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Showing 234cruise vacations: Caribbean,November 2024 - October 2026
Showing 234 cruise vacations that match your search
Picture of the cruise
Riviera Maya
Miami, Florida • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$1,190
per Cabin
5 nights
Valiant Lady, Scarlet Lady & Resilient Lady
BOOK NOW
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,190
per Cabin
Departing on:
2024Best Rate
Sun, Dec 01 - Fri, Dec 06
from Price$1,190
2025
Sun, Jan 12 - Fri, Jan 17
from Price$1,492
2025
Sun, Jan 26 - Fri, Jan 31
from Price$1,492
Picture of the cruise
San Juan to St. Lucia: Holiday Edition
San Juan • Tortola • Philipsburg • Bridgetown • Fort-de-France • Castries • Basseterre • San Juan
Insider cabins from
Price$1,904
per Cabin
8 nights
Resilient Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,904
per Cabin
Departing on:
2024
Fri, Dec 06 - Sat, Dec 14
from Price$1,904
Picture of the promotion

SAVINGS TO WRITE HOME ABOUT

80% off your 2nd Sailor + free drinks

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

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Eastern Caribbean Antilles
Miami, Florida • Puerto Plata • San Juan • St. Croix • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$1,744
per Cabin
8 nights
Scarlet Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,744
per Cabin
Departing on:
2025Best Rate
Sat, Jan 25 - Sun, Feb 02
from Price$1,744
2024
Sat, Dec 14 - Sun, Dec 22
from Price$1,904
2025
Sat, Jan 11 - Sun, Jan 19
from Price$2,224
Picture of the cruise
Saint (Isles) & Seas of the Caribbean
San Juan • Tortola • Bridgetown • Castries • St. John's • Philipsburg • San Juan
Insider cabins from
Price$1,668
per Cabin
7 nights
Resilient Lady & Valiant Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,668
per Cabin
Departing on:
2024Best Rate
Sat, Dec 14 - Sat, Dec 21
from Price$1,668
2025
Sat, Mar 08 - Sat, Mar 15
from Price$2,786
2025
Sat, Nov 08 - Sat, Nov 15
from Price$1,946
Picture of the cruise
Dominican Daze
Miami, Florida • Puerto Plata • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$1,490
per Cabin
5 nights
Valiant Lady, Scarlet Lady & Resilient Lady
BOOK NOW
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,490
per Cabin
Departing on:
2025Best Rate
Fri, Jan 31 - Wed, Feb 05
from Price$1,490
2024
Sun, Dec 15 - Fri, Dec 20
from Price$2,170
2025
Fri, Jan 03 - Wed, Jan 08
from Price$1,700
Picture of the cruise
Valiant Caribbean Holidays
Miami, Florida • Nassau • Puerto Plata • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$2,126
per Cabin
6 nights
Valiant Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,126
per Cabin
Departing on:
2024
Fri, Dec 20 - Thu, Dec 26
from Price$2,126
Picture of the cruise
Resilient Caribbean Holidays
San Juan • Philipsburg • Bridgetown • Castries • Fort-de-France • Basseterre • San Juan
Insider cabins from
Price$2,648
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,648
per Cabin
Departing on:
2024
Sat, Dec 21 - Sat, Dec 28
from Price$2,648
Picture of the cruise
Scarlet Caribbean Holidays
Miami, Florida • Costa Maya • Roatán • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$2,270
per Cabin
6 nights
Scarlet Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,270
per Cabin
Departing on:
2024
Sun, Dec 22 - Sat, Dec 28
from Price$2,270
Picture of the cruise
Resilient New Year's Ahoy
San Juan • Tortola • Bridgetown • Castries • St. John's • Philipsburg • San Juan
Insider cabins from
Price$3,206
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$3,206
per Cabin
Departing on:
2024
Sat, Dec 28 - Sat, Jan 04
from Price$3,206
Picture of the cruise
Scarlet New Year's Ahoy!
Miami, Florida • Puerto Plata • San Juan • St. Croix • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$3,984
per Cabin
8 nights
Scarlet Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$3,984
per Cabin
Departing on:
2024
Sat, Dec 28 - Sun, Jan 05
from Price$3,984
Picture of the cruise
Valiant New Year's Ahoy!
