
  • George Town, Grand Cayman
  • Ocho Rios, Jamaica
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026Best Rate
Sat, Jan 10 - Sat, Jan 17
from (US$)
2026
Sat, Mar 07 - Sat, Mar 14
from (US$)

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
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7 nights
Valiant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Sat, Jan 10 - Sat, Jan 17
from (US$)

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
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7 nights
Valiant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Sea View cabins from
per Cabin
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Departing on:
2026
Sat, Jan 17 - Sat, Jan 24
from (US$)

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
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7 nights
Valiant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Sea View cabins from
per Cabin
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Departing on:
2026
Sat, Jan 24 - Sat, Jan 31
from (US$)

Magnetic Miami to Gorgeous George Town

  • Miami, Florida
  • Willemstad, Curaçao
  • Oranjestad, Aruba
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Insider cabins from
per Cabin
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11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Sun, Feb 01 - Thu, Feb 12
from (US$) Brilliant Lady's Inaugural Season

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
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7 nights
Valiant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Sat, Feb 21 - Sat, Feb 28
from (US$)

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
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7 nights
Valiant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Sat, Mar 07 - Sat, Mar 14
from (US$)

Red Hot Sailing Club Voyage

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • St. John's, Antigua
  • Basseterre, St. Kitts and Nevis
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Thu, Mar 12 - Sat, Mar 21
from (US$) Brilliant Lady's Inaugural Season

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
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7 nights
Valiant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Sat, Mar 14 - Sat, Mar 21
from (US$)

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
per Cabin
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8 nights
Resilient Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Fri, Mar 20 - Sat, Mar 28
from (US$)

Puerto Plata, San Juan & Tortola

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Miami, Florida
Insider cabins from
per Cabin
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7 nights
Scarlet Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Sun, Apr 19 - Sun, Apr 26
from (US$)
Average starting price per cabin (incl. taxes & fees)