Sunlit mornings and effervescent nights. Kaleidoscopic reefs and exhilarating coastal hikes. Exclusive beach clubs and epic bonfire goodbyes. We’ve selected the most incredible destinations in the Caribbean to satisfy every part of yourself and all your exploratory cravings. And by curating itineraries with late stays, we’ll show you the real people and real experiences that make each port so special.
The Captivating Caribbean
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Fire & Sunset Soirées
4-Night, Scarlet Lady & Valiant Lady
Year-round
Round-trip from Miami to Key West and The Beach Club at Bimini. -
Dominican Daze
5-Night, Scarlet Lady & Valiant Lady
Year-roundRound-trip from Miami to Puerto Plata and The Beach Club at Bimini.
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Mayan Sol
5-Night, Valiant Lady
May 2024 - October 2025Round-trip from Miami to Costa Maya and The Beach Club at Bimini.
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Riviera Maya
5-Night, Scarlet Lady & Valiant Lady
Year-roundRound-trip from Miami to Cozumel (Playa del Carmen) and The Beach Club at Bimini.
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Miami, Grand Turk (& back)
5-Night, Scarlet Lady & Valiant Lady
April - September 2024, November 2025 - March 2026Roundtrip from Miami to Grand Turk, and The Beach Club at Bimini.
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Eastern Caribbean Antilles
8-Night, Scarlet Lady
December 2024 - April 2025Round-trip from Miami to Puerto Plata, San Juan, St. Croix, and The Beach Club at Bimini.
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Western Caribbean Charm
6-Night, Scarlet Lady
December 2024 - April 2025Round-trip from Miami to Roatán, Costa Maya, and The Beach Club at Bimini.
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A Virgin Celebration Voyage
5-Night, Valiant Lady
August 30 - September 4, 2024Round-trip from Miami to Puerto Plata and The Beach Club at Bimini.
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Costa Maya & Cozumel Charm
5-Night, Resilient Lady
November 10-15, 2024Round trip from Miami to Costa Maya and Cozumel.
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Grand Turk, Puerto Plata & Bimini
6-Night, Resilient Lady
November 15-21, 2024Round trip from Miami to Grand Turk, Puerto Plata, and The Beach Club at Bimini.
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One-Way San Juan Sojourn
6-Night, Resilient Lady
November 30 - December 6, 2024One-way trip from Miami to San Juan with stops in Grand Turk, Puerto Plata and St. Kitts & Nevis.
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Pre-Holiday Caribbean Refresh
8-Night, Resilient Lady
December 6-14, 2024Round-trip from San Juan to Tortola, St. Maarten, Barbados, Martinique, St. Lucia and St. Kitts and Nevis.
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Saint (Isles) & Seas of The Caribbean
7-Night, Resilient Lady & Valiant Lady
December 14-21, 2024; February - March 2025; November 8-15, 2025; January 24-31, 2026 and March 21-28, 2026Round-trip from San Juan to Tortola, Barbados, St. Lucia, Antigua, and St. Maarten.
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Sunsets in the Lesser Antilles
7-Night, Resilient Lady & Valiant Lady
January - March 2025 and March 14-21, 2026Round-trip from San Juan to Aruba, Curaçao, Martinique, and St. Kitts.
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San Juan, St. Vincent, Barbados & More
10-Night, Resilient Lady
January 11-21, 2025Round-trip from San Juan to Tortola, St. Kitts and Nevis, Antigua, Martinique, Barbados, St. Lucia, and St. Vincent.
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Idyllic Caribbean Isles & Colombia
11-Night, Resilient Lady & Valiant Lady
January 21 - February 1, 2025 and December 2-13, 2025Round-trip from San Juan to Cartagena, Curaçao, Aruba, St. Lucia, Antigua, and St. Maarten.
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San Juan, Barbados & Beyond
7-Night, Resilient Lady
March 1-8, 2025Round-trip from San Juan to St. Maarten, St. Lucia, Barbados, Martinique, and St. Kitts and Nevis.
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Puerto Rican Daze & Caribbean Nights
10-Night, Resilient Lady
March 22 - April 1, 2025Round-trip from San Juan to Tortola, Antigua, St. Kitts and Nevis, Martinique, St. Lucia, Barbados, and St. Vincent.
