Explore 408 cruise vacations

Showing cruise vacations: Caribbean, November 2025 - August 2026

Quick find:

2 Sailors , 1 Cabin

Sails Resilient Lady

Western Caribbean & Bimini Beach Club

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

Sea View cabins from

$1,308~~$1,802~~

per Cabin

6 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Sea View cabins from

$1,308~~$1,802~~

per Cabin

Departing on:

Sun, Nov 09 - Sat, Nov 15

from (US$)$1,308

San Juan Sunrises & Dominican Dreams

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

Insider cabins from

$1,386~~$2,008~~

per Cabin

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,386~~$2,008~~

per Cabin

Departing on:

Sat, Nov 15 - Sat, Nov 22

from (US$)$1,386

Sat, Mar 28 - Sat, Apr 04

from (US$)$2,366

Sat, Apr 18 - Sat, Apr 25

from (US$)$2,506

Cayman Coves & Jamaican Waterfalls

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

Insider cabins from

$1,386~~$1,998~~

per Cabin

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,386~~$1,998~~

per Cabin

Departing on:

Sat, Nov 22 - Sat, Nov 29

from (US$)$1,386

Sat, Dec 06 - Sat, Dec 13

from (US$)$1,386

Sat, Jan 24 - Sat, Jan 31

from (US$)$1,528

Eastern Caribbean & Bimini Beach Club

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

Insider cabins from

$1,386~~$2,022~~

per Cabin

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,386~~$2,022~~

per Cabin

Departing on:

Sat, Nov 29 - Sat, Dec 06

from (US$)$1,386

Sat, Jan 17 - Sat, Jan 24

from (US$)$1,386

Cayman Coves & Jamaican Waterfalls

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

Insider cabins from

$1,386~~$1,998~~

per Cabin

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,386~~$1,998~~

per Cabin

Departing on:

Sat, Dec 13 - Sat, Dec 20

from (US$)$1,386

Sat, Feb 07 - Sat, Feb 14

from (US$)$1,806

Resilient Caribbean Holidays

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

Sea View cabins from

$2,752~~$4,282~~

per Cabin

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Sea View cabins from

$2,752~~$4,282~~

per Cabin

Departing on:

Sat, Dec 20 - Sat, Dec 27

from (US$)$2,752

Resilient New Year's Ahoy!

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

Insider cabins from

$3,346~~$5,264~~

per Cabin

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$3,346~~$5,264~~

per Cabin

Departing on:

Sat, Dec 27 - Sat, Jan 03

from (US$)$3,346

Cozumel, Grand Cayman & Bimini

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

Insider cabins from

$1,386~~$1,930~~

per Cabin

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,386~~$1,930~~

per Cabin

Departing on:

Sat, Jan 03 - Sat, Jan 10

from (US$)$1,386

Cayman Isles & Jamaican Miles

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

Insider cabins from

$1,386~~$2,006~~

per Cabin

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,386~~$2,006~~

per Cabin

Departing on:

Sat, Jan 10 - Sat, Jan 17

from (US$)$1,386

Sat, Mar 07 - Sat, Mar 14

from (US$)$2,086

San Juan Sunrises & Dominican Dreams

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

Insider cabins from

$1,386~~$2,026~~

per Cabin

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,386~~$2,026~~

per Cabin

Departing on:

Sat, Jan 31 - Sat, Feb 07

from (US$)$1,386

Sat, Feb 28 - Sat, Mar 07

from (US$)$1,526

Resilient Valentine's Voyage

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

Insider cabins from

$1,946~~$2,938~~

per Cabin

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

$1,946~~$2,938~~

per Cabin

Departing on:

Sat, Feb 14 - Sat, Feb 21

from (US$)$1,946

Western Caribbean Cruise

Miami, Florida
Roatán, Honduras
Costa Maya, Mexico
Cozumel, Mexico
Miami, Florida

Sea View cabins from

$2,268~~$3,452~~

per Cabin

6 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Sea View cabins from

$2,268~~$3,452~~

per Cabin

Departing on:

Sat, Mar 14 - Fri, Mar 20

from (US$)$2,268

Puerto Rican Nights & St. Croix Delights

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

Sea View cabins from

$3,024~~$4,748~~

per Cabin

8 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Sea View cabins from

$3,024~~$4,748~~

per Cabin

Departing on:

Fri, Mar 20 - Sat, Mar 28

from (US$)$3,024

Miami, Grand Turk (& back)

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

Sea View cabins from

$1,990~~$3,006~~

per Cabin

5 nights

Resilient Lady

+ up to $100 free drinks

80% off second Sailor

Sea View cabins from

$1,990~~$3,006~~

per Cabin

Departing on:

Sat, Aug 08 - Thu, Aug 13

from (US$)$1,990

Sat, May 02 - Thu, May 07

from (US$)$2,252

Sat, May 16 - Thu, May 21

from (US$)$2,210

Fire & Sunset Soirées

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

Insider cabins from

$1,432~~$2,130~~

per Cabin

4 nights

Resilient Lady

+ up to $100 free drinks

80% off second Sailor

Insider cabins from

$1,432~~$2,130~~

per Cabin

Departing on:

Thu, Jul 02 - Mon, Jul 06

from (US$)$1,432

Thu, May 07 - Mon, May 11

from (US$)$1,692

Thu, May 21 - Mon, May 25

from (US$)$1,672

Riviera Maya

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

Insider cabins from

$1,690~~$2,484~~

per Cabin

5 nights

Resilient Lady

+ up to $100 free drinks

80% off second Sailor

Insider cabins from

$1,690~~$2,484~~

per Cabin

Departing on:

Mon, May 11 - Sat, May 16

from (US$)$1,690

Mon, Jul 20 - Sat, Jul 25

from (US$)$1,790

Dominican Daze

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

Insider cabins from

$1,790~~$2,728~~

per Cabin

5 nights

Resilient Lady

+ up to $100 free drinks

80% off second Sailor

Insider cabins from

$1,790~~$2,728~~

per Cabin

Departing on:

Mon, Aug 03 - Sat, Aug 08

from (US$)$1,790

Mon, May 25 - Sat, May 30

from (US$)$2,112

Mon, Jul 06 - Sat, Jul 11

from (US$)$2,158

Cayman Isles & Bimini Beach Miles

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

Sea View cabins from

$2,090~~$3,150~~

per Cabin

5 nights

Resilient Lady

+ up to $100 free drinks

80% off second Sailor

Sea View cabins from

$2,090~~$3,150~~

per Cabin

Departing on:

Mon, Jun 08 - Sat, Jun 13

from (US$)$2,090

Sat, Jun 13 - Thu, Jun 18

from (US$)$2,348

Mayan Sol

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

Sea View cabins from

$2,090~~$3,174~~

per Cabin

5 nights

Resilient Lady

+ up to $100 free drinks

80% off second Sailor

Sea View cabins from

$2,090~~$3,174~~

per Cabin

Departing on:

Mon, Jun 22 - Sat, Jun 27

from (US$)$2,090