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Explore 403 cruise vacations

Showing Loading cruise vacations: Caribbean, July 2025 - April 2027
Showing 65 cruise vacations that match your search
Showing 65 cruise vacations that match your search
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Dominican Daze

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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5 nights
Valiant Lady, Scarlet Lady, Resilient Lady & Brilliant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026Best Rate
Mon, Aug 31 - Sat, Sep 05
from (US$)
2025
Fri, Jul 04 - Wed, Jul 09
from (US$)
2025
Fri, Aug 01 - Wed, Aug 06
from (US$)

Grand Turk, Puerto Plata & More

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • Grand Turk, Turks and Caicos
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
per Cabin
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7 nights
Valiant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Sea Terrace cabins from
per Cabin
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Departing on:
2025
Sun, Jul 20 - Sun, Jul 27
from (US$)

Dominican Daze: Halloween Edition

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
per Cabin
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5 nights
Valiant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Sea View cabins from
per Cabin
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Departing on:
2025
Fri, Oct 24 - Wed, Oct 29
from (US$)

One-way to SJ: DR, St. Maarten & BVI

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • San Juan, Puerto Rico
Insider cabins from
per Cabin
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6 nights
Valiant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2025
Sun, Nov 02 - Sat, Nov 08
from (US$)

San Juan Sunrises & Dominican Dreams

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026Best Rate
Sat, Mar 28 - Sat, Apr 04
from (US$)
2025
Sat, Nov 15 - Sat, Nov 22
from (US$)
2026
Sat, Apr 18 - Sat, Apr 25
from (US$)

Sunny San Juan & Isles of Beach Miles

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • St. Croix, U.S. Virgin Islands
  • Miami, Florida
Insider cabins from
per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2025
Thu, Nov 20 - Fri, Nov 28
from (US$) Brilliant Lady's Inaugural Season

Brilliant Caribbean Holidays

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Samaná, Dominican Republic
  • Miami, Florida
Insider cabins from
per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2025
Thu, Dec 18 - Fri, Dec 26
from (US$) Brilliant Lady's Inaugural Season

Resilient Caribbean Holidays

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from (US$)

Grand Turk, Puerto Plata & Bimini

  • Miami, Florida
  • The Beach Club at Bimini, Bahamas
  • Puerto Plata, Dominican Republic
  • Grand Turk, Turks and Caicos
  • Miami, Florida
Insider cabins from
per Cabin
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6 nights
Brilliant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Mon, Jan 26 - Sun, Feb 01
from (US$)

San Juan Sunrises & Dominican Dreams

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026Best Rate
Sat, Jan 31 - Sat, Feb 07
from (US$)
2026
Sat, Feb 28 - Sat, Mar 07
from (US$)
2026
Sun, Dec 06 - Sun, Dec 13
from (US$)

Brilliant Valentine's Voyage

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • St. Croix, U.S. Virgin Islands
  • Miami, Florida
Sea View cabins from
per Cabin
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8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Sea View cabins from
per Cabin
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Departing on:
2026
Thu, Feb 12 - Fri, Feb 20
from (US$) Brilliant Lady's Inaugural Season

Scarlet Valentine's Voyage

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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5 nights
Scarlet Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Fri, Feb 13 - Wed, Feb 18
from (US$)

Red Hot Sailing Club Voyage

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • St. John's, Antigua
  • Basseterre, St. Kitts and Nevis
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Thu, Mar 12 - Sat, Mar 21
from (US$) Brilliant Lady's Inaugural Season

Puerto Rican Nights & St. Croix Delights

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • St. Croix, U.S. Virgin Islands
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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8 nights
Resilient Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Fri, Mar 20 - Sat, Mar 28
from (US$)

Tortola, Charleston, Newport & More

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Puerto Plata, Dominican Republic
  • Charleston, South Carolina
  • Newport, Rhode Island
  • New York City, New York
Insider cabins from
per Cabin
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9 nights
Valiant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Sat, Mar 28 - Mon, Apr 06
from (US$)

Puerto Plata, San Juan & Tortola

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Miami, Florida
Insider cabins from
per Cabin
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7 nights
Scarlet Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Sun, Apr 19 - Sun, Apr 26
from (US$)

Miami to Grand Turk: Halloween Edition

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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6 nights
Scarlet Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Sun, Oct 25 - Sat, Oct 31
from (US$)

November Nights in the Eastern Caribbean

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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8 nights
Resilient Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Sun, Nov 08 - Mon, Nov 16
from (US$)

St. Maarten, Tortola, San Juan & more

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • St. Croix, U.S. Virgin Islands
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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10 nights
Brilliant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
Loading
Departing on:
2027Best Rate
Mon, Jan 11 - Thu, Jan 21
from (US$)
2026
Mon, Nov 30 - Thu, Dec 10
from (US$)
2027
Mon, Mar 08 - Thu, Mar 18
from (US$)

Resilient Caribbean Holidays

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
Loading
Departing on:
2026
Sun, Dec 20 - Sun, Dec 27
from (US$)

Brilliant Caribbean Holidays

  • Miami, Florida
  • The Beach Club at Bimini, Bahamas
  • Puerto Plata, Dominican Republic
  • Miami, Florida
Insider cabins from
per Cabin
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5 nights
Brilliant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Wed, Dec 23 - Mon, Dec 28
from (US$)

Scarlet New Year's Ahoy!

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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5 nights
Scarlet Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2026
Wed, Dec 30 - Mon, Jan 04
from (US$)

San Juan & St. Isles: Valentine’s Voyage

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • St. Croix, U.S. Virgin Islands
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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10 nights
Brilliant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2027
Mon, Feb 08 - Thu, Feb 18
from (US$)

PR, DR & Bimini: Valentine’s Voyage

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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7 nights
Resilient Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2027
Sun, Feb 14 - Sun, Feb 21
from (US$)

San Juan to Miami: Dominican Daze

  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
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5 nights
Valiant Lady
BOOK NOW
+ free drinks
70% off 2nd Sailor + Balcony upgrades
Insider cabins from
per Cabin
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Departing on:
2027
Sat, Apr 10 - Thu, Apr 15
from (US$)
Average starting price per cabin (incl. taxes & fees)