The Captivating Caribbean

4-Night
Scarlet, Valiant, Resilient & 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.

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

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

5-Night
Scarlet, Valiant & 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.

5-Night
Scarlet, Valiant & 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.

5-Night
Valiant Lady
October 19-24, 2025
& October 30 - November 4, 2027

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

5-Night
Valiant Lady
October 24-29, 2025

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

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

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

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

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

5-Night
Scarlet, Valiant & Resilient Lady
November 2025 - October 2026;
April - October 2027

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

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

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.

7-Night
Brilliant Lady
November 1-8, 2025

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

6-Night
Valiant Lady
November 2-8, 2025

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

12-Night
Brilliant Lady
November 8-20, 2025

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

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.

6-Night
Scarlet & 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.

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.

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.

7-Night
Valiant Lady
November 22-29, 2025

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

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.

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

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

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.

11-Night
Valiant Lady
December 2-13, 2025

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

8-Night
Valiant Lady
December 5-13, 2025

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

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

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

7-Night
Valiant Lady
December 13-20, 2025

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

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

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

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.

11-Night
Brilliant Lady
January 4-15, 2026

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

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.

*The itinerary departing January 17, 2027 swaps Day 3 in George Town, Grand Cayman to Ocho Rios, Jamaica and Day 4 with Ocho Rios, Jamaica to George Town, Grand Cayman, the rest of the itinerary is unchanged

7-Night
Valiant Lady
January 10-17, 2026

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

7-Night
Valiant Lady
January 17-24, 2026

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

7-Night
Valiant Lady
January 24-31, 2026

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

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

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

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

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

11-Night
Brilliant Lady
February 1-12, 2026

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

7-Nights
Valiant Lady
February 7-14, 2026

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

8-Night
Brilliant Lady
February 12-20, 2026

Round-trip sailing from Miami with stops in Puerto Plata, San Juan, Philipsburg, and Frederiksted.

5-Night
Scarlet Lady
February 13-18, 2026

Round-trip sailing from Miami with stops in Puerto Plata, and The Beach Club at Bimini.

7-Night
Resilient Lady
February 14-21, 2026

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

8-Night
Valiant Lady
Februrary 14-21, 2026

Round-trip sailing from San Juan with stops in Oranjestad, Willemstad, Frederiksted, and Philipsburg.

7-Night
Valiant Lady
February 21-28, 2026

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

7-Night
Valiant Lady
March 7-14, 2026

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

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

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

9-Night
Brilliant Lady
March 12-21, 2026

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

6-Night
Resilient Lady
March 14-20, 2026

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

8-Night
Resilient Lady
March 20-28, 2026

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

3-Night
Scarlet Lady
April 19 - 22, 2026

Round trip from Miami with a stop in Bimini.

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.

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.

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

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

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.

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.

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.

5-Night
Scarlet, Valiant & Resilient Lady
June 2026 ; November 9-14, 2026 ;
January - October, 2027

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

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.

*The itinerary departing November 14, 2026 swaps Day 3 in Basseterre, St Kitts to a Sea Day and Day 6 with a Sea Day to Basseterre, St Kitts, the rest of the itinerary is unchanged.

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.

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.

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.

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.

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.

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.

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.

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.

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.

4-Night
Scarlet Lady
February 11-15, 2027

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

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.

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.

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.

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.

4-Nights
Brilliant Lady
March 22-26, 2027

Round trip from Miami with stops in Freeport and The Beach Club at Bimini.

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.

5-Night
Valiant Lady
April 10 - April 15, 2027

One-way sailing from San Juan to Miami with stops in Puerto Plata and The Beach Club at Bimini

5-Nights
Resilient Lady
April 23-28, 2027

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