Explore cruise vacations

Showing cruise vacations: Caribbean, December 2025 - November 2027

Quick find:

Eclipse Sailings 2026
Holiday Sailings

9-12 & 13+ nights

Departs Miami, Florida & San Juan, Puerto Rico

Brilliant New Year's Ahoy!

Miami, Florida
Grand Turk, Turks and Caicos
Philipsburg, St. Maarten
Basseterre, St. Kitts and Nevis
San Juan, Puerto Rico
Miami, Florida

Insider cabins from

$3,942~~$6,340~~

per Cabin

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

Up to $300 in drinks

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,942~~$6,340~~

per Cabin

Departing on:

Fri, Dec 26 - Sun, Jan 04

from (US$)$3,942

Aruba, Bonaire, Colombia, Jamaica & More

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

Sea View cabins from

$3,058~~$4,786~~

per Cabin

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

Up to $400 in drinks

Getaways for 80% off 2nd Sailor

Sea View cabins from

$3,058~~$4,786~~

per Cabin

Departing on:

Sun, Jan 04 - Thu, Jan 15

from (US$)$3,058

WITH LOVE, FROM US

80% off second Sailor + free drinks

Book a voyage now to receive 80% off 2nd Sailor and up to $400 in free drinks.

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

$2,618~~$4,048~~

per Cabin

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

Up to $400 in drinks

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,618~~$4,048~~

per Cabin

Departing on:

Sun, Feb 01 - Thu, Feb 12

from (US$)$2,618

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

$3,042~~$4,830~~

per Cabin

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

Up to $300 in drinks

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,042~~$4,830~~

per Cabin

Departing on:

Fri, Feb 20 - Sun, Mar 01

from (US$)$3,042

Aruban Sunsets & Calm Cayman Days

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

Insider cabins from

$2,618~~$4,070~~

per Cabin

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

Up to $400 in drinks

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,618~~$4,070~~

per Cabin

Departing on:

Sun, Mar 01 - Thu, Mar 12

from (US$)$2,618

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

$2,502~~$3,876~~

per Cabin

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

Up to $300 in drinks

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,502~~$3,876~~

per Cabin

Departing on:

Thu, Mar 12 - Sat, Mar 21

from (US$)$2,502

St. Isles & Sun-soaked Seas

Miami, Florida
Philipsburg, St. Maarten
Tortola, British Virgin Islands
Basseterre, St. Kitts and Nevis
St. John's, Antigua
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$2,580~~$3,846~~

per Cabin

10 nights

Brilliant Lady

Up to $400 in drinks

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,580~~$3,846~~

per Cabin

Departing on:

Mon, Jan 25 - Thu, Feb 04

from (US$)$2,580

Sun, Nov 15 - Wed, Nov 25

from (US$)$3,066

Mon, Feb 22 - Thu, Mar 04

from (US$)$2,780

St. Maarten, Tortola, San Juan & more

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

Insider cabins from

$2,980~~$4,490~~

per Cabin

10 nights

Brilliant Lady

Up to $400 in drinks

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,980~~$4,490~~

per Cabin

Departing on:

Mon, Mar 08 - Thu, Mar 18

from (US$)$2,980

Mon, Nov 30 - Thu, Dec 10

from (US$)$3,068

Mon, Jan 11 - Thu, Jan 21

from (US$)$2,982

Pre-Holiday Caribbean Getaway

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

Insider cabins from

$2,504~~$3,856~~

per Cabin

9 nights

Brilliant Lady

Up to $300 in drinks

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,504~~$3,856~~

per Cabin

Departing on:

Mon, Dec 14 - Wed, Dec 23

from (US$)$2,504

Brilliant New Year's Ahoy!

Miami, Florida
Philipsburg, St. Maarten
Basseterre, St. Kitts and Nevis
Tortola, British Virgin Islands
St. John's, Antigua
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$4,980~~$7,968~~

per Cabin

10 nights

Brilliant Lady

Up to $400 in drinks

Getaways for 80% off 2nd Sailor

Insider cabins from

$4,980~~$7,968~~

per Cabin

Departing on:

Mon, Dec 28 - Thu, Jan 07

from (US$)$4,980

San Juan & St. Isles: Valentine’s Voyage

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

Insider cabins from

$2,780~~$4,156~~

per Cabin

10 nights

Brilliant Lady

Up to $400 in drinks

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,780~~$4,156~~

per Cabin

Departing on:

Mon, Feb 08 - Thu, Feb 18

from (US$)$2,780