Showing cruise vacations: Caribbean, July 2026 - April 2027

Quick find:

Up to $400 onboard credit on 2027 voyages

Showing 125 cruise vacations that match your search

Grand Turk & Bimini Beach Club

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

Insider cabins from

$695~~$964~~

per Sailor

5 nights

Resilient Lady, Scarlet Lady, Brilliant Lady & Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$695~~$964~~

per Sailor

Departing on:

2026Best Rate

Mon, Dec 07 - Sat, Dec 12

from (US$)$695

2026

Sat, Aug 08 - Thu, Aug 13

from (US$)$1,530

2026

Sat, Aug 22 - Thu, Aug 27

from (US$)$1,145

Key West & Bimini Beach Club

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

Insider cabins from

$556~~$745~~

per Sailor

4 nights

Resilient Lady, Scarlet Lady, Brilliant Lady & Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$556~~$745~~

per Sailor

Departing on:

2026Best Rate

Thu, Sep 10 - Mon, Sep 14

from (US$)$556

2026

Thu, Aug 13 - Mon, Aug 17

from (US$)$1,036

2026

Thu, Aug 27 - Mon, Aug 31

from (US$)$796

BOOK YOUR 2027 GETAWAY

UNTIL JULY 31ST: UP TO $400 ONBOARD CREDIT

Get started planning next year’s vacation & get up to $400 for your voyage!

Dominican Republic & Bimini Beach Club

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

Insider cabins from

$545~~$734~~

per Sailor

5 nights

Resilient Lady & Scarlet Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$545~~$734~~

per Sailor

Departing on:

2026Best Rate

Mon, Sep 28 - Sat, Oct 03

from (US$)$545

2026

Mon, Aug 17 - Sat, Aug 22

from (US$)$845

2026

Mon, Aug 31 - Sat, Sep 05

from (US$)$645

Eastern Caribbean & Bimini Halloween

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

Insider cabins from

$1,134~~$1,626~~

per Sailor

6 nights

Scarlet Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$1,134~~$1,626~~

per Sailor

Departing on:

2026

Sun, Oct 25 - Sat, Oct 31

from (US$)$1,134

Mexico & Bimini Beach Club Halloween

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

Insider cabins from

$745~~$1,027~~

per Sailor

5 nights

Scarlet Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$745~~$1,027~~

per Sailor

Departing on:

2026

Sat, Oct 31 - Thu, Nov 05

from (US$)$745

Southern Caribbean Halloween Cruise

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

Insider cabins from

$1,253~~$1,852~~

per Sailor

7 nights

Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$1,253~~$1,852~~

per Sailor

Departing on:

2026

Sat, Oct 31 - Sat, Nov 07

from (US$)$1,253

Western Caribbean & Bimini Beach Club

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

Insider cabins from

$833~~$1,156~~

per Sailor

7 nights

Resilient Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$833~~$1,156~~

per Sailor

Departing on:

2027Best Rate

Sun, Feb 21 - Sun, Feb 28

from (US$)$833

2026

Sun, Nov 01 - Sun, Nov 08

from (US$)$903

Bahamas & Bimini Beach Club

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

Sea View cabins from

$716~~$998~~

per Sailor

4 nights

Scarlet Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Sea View cabins from

$716~~$998~~

per Sailor

Departing on:

2026Best Rate

Thu, Nov 05 - Mon, Nov 09

from (US$)$716

2026

Sat, Dec 26 - Wed, Dec 30

from (US$)$716

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

Insider cabins from

$1,113~~$1,630~~

per Sailor

7 nights

Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$1,113~~$1,630~~

per Sailor

Departing on:

2026Best Rate

Sat, Dec 12 - Sat, Dec 19

from (US$)$1,113

2026

Sat, Nov 07 - Sat, Nov 14

from (US$)$1,393

2027

Sat, Jan 16 - Sat, Jan 23

from (US$)$1,113

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

Insider cabins from

$872~~$1,213~~

per Sailor

8 nights

Resilient Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$872~~$1,213~~

per Sailor

Departing on:

2026

Sun, Nov 08 - Mon, Nov 16

from (US$)$872

Grand Cayman & Bimini Beach Club

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

Insider cabins from

$545~~$728~~

per Sailor

5 nights

Scarlet Lady & Resilient Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$545~~$728~~

per Sailor

Departing on:

2026Best Rate

Mon, Nov 09 - Sat, Nov 14

from (US$)$545

2027

Mon, Mar 29 - Sat, Apr 03

from (US$)$823

2027

Fri, Apr 23 - Wed, Apr 28

from (US$)$771

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

Insider cabins from

$714~~$1,023~~

per Sailor

6 nights

Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$714~~$1,023~~

per Sailor

Departing on:

2026Best Rate

Sat, Nov 14 - Fri, Nov 20

from (US$)$714

2027

Sat, Jan 23 - Fri, Jan 29

from (US$)$834

2027

Sat, Mar 13 - Fri, Mar 19

from (US$)$894

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

Insider cabins from

$1,090~~$1,493~~

per Sailor

10 nights

Brilliant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$1,090~~$1,493~~

per Sailor

Departing on:

2027Best Rate

Mon, Jan 25 - Thu, Feb 04

from (US$)$1,090

2026

Sun, Nov 15 - Wed, Nov 25

from (US$)$1,091

2027

Mon, Feb 22 - Thu, Mar 04

from (US$)$1,090

Mexico & Bimini Beach Club

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

Insider cabins from

$594~~$781~~

per Sailor

6 nights

Resilient Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$594~~$781~~

per Sailor

Departing on:

2026

Mon, Nov 16 - Sun, Nov 22

from (US$)$594

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

Insider cabins from

$952~~$1,375~~

per Sailor

8 nights

Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$952~~$1,375~~

per Sailor

Departing on:

2026

Fri, Nov 20 - Sat, Nov 28

from (US$)$952

Jamaica & Bimini Beach Club

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

Sea View cabins from

$845~~$1,193~~

per Sailor

5 nights

Scarlet Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Sea View cabins from

$845~~$1,193~~

per Sailor

Departing on:

2026

Mon, Nov 23 - Sat, Nov 28

from (US$)$845

Mexico & Bimini Beach Club

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

Insider cabins from

$545~~$723~~

per Sailor

5 nights

Scarlet Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$545~~$723~~

per Sailor

Departing on:

2026Best Rate

Sat, Nov 28 - Thu, Dec 03

from (US$)$545

2027

Mon, Jan 04 - Sat, Jan 09

from (US$)$645

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

Insider cabins from

$833~~$1,195~~

per Sailor

7 nights

Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$833~~$1,195~~

per Sailor

Departing on:

2026

Sat, Nov 28 - Sat, Dec 05

from (US$)$833

Western Caribbean & Bimini Beach Club

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

Insider cabins from

$834~~$1,158~~

per Sailor

6 nights

Resilient Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$834~~$1,158~~

per Sailor

Departing on:

2026Best Rate

Sun, Dec 13 - Sat, Dec 19

from (US$)$834

2026

Sun, Nov 29 - Sat, Dec 05

from (US$)$894

2027

Sun, Jan 10 - Sat, Jan 16

from (US$)$954

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

Insider cabins from

$990~~$1,380~~

per Sailor

10 nights

Brilliant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$990~~$1,380~~

per Sailor

Departing on:

2026Best Rate

Mon, Nov 30 - Thu, Dec 10

from (US$)$990

2027

Mon, Jan 11 - Thu, Jan 21

from (US$)$990

2027

Mon, Mar 08 - Thu, Mar 18

from (US$)$990

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

Insider cabins from

$952~~$1,339~~

per Sailor

8 nights

Resilient Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$952~~$1,339~~

per Sailor

Departing on:

2026Best Rate

Sat, Dec 05 - Sun, Dec 13

from (US$)$952

2027

Sat, Mar 27 - Sun, Apr 04

from (US$)$1,192

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

Insider cabins from

$973~~$1,380~~

per Sailor

7 nights

Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$973~~$1,380~~

per Sailor

Departing on:

2027Best Rate

Sat, Jan 09 - Sat, Jan 16

from (US$)$973

2026

Sat, Dec 05 - Sat, Dec 12

from (US$)$1,253

2027

Sat, Feb 27 - Sat, Mar 06

from (US$)$1,043

Eastern Caribbean & Bimini Holiday

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

Insider cabins from

$891~~$1,241~~

per Sailor

9 nights

Brilliant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$891~~$1,241~~

per Sailor

Departing on:

2026

Mon, Dec 14 - Wed, Dec 23

from (US$)$891

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

Insider cabins from

$1,192~~$1,701~~

per Sailor

8 nights

Resilient Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$1,192~~$1,701~~

per Sailor

Departing on:

2026

Sat, Dec 19 - Sun, Dec 27

from (US$)$1,192

Southern Caribbean Holiday Cruise

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

Insider cabins from

$1,113~~$1,636~~

per Sailor

7 nights

Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$1,113~~$1,636~~

per Sailor

Departing on:

2026

Sat, Dec 19 - Sat, Dec 26

from (US$)$1,113

Mexico & Bimini Beach Club Holiday

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

Insider cabins from

$745~~$1,028~~

per Sailor

5 nights

Scarlet Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$745~~$1,028~~

per Sailor

Departing on:

2026

Mon, Dec 21 - Sat, Dec 26

from (US$)$745

Grand Turk & Bimini Holiday Cruise

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

Insider cabins from

$1,045~~$1,502~~

per Sailor

5 nights

Brilliant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$1,045~~$1,502~~

per Sailor

Departing on:

2026

Wed, Dec 23 - Mon, Dec 28

from (US$)$1,045

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

Insider cabins from

$2,023~~$3,028~~

per Sailor

7 nights

Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$2,023~~$3,028~~

per Sailor

Departing on:

2026

Sat, Dec 26 - Sat, Jan 02

from (US$)$2,023

Western Caribbean & Bimini New Year's

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

Insider cabins from

$1,463~~$2,125~~

per Sailor

7 nights

Resilient Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$1,463~~$2,125~~

per Sailor

Departing on:

2026

Sun, Dec 27 - Sun, Jan 03

from (US$)$1,463

Eastern Caribbean & Bimini New Year's

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

$1,490~~$2,158~~

per Sailor

10 nights

Brilliant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$1,490~~$2,158~~

per Sailor

Departing on:

2026

Mon, Dec 28 - Thu, Jan 07

from (US$)$1,490

Dominican Republic & Bimini New Year's

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

Insider cabins from

$1,345~~$1,957~~

per Sailor

5 nights

Scarlet Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$1,345~~$1,957~~

per Sailor

Departing on:

2026

Wed, Dec 30 - Mon, Jan 04

from (US$)$1,345

Southern Caribbean Cruise

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

Insider cabins from

$973~~$1,367~~

per Sailor

7 nights

Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$973~~$1,367~~

per Sailor

Departing on:

2027Best Rate

Sat, Jan 02 - Sat, Jan 09

from (US$)$973

2027

Sat, Mar 06 - Sat, Mar 13

from (US$)$1,043

Eastern Caribbean & Bimini Beach Club

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

Insider cabins from

$763~~$1,054~~

per Sailor

7 nights

Resilient Lady & Scarlet Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$763~~$1,054~~

per Sailor

Departing on:

2027Best Rate

Sun, Jan 03 - Sun, Jan 10

from (US$)$763

2027

Sat, Apr 17 - Sat, Apr 24

from (US$)$973

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

Insider cabins from

$1,112~~$1,549~~

per Sailor

8 nights

Resilient Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$1,112~~$1,549~~

per Sailor

Departing on:

2027Best Rate

Sat, Jan 16 - Sun, Jan 24

from (US$)$1,112

2027

Sat, Mar 13 - Sun, Mar 21

from (US$)$1,192

Eastern Caribbean Cruise

Miami, Florida
Key West, Florida
Grand Turk, Turks and Caicos
Puerto Plata, Dominican Republic
Miami, Florida

Insider cabins from

$774~~$1,089~~

per Sailor

6 nights

Resilient Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$774~~$1,089~~

per Sailor

Departing on:

2027

Sun, Jan 24 - Sat, Jan 30

from (US$)$774

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

Insider cabins from

$1,352~~$1,947~~

per Sailor

8 nights

Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$1,352~~$1,947~~

per Sailor

Departing on:

2027

Fri, Jan 29 - Sat, Feb 06

from (US$)$1,352

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

Insider cabins from

$1,032~~$1,456~~

per Sailor

8 nights

Resilient Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$1,032~~$1,456~~

per Sailor

Departing on:

2027

Sat, Jan 30 - Sun, Feb 07

from (US$)$1,032

Southern Caribbean & Aruban Nights

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

Insider cabins from

$833~~$1,157~~

per Sailor

7 nights

Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$833~~$1,157~~

per Sailor

Departing on:

