Explore 400 cruise vacations

+ Balcony upgrades

70% off 2nd Sailor

Sea Terrace cabins from

per Cabin

Departing on:

Sun, Jul 13 - Sun, Jul 20

DEAL

Brilliant Lady Miami MerMaiden

Miami, Florida
Philipsburg, St. Maarten
Tortola, British Virgin Islands
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

per Cabin

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Fri, Oct 17 - Sat, Oct 25

DEAL

Honduras, Mexico & Bahamas

Miami, Florida
Roatán, Honduras
Costa Maya, Mexico
Cozumel, Mexico
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

per Cabin

7 nights

Scarlet Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Fri, Oct 31 - Fri, Nov 07

DEAL

Western Caribbean: From Miami to Bimini

Miami, Florida
Ocho Rios, Jamaica
George Town, Grand Cayman
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

per Cabin

7 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Nov 01 - Sat, Nov 08

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

Miami, Florida
Puerto Plata, Dominican Republic
Philipsburg, St. Maarten
Tortola, British Virgin Islands
San Juan, Puerto Rico

Insider cabins from

per Cabin

6 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Nov 02 - Sat, Nov 08

DEAL

Colorful Curaçao to the Charming Caymans

Miami, Florida
Oranjestad, Aruba
Willemstad, Curaçao
Cartagena, Colombia
Ocho Rios, Jamaica
George Town, Grand Cayman
Miami, Florida

Insider cabins from

per Cabin

12 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Nov 08 - Thu, Nov 20

DEAL

San Juan Sunrises & Dominican Dreams

Miami, Florida
San Juan, Puerto Rico
Puerto Plata, Dominican Republic
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

per Cabin

7 nights

Resilient Lady

Sat, Mar 28 - Sat, Apr 04

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

2026Best Rate

Sat, Nov 15 - Sat, Nov 22

Sat, Apr 18 - Sat, Apr 25

DEAL

Sunny San Juan & Isles of Beach Miles

Miami, Florida
Puerto Plata, Dominican Republic
San Juan, Puerto Rico
Philipsburg, St. Maarten
St. Croix, U.S. Virgin Islands
Miami, Florida

Insider cabins from

per Cabin

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Thu, Nov 20 - Fri, Nov 28

DEAL

Cayman Coves & Jamaican Waterfalls

Miami, Florida
Ocho Rios, Jamaica
George Town, Grand Cayman
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

per Cabin

7 nights

Resilient Lady

Sat, Dec 06 - Sat, Dec 13

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

2025Best Rate

Sat, Nov 22 - Sat, Nov 29

Sat, Dec 13 - Sat, Dec 20

DEAL

Antigua Waves & Grand Turk Caves

Miami, Florida
Grand Turk, Turks and Caicos
St. John's, Antigua
Basseterre, St. Kitts and Nevis
San Juan, Puerto Rico
Miami, Florida

Insider cabins from

per Cabin

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

Fri, Nov 28 - Sun, Dec 07

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

2025Best Rate

Fri, Feb 20 - Sun, Mar 01

DEAL

San Juan, Samaná & Bimini

Miami, Florida
San Juan, Puerto Rico
Samaná, Dominican Republic
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

per Cabin

7 nights

Resilient Lady

Sat, Nov 29 - Sat, Dec 06

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

2025Best Rate

Sat, Jan 17 - Sat, Jan 24

DEAL

Aruban Sunsets & Calm Cayman Days

Miami, Florida
Oranjestad, Aruba
Cartagena, Colombia
Ocho Rios, Jamaica
George Town, Grand Cayman
Miami, Florida

Insider cabins from

per Cabin

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

Sun, Mar 01 - Thu, Mar 12

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

2026Best Rate

Sun, Dec 07 - Thu, Dec 18

DEAL

Brilliant Caribbean Holidays

Miami, Florida
Grand Turk, Turks and Caicos
Puerto Plata, Dominican Republic
San Juan, Puerto Rico
Samaná, Dominican Republic
Miami, Florida

Insider cabins from

per Cabin

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Thu, Dec 18 - Fri, Dec 26

DEAL

Brilliant New Year's Ahoy!

Miami, Florida
Grand Turk, Turks and Caicos
St. John's, Antigua
Basseterre, St. Kitts and Nevis
San Juan, Puerto Rico
Miami, Florida

Insider cabins from

per Cabin

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Fri, Dec 26 - Sun, Jan 04

DEAL

Resilient New Year's Ahoy!

Miami, Florida
Ocho Rios, Jamaica
George Town, Grand Cayman
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

per Cabin

7 nights

Resilient Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Dec 27 - Sat, Jan 03

DEAL

Cozumel, Grand Cayman & Bimini

Miami, Florida
George Town, Grand Cayman
Cozumel, Mexico
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

per Cabin

7 nights

Resilient Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Jan 03 - Sat, Jan 10

DEAL

Aruba, Bonaire, Colombia, Jamaica & More

Miami, Florida
Oranjestad, Aruba
Kralendijk, Bonaire
Cartagena, Colombia
Ocho Rios, Jamaica
George Town, Grand Cayman
Miami, Florida

Insider cabins from

per Cabin

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Jan 04 - Thu, Jan 15

DEAL

Cayman Isles & Jamaican Miles

Miami, Florida
George Town, Grand Cayman
Ocho Rios, Jamaica
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

per Cabin

7 nights

Resilient Lady

Sat, Mar 07 - Sat, Mar 14

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

2026Best Rate

Sat, Jan 10 - Sat, Jan 17

DEAL

Magnetic Miami to Gorgeous George Town

Miami, Florida
Willemstad, Curaçao
Oranjestad, Aruba
Cartagena, Colombia
Ocho Rios, Jamaica
George Town, Grand Cayman
Miami, Florida

Insider cabins from

per Cabin

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Feb 01 - Thu, Feb 12

DEAL

Red Hot Sailing Club Voyage

Miami, Florida
Puerto Plata, Dominican Republic
St. John's, Antigua
Basseterre, St. Kitts and Nevis
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

per Cabin

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Thu, Mar 12 - Sat, Mar 21

DEAL

Puerto Rican Nights & St. Croix Delights

Miami, Florida
Puerto Plata, Dominican Republic
San Juan, Puerto Rico
St. Croix, U.S. Virgin Islands
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

per Cabin

8 nights

Resilient Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Fri, Mar 20 - Sat, Mar 28

DEAL

Puerto Plata, San Juan & Tortola

Miami, Florida
Puerto Plata, Dominican Republic
San Juan, Puerto Rico
Tortola, British Virgin Islands
Miami, Florida

Insider cabins from

per Cabin

7 nights

Scarlet Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Apr 19 - Sun, Apr 26