Showing 107 cruise vacations: Caribbean, August 2026 - April 2027

Quick find:

1 Sailor , 1 Cabin

The Europe Sale: Up to $500 in onboard credit

Showing 107 cruise vacations that match your search

Key West & Bimini Beach Club

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

from

$665~~$911~~

per Sailor

4 nights

Resilient Lady, Scarlet Lady, Brilliant Lady & Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$665~~$911~~

per Sailor

Departing on:

2026Best Rate

Thu, Dec 10 - Mon, Dec 14

from (US$)$665

2026

Thu, Aug 13 - Mon, Aug 17

from (US$)$1,707

2026

Thu, Aug 27 - Mon, Aug 31

from (US$)$1,788

Dominican Republic & Bimini Beach Club

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

from

$897~~$1,275~~

per Sailor

5 nights

Resilient Lady & Scarlet Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$897~~$1,275~~

per Sailor

Departing on:

2026Best Rate

Mon, Sep 28 - Sat, Oct 03

from (US$)$897

2026

Mon, Aug 17 - Sat, Aug 22

from (US$)$3,797

Only suites remaining

2026

Mon, Aug 31 - Sat, Sep 05

from (US$)$1,418

LOCK IN NEXT SUMMER

THE EUROPE SALE COMES WITH UP TO $500 IN ONBOARD CREDIT

And there's more: You also get free balcony upgrades and 70% off your second Sailor.

Grand Turk & Bimini Beach Club

Miami, Florida
Grand Turk, Turks and Caicos
The Beach Club at Bimini, Bahamas
Miami, Florida

from

$870~~$1,233~~

per Sailor

5 nights

Resilient Lady, Scarlet Lady, Brilliant Lady & Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$870~~$1,233~~

per Sailor

Departing on:

2026Best Rate

Mon, Dec 07 - Sat, Dec 12

from (US$)$870

2026

Sat, Aug 22 - Thu, Aug 27

from (US$)$2,497

2026

Sat, Sep 05 - Thu, Sep 10

from (US$)$3,152

Eastern Caribbean & Bimini Halloween

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

from

$2,049~~$3,033~~

per Sailor

6 nights

Scarlet Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$2,049~~$3,033~~

per Sailor

Departing on:

2026

Sun, Oct 25 - Sat, Oct 31

from (US$)$2,049

Mexico & Bimini Beach Club Halloween

Miami, Florida
Cozumel, Mexico
The Beach Club at Bimini, Bahamas
Miami, Florida

from

$1,369~~$1,987~~

per Sailor

5 nights

Scarlet Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$1,369~~$1,987~~

per Sailor

Departing on:

2026

Sat, Oct 31 - Thu, Nov 05

from (US$)$1,369

Western Caribbean & Bimini Beach Club

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

from

$877

per Sailor

7 nights

Resilient Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$877

per Sailor

Departing on:

2026Best Rate

Sun, Nov 01 - Sun, Nov 08

from (US$)$877

2027

Sun, Feb 21 - Sun, Feb 28

from (US$)$943

Southern Caribbean Cruise

San Juan, Puerto Rico
Philipsburg, St. Maarten
Bridgetown, Barbados
Castries, St. Lucia
Fort-de-France, Martinique
Basseterre, St. Kitts and Nevis
San Juan, Puerto Rico

from

$1,803

per Sailor

7 nights

Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$1,803

per Sailor

Departing on:

2027Best Rate

Sat, Jan 16 - Sat, Jan 23

from (US$)$1,803

2026

Sat, Nov 07 - Sat, Nov 14

from (US$)$2,353

2026

Sat, Dec 12 - Sat, Dec 19

from (US$)$1,837

Eastern Caribbean & Bimini Beach Club

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

from

$1,000

per Sailor

8 nights

Resilient Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$1,000

per Sailor

Departing on:

2026

Sun, Nov 08 - Mon, Nov 16

from (US$)$1,000

Grand Cayman & Bimini Beach Club

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

from

$961

per Sailor

5 nights

Scarlet Lady & Resilient Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$961

per Sailor

Departing on:

2027Best Rate

Fri, Apr 23 - Wed, Apr 28

from (US$)$961

2026

Mon, Nov 09 - Sat, Nov 14

from (US$)$1,084

2027

Mon, Mar 29 - Sat, Apr 03

from (US$)$1,198

Southern Caribbean Cruise

San Juan, Puerto Rico
Tortola, British Virgin Islands
St. John's, Antigua
Castries, St. Lucia
Basseterre, St. Kitts and Nevis
San Juan, Puerto Rico

from

$1,289~~$1,907~~

per Sailor

6 nights

Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$1,289~~$1,907~~

per Sailor

Departing on:

2026Best Rate

Sat, Nov 14 - Fri, Nov 20

from (US$)$1,289

2027

Sat, Jan 23 - Fri, Jan 29

from (US$)$1,533

2027

Sat, Mar 13 - Fri, Mar 19

from (US$)$1,654

Eastern Caribbean & Bimini Beach Club

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

from

$1,932~~$2,837~~

per Sailor

10 nights

Brilliant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$1,932~~$2,837~~

per Sailor

Departing on:

2026Best Rate

Sun, Nov 15 - Wed, Nov 25

from (US$)$1,932

2027

Mon, Jan 25 - Thu, Feb 04

from (US$)$1,936

2027

Mon, Feb 22 - Thu, Mar 04

from (US$)$2,537

Mexico & Bimini Beach Club

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

from

$725

per Sailor

6 nights

Resilient Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$725

per Sailor

Departing on:

2026

Mon, Nov 16 - Sun, Nov 22

from (US$)$725

Southern Caribbean Cruise

San Juan, Puerto Rico
Charlotte Amalie, St. Thomas
Willemstad, Curaçao
Oranjestad, Aruba
Basseterre, St. Kitts and Nevis
Philipsburg, St. Maarten
San Juan, Puerto Rico

from

$1,898~~$2,831~~

per Sailor

8 nights

Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$1,898~~$2,831~~

per Sailor

Departing on:

2026

Fri, Nov 20 - Sat, Nov 28

from (US$)$1,898

Jamaica & Bimini Beach Club

Miami, Florida
Ocho Rios, Jamaica
The Beach Club at Bimini, Bahamas
Miami, Florida

from

$1,392~~$2,034~~

per Sailor

5 nights

Scarlet Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$1,392~~$2,034~~

per Sailor

Departing on:

2026

Mon, Nov 23 - Sat, Nov 28

from (US$)$1,392

Mexico & Bimini Beach Club

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

from

$866

per Sailor

5 nights

Scarlet Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$866

per Sailor

Departing on:

2027Best Rate

Mon, Jan 04 - Sat, Jan 09

from (US$)$866

2026

Sat, Nov 28 - Thu, Dec 03

from (US$)$876

Southern Caribbean Cruise

San Juan, Puerto Rico
Charlotte Amalie, St. Thomas
Tortola, British Virgin Islands
Basseterre, St. Kitts and Nevis
St. John's, Antigua
Philipsburg, St. Maarten
San Juan, Puerto Rico

from

$973

per Sailor

7 nights

Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$973

per Sailor

Departing on:

2026

Sat, Nov 28 - Sat, Dec 05

from (US$)$973

Western Caribbean & Bimini Beach Club

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

from

$1,315~~$1,898~~

per Sailor

6 nights

Resilient Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$1,315~~$1,898~~

per Sailor

Departing on:

2026Best Rate

Sun, Nov 29 - Sat, Dec 05

from (US$)$1,315

2026

Sun, Dec 13 - Sat, Dec 19

from (US$)$1,352

2027

Sun, Jan 10 - Sat, Jan 16

from (US$)$1,551

Eastern Caribbean & Bimini Beach Club

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

from

$1,713~~$2,492~~

per Sailor

10 nights

Brilliant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$1,713~~$2,492~~

per Sailor

Departing on:

2027Best Rate

Mon, Jan 11 - Thu, Jan 21

from (US$)$1,713

2026

Mon, Nov 30 - Thu, Dec 10

from (US$)$1,715

2027

Mon, Mar 08 - Thu, Mar 18

from (US$)$1,713

Eastern Caribbean & Bimini Beach Club

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

from

$1,192~~$1,708~~

per Sailor

8 nights

Resilient Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$1,192~~$1,708~~

per Sailor

Departing on:

2026Best Rate

Sat, Dec 05 - Sun, Dec 13

from (US$)$1,192

2027

Sat, Mar 27 - Sun, Apr 04

from (US$)$1,950

Southern Caribbean & Aruban Nights

San Juan, Puerto Rico
Oranjestad, Aruba
Willemstad, Curaçao
Fort-de-France, Martinique
Basseterre, St. Kitts and Nevis
San Juan, Puerto Rico

from

$1,946~~$2,918~~

per Sailor

7 nights

Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$1,946~~$2,918~~

per Sailor

Departing on:

2026Best Rate

Sat, Dec 05 - Sat, Dec 12

from (US$)$1,946

2027

Sat, Jan 09 - Sat, Jan 16

from (US$)$2,092

2027

Sat, Feb 27 - Sat, Mar 06

from (US$)$1,952

Eastern Caribbean & Bimini Holiday

Miami, Florida
San Juan, Puerto Rico
Charlotte Amalie, St. Thomas
Philipsburg, St. Maarten
The Beach Club at Bimini, Bahamas
Miami, Florida

from

$1,541~~$2,241~~

per Sailor

9 nights

Brilliant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$1,541~~$2,241~~

per Sailor

Departing on:

2026

Mon, Dec 14 - Wed, Dec 23

from (US$)$1,541

Eastern Caribbean & Bimini Holiday

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

from

$1,978~~$2,910~~

per Sailor

8 nights

Resilient Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$1,978~~$2,910~~

per Sailor

Departing on:

2026

Sat, Dec 19 - Sun, Dec 27

from (US$)$1,978

Grand Turk & Bimini Holiday Cruise

Miami, Florida
The Beach Club at Bimini, Bahamas
Grand Turk, Turks and Caicos
Miami, Florida

from

$1,981

per Sailor

5 nights

Brilliant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$1,981

per Sailor

Departing on:

