Celebrate special occasions at sea with sailings that take you to dreamy destinations on dates you already have marked on your calendar. Whether you’re toasting at midnight to a new year off Tulum or welcoming the holidays with a suntan on Roatán, these special itineraries make already festive times of the year even more unforgettable.
Caribbean Holiday Itineraries
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Brilliant Caribbean Holidays 2025
8-Night, Brilliant Lady
December 18-26, 2025Roundtrip from Miami to Grand Turk, Puerto Plata, San Juan, and Samana.
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Valiant Caribbean Holidays 2025
7-Night, Valiant Lady
December 20-27, 2025Roundtrip from San Juan to St. Maarten, St. Kitts, Antigua, St. Lucia, and Tortola.
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Resilient Caribbean Holidays 2025
7-Night, Resilient Lady
December 20-27, 2025Roundtrip from Miami to San Juan, Puerto Plata and The Beach Club at Bimini.
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Scarlet Caribbean Holidays 2025
4-Night, Scarlet Lady
December 24-28, 2025Round-trip from Miami to Nassau and The Beach Club at Bimini.
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Brilliant 2025 New Year’s Ahoy!
9-Night, Brilliant Lady
December 26, 2025 - January 4, 2026Round trip Miami to Grand Turk, Philipsburg, St. Kitts, and San Juan.
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Valiant 2025 New Year’s Ahoy!
7-Night, Valiant Lady
December 27, 2025 - January 3, 2026Roundtrip from San Juan to St. Maarten, St. Kitts, St. Lucia, Barbados, and St. Croix.
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Resilient 2025 New Year’s Ahoy!
7-Night, Resilient Lady
December 27, 2025 - January 3, 2026Roundtrip from Miami to Ocho Rios, George Town and The Beach Club at Bimini.
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Scarlet 2025 New Year's Ahoy!
5-Night, Scarlet Lady
December 28, 2025 - January 2, 2026Round-trip from Miami to Cozumel, Cozumel (Playa del Carmen), and The Beach Club at Bimini.
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Valiant Caribbean Holidays 2026
7-Night, Valiant Lady
December 19-26, 2026
Round-trip from San Juan, Puerto Rico to Basseterre, St. Kitts with stops in Fort-de-France, Martinique, Oranjestad, Aruba and Willemstad, Curaçao. -
Resilient Caribbean Holidays 2026
7-Night, Resilient Lady
December 20-27, 2026
Round-trip from Miami to Puerto Plata, Dominican Republic, San Juan, Puerto Rico and The Beach Club at Bimini, Bahamas. -
Scarlet Caribbean Holidays 2026
5-Night, Scarlet Lady
December 21-26, 2026
Round-trip from Miami to Cozumel (Playa del Carmen), Mexico and The Beach Club at Bimini, Bahamas. -
Brilliant Caribbean Holidays 2026
5-Night, Brilliant Lady
December 23-28, 2026
Round-trip Miami to The Beach Club at Bimini, and Puerto Plata. -
Valiant 2026 New Year's Ahoy!
7-Night, Valiant Lady
December 26, 2026 - January 2, 2027
Round-trip from San Juan, Puerto Rico to Philipsburg, St. Maarten, Fort-de-France, Martinique, Bridgetown, Barbados, Castries, St. Lucia and St. Johns, Antigua. -
Resilient 2026 New Year's Ahoy!
7-Night, Resilient Lady
December 27, 2026 - January 3, 2027
Round-trip from Miami to George Town, Grand Cayman, Ocho Rios, Jamaica and The Beach Club at Bimini, Bahamas. -
Brilliant 2026 New Year's Ahoy!
10-Night, Brilliant Lady
December 28, 2026 - January 7, 2027
Round-trip from Miami with stops in St. Maarten, St. Kitts & Nevis, Tortola, Antigua, and The Beach Club at Bimini. -
Scarlet 2026 New Year's Ahoy!
5-Night, Scarlet Lady
December 30, 2026 - January 4, 2027
Round-trip from Miami to Puerto Plata, Dominican Republic and The Beach Club at Bimini, Bahamas.
Itinerary details, including arrival/departure times and days of port calls, are subject to change.
To best take advantage of the incredible sunsets in Bimini, our ship departure time may change with the seasons.
Please refer to www.firstmates.com/fmdc/s/destinations for the most updated itineraries.