Miami, Florida • Key West, Florida • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$2,794
per Cabin
4 nights
Valiant Lady
BOOK NOW
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,794
per Cabin
Departing on:
2024
Mon, Dec 30 - Fri, Jan 03
from Price$2,794
Picture of the cruise
Sunsets in the Lesser Antilles
San Juan • Oranjestad • Willemstad • Fort-de-France • Basseterre • San Juan
Insider cabins from
Price$2,226
per Cabin
7 nights
Resilient Lady & Valiant Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,226
per Cabin
Departing on:
2025Best Rate
Sat, Jan 04 - Sat, Jan 11
from Price$2,226
2025
Sat, Feb 01 - Sat, Feb 08
from Price$2,506
2025
Sat, Feb 15 - Sat, Feb 22
from Price$2,366
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Western Caribbean Charm
Miami, Florida • Roatán • Costa Maya • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$1,428
per Cabin
6 nights
Scarlet Lady & Resilient Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,428
per Cabin
Departing on:
2025Best Rate
Sun, Feb 02 - Sat, Feb 08
from Price$1,428
2025
Sun, Jan 05 - Sat, Jan 11
from Price$1,668
2025
Sun, Jan 19 - Sat, Jan 25
from Price$1,668
* Port changes in place on select sailings — see full cruise details
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Fire & Sunset Soirées
Miami, Florida • Key West, Florida • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$1,192
per Cabin
4 nights
Valiant Lady, Scarlet Lady & Resilient Lady
BOOK NOW
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,192
per Cabin
Departing on:
2025Best Rate
Wed, Jan 22 - Sun, Jan 26
from Price$1,192
2025
Wed, Jan 08 - Sun, Jan 12
from Price$1,360
2025
Wed, Feb 05 - Sun, Feb 09
from Price$1,354
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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
Price$2,580
per Cabin
10 nights
Resilient Lady
BOOK NOW
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Sea View cabins from
Price$2,580
per Cabin
Departing on:
2025
Sat, Jan 11 - Tue, Jan 21
from Price$2,580
Picture of the cruise
Idyllic Caribbean Isles & Colombia
San Juan • Cartagena • Willemstad • Oranjestad • Castries • St. John's • Philipsburg • San Juan
Insider cabins from
Price$2,178
per Cabin
11 nights
Resilient Lady
BOOK NOW
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,178
per Cabin
Departing on:
2025
Tue, Jan 21 - Sat, Feb 01
from Price$2,178
Picture of the cruise
Resilient Valentine's Voyage
San Juan • Tortola • Bridgetown • Castries • St. John's • Philipsburg • San Juan
Insider cabins from
Price$2,648
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,648
per Cabin
Departing on:
2025
Sat, Feb 08 - Sat, Feb 15
from Price$2,648
Picture of the cruise
Scarlet Valentine's Voyage
Miami, Florida • Puerto Plata • San Juan • St. Croix • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$1,904
per Cabin
8 nights
Scarlet Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,904
per Cabin
Departing on:
2025
Sat, Feb 08 - Sun, Feb 16
from Price$1,904
Picture of the cruise
Valiant Valentine's Voyage
Miami, Florida • Puerto Plata • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$1,490
per Cabin
5 nights
Valiant Lady
BOOK NOW
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,490
per Cabin
Departing on:
2025
Fri, Feb 14 - Wed, Feb 19
from Price$1,490
Picture of the cruise
San Juan, Barbados & Beyond
San Juan • Philipsburg • Castries • Bridgetown • Fort-de-France • Basseterre • San Juan
Insider cabins from
Price$2,366
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,366
per Cabin
Departing on:
2025
Sat, Mar 01 - Sat, Mar 08
from Price$2,366
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Puerto Rican Daze & Caribbean Nights
San Juan • Tortola • St. John's • Basseterre • Fort-de-France • Castries • Bridgetown • Kingstown • San Juan
Insider cabins from
Price$2,182
per Cabin
10 nights
Resilient Lady
BOOK NOW
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,182
per Cabin
Departing on:
2025
Sat, Mar 22 - Tue, Apr 01
from Price$2,182
Picture of the cruise
Colombia & Caribbean Islands
San Juan • Cartagena • Oranjestad • Willemstad • Roseau • St. John's • Philipsburg • San Juan
Insider cabins from
Price$2,400
per Cabin
11 nights
Resilient Lady
BOOK NOW
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,400
per Cabin
Departing on:
2025
Tue, Apr 01 - Sat, Apr 12
from Price$2,400
Picture of the cruise
Sunny Daze in Puerto Plata & Nassau
Miami, Florida • Puerto Plata • Nassau • Miami, Florida
Sea View cabins from
Price$2,092
per Cabin
5 nights
Valiant Lady
BOOK NOW
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Sea View cabins from
Price$2,092
per Cabin
Departing on:
2025
Fri, Apr 11 - Wed, Apr 16
from Price$2,092
Picture of the cruise
A Virgin Celebration Voyage (Miami)
Miami, Florida • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$1,690
per Cabin
5 nights
Valiant Lady
BOOK NOW
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,690
per Cabin
Departing on:
2025
Sun, May 04 - Fri, May 09
from Price$1,690
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Mayan Sol
Miami, Florida • Costa Maya • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$1,490
per Cabin
5 nights
Valiant Lady & Resilient Lady
BOOK NOW
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,490
per Cabin
Departing on:
2025Best Rate
Sun, Sep 07 - Fri, Sep 12
from Price$1,490
2025
Sun, May 18 - Fri, May 23
from Price$1,890
2025
Sun, Jun 15 - Fri, Jun 20
from Price$1,890
Picture of the cruise
Grand Cayman, Costa Maya & More
Miami, Florida • George Town • Costa Maya • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$2,788
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,788
per Cabin
Departing on:
2025
Sun, Jul 13 - Sun, Jul 20
from Price$2,788
Picture of the cruise
Grand Turk, Puerto Plata & More
Miami, Florida • Puerto Plata • Grand Turk • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$2,926
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,926
per Cabin
Departing on:
2025
Sun, Jul 20 - Sun, Jul 27
from Price$2,926
Picture of the cruise
Virgin Voyages Comedy Fest from Miami
Miami, Florida • Costa Maya • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$1,692
per Cabin
5 nights
Valiant Lady
BOOK NOW
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,692
per Cabin
Departing on:
2025
Sun, Aug 10 - Fri, Aug 15
from Price$1,692
Picture of the cruise
Brilliant Lady Miami MerMaiden
Miami, Florida • Philipsburg • Tortola • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$3,186
per Cabin
8 nights
Brilliant Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$3,186
per Cabin
Departing on:
2025
Fri, Oct 17 - Sat, Oct 25
from Price$3,186
Picture of the cruise
Riviera Maya: Halloween Edition
Miami, Florida • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$1,490
per Cabin
5 nights
Valiant Lady
BOOK NOW
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,490
per Cabin
Departing on:
2025
Sun, Oct 19 - Fri, Oct 24
from Price$1,490
Picture of the cruise
Dominican Daze: Halloween Edition
Miami, Florida • Puerto Plata • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$1,590
per Cabin
5 nights
Valiant Lady
BOOK NOW
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,590
per Cabin
Departing on:
2025
Fri, Oct 24 - Wed, Oct 29
from Price$1,590
Picture of the cruise
Valiant's Haunted Halloween Soriées
Miami, Florida • Key West, Florida • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$1,274
per Cabin
4 nights
Valiant Lady
BOOK NOW
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,274
per Cabin
Departing on:
2025
Wed, Oct 29 - Sun, Nov 02
from Price$1,274
Picture of the cruise
Honduras, Mexico & Bahamas
Miami, Florida • Roatán • Costa Maya • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$2,088
per Cabin
7 nights
Scarlet Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,088
per Cabin
Departing on:
2025
Fri, Oct 31 - Fri, Nov 07
from Price$2,088
Picture of the cruise
Western Caribbean: From Miami to Bimini
Miami, Florida • Ocho Rios • George Town • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$2,086
per Cabin
7 nights
Brilliant Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,086
per Cabin
Departing on:
2025
Sat, Nov 01 - Sat, Nov 08
from Price$2,086
Picture of the cruise
One-way to SJ: DR, St. Maarten & BVI
Miami, Florida • Puerto Plata • Philipsburg • Tortola • San Juan
Insider cabins from
Price$1,788
per Cabin
6 nights
Valiant Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,788
per Cabin
Departing on:
2025
Sun, Nov 02 - Sat, Nov 08
from Price$1,788
Picture of the cruise
Colorful Curacao to the Charming Caymans
Miami, Florida • Oranjestad • Willemstad • Cartagena • Ocho Rios • George Town • Miami, Florida
Insider cabins from
Price$3,096
per Cabin
12 nights
Brilliant Lady
BOOK NOW
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$3,096
per Cabin
Departing on:
2025
Sat, Nov 08 - Thu, Nov 20
from Price$3,096
Picture of the cruise
San Juan Sunrises & Dominican Dreams
Miami, Florida • San Juan • Puerto Plata • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$2,086
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,086
per Cabin
Departing on:
2025Best Rate
Sat, Nov 15 - Sat, Nov 22
from Price$2,086
2026
Sat, Jan 31 - Sat, Feb 07
from Price$2,086
2026
Sat, Feb 28 - Sat, Mar 07
from Price$2,086
Picture of the cruise
Sunny Miles of Tropical Isles
San Juan • Philipsburg • Bridgetown • Castries • Fort-de-France • Basseterre • San Juan
Insider cabins from
Price$1,948
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,948
per Cabin
