Explore 419 cruise vacations

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

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Departing on:

Fri, Oct 17 - Sat, Oct 25

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

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per Cabin

Departing on:

Sat, Nov 01 - Sat, Nov 08

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Nov 08 - Thu, Nov 20

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

Thu, Nov 20 - Fri, Nov 28

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

2025Best Rate

Thu, Feb 12 - Fri, Feb 20

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

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per Cabin

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

Fri, Nov 28 - Sun, Dec 07

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

2025Best Rate

Fri, Feb 20 - Sun, Mar 01

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, Dec 07 - Thu, Dec 18

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

2025Best Rate

Sun, Mar 01 - Thu, Mar 12

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Thu, Dec 18 - Fri, Dec 26

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Fri, Dec 26 - Sun, Jan 04

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Jan 04 - Thu, Jan 15

Grand Turk, Puerto Plata & Bimini

Miami, Florida
The Beach Club at Bimini, Bahamas
Puerto Plata, Dominican Republic
Grand Turk, Turks and Caicos
Miami, Florida

Insider cabins from

per Cabin

6 nights

Brilliant Lady

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Mon, Jan 26 - Sun, Feb 01

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Feb 01 - Thu, Feb 12

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Thu, Mar 12 - Sat, Mar 21

Panama Canal & Pacific Wonders

Miami, Florida
Cartagena, Colombia
Colón, Panama
Panama Canal (Cruising), Panama
Puntarenas, Costa Rica
Puerto Quetzal, Guatemala
Cabo San Lucas, Mexico
Los Angeles, California

Insider cabins from

per Cabin

16 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Mar 21 - Mon, Apr 06