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

  • Fire & Sunset Soirées

    4-Night, Scarlet Lady, Valiant Lady, Resilient Lady & Brilliant 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.

    View Itinerary

  • Dominican Daze

    5-Night, Scarlet Lady, Valiant Lady, Resilient Lady & Brilliant Lady
    Year-round

    Round-trip from Miami to Puerto Plata and The Beach Club at Bimini.

    View Itinerary

  • Mayan Sol

    5-Night, Scarlet Lady, Valiant Lady
    & Resilient Lady
    May - October 2025; June 22-27, 2026; November 2026 - January 2027; March 20-25, 2027

    Round-trip from Miami to Costa Maya and The Beach Club at Bimini.

    View Itinerary

  • Riviera Maya

    5-Night, Scarlet Lady, Valiant Lady & Resilient Lady
    April 2025 - may 2026; July 2026; January - February 2027

    Round-trip from Miami to Cozumel (Playa del Carmen) and The Beach Club at Bimini.

    View Itinerary

  • Eastern Caribbean Antilles

    8-Night, Scarlet Lady
    December 2024 - April 2025

    Round-trip from Miami to Puerto Plata, San Juan, St. Croix, and The Beach Club at Bimini.

    View Itinerary

  • Saint (Isles) & Seas of The Caribbean

    7-Night, Valiant Lady
    November 8-15, 2025; January 24-31, 2026; March 21-28, 2026; January 2-9, 2027 & March 6-13, 2027

    Round-trip from San Juan to Tortola, Barbados, St. Lucia, Antigua, and St. Maarten.

    View Itinerary

  • Western Caribbean Charm

    6-Night, Scarlet Lady & Resilient Lady
    December 2024 - April 2025,
    November 9-15, 2025

    Round-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.

    View Itinerary

  • Sunsets in the Lesser Antilles

    7-Night, Valiant Lady
    March 14-21, 2026 & December 2026 - April 2027

    Round-trip from San Juan to Aruba, Curaçao, Martinique, and St. Kitts.

    View Itinerary

  • Miami, Grand Turk (& back)

    5-Night, Scarlet Lady & Resilient Lady
    November 2025 - October 2026

    Round-trip from Miami to Grand Turk, and The Beach Club at Bimini.

    View Itinerary

  • Idyllic Caribbean Isles & Colombia

    11-Night, Valiant Lady
    December 2-13, 2025

    Round-trip from San Juan to Cartagena, Curaçao, Aruba, St. Lucia, Antigua, and St. Maarten.

    View Itinerary

  • Puerto Rican Daze & Caribbean Nights

    10-Night, Resilient Lady
    March 22 - April 1, 2025

    Round-trip from San Juan to Tortola, Antigua, St. Kitts and Nevis, Martinique, St. Lucia, Barbados, and St. Vincent.

    View Itinerary

  • Colombia & Caribbean Islands

    11-Night, Resilient Lady
    April 1-12, 2025

    Round-trip from San Juan to Cartagena, Aruba, Curaçao, Dominica, Antigua, and St. Maarten.

    View Itinerary

  • Sunny Daze in Puerto Plata & Nassau

    5-Night, Valiant Lady
    April 11-16, 2025

    Round-trip from Miami with stops in Puerto Plata and Nassau.

    VIEW ITINERARY

  • A Virgin Celebration Voyage

    5-Night, Valiant Lady
    May 4-9, 2025

    Round-trip from Miami to Cozumel, and Bimini

    VIEW ITINERARY

  • Grand Cayman, Costa Maya & More

    7-Night, Valiant Lady
    July 13-20, 2025

    Round-trip from Miami with stops in Grand Cayman, Costa Maya, and Bimini.

    View Itinerary

  • Grand Turk, Puerto Plata & more

    7-Night, Valiant Lady
    July 20-27, 2025

    Round-trip from Miami with stops in Grand Turk, Puerto Plata, and Bimini.

    View Itinerary

  • Virgin Voyages Comedy Fest

    5-Night, Valiant Lady
    August 10-15, 2025

    Round-trip from Miami to Costa Maya and The Beach Club at Bimini.

