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
& Resilient Lady
Year-round
Round-trip from Miami to Key West and The Beach Club at Bimini.The 12/10/25 sailing visits Key West on Day 2 followed by a sea day. The rest of the itinerary remains the same. The 12/24/25 sailing has a sea day on Day 1, Nassau on Day 2 and Bimini on Day 3.
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Dominican Daze
5-Night, Scarlet Lady, Valiant Lady
& Resilient Lady
Year-roundRound-trip from Miami to Puerto Plata and The Beach Club at Bimini.
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Mayan Sol
5-Night, Scarlet Lady, Valiant Lady
& Resilient Lady
Year-roundRound-trip from Miami to Costa Maya and The Beach Club at Bimini.
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Riviera Maya
5-Night, Scarlet Lady, Valiant Lady
& Resilient Lady
Year-roundRound-trip from Miami to Cozumel (Playa del Carmen) 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 & Resilient Lady
December 2024 - April 2025,
November 9-15, 2025Round-trip from Miami to Roatán, Costa Maya, and The Beach Club at Bimini.
*The sailing departing April 27, 2025 replaces the sailing day on Day 5 with Cozumel (Playa del Carmen) followed by a sea day on Day 6, replacing The Beach Club at Bimini, Bahamas. The rest of the itinerary is unchanged.
**The sailing departing November 9, 2025 flip the order of days 3 and 4 to first stop at Costa Maya, followed by Roatán. The rest of the itinerary is unchanged.
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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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Virgin Voyages Comedy Fest
5-Night, Valiant Lady
August 10-15, 2025Round-trip from Miami to Costa Maya and The Beach Club at 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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Riviera Maya: Halloween Edition
5-Night, Valiant Lady
October 19-24, 20255 Night Round Trip Sailing from Miami, stopping in Cozumel and The Beach Club at Bimini.
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Dominican Daze: Halloween Edition
5-Night, Valiant Lady
October 24-29, 20255 Night Round Trip Sailing from Miami, stopping in Puerto Plata and The Beach Club at Bimini.
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Valiant's Haunted Halloween Soirée
4-Night, Valiant Lady
October 29 - November 2, 20254 Night Round Trip Sailing from Miami, stopping in Key West 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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Miami, Grand Turk (& back)
5-Night, Scarlet Lady & Resilient Lady
November 2025 - March 2026Roundtrip from Miami to Grand Turk, and The Beach Club at Bimini.
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San Juan Sunrises & Dominican Dreams
7-Night, Resilient Lady
November 2024 - April 2026Roundtrip from Miami to San Juan, Puerto Plata, and The Beach Club at Bimini.
*The sailing departing January 31, 2025 and February 28, 2025 replaces the sea day on Day 3 with Puerto Plata, Dominican Republic followed by a sea day on Day 5, replacing Puerto Plata, Dominican Republic. The rest of the itinerary is unchanged.
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Cayman Coves & Jamaican Waterfalls
7-Night, Resilient Lady
November 2025 - February 2026 and April 24 - May 2, 2026Round trip from Miami to Ocho Rios, George Town and The Beach Club at Bimini.
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Western Caribbean: From Miami to Bimini
7-Night, Brilliant Lady
November 1-8, 2025Round trip from Miami to Ocho Rios, George Town and 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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Colorful Curaçao to the Charming Caymans
12-Night, Brilliant Lady
November 8-20, 2025Roundtrip from Miami to Aruba, Curaçao, Cartagena, Cartagena, Ocho Rios, and George Town.
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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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From Miami to St. Croix
8-Night, Brilliant Lady
November 20-28, 2025 & February 12-20, 2026Roundtrip from Miami to Puerto Plata, San Juan, St. Maarten, and St. Croix.
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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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Miami to San Juan
9-Night, Brilliant Lady
November 28th - December 8rd, 2025 & January 23rd - February 1st, 2026 & February 20th - March 1st, 2026Roundtrip from Miami to Grand Turk, Antigua, St. Kitts & Nevis and San Juan.
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San Juan, Samaná & Bimini
7-Night, Resilient Lady
November 29 - December 6, 2025 & January 17-24, 2026Round trip from Miami to San Juan, Samaná and The Beach Club at Bimini.
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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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Aruban Sunsets & Calm Cayman Days
11-Night, Brilliant Lady
December 7-18, 2025 and March 1-12, 2026Round trip from Miami to Aruba, Cartagena, Ocho Rios, and George Town.
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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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Cozumel, Grand Cayman & Bimini
7-Night, Resilient Lady
January 3-10, 2026Roundtrip from Miami to George Town, Cozumel (Playa del Carmen) and The Beach Club at Bimini.
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Miami to the Cayman Islands
11-Night, Brilliant Lady
January 4-15, 2026Round trip from Miami to Aruba, Bonaire, Cartagena, Ocho Rios, and George Town.
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Cayman Isles & Jamaican Miles
7-Night, Resilient Lady
January 10-17, 2026 & March 7-13, 2026Roundtrip from Miami to George Town, Ocho Rios and The Beach Club at Bimini.
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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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Grand Turk Tranquility & St. Croix Charm
8-Night, Brilliant Lady
January 15-23, 2026Roundtrip from Miami to Grand Turk, Puerto Plata, San Juan, 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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Magnetic Miami to Gorgeous George Town
11-Night, Brilliant Lady
February 1-12, 2026Round trip from Miami to Curaçao, Aruba, Cartagena, Ocho Rios, and George Town.
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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.
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Gorgeous Antigua, St. Kitts & Bimini
9-Night, Brilliant Lady
March 12-21, 2026Round trip from Miami to Puerto Plata, Antigua, St. Kitts, and Bimini.
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Costa Mayan Caves & Honduran Waves
6-Night, Resilient Lady
March 14-20, 2026Roundtrip from Miami to Costa Maya, Roatan, and Cozumel (Playa del Carmen).
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Puerto Rican Nights & St. Croix Delights
8-Night, Resilient Lady
March 20-28, 2026Roundtrip from Miami to Puerto Plata, San Juan, Frederiksted and The Beach Club at Bimini.
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Puerto Plata, San Juan & Tortola
7-Night, Scarlet Lady
April 19 - 26, 2026Sailing from Miami, Florida with stops in Puerto Plata, San Juan, and Tortola, BVI.
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.