2026

Wed, Dec 23 - Mon, Dec 28

from (US$)$1,981

Southern Caribbean New Year's Cruise

San Juan, Puerto Rico
Philipsburg, St. Maarten
Fort-de-France, Martinique
Bridgetown, Barbados
Castries, St. Lucia
St. John's, Antigua
San Juan, Puerto Rico

from

$2,702

per Sailor

7 nights

Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$2,702

per Sailor

Departing on:

2026

Sat, Dec 26 - Sat, Jan 02

from (US$)$2,702

Southern Caribbean Cruise

San Juan, Puerto Rico
Philipsburg, St. Maarten
Bridgetown, Barbados
Castries, St. Lucia
St. John's, Antigua
Tortola, British Virgin Islands
San Juan, Puerto Rico

from

$1,929~~$2,883~~

per Sailor

7 nights

Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$1,929~~$2,883~~

per Sailor

Departing on:

2027Best Rate

Sat, Mar 06 - Sat, Mar 13

from (US$)$1,929

2027

Sat, Jan 02 - Sat, Jan 09

from (US$)$2,209

Eastern Caribbean & Bimini Beach Club

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

from

$976

per Sailor

7 nights

Resilient Lady & Scarlet Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$976

per Sailor

Departing on:

2027Best Rate

Sun, Jan 03 - Sun, Jan 10

from (US$)$976

2027

Sat, Apr 17 - Sat, Apr 24

from (US$)$1,275

Western Caribbean & Bimini Beach Club

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

from

$1,763~~$2,549~~

per Sailor

8 nights

Resilient Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$1,763~~$2,549~~

per Sailor

Departing on:

2027Best Rate

Sat, Jan 16 - Sun, Jan 24

from (US$)$1,763

2027

Sat, Mar 13 - Sun, Mar 21

from (US$)$1,922

Southern Caribbean & Aruban Nights

San Juan, Puerto Rico
Oranjestad, Aruba
Willemstad, Curaçao
Kralendijk, Bonaire
Fort-de-France, Martinique
Philipsburg, St. Maarten
San Juan, Puerto Rico

from

$2,708~~$4,082~~

per Sailor

8 nights

Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$2,708~~$4,082~~

per Sailor

Departing on:

2027

Fri, Jan 29 - Sat, Feb 06

from (US$)$2,708

Eastern Caribbean & Bimini Beach Club

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

from

$1,381

per Sailor

8 nights

Resilient Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$1,381

per Sailor

Departing on:

2027

Sat, Jan 30 - Sun, Feb 07

from (US$)$1,381

Southern Caribbean & Aruban Nights

San Juan, Puerto Rico
Oranjestad, Aruba
Willemstad, Curaçao
St. John's, Antigua
Philipsburg, St. Maarten
San Juan, Puerto Rico

from

$1,937~~$2,900~~

per Sailor

7 nights

Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$1,937~~$2,900~~

per Sailor

Departing on:

2027

Sat, Feb 06 - Sat, Feb 13

from (US$)$1,937

Western Caribbean & Bimini Beach Club

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

from

$1,044

per Sailor

7 nights

Resilient Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$1,044

per Sailor

Departing on:

2027Best Rate

Sun, Feb 07 - Sun, Feb 14

from (US$)$1,044

2027

Sun, Feb 28 - Sun, Mar 07

from (US$)$1,044

2027

Sun, Apr 11 - Sun, Apr 18

from (US$)$1,210

Sisters at Sea: Brilliant Lady

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

from

$3,313~~$4,953~~

per Sailor

10 nights

Brilliant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$3,313~~$4,953~~

per Sailor

Departing on:

2027

Mon, Feb 08 - Thu, Feb 18

from (US$)$3,313

Southern Caribbean Cruise

San Juan, Puerto Rico
Tortola, British Virgin Islands
Castries, St. Lucia
Bridgetown, Barbados
Roseau, Dominica
Philipsburg, St. Maarten
San Juan, Puerto Rico

from

$1,936

per Sailor

7 nights

Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$1,936

per Sailor

Departing on:

2027

Sat, Feb 20 - Sat, Feb 27

from (US$)$1,936

Southern Caribbean Cruise

San Juan, Puerto Rico
Charlotte Amalie, St. Thomas
Bridgetown, Barbados
Kingstown, St. Vincent
Roseau, Dominica
Philipsburg, St. Maarten
San Juan, Puerto Rico

from

$1,762~~$2,634~~

per Sailor

8 nights

Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$1,762~~$2,634~~

per Sailor

Departing on:

2027

Fri, Mar 19 - Sat, Mar 27

from (US$)$1,762

Western Caribbean & Bimini Beach Club

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

from

$1,343

per Sailor

7 nights

Resilient Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

from

$1,343

per Sailor

Departing on:

2027

Sun, Apr 04 - Sun, Apr 11

from (US$)$1,343

Average starting price per Sailor (incl. taxes & fees)