    View Itinerary

  • Brilliant Lady Miami MerMaiden

    8-Night, Brilliant Lady
    October 17-25, 2025

    Roundtrip from Miami to St. Maarten, Tortola, and The Beach Club at Bimini.

    View Itinerary

  • Riviera Maya: Halloween Edition

    5-Night, Valiant Lady
    October 19-24, 2025

    Round-trip Sailing from Miami, stopping in Cozumel and The Beach Club at Bimini.

    VIEW ITINERARY

  • Dominican Daze: Halloween Edition

    5-Night, Valiant Lady
    October 24-29, 2025

    Round-trip Sailing from Miami, stopping in Puerto Plata and The Beach Club at Bimini.

    VIEW ITINERARY

  • Valiant's Haunted Halloween Soirée

    4-Night, Valiant Lady
    October 29 - November 2, 2025

    Round-trip Sailing from Miami, stopping in Key West and The Beach Club at Bimini.

    VIEW ITINERARY

  • Honduras, Mexico & Bahamas

    7-Night, Scarlet Lady
    October 31 - November 7, 2025

    Round-trip from Miami to Roatan, Costa Maya, Cozumel, and The Beach Club at Bimini.

    View Itinerary

  • San Juan Sunrises & Dominican Dreams

    7-Night, Resilient Lady
    November 2025 - April 2026; December 2026; January & March 2027

    Round-trip 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.

    View Itinerary

  • Cayman Coves & Jamaican Waterfalls

    7-Night, Resilient Lady
    November 2025 - February 2026; April 25 - May 2026; November 2026 & January - April 2027

    Round-trip from Miami to Ocho Rios, George Town and The Beach Club at Bimini.

    View Itinerary

  • Western Caribbean: From Miami to Bimini

    7-Night, Brilliant Lady
    November 1-8, 2025

    Round-trip from Miami to Ocho Rios, George Town and Bimini.

    View Itinerary

  • One-way to SJ: DR, St. Maarten & BVI

    6-Night, Valiant Lady
    November 2-8, 2025

    One-way from Miami to San Juan with stops in Puerto Plata, St. Maarten, and Tortola.

    View Itinerary

  • Colorful Curaçao to the Charming Caymans

    12-Night, Brilliant Lady
    November 8-20, 2025

    Round-trip from Miami to Aruba, Curaçao, Cartagena, Cartagena, Ocho Rios, and George Town.

    View Itinerary

  • Sunny Miles of Tropical Isles

    7-Night, Valiant Lady
    November 15-22, 2025 & February 28 - March 7, 2026; November 7-14, 2026; December 12-19, 2026 & January 16-23, 2027

    Round-trip from San Juan to St. Maarten, Barbados, St. Lucia, Martinique, and St. Kitts.

    View Itinerary

  • Sunny San Juan & Isles of Beach Miles

    8-Night, Brilliant Lady
    November 20-28, 2025 & February 12-20, 2026

    Round-trip from Miami to Puerto Plata, San Juan, St. Maarten, and St. Croix.

    View Itinerary

  • Thanksgiving In The Lesser Antilles

    7-Night, Valiant Lady
    November 22-29, 2025

    Round-trip from San Juan to Road Town, Basseterre, St. Johns, Castries, and St. Thomas.

    View Intinerary

  • Antigua Waves & Grand Turk Caves

    9-Night, Brilliant Lady
    November 28 - December 7, 2025 & February 20 - March 1, 2026

    Round-trip from Miami to Grand Turk, Antigua, St. Kitts & Nevis and San Juan.

    View Itinerary

  • San Juan to Barbados & The St.Isles

    6-Night, Valiant Lady
    November 29 - December 5, 2025

    Round-trip from San Juan to Philipsburg, Basseterre, Roseau, and Bridgetown.

    View Itinerary

  • San Juan, Samaná & Bimini

    7-Night, Resilient Lady
    November 29 - December 6, 2025 & January 17-24, 2026

    Round-trip from Miami to San Juan, Samaná and The Beach Club at Bimini.

    View Itinerary

  • Aruba, Curaçao and the Lesser Antilles

    8-Night, Valiant Lady
    December 5-13, 2025

    Round-trip from San Juan to Willemstad, Oranjestad, Roseau, St. Johns, and Philipsburg.

    View Itinerary

  • Aruban Sunsets & Calm Cayman Days

    11-Night, Brilliant Lady
    December 7-18, 2025 and March 1-12, 2026

    Round-trip from Miami to Aruba, Cartagena, Ocho Rios, and George Town.

    View Itinerary

  • St. Lucia, St. Maarten, Barbados & More

    7-Night, Valiant Lady
    December 13-20, 2025

    Round-trip from San Juan to St. Kitts, St. Lucia, Dominica, Barbados, St. Maarten.

    View Itinerary

  • Aruban Sights & Antiguan Nights

    7-Night, Valiant Lady
    January 3-10, 2026; February 6-13, 2027

    Round-trip from San Juan to Aruba, Curaçao, Antigua, and St. Maarten.

    View Itinerary

  • Cozumel, Grand Cayman & Bimini

    7-Night, Resilient Lady
    January 3-10, 2026

    Round-trip from Miami to George Town, Cozumel (Playa del Carmen) and The Beach Club at Bimini.

    View Itinerary

  • Aruba, Bonaire, Colombia, Jamaica & More

    11-Night, Brilliant Lady
    January 4-15, 2026

    Round-trip from Miami to Aruba, Bonaire, Cartagena, Ocho Rios, and George Town.

    View Itinerary

  • Cayman Isles & Jamaican Miles

    7-Night, Resilient Lady
    January 10-17, 2026; March 7-13, 2026 & November 2026 - March 2027

    Round-trip from Miami to George Town, Ocho Rios and The Beach Club at Bimini.

    View Itinerary

  • Virgin Island Views and Saint Isles Blues

    7-Night, Valiant Lady
    January 10-17, 2026

    Round-trip from San Juan to Tortola, Barbados, St. Vincent, St. Kitts, and St. Croix.

    View Itinerary

  • St. Kitts, Barbados, Martinique & More

    7-Night, Valiant Lady
    January 17-24, 2026

    Round-trip from San Juan to St. Kitts, Barbados, Martinique, Antigua, and St. Maarten.

    View Itinerary

  • Barbados, Antigua, BVI & More

    7-Night, Valiant Lady
    January 24-31, 2026

    Round-trip from San Juan to Tortola, Barbados, Martinique, Antigua, and St. Maarten.

    View Itinerary

  • Grand Turk, Puerto Plata & Bimini

    6-Night, Brilliant Lady
    January 26 - February 1, 2026

    Round-trip from Miami to The Beach Club at Bimini, Puerto Plata, and Grand Turk.

    VIEW ITINERARY

  • Antigua & the St. Isles

    7-Night, Valiant Lady
    January 31-February 7, 2026

    Round-trip from San Juan to Philipsburg, Basseterre, St. Johns, Castries, and St. Thomas.

    View itinerary

  • Magnetic Miami to Gorgeous George Town

    11-Night, Brilliant Lady
    February 1-12, 2026

    Round-trip from Miami to Curaçao, Aruba, Cartagena, Ocho Rios, and George Town.

    View Itinerary

  • St. Lucia, Barbados & More

    7-Nights, Valiant Lady
    February 7-14, 2026

    Round-trip from San Juan to Philipsburg, Basseterre, Castries, Bridgetown, and St. Thomas.

    View Itinerary

  • Aruba, Curaçao and the St. Isles

    7-Night, Valiant Lady
    February 14-21, 2026

    Round-trip from San Juan to Oranjestad, Willemstad, Frederiksted, and Philipsburg.

    View Itinerary

  • Antigua, Martinique, & Barbados & More

    7-Night, Valiant Lady
    February 21-28, 2026

    Round-trip from San Juan to St. Maarten, Barbados, Martinique, Antigua, and Tortola.

    View Itinerary

  • Quaint Castries to Elegant Antigua

    7-Night, Valiant Lady
    March 7-14, 2026

    Round-trip from San Juan to St. Kitts, St. Lucia, Martinique, Antigua, and Tortola.

    View Itinerary

  • Gorgeous Antigua, St. Kitts & Bimini

    9-Night, Brilliant Lady
    March 12-21, 2026

    Round-trip from Miami to Puerto Plata, Antigua, St. Kitts, and Bimini.

    View Itinerary

  • Costa Mayan Caves & Honduran Waves

    6-Night, Resilient Lady
    March 14-20, 2026

    Round-trip from Miami to Costa Maya, Roatan, and Cozumel (Playa del Carmen).

    View Itinerary

  • Puerto Rican Nights & St. Croix Delights

    8-Night, Resilient Lady
    March 20-28, 2026

    Round-trip from Miami to Puerto Plata, San Juan, Frederiksted and The Beach Club at Bimini.

    View Itinerary

  • Puerto Plata, San Juan & Tortola

    7-Night, Scarlet Lady
    April 19 - 26, 2026

    Sailing from Miami, Florida with stops in Puerto Plata, San Juan, and Tortola, BVI.

    View Itinerary

  • Miami to Grand Turk: Halloween Edition

    6-Night, Scarlet Lady
    October 25-31, 2026

    Round-trip from Miami to Grand Turk, Turks & Caicos with stops in Puerto Plata, Dominican Republic and The Beach Club at Bimini, Bahamas.

    View Itinerary

  • Mexico & Bimini: Halloween Edition

    6-Night, Resilient Lady
    October 26 - November 1, 2026

    Round-trip from Miami to Cozumel (Playa del Carmen), Mexico with stops in Costa Maya, Mexico and The Beach Club at Bimini, Bahamas.

    View Itinerary

  • Scarlet's Haunted Halloween Soirée

    5-Night, Scarlet Lady
    October 31 - November 5, 2026

    Round-trip from Miami to Cozumel (Playa del Carmen) and The Beach Club at Bimini.

    View Itinerary

  • Valiant's Haunted Halloween Soirée

    7-Night, Valiant Lady
    October 31 - November 7, 2026

    Round-trip from San Juan, Puerto Rico to Willemstad, Curaçao with stops in Oranjestad, Aruba, Fort-de-France, Martinique and Basseterre, St. Kitts & Nevis.

    View Itinerary

  • Fire & Sunsets Soirées - with Nassau

    4-Night, Scarlet Lady
    November 5-9, 2026; December 26-30, 2026; January 14-18, 2027

    Round-trip from Miami to Nassau, Bahamas and The Beach Club at Bimini, Bahamas.

    View Itinerary

  • November Nights In The Eastern Caribbean

    8-Night, Resilient Lady
    November 8-16, 2026

    Round-trip from Miami toPuerto Plata, Dominican Republic with stops in San Juan, Puerto Rico, Road Town, Tortola, BVI and The Beach Club at Bimini, Bahamas.

    View Itinerary

  • Cayman Isles & Bimini Beach Miles

    5-Night, Scarlet Lady
    November 9-14; January 23-28; March 6-11 & March 29 - April 3, 2027

    Round-trip sailing from Miami with stops in George Town and The Beach Club at Bimini.

    View Itinerary

  • Caribbean East: Virgin & Saint Isles

    6-Night, Valiant Lady
    November 14-20, 2026; January 23-29 & March 13-19, 2027

    Round-trip sailing from San Juan with stops in Tortola, St. Kitts & Nevis, Antigua and St. Lucia.

    View Itinerary

  • St. Isles & Sun-Soaked Seas

    10-Night, Brilliant Lady
    November 15-25, 2026; January 25 - February 4, 2027 & February 22 - March 4, 2027

    Round-trip from Miami with stops in St. Maarten, Tortola, St. Kitts & Nevis, Antigua, and The Beach Club at Bimini.

    View Itinerary

  • Captivating Costa Maya & Cozumel Charm

    6-Night, Resilient Lady
    November 16-22, 2026

    Round-trip from Miami to Costa Maya, Mexico, Cozumel (Playa del Carmen), Mexico and The Beach Club at Bimini, Bahamas.

    View Itinerary

  • Thanksgiving: St. Isles, Aruba & Curaçao

    8-Night, Valiant Lady
    November 20-28, 2026

    Round-trip sailing from San Juan with stops in St. Thomas, Curaçao, Aruba, St. Kitts & Nevis and St. Maarten.

    View Itinerary

  • Jamaican Waves & Bimini Breeze

    5-Night, Scarlet Lady
    November 23-28, 2026 & February 15-20, 2027

    Round-trip sailing from Miami with stops in Ocho Rios and The Beach Club at Bimini.

    View Itinerary

  • Antiguan Elegance & Sunny St. Isles

    7-Night, Valiant Lady
    November 28 - December 5, 2026

    Round-trip sailing from San Juan with stops in St. Thomas, Tortola, St. Kitts & Nevis, Antigua, and St. Maarten.

    View Itinerary

  • St. Maarten, Tortola, San Juan & More

    10-Night, Brilliant Lady
    November 30 - December 10, 2026; January 11-21, 2027 & March 8-18, 2027

    Round-trip from Miami with stops in St. Maarten, Tortola, St. Croix, San Juan, Puerto Plata, and The Beach Club at Bimini.

    View Itinerary

  • Pre-Holiday Caribbean Getaway

    9-Night, Brilliant Lady
    December 14-23, 2026

    Round-trip from Miami with stops in St. Maarten, Tortola, San Juan, and The Beach Club at Bimini.

    View Itinerary

  • Puerto Rico to Aruba, Bonaire & More

    8-Night, Valiant Lady
    January 29 - February 6, 2027

    Round-trip from San Juan, Puerto Rico to Oranjestad, Aruba with stops in Willemstad, Curaçao, Kralendijk, Bonaire, Fort-de-France, Martinique and Philipsburg, St. Maarten.

    View Itinerary

  • San Juan & St. Isles: Valentine’s Voyage

    10-Night, Brilliant Lady
    February 8-18, 2027

    Round-trip from Miami with stops in St. Maarten, Tortola, St. Croix, San Juan, Puerto Plata, and The Beach Club at Bimini.

    View Itinerary

  • Key West & Bimini: Valentine's Voyage

    4-Night, Scarlet Lady
    February 11-15, 2027

    Round-trip from Miami to Key West, Florida and The Beach Club at Bimini, Bahamas.

    View Itinerary

  • Lesser Antilles: Valentine's Day

    7-Night, Valiant Lady
    February 13-30, 2027

    Round-trip from San Juan, Puerto Rico to Oranjestad, Aruba with stops in Willemstad, Curaçao, Fort-de-France, Martinique and Basseterre, St. Kitts and Nevis.

    View Itinerary

  • PR, DR & Bimini: Valentine's Voyage

    7-Night, Resilient Lady
    February 14-21, 2027

    Round-trip from Miami to San Juan, Puerto Rico with stops in Puerto Plata, Dominican Republic and The Beach Club at Bimini, Bahamas.

    View Itinerary

  • Saint Isles & The Greater Antilles

    7-Night, Valiant Lady
    February 20-27, 2027

    Round-trip from San Juan, Puerto Rico to Road Town, Tortola, BVI with stops in Castries, St. Lucia, Bridgetown, Barbados, Roseau, Dominica and Philipsburg, St. Maarten.

    View Itinerary

  • Barbados, Dominica & St. Isles Spring

    8-Night, Valiant Lady
    March 19-27, 2027

    Round-trip from San Juan, Puerto Rico to St. Thomas, U.S. Virgin Islands with stops in Bridgetown, Barbados, Kingstown, St. Vincent, Roseau, Dominica and Philipsburg, St. Maarten.

    View Itinerary

  • Colorful Curaçao, Aruba & Antigua

    7-Night, Valiant Lady
    March 27 - April 3, 2027

    Round-trip from San Juan, Puerto Rico to Willemstad, Curaçao with stops in Oranjestad, Aruba, St. Johns, Antigua and Philipsburg, St. Maarten.

    View Itinerary

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.