Explore 411 cruise vacations

Showing cruise vacations: All Destinations, October 2025 - March 2026

2 Sailors , 1 Cabin

Sails Brilliant Lady

UP TO $300 IN ONBOARD CREDIT

On Caribbean sailings 7 nights or longer

On top of 70% off 2nd Sailor + balcony upgrades

Showing 18 cruise vacations that match your search

Autumn Leaves: New York to Quebec

New York City, New York
Boston, Massachusetts
Eastport, Maine
Saint John, New Brunswick
Halifax, Nova Scotia
Quebec City, Quebec

Sea View cabins from

per Cabin

10 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Sea View cabins from

per Cabin

Departing on:

Tue, Sep 23 - Fri, Oct 03

Fall Leaves to Miami Scenes

Quebec City, Quebec
Halifax, Nova Scotia
Saint John, New Brunswick
Eastport, Maine
Boston, Massachusetts
Charleston, South Carolina
Miami, Florida

Insider cabins from

per Cabin

13 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Fri, Oct 03 - Thu, Oct 16

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

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Fri, Oct 17 - Sat, Oct 25

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

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Nov 01 - 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

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Nov 08 - Thu, Nov 20

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

Sea View cabins from

per Cabin

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Sea View cabins from

per Cabin

Departing on:

Thu, Nov 20 - Fri, Nov 28

Thu, Feb 12 - Fri, Feb 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

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Fri, Nov 28 - Sun, Dec 07

Fri, Feb 20 - Sun, Mar 01

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

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Dec 07 - Thu, Dec 18

Sun, Mar 01 - Thu, Mar 12

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

+ free balcony upgrade

SWING INTO SUMMER: 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

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Fri, Dec 26 - Sun, Jan 04

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

+ free balcony upgrade

SWING INTO SUMMER: 70% 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

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Mon, Jan 26 - Sun, Feb 01

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

+ free balcony upgrade

SWING INTO SUMMER: 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

+ free balcony upgrade

SWING INTO SUMMER: 70% 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

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Mar 21 - Mon, Apr 06