2027

Sat, Feb 06 - Sat, Feb 13

from (US$)$833

Western Caribbean & Bimini Beach Club

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

Insider cabins from

$903~~$1,256~~

per Sailor

7 nights

Resilient Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$903~~$1,256~~

per Sailor

Departing on:

2027Best Rate

Sun, Feb 07 - Sun, Feb 14

from (US$)$903

2027

Sun, Feb 28 - Sun, Mar 07

from (US$)$903

2027

Sun, Apr 11 - Sun, Apr 18

from (US$)$1,043

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

Insider cabins from

$1,490~~$2,100~~

per Sailor

10 nights

Brilliant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$1,490~~$2,100~~

per Sailor

Departing on:

2027

Mon, Feb 08 - Thu, Feb 18

from (US$)$1,490

Sisters at Sea: Valiant Lady

San Juan, Puerto Rico
Samaná, Dominican Republic
Grand Turk, Turks and Caicos
Cabo Rojo, Dominican Republic
San Juan, Puerto Rico

Insider cabins from

$1,323~~$1,953~~

per Sailor

7 nights

Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$1,323~~$1,953~~

per Sailor

Departing on:

2027

Sat, Feb 13 - Sat, Feb 20

from (US$)$1,323

Sisters at Sea: Resilient Lady

Miami, Florida
Freeport, Grand Bahama Island, Bahamas
Progreso, Mexico
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$1,113~~$1,564~~

per Sailor

7 nights

Resilient Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$1,113~~$1,564~~

per Sailor

Departing on:

2027

Sun, Feb 14 - Sun, Feb 21

from (US$)$1,113

Sisters at Sea: Scarlet Lady

Miami, Florida
Freeport, Grand Bahama Island, Bahamas
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$1,045~~$1,496~~

per Sailor

5 nights

Scarlet Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$1,045~~$1,496~~

per Sailor

Departing on:

2027

Mon, Feb 15 - Sat, Feb 20

from (US$)$1,045

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

Insider cabins from

$1,043~~$1,480~~

per Sailor

7 nights

Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$1,043~~$1,480~~

per Sailor

Departing on:

2027

Sat, Feb 20 - Sat, Feb 27

from (US$)$1,043

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

Insider cabins from

$1,272~~$1,832~~

per Sailor

8 nights

Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$1,272~~$1,832~~

per Sailor

Departing on:

2027

Fri, Mar 19 - Sat, Mar 27

from (US$)$1,272

True Crime Voyage

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

Sea View cabins from

$1,127~~$1,629~~

per Sailor

5 nights

Scarlet Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Sea View cabins from

$1,127~~$1,629~~

per Sailor

Departing on:

2027

Sat, Mar 20 - Thu, Mar 25

from (US$)$1,127

Eastern Caribbean Cruise

Miami, Florida
Grand Turk, Turks and Caicos
Samaná, Dominican Republic
Puerto Plata, Dominican Republic
Miami, Florida

Insider cabins from

$834~~$1,191~~

per Sailor

6 nights

Resilient Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$834~~$1,191~~

per Sailor

Departing on:

2027

Sun, Mar 21 - Sat, Mar 27

from (US$)$834

Bahamas & Bimini Beach Club

Miami, Florida
Freeport, Grand Bahama Island, Bahamas
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$581~~$782~~

per Sailor

4 nights

Brilliant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$581~~$782~~

per Sailor

Departing on:

2027

Mon, Mar 22 - Fri, Mar 26

from (US$)$581

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

Insider cabins from

$973~~$1,354~~

per Sailor

7 nights

Resilient Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$973~~$1,354~~

per Sailor

Departing on:

2027

Sun, Apr 04 - Sun, Apr 11

from (US$)$973

Eastern Caribbean: San Juan to Miami

San Juan, Puerto Rico
Grand Turk, Turks and Caicos
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$545~~$718~~

per Sailor

5 nights

Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$545~~$718~~

per Sailor

Departing on:

2027

Sat, Apr 10 - Thu, Apr 15

from (US$)$545

Grand Turk Cruise

Miami, Florida
Grand Turk, Turks and Caicos
Miami, Florida

Insider cabins from

$501~~$700~~

per Sailor

4 nights

Valiant Lady

BOOK NOW

70% off 2nd Sailor

Limited time: free balcony upgrades

Insider cabins from

$501~~$700~~

per Sailor

Departing on:

2027

Thu, Apr 15 - Mon, Apr 19

from (US$)$501

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