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70% off 2nd Sailor + up to $500 in savings
Showing 10 cruise vacations that match your search
Saint (Isles) & Seas of the Caribbean
San Juan • Tortola • Bridgetown • Castries • St. John's • Philipsburg • San Juan
Up to $500 off 2025-2026 sailings
from
Price$187
per Sailor per night
Resilient Caribbean Holidays
San Juan • Philipsburg • Bridgetown • Castries • Fort-de-France • Basseterre • San Juan
Up to $500 off 2025-2026 sailings
from
Price$189
per Sailor per night
SAVE NOW, SAIL LATER
70% off 2nd Sailor + up to $500 off
Always Included Luxury: Wi-Fi, tips & gratuities, all dining, entertainment, and more.
Resilient New Year's Ahoy
San Juan • Tortola • Bridgetown • Castries • St. John's • Philipsburg • San Juan
Up to $500 off 2025-2026 sailings
from
Price$259
per Sailor per night
San Juan, St. Vincent, Barbados & More
San Juan • Tortola • Basseterre • St. John's • Fort-de-France • Bridgetown • Castries • Kingstown • San Juan
Up to $500 off 2025-2026 sailings
from
Price$189
per Sailor per night
Idyllic Caribbean Isles & Colombia
San Juan • Cartagena • Willemstad • Oranjestad • Castries • St. John's • Philipsburg • San Juan
Up to $500 off 2025-2026 sailings
from
Price$186
per Sailor per night
San Juan, Barbados & Beyond
San Juan • Philipsburg • Castries • Bridgetown • Fort-de-France • Basseterre • San Juan
Up to $500 off 2025-2026 sailings
from
Price$227
per Sailor per night
Puerto Rican Daze & Caribbean Nights
San Juan • Tortola • St. John's • Basseterre • Fort-de-France • Castries • Bridgetown • Kingstown • San Juan
Up to $500 off 2025-2026 sailings
from
Price$176
per Sailor per night
Colombia & Caribbean Islands
San Juan • Cartagena • Oranjestad • Willemstad • Roseau • St. John's • Philipsburg • San Juan
Up to $500 off 2025-2026 sailings
from
Price$189
per Sailor per night