Departing on:
2025Best Rate
Sat, Nov 15 - Sat, Nov 22
from Price$1,948
2026
Sat, Feb 28 - Sat, Mar 07
from Price$2,086
Picture of the cruise
From Miami to St. Croix
Miami, Florida • Puerto Plata • San Juan • Philipsburg • St. Croix • Miami, Florida
Insider cabins from
Price$2,384
per Cabin
8 nights
Brilliant Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,384
per Cabin
Departing on:
2026Best Rate
Thu, Feb 12 - Fri, Feb 20
from Price$2,384
2025
Thu, Nov 20 - Fri, Nov 28
from Price$2,386
Picture of the cruise
Miami, Grand Turk (& back)
Miami, Florida • Grand Turk • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$1,590
per Cabin
5 nights
Scarlet Lady & Resilient Lady
BOOK NOW
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,590
per Cabin
Departing on:
2025Best Rate
Fri, Dec 19 - Wed, Dec 24
from Price$1,590
2025
Fri, Nov 21 - Wed, Nov 26
from Price$1,592
2026
Fri, Jan 16 - Wed, Jan 21
from Price$1,690
Picture of the cruise
Cayman Coves & Jamaican Waterfalls
Miami, Florida • Ocho Rios • George Town • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$1,948
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,948
per Cabin
Departing on:
2026Best Rate
Sat, Jan 24 - Sat, Jan 31
from Price$1,948
2025
Sat, Nov 22 - Sat, Nov 29
from Price$2,228
2025
Sat, Dec 06 - Sat, Dec 13
from Price$2,086
Picture of the cruise
Sun-Soaked Seas & Saint Isles
San Juan • Tortola • Basseterre • St. John's • Fort-de-France • Bridgetown • Castries • Philipsburg • San Juan
Insider cabins from
Price$2,780
per Cabin
10 nights
Valiant Lady
BOOK NOW
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,780
per Cabin
Departing on:
2025
Sat, Nov 22 - Tue, Dec 02
from Price$2,780
Picture of the cruise
Miami to San Juan
Miami, Florida • Grand Turk • St. John's • Basseterre • San Juan • Miami, Florida
Insider cabins from
Price$2,324
per Cabin
9 nights
Brilliant Lady
BOOK NOW
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,324
per Cabin
Departing on:
2025Best Rate
Fri, Nov 28 - Sun, Dec 07
from Price$2,324
2026
Fri, Jan 23 - Sun, Feb 01
from Price$2,502
2026
Fri, Feb 20 - Sun, Mar 01
from Price$2,502
Picture of the cruise
San Juan, Samaná & Bimini
Miami, Florida • San Juan • Samaná • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$1,948
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,948
per Cabin
Departing on:
2026Best Rate
Sat, Jan 17 - Sat, Jan 24
from Price$1,948
2025
Sat, Nov 29 - Sat, Dec 06
from Price$2,086
Picture of the cruise
Cartagena & Caribbean Faves
San Juan • Cartagena • Willemstad • Oranjestad • Fort-de-France • St. John's • Philipsburg • San Juan
Insider cabins from
Price$3,060
per Cabin
11 nights
Valiant Lady
BOOK NOW
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$3,060
per Cabin
Departing on:
2025
Tue, Dec 02 - Sat, Dec 13
from Price$3,060
Picture of the cruise
Aruban Sunsets & Calm Cayman Days
Miami, Florida • Oranjestad • Cartagena • Ocho Rios • George Town • Miami, Florida
Insider cabins from
Price$2,838
per Cabin
11 nights
Brilliant Lady
BOOK NOW
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,838
per Cabin
Departing on:
2025Best Rate
Sun, Dec 07 - Thu, Dec 18
from Price$2,838
2026
Sun, Mar 01 - Thu, Mar 12
from Price$2,838
Picture of the cruise
St. Lucia, St. Maarten, Barbados & More
San Juan • Basseterre • Castries • Roseau • Bridgetown • Philipsburg • San Juan
Insider cabins from
Price$1,946
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,946
per Cabin
Departing on:
2025
Sat, Dec 13 - Sat, Dec 20
from Price$1,946
Picture of the cruise
Brilliant Caribbean Holidays
Miami, Florida • Grand Turk • Puerto Plata • San Juan • Samaná • Miami, Florida
Insider cabins from
Price$3,186
per Cabin
8 nights
Brilliant Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$3,186
per Cabin
Departing on:
2025
Thu, Dec 18 - Fri, Dec 26
from Price$3,186
Picture of the cruise
Resilient Caribbean Holidays
Miami, Florida • San Juan • Puerto Plata • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$2,786
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,786
per Cabin
Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from Price$2,786
Picture of the cruise
Valiant Caribbean Holidays
San Juan • Philipsburg • Basseterre • St. John's • Castries • Tortola • San Juan
Insider cabins from
Price$2,368
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,368
per Cabin
Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from Price$2,368
Picture of the cruise
Scarlet Caribbean Holidays
Miami, Florida • Nassau • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$1,512
per Cabin
4 nights
Scarlet Lady
BOOK NOW
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,512
per Cabin
Departing on:
2025
Wed, Dec 24 - Sun, Dec 28
from Price$1,512
Picture of the cruise
Brilliant New Year's Ahoy!
Miami, Florida • Grand Turk • St. John's • Basseterre • San Juan • Miami, Florida
Insider cabins from
Price$4,664
per Cabin
9 nights
Brilliant Lady
BOOK NOW
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$4,664
per Cabin
Departing on:
2025
Fri, Dec 26 - Sun, Jan 04
from Price$4,664
Picture of the cruise
Resilient New Year's Ahoy!
Miami, Florida • Ocho Rios • George Town • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$3,766
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$3,766
per Cabin
Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from Price$3,766
Picture of the cruise
Valiant New Year’s Ahoy!
San Juan • Philipsburg • Basseterre • Castries • Bridgetown • St. Croix • San Juan
Insider cabins from
Price$3,768
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$3,768
per Cabin
Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from Price$3,768
Picture of the cruise
Scarlet New Year's Ahoy!
Miami, Florida • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$2,918
per Cabin
5 nights
Scarlet Lady
BOOK NOW
+ $100 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,918
per Cabin
Departing on:
2025
Sun, Dec 28 - Fri, Jan 02
from Price$2,918
Picture of the cruise
Aruban Sights & Antiguan Nights
San Juan • Oranjestad • Willemstad • St. John's • Philipsburg • San Juan
Insider cabins from
Price$2,086
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,086
per Cabin
Departing on:
2026
Sat, Jan 03 - Sat, Jan 10
from Price$2,086
Picture of the cruise
Cozumel, Grand Cayman & Bimini
Miami, Florida • George Town • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$1,948
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,948
per Cabin
Departing on:
2026
Sat, Jan 03 - Sat, Jan 10
from Price$1,948
Picture of the cruise
Miami to the Cayman Islands
Miami, Florida • Oranjestad • Kralendijk • Cartagena • Ocho Rios • George Town • Miami, Florida
Insider cabins from
Price$2,840
per Cabin
11 nights
Brilliant Lady
BOOK NOW
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,840
per Cabin
Departing on:
2026
Sun, Jan 04 - Thu, Jan 15
from Price$2,840
Picture of the cruise
Cayman Isles & Jamaican Miles
Miami, Florida • George Town • Ocho Rios • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$1,948
per Cabin
7 nights
Resilient Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,948
per Cabin
Departing on:
2026Best Rate
Sat, Jan 10 - Sat, Jan 17
from Price$1,948
2026
Sat, Mar 07 - Sat, Mar 14
from Price$2,226
Picture of the cruise
Virgin Island Views & Saint Isle Blues
San Juan • Tortola • Bridgetown • Kingstown • Basseterre • St. Croix • San Juan
Insider cabins from
Price$1,946
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,946
per Cabin
Departing on:
2026
Sat, Jan 10 - Sat, Jan 17
from Price$1,946
Picture of the cruise
Grand Turk Tranquility & St. Croix Charm
Miami, Florida • Grand Turk • Puerto Plata • San Juan • St. Croix • Miami, Florida
Insider cabins from
Price$2,384
per Cabin
8 nights
Brilliant Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,384
per Cabin
Departing on:
2026
Thu, Jan 15 - Fri, Jan 23
from Price$2,384
Picture of the cruise
St. Kitts, Barbados, Martinique & More
San Juan • Basseterre • Bridgetown • Fort-de-France • St. John's • Philipsburg • San Juan
Insider cabins from
Price$1,946
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,946
per Cabin
Departing on:
2026
Sat, Jan 17 - Sat, Jan 24
from Price$1,946
Picture of the cruise
Barbados, Antigua, BVI & More
San Juan • Tortola • Bridgetown • Fort-de-France • St. John's • Philipsburg • San Juan
Insider cabins from
Price$1,946
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,946
