Explore over 320 cruise vacations

Sat, Dec 14 - Sun, Dec 22

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,904

per Cabin

Departing on:

2024Best Rate

from $1,904

Sat, Jan 11 - Sun, Jan 19

from $2,224

Sat, Jan 25 - Sun, Feb 02

from $2,240

Saint (Isles) & Seas of the Caribbean

San Juan • Tortola • Bridgetown • Castries • St. John's • Philipsburg • San Juan

Insider cabins from

$1,668

per Cabin

7 nights

Resilient Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,668

per Cabin

Departing on:

Sat, Dec 14 - Sat, Dec 21

from $1,668

SAVINGS TO WRITE HOME ABOUT

80% off your 2nd Sailor + free drinks

Always Included Luxury covers your WiFi, tips & gratuities, all dining, & more.

Dominican Daze

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

Insider cabins from

$1,490

per Cabin

5 nights

Valiant Lady

+ $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,490

per Cabin

Departing on:

Fri, Jan 31 - Wed, Feb 05

from $1,490

Sun, Dec 15 - Fri, Dec 20

from $1,870

Fri, Jan 03 - Wed, Jan 08

from $2,500

Resilient Caribbean Holidays

San Juan • Philipsburg • Bridgetown • Castries • Fort-de-France • Basseterre • San Juan

Sea View cabins from

$2,926

per Cabin

7 nights

Resilient Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Sea View cabins from

$2,926

per Cabin

Departing on:

Sat, Dec 21 - Sat, Dec 28

from $2,926

Scarlet New Year's Ahoy!

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

Insider cabins from

$4,464

per Cabin

8 nights

Scarlet Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$4,464

per Cabin

Departing on:

Sat, Dec 28 - Sun, Jan 05

from $4,464

Valiant New Year's Ahoy!

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

Sea View cabins from

$3,202

per Cabin

4 nights

Valiant Lady

+ $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Sea View cabins from

$3,202

per Cabin

Departing on:

Mon, Dec 30 - Fri, Jan 03

from $3,202

Sunsets in the Lesser Antilles

San Juan • Oranjestad • Willemstad • Fort-de-France • Basseterre • San Juan

Insider cabins from

$1,806

per Cabin

7 nights

Resilient Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,806

per Cabin

Departing on:

Sat, Jan 04 - Sat, Jan 11

from $1,806

Sat, Feb 01 - Sat, Feb 08

from $2,926

Sat, Feb 15 - Sat, Feb 22

from $2,660

Western Caribbean Charm

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

Insider cabins from

$1,740

per Cabin

6 nights

Scarlet Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,740

per Cabin

Departing on:

Sun, Feb 02 - Sat, Feb 08

from $1,740

Sun, Jan 05 - Sat, Jan 11

from $6,340

Only suites remaining

Sun, Jan 19 - Sat, Jan 25

from $2,640

Fire & Sunset Soirées

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

Insider cabins from

$1,192

per Cabin

4 nights

Valiant Lady

+ $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,192

per Cabin

Departing on:

Wed, Feb 05 - Sun, Feb 09

from $1,192

Wed, Jan 08 - Sun, Jan 12

from $2,800

Wed, Jan 22 - Sun, Jan 26

from $1,752

San Juan, St. Vincent, Barbados & More

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

Sea View cabins from

$3,402

per Cabin

10 nights

Resilient Lady

+ $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Sea View cabins from

$3,402

per Cabin

Departing on:

Sat, Jan 11 - Tue, Jan 21

from $3,402

Riviera Maya

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

Insider cabins from

$1,492

per Cabin

5 nights

Valiant Lady

+ $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,492

per Cabin

Departing on:

Sun, Jan 12 - Fri, Jan 17

from $1,492

Sun, Jan 26 - Fri, Jan 31

from $1,990

Sun, Feb 09 - Fri, Feb 14

from $1,492

Idyllic Caribbean Isles & Colombia

San Juan • Cartagena • Willemstad • Oranjestad • Castries • St. John's • Philipsburg • San Juan

Insider cabins from

$2,310

per Cabin

11 nights

Resilient Lady

+ $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,310

per Cabin

Departing on:

Tue, Jan 21 - Sat, Feb 01

from $2,310

Resilient Valentine's Voyage

San Juan • Tortola • Bridgetown • Castries • St. John's • Philipsburg • San Juan

Sea View cabins from

$3,206

per Cabin

7 nights

Resilient Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Sea View cabins from

$3,206

per Cabin

Departing on:

Sat, Feb 08 - Sat, Feb 15

from $3,206

Scarlet Valentine's Voyage

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

Insider cabins from

$2,320

per Cabin

8 nights

Scarlet Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,320

per Cabin

Departing on:

Sat, Feb 08 - Sun, Feb 16

from $2,320

Valiant Valentine's Voyage

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

Sea View cabins from

$1,690

per Cabin

5 nights

Valiant Lady

+ $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Sea View cabins from

$1,690

per Cabin

Departing on: