Explore over 320 cruise vacations

+ $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,300

per Cabin

Departing on:

Thu, Nov 28 - Sat, Dec 14

from $3,300

Riviera Maya

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

Insider cabins from

$1,190

per Cabin

5 nights

Valiant Lady

Sun, Dec 01 - Fri, Dec 06

+ $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,190

per Cabin

Departing on:

2024Best Rate

from $1,190

Sun, Jan 12 - Fri, Jan 17

from $1,492

Sun, Jan 26 - Fri, Jan 31

from $1,492

SAVINGS TO WRITE HOME ABOUT

80% off your 2nd Sailor + free drinks

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

San Juan to St. Lucia: Holiday Edition

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

Insider cabins from

$1,904

per Cabin

8 nights

Resilient Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,904

per Cabin

Departing on:

Fri, Dec 06 - Sat, Dec 14

from $1,904

Eastern Caribbean Antilles

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

Insider cabins from

$1,744

per Cabin

8 nights

Scarlet Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,744

per Cabin

Departing on:

Sat, Jan 11 - Sun, Jan 19

from $1,744

Sat, Dec 14 - Sun, Dec 22

from $1,904

Sat, Jan 25 - Sun, Feb 02

from $1,744

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

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 $2,170

Fri, Jan 03 - Wed, Jan 08

from $1,700

Valiant Caribbean Holidays

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

Insider cabins from

$2,126

per Cabin

6 nights

Valiant Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,126

per Cabin

Departing on:

Fri, Dec 20 - Thu, Dec 26

from $2,126

Resilient Caribbean Holidays

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

Insider cabins from

$2,648

per Cabin

7 nights

Resilient Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,648

per Cabin

Departing on:

Sat, Dec 21 - Sat, Dec 28

from $2,648

Scarlet Caribbean Holidays

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

Insider cabins from

$2,270

per Cabin

6 nights

Scarlet Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,270

per Cabin

Departing on:

Sun, Dec 22 - Sat, Dec 28

from $2,270

Resilient New Year's Ahoy

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

Insider cabins from

$3,206

per Cabin

7 nights

Resilient Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,206

per Cabin

Departing on:

Sat, Dec 28 - Sat, Jan 04

from $3,206

Scarlet New Year's Ahoy!

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

Insider cabins from

$3,984

per Cabin

8 nights

Scarlet Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,984

per Cabin

Departing on:

Sat, Dec 28 - Sun, Jan 05

from $3,984

Valiant New Year's Ahoy!

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

Insider cabins from

$2,794

per Cabin

4 nights

Valiant Lady

+ $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,794

per Cabin

Departing on:

Mon, Dec 30 - Fri, Jan 03

from $2,794

Sunsets in the Lesser Antilles

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

Insider cabins from

$2,226

per Cabin

7 nights

Resilient Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,226

per Cabin

Departing on:

Sat, Jan 04 - Sat, Jan 11

from $2,226

Western Caribbean Charm

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

Insider cabins from

$1,308

per Cabin

6 nights

Scarlet Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,308

per Cabin

Departing on:

Sun, Jan 05 - Sat, Jan 11

from $1,308

Sun, Jan 19 - Sat, Jan 25

from $1,668

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, Jan 22 - Sun, Jan 26

from $1,192

Wed, Jan 08 - Sun, Jan 12

from $1,360

San Juan, St. Vincent, Barbados & More

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

Insider cabins from

$1,980

per Cabin

10 nights

Resilient Lady

+ $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,980

per Cabin

Departing on:

Sat, Jan 11 - Tue, Jan 21

from $1,980

Idyllic Caribbean Isles & Colombia

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

Insider cabins from

$2,178

per Cabin

11 nights

Resilient Lady

+ $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,178

per Cabin

Departing on: