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70% off 2nd Sailor + up to $500 in savings

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from $2,548

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from $3,234

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Caribbean

from $1,728

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North America

from $3,926

per cabin

Showing 123 cruise vacations that match your search
Picture of the cruise
Dominican Daze
Miami, Florida • Puerto Plata • Beach Club at Bimini • Miami, Florida
from
Price$1,488
per Cabin
5 nights
Valiant Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$1,488
per Cabin
2025Best Rate★
Fri, Jan 03 - Wed, Jan 08
from Price$1,488
2024
Fri, Oct 11 - Wed, Oct 16
from Price$2,252
2024
Fri, Nov 08 - Wed, Nov 13
from Price$1,788
Picture of the cruise
Fire & Sunset Soirées: Halloween Edition
Miami, Florida • Key West, Florida • Beach Club at Bimini • Miami, Florida
from
Price$1,856
per Cabin
4 nights
Valiant Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$1,856
per Cabin
2024
Wed, Oct 16 - Sun, Oct 20
from Price$1,856
Picture of the promotion

DON'T MISS OUT - SAVE NOW, SAIL LATER

70% off 2nd Sailor + up to $500 off

Always Included Luxury: Wi-Fi, tips & gratuities, all dining, entertainment, and more.

Picture of the cruise
Riviera Maya: Halloween Edition
Miami, Florida • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida
from
Price$1,792
per Cabin
5 nights
Valiant Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$1,792
per Cabin
2024
Sun, Oct 20 - Fri, Oct 25
from Price$1,792
Picture of the cruise
Dominican Daze: Halloween Edition
Miami, Florida • Puerto Plata • Beach Club at Bimini • Miami, Florida
from
Price$1,692
per Cabin
5 nights
Valiant Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$1,692
per Cabin
2024
Fri, Oct 25 - Wed, Oct 30
from Price$1,692
Picture of the cruise
A Caribbean Breeze & Haunted Seas
Miami, Florida • Key West, Florida • Beach Club at Bimini • Miami, Florida
from
Price$2,328
per Cabin
4 nights
Valiant Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$2,328
per Cabin
2024
Wed, Oct 30 - Sun, Nov 03
from Price$2,328
Picture of the cruise
Mayan Sol
Miami, Florida • Costa Maya • Beach Club at Bimini • Miami, Florida
from
Price$1,490
per Cabin
5 nights
Valiant Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$1,490
per Cabin
2024Best Rate★
Sun, Nov 03 - Fri, Nov 08
from Price$1,490
2025
Sun, May 18 - Fri, May 23
from Price$2,480
2025
Sun, Jun 15 - Fri, Jun 20
from Price$2,610
Picture of the cruise
Costa Maya & Cozumel Charm
Miami, Florida • Costa Maya • Cozumel (Playa del Carmen) • Miami, Florida
from
Price$1,800
per Cabin
5 nights
Resilient Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$1,800
per Cabin
2024
Sun, Nov 10 - Fri, Nov 15
from Price$1,800
Picture of the cruise
Fire & Sunset Soirées
Miami, Florida • Key West, Florida • Beach Club at Bimini • Miami, Florida
from
Price$1,352
per Cabin
4 nights
Valiant Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$1,352
per Cabin
2024Best Rate★
Wed, Nov 13 - Sun, Nov 17
from Price$1,352
2024
Wed, Nov 27 - Sun, Dec 01
from Price$1,610
2024
Thu, Dec 26 - Mon, Dec 30
from Price$1,482
Picture of the cruise
Grand Turk, Puerto Plata & Bimini
Miami, Florida • Grand Turk • Puerto Plata • Beach Club at Bimini • Miami, Florida
from
Price$2,710
per Cabin
6 nights
Resilient Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$2,710
per Cabin
2024
Fri, Nov 15 - Thu, Nov 21
from Price$2,710
Picture of the cruise
Riviera Maya
Miami, Florida • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida
from
Price$1,486
per Cabin
5 nights
Valiant Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$1,486
per Cabin
2024Best Rate★
Sun, Dec 01 - Fri, Dec 06
from Price$1,486
2024
Sun, Nov 17 - Fri, Nov 22
from Price$1,490
2025
Sun, Jan 12 - Fri, Jan 17
from Price$1,690
Picture of the cruise
The Virgin Voyages Weekend w/ Sam Feldt
Miami, Florida • Miami, Florida
from
Price$756
per Cabin
2 nights
Resilient Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$756
per Cabin
2024
Sat, Nov 23 - Mon, Nov 25
from Price$756
Picture of the cruise
One-Way San Juan Sojourn
Miami, Florida • Grand Turk • Puerto Plata • Basseterre • San Juan
from
Price$2,096
per Cabin
6 nights
Resilient Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$2,096
per Cabin
2024
Sat, Nov 30 - Fri, Dec 06
from Price$2,096
Picture of the cruise
Dominican Daze: Holiday Edition
Miami, Florida • Puerto Plata • Beach Club at Bimini • Miami, Florida
from
Price$1,588
per Cabin
5 nights
Valiant Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$1,588
per Cabin
2024
Fri, Dec 06 - Wed, Dec 11
from Price$1,588
Picture of the cruise
San Juan to St. Lucia: Holiday Edition
San Juan • Tortola • Philipsburg • Bridgetown • Fort-de-France • Castries • Basseterre • San Juan
from
Price$3,014
per Cabin
8 nights
Resilient Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$3,014
per Cabin
2024
Fri, Dec 06 - Sat, Dec 14
from Price$3,014
Picture of the cruise
Fire & Sunset Soirées: Holiday Edition
Miami, Florida • Key West, Florida • Beach Club at Bimini • Miami, Florida
from
Price$1,356
per Cabin
4 nights
Valiant Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$1,356
per Cabin
2024
Wed, Dec 11 - Sun, Dec 15
from Price$1,356
Picture of the cruise
Eastern Caribbean Antilles
Miami, Florida • Puerto Plata • San Juan • St. Croix • Beach Club at Bimini • Miami, Florida
from
Price$2,804
per Cabin
8 nights
Scarlet Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$2,804
per Cabin
2025Best Rate★
Sat, Mar 08 - Sun, Mar 16
from Price$2,804
2024
Sat, Dec 14 - Sun, Dec 22
from Price$3,604
2025
Sat, Jan 11 - Sun, Jan 19
from Price$2,808
Picture of the cruise
Saint (Isles) & Seas of the Caribbean
San Juan • Tortola • Bridgetown • Castries • St. John's • Philipsburg • San Juan
from
Price$2,610
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$2,610
per Cabin
2024Best Rate★
Sat, Dec 14 - Sat, Dec 21
from Price$2,610
2025
Sat, Feb 08 - Sat, Feb 15
from Price$3,236
2025
Sat, Mar 08 - Sat, Mar 15
from Price$3,370
Picture of the cruise
Valiant Caribbean Holidays
Miami, Florida • Nassau • Puerto Plata • Beach Club at Bimini • Miami, Florida
from
Price$1,924
per Cabin
6 nights
Valiant Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$1,924
per Cabin
2024
Fri, Dec 20 - Thu, Dec 26
from Price$1,924
Picture of the cruise
Resilient Caribbean Holidays
San Juan • Philipsburg • Bridgetown • Castries • Fort-de-France • Basseterre • San Juan
from
Price$2,896
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$2,896
per Cabin
2024
Sat, Dec 21 - Sat, Dec 28
from Price$2,896
Picture of the cruise
Scarlet Caribbean Holidays
Miami, Florida • Costa Maya • Roatán • Beach Club at Bimini • Miami, Florida
from
Price$2,816
per Cabin
6 nights
Scarlet Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$2,816
per Cabin
2024
Sun, Dec 22 - Sat, Dec 28
from Price$2,816
Picture of the cruise
Resilient New Year's Ahoy
San Juan • Tortola • Bridgetown • Castries • St. John's • Philipsburg • San Juan
from
Price$2,912
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$2,912
per Cabin
2024
Sat, Dec 28 - Sat, Jan 04
from Price$2,912
Picture of the cruise
Scarlet New Year's Ahoy!
Miami, Florida • Puerto Plata • San Juan • St. Croix • Beach Club at Bimini • Miami, Florida
from
Price$4,862
per Cabin
8 nights
Scarlet Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$4,862
per Cabin
2024
Sat, Dec 28 - Sun, Jan 05
from Price$4,862
Picture of the cruise
Valiant New Year's Ahoy!
Miami, Florida • Key West, Florida • Beach Club at Bimini • Miami, Florida
from
Price$3,604
per Cabin
4 nights
Valiant Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$3,604
per Cabin
2024
Mon, Dec 30 - Fri, Jan 03
from Price$3,604
Picture of the cruise
Sunsets in the Lesser Antilles
San Juan • Oranjestad • Willemstad • Fort-de-France • Basseterre • San Juan
from
Price$2,878
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$2,878
per Cabin
2025Best Rate★
Sat, Jan 04 - Sat, Jan 11
from Price$2,878
2025
Sat, Feb 01 - Sat, Feb 08
from Price$3,132
2025
Sat, Feb 15 - Sat, Feb 22
from Price$3,006
Picture of the cruise
Western Caribbean Charm
Miami, Florida • Roatán • Costa Maya • Beach Club at Bimini • Miami, Florida
from
Price$2,044
per Cabin
6 nights
Scarlet Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$2,044
per Cabin
2025Best Rate★
Sun, Feb 02 - Sat, Feb 08
from Price$2,044
2025
Sun, Jan 05 - Sat, Jan 11
from Price$2,104
2025
Sun, Jan 19 - Sat, Jan 25
from Price$2,104
* Port changes in place on select sailings — see full cruise details
Picture of the cruise
San Juan, St. Vincent, Barbados & More
San Juan • Tortola • Basseterre • St. John's • Fort-de-France • Bridgetown • Castries • Kingstown • San Juan
from
Price$3,780
per Cabin
10 nights
Resilient Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$3,780
per Cabin
2025
Sat, Jan 11 - Tue, Jan 21
from Price$3,780
Picture of the cruise
Idyllic Caribbean Isles & Colombia
San Juan • Cartagena • Willemstad • Oranjestad • Castries • St. John's • Philipsburg • San Juan
from
Price$4,092
per Cabin
11 nights
Resilient Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$4,092
per Cabin
2025
Tue, Jan 21 - Sat, Feb 01
from Price$4,092
Picture of the cruise
San Juan, Barbados & Beyond
San Juan • Philipsburg • Castries • Bridgetown • Fort-de-France • Basseterre • San Juan
from
Price$3,168
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$3,168
per Cabin
2025
Sat, Mar 01 - Sat, Mar 08
from Price$3,168
Picture of the cruise
Puerto Rican Daze & Caribbean Nights
San Juan • Tortola • St. John's • Basseterre • Fort-de-France • Castries • Bridgetown • Kingstown • San Juan
from
Price$3,504
per Cabin
10 nights
Resilient Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$3,504
per Cabin
2025
Sat, Mar 22 - Tue, Apr 01
from Price$3,504
Picture of the cruise
Colombia & Caribbean Islands
San Juan • Cartagena • Oranjestad • Willemstad • Roseau • St. John's • Philipsburg • San Juan
from
Price$4,146
per Cabin
11 nights
Resilient Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$4,146
per Cabin
2025
Tue, Apr 01 - Sat, Apr 12
from Price$4,146
Picture of the cruise
Sunny Daze in Puerto Plata & Nassau
Miami, Florida • Puerto Plata • Nassau • Miami, Florida
from
Price$2,204
per Cabin
5 nights
Valiant Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$2,204
per Cabin
2025
Fri, Apr 11 - Wed, Apr 16
from Price$2,204
Picture of the cruise
Grand Cayman, Costa Maya & More
Miami, Florida • George Town • Costa Maya • Beach Club at Bimini • Miami, Florida
from
Price$3,598
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$3,598
per Cabin
2025
Sun, Jul 13 - Sun, Jul 20
from Price$3,598
Picture of the cruise
Grand Turk, Puerto Plata & More
Miami, Florida • Puerto Plata • Grand Turk • Beach Club at Bimini • Miami, Florida
from
Price$3,760
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$3,760
per Cabin
2025
Sun, Jul 20 - Sun, Jul 27
from Price$3,760
Picture of the cruise
Virgin Voyages Comedy Fest from Miami
Miami, Florida • Costa Maya • Beach Club at Bimini • Miami, Florida
from
Price$2,578
per Cabin
5 nights
Valiant Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$2,578
per Cabin
2025
Sun, Aug 10 - Fri, Aug 15
from Price$2,578
Picture of the cruise
Brilliant Lady Miami MerMaiden
Miami, Florida • Philipsburg • Tortola • Beach Club at Bimini • Miami, Florida
from
Price$5,486
per Cabin
8 nights
Brilliant Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$5,486
per Cabin
2025
Fri, Oct 17 - Sat, Oct 25
from Price$5,486
Picture of the cruise
Honduras, Mexico & Bahamas
Miami, Florida • Roatán • Costa Maya • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida
from
Price$3,562
per Cabin
7 nights
Scarlet Lady
BOOK NOW
+ 70% off 2nd Sailor
Up to $500 off 2025-2026 sailings
from
Price$3,562
per Cabin
2025
Fri, Oct 31 - Fri, Nov 07
from Price$3,562
Average starting price per cabin (incl. taxes & fees)