per Cabin
Departing on:
2026
Sat, Jan 24 - Sat, Jan 31
from Price$1,946
Picture of the cruise
Quintessential Caribbean Highlights
San Juan • Philipsburg • Basseterre • St. John's • Fort-de-France • Castries • Kingstown • Bridgetown • San Juan
Insider cabins from
Price$2,780
per Cabin
10 nights
Valiant Lady
BOOK NOW
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,780
per Cabin
Departing on:
2026
Sat, Jan 31 - Tue, Feb 10
from Price$2,780
Picture of the cruise
Magnetic Miami to Gorgeous George Town
Miami, Florida • Willemstad • Oranjestad • Cartagena • Ocho Rios • George Town • Miami, Florida
Insider cabins from
Price$2,840
per Cabin
11 nights
Brilliant Lady
BOOK NOW
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,840
per Cabin
Departing on:
2026
Sun, Feb 01 - Thu, Feb 12
from Price$2,840
Picture of the cruise
Cartagena, Aruba, Antigua & More
San Juan • Cartagena • Willemstad • Oranjestad • St. John's • St. Croix • Philipsburg • San Juan
Insider cabins from
Price$3,058
per Cabin
11 nights
Valiant Lady
BOOK NOW
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$3,058
per Cabin
Departing on:
2026
Tue, Feb 10 - Sat, Feb 21
from Price$3,058
Picture of the cruise
Antigua, Martinique, & Barbados & More
San Juan • Philipsburg • Bridgetown • Fort-de-France • St. John's • Tortola • San Juan
Insider cabins from
Price$2,086
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,086
per Cabin
Departing on:
2026
Sat, Feb 21 - Sat, Feb 28
from Price$2,086
Picture of the cruise
Quaint Castries to Elegant Antigua
San Juan • Basseterre • Castries • Fort-de-France • St. John's • Tortola • San Juan
Insider cabins from
Price$2,228
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,228
per Cabin
Departing on:
2026
Sat, Mar 07 - Sat, Mar 14
from Price$2,228
Picture of the cruise
Gorgeous Antigua, St. Kitts & Bimini
Miami, Florida • Puerto Plata • St. John's • Basseterre • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$2,682
per Cabin
9 nights
Brilliant Lady
BOOK NOW
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,682
per Cabin
Departing on:
2026
Thu, Mar 12 - Sat, Mar 21
from Price$2,682
Picture of the cruise
Costa Mayan Caves & Honduran Waves
Miami, Florida • Costa Maya • Roatán • Cozumel (Playa del Carmen) • Miami, Florida
Insider cabins from
Price$1,910
per Cabin
6 nights
Resilient Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,910
per Cabin
Departing on:
2026
Sat, Mar 14 - Fri, Mar 20
from Price$1,910
Picture of the cruise
Puerto Rican Nights & St. Croix Delights
Miami, Florida • Puerto Plata • San Juan • St. Croix • Beach Club at Bimini • Miami, Florida
Insider cabins from
Price$2,544
per Cabin
8 nights
Resilient Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,544
per Cabin
Departing on:
2026
Fri, Mar 20 - Sat, Mar 28
from Price$2,544
Picture of the cruise
Panama Canal & Pacific Wonders
Miami, Florida • Cartagena • Colón • Panama Canal (Cruising) • Puntarenas • Puerto Quetzal • Cabo San Lucas • Los Angeles, California
Insider cabins from
Price$6,370
per Cabin
16 nights
Brilliant Lady
BOOK NOW
+ $300 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$6,370
per Cabin
Departing on:
2026
Sat, Mar 21 - Mon, Apr 06
from Price$6,370
Picture of the cruise
Puerto Plata, San Juan & Tortola
Miami, Florida • Puerto Plata • San Juan • Tortola • Miami, Florida
Insider cabins from
Price$2,228
per Cabin
7 nights
Scarlet Lady
BOOK NOW
+ $200 in drinks — on us
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,228
per Cabin
Departing on:
2026
Sun, Apr 19 - Sun, Apr 26
from Price$2,228
Average starting price per cabin (incl. taxes & fees)