Explore 381 cruise vacations

Showing 32 cruise vacations: All Destinations, November 2025 - December 2025

Extra $100 onboard credit ending soon

Showing 21 cruise vacations that match your search

Sunny San Juan & Isles of Beach Miles

Miami, Florida • Puerto Plata • San Juan, Puerto Rico • Philipsburg • St. Croix • Miami, Florida

Insider cabins from

$2,384

per Cabin

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$2,384

per Cabin

Departing on:

2025

Thu, Nov 20 - Fri, Nov 28

from (US$)$2,384

Cayman Coves & Jamaican Waterfalls

Miami, Florida • Ocho Rios • George Town • The Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,086

per Cabin

7 nights

Resilient Lady

BOOK NOW

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$2,086

per Cabin

Departing on:

2025Best Rate

Sat, Dec 06 - Sat, Dec 13

from (US$)$2,086

2025

Sat, Nov 22 - Sat, Nov 29

from (US$)$2,226

2025

Sat, Dec 13 - Sat, Dec 20

from (US$)$2,086

Thanksgiving in the Lesser Antilles

San Juan, Puerto Rico • Tortola • Basseterre • St. John's • Castries • St. Thomas • San Juan, Puerto Rico

Insider cabins from

$2,088

per Cabin

7 nights

Valiant Lady

BOOK NOW

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$2,088

per Cabin

Departing on:

2025

Sat, Nov 22 - Sat, Nov 29

from (US$)$2,088

Fire & Sunset Soirées

Miami, Florida • Key West, Florida • The Beach Club at Bimini • Miami, Florida

Sea View cabins from

$1,602

per Cabin

4 nights

Scarlet Lady

BOOK NOW

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Sea View cabins from

$1,602

per Cabin

Departing on:

2025Best Rate

Wed, Dec 10 - Sun, Dec 14

from (US$)$1,602

2025

Wed, Nov 26 - Sun, Nov 30

from (US$)$1,802

Antigua Waves & Grand Turk Caves

Miami, Florida • Grand Turk • St. John's • Basseterre • San Juan, Puerto Rico • Miami, Florida

Insider cabins from

$2,322

per Cabin

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$2,322

per Cabin

Departing on:

2025

Fri, Nov 28 - Sun, Dec 07

from (US$)$2,322

San Juan to Barbados & the St. Isles

San Juan, Puerto Rico • Philipsburg • Basseterre • Roseau • Bridgetown • San Juan, Puerto Rico

Insider cabins from

$1,550

per Cabin

6 nights

Valiant Lady

BOOK NOW

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$1,550

per Cabin

Departing on:

2025

Sat, Nov 29 - Fri, Dec 05

from (US$)$1,550

San Juan, Samaná & Bimini

Miami, Florida • San Juan, Puerto Rico • Samaná • The Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,948

per Cabin

7 nights

Resilient Lady

BOOK NOW

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$1,948

per Cabin

Departing on:

2025

Sat, Nov 29 - Sat, Dec 06

from (US$)$1,948

Miami, Grand Turk (& back)

Miami, Florida • Grand Turk • The Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,500

per Cabin

5 nights

Scarlet Lady

BOOK NOW

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$1,500

per Cabin

Departing on:

2025Best Rate

Sun, Nov 30 - Fri, Dec 05

from (US$)$1,500

2025

Fri, Dec 19 - Wed, Dec 24

from (US$)$1,802

Aruba, Curaçao and the Lesser Antilles

San Juan, Puerto Rico • Willemstad • Oranjestad • Roseau • St. John's • Philipsburg • San Juan, Puerto Rico

Insider cabins from

$2,480

per Cabin

8 nights

Valiant Lady

BOOK NOW

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$2,480

per Cabin

Departing on:

2025

Fri, Dec 05 - Sat, Dec 13

from (US$)$2,480

Dominican Daze

Miami, Florida • Puerto Plata • The Beach Club at Bimini • Miami, Florida

Sea View cabins from

$2,002

per Cabin

5 nights

Scarlet Lady

BOOK NOW

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Sea View cabins from

$2,002

per Cabin

Departing on:

2025

Fri, Dec 05 - Wed, Dec 10

from (US$)$2,002

Aruban Sunsets & Calm Cayman Days

Miami, Florida • Oranjestad • Cartagena • Ocho Rios • George Town • Miami, Florida

Insider cabins from

$2,838

per Cabin

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$2,838

per Cabin

Departing on:

2025

Sun, Dec 07 - Thu, Dec 18

from (US$)$2,838

St. Lucia, St. Maarten, Barbados & More

San Juan, Puerto Rico • Basseterre • Castries • Roseau • Bridgetown • Philipsburg • San Juan, Puerto Rico

Insider cabins from

$2,086

per Cabin

7 nights

Valiant Lady

BOOK NOW

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$2,086

per Cabin

Departing on:

2025

Sat, Dec 13 - Sat, Dec 20

from (US$)$2,086

Riviera Maya

Miami, Florida • Cozumel • The Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,700

per Cabin

5 nights

Scarlet Lady

BOOK NOW

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$1,700

per Cabin

Departing on:

2025

Sun, Dec 14 - Fri, Dec 19

from (US$)$1,700

Brilliant Caribbean Holidays

Miami, Florida • Grand Turk • Puerto Plata • San Juan, Puerto Rico • Samaná • Miami, Florida

Insider cabins from

$3,184

per Cabin

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$3,184

per Cabin

Departing on:

2025

Thu, Dec 18 - Fri, Dec 26

from (US$)$3,184

Resilient Caribbean Holidays

Miami, Florida • San Juan, Puerto Rico • Puerto Plata • The Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,786

per Cabin

7 nights

Resilient Lady

BOOK NOW

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$2,786

per Cabin

Departing on:

2025

Sat, Dec 20 - Sat, Dec 27

from (US$)$2,786

Valiant Caribbean Holidays

San Juan, Puerto Rico • Philipsburg • Basseterre • St. John's • Castries • Tortola • San Juan, Puerto Rico

Insider cabins from

$2,368

per Cabin

7 nights

Valiant Lady

BOOK NOW

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$2,368

per Cabin

Departing on:

2025

Sat, Dec 20 - Sat, Dec 27

from (US$)$2,368

Scarlet Caribbean Holidays

Miami, Florida • Nassau • The Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,802

per Cabin

4 nights

Scarlet Lady

BOOK NOW

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

$1,802

per Cabin

Departing on:

2025

Wed, Dec 24 - Sun, Dec 28

from (US$)$1,802

Explore 381 cruise vacations

Extra $100 onboard credit ending soon

Sunny San Juan & Isles of Beach Miles

Cayman Coves & Jamaican Waterfalls

Thanksgiving in the Lesser Antilles

Fire & Sunset Soirées

Antigua Waves & Grand Turk Caves

San Juan to Barbados & the St. Isles

San Juan, Samaná & Bimini

Miami, Grand Turk (& back)

Aruba, Curaçao and the Lesser Antilles

Dominican Daze

Aruban Sunsets & Calm Cayman Days

St. Lucia, St. Maarten, Barbados & More

Riviera Maya

Brilliant Caribbean Holidays

Resilient Caribbean Holidays

Valiant Caribbean Holidays

Scarlet Caribbean Holidays

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Woop woop, you're signed up!

Extra $100 onboard credit ending soon

Sunny San Juan & Isles of Beach Miles

Cayman Coves & Jamaican Waterfalls

Thanksgiving in the Lesser Antilles

Fire & Sunset Soirées

Antigua Waves & Grand Turk Caves

San Juan to Barbados & the St. Isles

San Juan, Samaná & Bimini

Miami, Grand Turk (& back)

Aruba, Curaçao and the Lesser Antilles

Dominican Daze

Aruban Sunsets & Calm Cayman Days

St. Lucia, St. Maarten, Barbados & More

Riviera Maya

Brilliant Caribbean Holidays

Resilient Caribbean Holidays

Valiant Caribbean Holidays

Scarlet Caribbean Holidays

75% Off 2nd Sailor + USD$500* in Savings