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Colombia & Caribbean Islands
11-Night, Resilient Lady
April 1-12, 2025Round-trip from San Juan to Cartagena, Aruba, Curaçao, Dominica, Antigua, and St. Maarten.
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Sunny Daze in Puerto Plata & Nassau
5-Night, Valiant Lady
April 11-16, 2025Round trip from Miami with stops in Puerto Plata and Nassau.
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Grand Cayman, Costa Maya & More
7-Night, Valiant Lady
July 13-20, 2025Round trip from Miami with stops in Grand Cayman, Costa Maya, and Bimini.
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Grand Turk, Puerto Plata & more
7-Night, Valiant Lady
July 20-27, 2025Round trip from Miami with stops in Grand Turk, Puerto Plata, and Bimini.
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Brilliant Lady Miami MerMaiden
8-Night, Brilliant Lady
October 17-25, 2025Roundtrip from Miami to St. Maarten, Tortola, and The Beach Club at Bimini.
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Honduras, Mexico & Bahamas
7-Night, Scarlet Lady
October 31 - November 7, 2025Roundtrip from Miami to Roatan, Costa Maya, Cozumel, and The Beach Club at Bimini.
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One-way to SJ: DR, St. Maarten & BVI
6-Night, Valiant Lady
November 2-8, 2025One-way from Miami to San Juan with stops in Puerto Plata, St. Maarten, and Tortola.
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Sunny Miles of Tropical Isles
7-Night, Valiant Lady
November 15-22, 2025 & February 28 - March 7, 2026Roundtrip from San Juan to St. Maarten, Barbados, St. Lucia, Martinique, and St. Kitts.
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Sun-Soaked Seas & Saint Isles
10-Night, Valiant Lady
November 22 - December 2, 2025Roundtrip from San Juan to Tortola, St. Kitts, Antigua, Martinique, Barbados, St. Lucia, and St. Maarten.
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Cartagena & Caribbean Faves
11-Night, Valiant Lady
December 2-13, 2025Roundtrip from San Juan to Cartagena, Curaçao, Aruba, Martinique, Antigua, and St. Maarten.
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St. Lucia, St. Maarten, Barbados & More
7-Night, Valiant Lady
December 13-20, 2025Roundtrip from San Juan to St. Kitts, St. Lucia, Dominica, Barbados, St. Maarten.
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Aruban Sights & Antiguan Nights
7-Night, Valiant Lady
January 3-10, 2026Roundtrip from San Juan to Aruba, Curaçao, Antigua, and St. Maarten.
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Virgin Island Views and Saint Isles Blues
7-Night, Valiant Lady
January 10-17, 2026Roundtrip from San Juan to Tortola, Barbados, St. Vincent, St. Kitts, and St. Croix.
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St. Kitts, Barbados, Martinique & More
7-Night, Valiant Lady
January 17-24, 2026Roundtrip from San Juan to St. Kitts, Barbados, Martinique, Antigua, and St. Maarten.
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Barbados, Antigua, BVI & More
7-Night, Valiant Lady
January 24-31, 2026Roundtrip from San Juan to Tortola, Barbados, Martinique, Antigua, and St. Maarten.
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Quintessential Caribbean Highlights
10-Night, Valiant Lady
January 31 - February 10, 2026Roundtrip from San Juan to St. Maarten, St. Kitts, Antigua, Martinique, St. Lucia, St. Vincent, and Barbados.
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Cartagena, Aruba, Antigua & More
11-Night, Valiant Lady
February 10-21, 2026Roundtrip from San Juan to Cartagena, Curaçao, Aruba, Antigua, St. Croix, and St. Maarten
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Antigua, Martinique, & Barbados & More
7-Night, Valiant Lady
February 21-28, 2026Roundtrip from San Juan to St. Maarten, Barbados, Martinique, Antigua, and Tortola.
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Quaint Castries to Elegant Antigua
7-Night, Valiant Lady
March 7-14, 2026Roundtrip from San Juan to St. Kitts, St. Lucia, Martinique, Antigua, and Tortola.
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.