Explore 390 cruise vacations

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Mega RockStar Quarters suites from

$13,700

per Cabin

‌

Departing on:

Sat, Mar 22 - Tue, Apr 01

from (US$)$13,700

Only suites remaining

Colombia & Caribbean Islands

San Juan • Cartagena • Oranjestad • Willemstad • Roseau • St. John's • Philipsburg, St. Maarten • San Juan

Sea Terrace cabins from

$6,960

per Cabin

‌

11 nights

Resilient Lady

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Sea Terrace cabins from

$6,960

per Cabin

‌

Departing on:

Tue, Apr 01 - Sat, Apr 12

from (US$)$6,960

Western Caribbean Charm

Miami, Florida • Costa Maya • Roatán • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,100

per Cabin

‌

6 nights

Resilient Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,100

per Cabin

‌

Departing on:

Sun, Nov 09 - Sat, Nov 15

San Juan Sunrises & Dominican Dreams

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

Insider cabins from

$1,974

per Cabin

‌

7 nights

Resilient Lady

Sat, Nov 15 - Sat, Nov 22

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,974

per Cabin

‌

Departing on:

2025Best Rate

from (US$)$1,974

Sat, Jan 31 - Sat, Feb 07

Sat, Feb 28 - Sat, Mar 07

Cayman Coves & Jamaican Waterfalls

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

Insider cabins from

$1,948

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,948

per Cabin

‌

Departing on:

Sat, Jan 24 - Sat, Jan 31

Sat, Nov 22 - Sat, Nov 29

from (US$)$2,242

Sat, Dec 06 - Sat, Dec 13

San Juan, Samaná & Bimini

Miami, Florida • San Juan • Samaná • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,948

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,948

per Cabin

‌

Departing on:

Sat, Jan 17 - Sat, Jan 24

Sat, Nov 29 - Sat, Dec 06

from (US$)$1,976

Resilient Caribbean Holidays

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

Insider cabins from

$2,814

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,814

per Cabin

‌

Departing on:

Sat, Dec 20 - Sat, Dec 27

from (US$)$2,814

Resilient New Year's Ahoy!

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

Insider cabins from

$3,780

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,780

per Cabin

‌

Departing on:

Sat, Dec 27 - Sat, Jan 03

from (US$)$3,780

Cozumel, Grand Cayman & Bimini

Miami, Florida • George Town • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,946

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,946

per Cabin

‌

Departing on:

Sat, Jan 03 - Sat, Jan 10

from (US$)$1,946

Cayman Isles & Jamaican Miles

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

Insider cabins from

$1,948

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,948

per Cabin

‌

Departing on:

Sat, Jan 10 - Sat, Jan 17

Sat, Mar 07 - Sat, Mar 14

from (US$)$2,226

Costa Mayan Caves & Honduran Waves

Miami, Florida • Costa Maya • Roatán • Cozumel (Playa del Carmen) • Miami, Florida

Insider cabins from

$2,006

per Cabin

‌

6 nights

Resilient Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,006

per Cabin

‌

Departing on:

Sat, Mar 14 - Fri, Mar 20

from (US$)$2,006

RED HOT

Puerto Rican Nights & St. Croix Delights

Miami, Florida • Puerto Plata • San Juan • St. Croix • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,544

per Cabin

‌

8 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,544

per Cabin

‌

Departing on:

Fri, Mar 20 - Sat, Mar 28

from (US$)$2,544

Miami, Grand Turk (& back)

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

Insider cabins from

$1,890

per Cabin

‌

5 nights

Resilient Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,890

per Cabin

‌

Departing on:

Sat, May 02 - Thu, May 07

Sat, May 30 - Thu, Jun 04

Sat, Jun 13 - Thu, Jun 18

Fire & Sunset Soirées

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

Insider cabins from

$1,432

per Cabin

‌

4 nights

Resilient Lady

+ up to $50 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,432

per Cabin

‌

Departing on:

Thu, May 07 - Mon, May 11

from (US$)$1,432

Thu, May 21 - Mon, May 25

Thu, Jun 04 - Mon, Jun 08

Riviera Maya

Miami, Florida • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,888

per Cabin

‌

5 nights

Resilient Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,888

per Cabin

‌

Departing on:

Mon, May 11 - Sat, May 16

from (US$)$1,888

Mon, Jun 08 - Sat, Jun 13

Sat, Jun 27 - Thu, Jul 02

Mayan Sol

Miami, Florida • Costa Maya • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,886

per Cabin

‌

5 nights

Resilient Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,886

per Cabin

‌

Departing on:

Sat, May 16 - Thu, May 21

from (US$)$1,886

Mon, Jun 22 - Sat, Jun 27

Sat, Jul 25 - Thu, Jul 30

Dominican Daze

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

Insider cabins from

$1,892

per Cabin

‌

5 nights

Resilient Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,892

per Cabin

‌

Departing on:

Mon, May 25 - Sat, May 30

Mon, Jul 06 - Sat, Jul 11

Mon, Aug 03 - Sat, Aug 08

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Showing 49 cruise vacations that match your search

Puerto Rican Daze & Caribbean Nights

San Juan • Tortola • St. John's • Basseterre • Fort-de-France • Castries • Bridgetown • Kingstown • San Juan

Mega RockStar Quarters suites from

$13,700

per Cabin

‌

10 nights

Resilient Lady

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Mega RockStar Quarters suites from

$13,700

per Cabin

‌

Departing on:

Sat, Mar 22 - Tue, Apr 01

from (US$)$13,700

Only suites remaining

Colombia & Caribbean Islands

San Juan • Cartagena • Oranjestad • Willemstad • Roseau • St. John's • Philipsburg, St. Maarten • San Juan

Sea Terrace cabins from

$6,960

per Cabin

‌

11 nights

Resilient Lady

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Sea Terrace cabins from

$6,960

per Cabin

‌

Departing on:

Tue, Apr 01 - Sat, Apr 12

from (US$)$6,960

Western Caribbean Charm

Miami, Florida • Costa Maya • Roatán • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,100

per Cabin

‌

6 nights

Resilient Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,100

per Cabin

‌

Departing on:

Sun, Nov 09 - Sat, Nov 15

San Juan Sunrises & Dominican Dreams

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

Insider cabins from

$1,974

per Cabin

‌

7 nights

Resilient Lady

Sat, Nov 15 - Sat, Nov 22

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,974

per Cabin

‌

Departing on:

2025Best Rate

from (US$)$1,974

Sat, Jan 31 - Sat, Feb 07

Sat, Feb 28 - Sat, Mar 07

Cayman Coves & Jamaican Waterfalls

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

Insider cabins from

$1,948

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,948

per Cabin

‌

Departing on:

Sat, Jan 24 - Sat, Jan 31

Sat, Nov 22 - Sat, Nov 29

from (US$)$2,242

Sat, Dec 06 - Sat, Dec 13

San Juan, Samaná & Bimini

Miami, Florida • San Juan • Samaná • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,948

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,948

per Cabin

‌

Departing on:

Sat, Jan 17 - Sat, Jan 24

Sat, Nov 29 - Sat, Dec 06

from (US$)$1,976

Resilient Caribbean Holidays

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

Insider cabins from

$2,814

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,814

per Cabin

‌

Departing on:

Sat, Dec 20 - Sat, Dec 27

from (US$)$2,814

Resilient New Year's Ahoy!

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

Insider cabins from

$3,780

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,780

per Cabin

‌

Departing on:

Sat, Dec 27 - Sat, Jan 03

from (US$)$3,780

Cozumel, Grand Cayman & Bimini

Miami, Florida • George Town • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,946

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,946

per Cabin

‌

Departing on:

Sat, Jan 03 - Sat, Jan 10

from (US$)$1,946

Cayman Isles & Jamaican Miles

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

Insider cabins from

$1,948

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,948

per Cabin

‌

Departing on:

Sat, Jan 10 - Sat, Jan 17

Sat, Mar 07 - Sat, Mar 14

from (US$)$2,226

Costa Mayan Caves & Honduran Waves

Miami, Florida • Costa Maya • Roatán • Cozumel (Playa del Carmen) • Miami, Florida

Insider cabins from

$2,006

per Cabin

‌

6 nights

Resilient Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,006

per Cabin

‌

Departing on:

Sat, Mar 14 - Fri, Mar 20

from (US$)$2,006

RED HOT

Puerto Rican Nights & St. Croix Delights

Miami, Florida • Puerto Plata • San Juan • St. Croix • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,544

per Cabin

‌

8 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,544

per Cabin

‌

Departing on:

Fri, Mar 20 - Sat, Mar 28

from (US$)$2,544

Miami, Grand Turk (& back)

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

Insider cabins from

$1,890

per Cabin

‌

5 nights

Resilient Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,890

per Cabin

‌

Departing on:

Sat, May 02 - Thu, May 07

Sat, May 30 - Thu, Jun 04

Sat, Jun 13 - Thu, Jun 18

Fire & Sunset Soirées

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

Insider cabins from

$1,432

per Cabin

‌

4 nights

Resilient Lady

+ up to $50 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,432

per Cabin

‌

Departing on:

Thu, May 07 - Mon, May 11

from (US$)$1,432

Thu, May 21 - Mon, May 25

Thu, Jun 04 - Mon, Jun 08

Riviera Maya

Miami, Florida • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,888

per Cabin

‌

5 nights

Resilient Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,888

per Cabin

‌

Departing on:

Mon, May 11 - Sat, May 16

from (US$)$1,888

Mon, Jun 08 - Sat, Jun 13

Sat, Jun 27 - Thu, Jul 02

Mayan Sol

Miami, Florida • Costa Maya • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,886

per Cabin

‌

5 nights

Resilient Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,886

per Cabin

‌

Departing on:

Sat, May 16 - Thu, May 21

from (US$)$1,886

Mon, Jun 22 - Sat, Jun 27

Sat, Jul 25 - Thu, Jul 30

Dominican Daze

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

Insider cabins from

$1,892

per Cabin

‌

5 nights

Resilient Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,892

per Cabin

‌

Departing on:

Mon, May 25 - Sat, May 30

Mon, Jul 06 - Sat, Jul 11

Mon, Aug 03 - Sat, Aug 08