Currency, current value
$USD

Explore 400 cruise vacations

Showing Loading cruise vacations: All Destinations, July 2025 - December 2025
2 Sailors , 1 Cabin
Showing 84 cruise vacations that match your search
Showing 84 cruise vacations that match your search
Sort price type, current value Price per cabin
Sort options, current value Sails first
DEAL

Grand Cayman, Costa Maya & More

  • Miami, Florida
  • George Town, Grand Cayman
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
per Cabin
7 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea Terrace cabins from
per Cabin
Departing on:
2025
Sun, Jul 13 - Sun, Jul 20
from (US$)

Greek Island Glow

  • Athens (Piraeus)
  • Santorini, Greece
  • Rhodes, Greece
  • Bodrum, Turkey
  • Mykonos, Greece
  • Athens (Piraeus)
Sea View cabins from
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025Best Rate
Sun, Oct 12 - Sun, Oct 19
from (US$)
2025
Sun, Jul 20 - Sun, Jul 27
from (US$)
2025
Sun, Aug 03 - Sun, Aug 10
from (US$)
Only suites remaining

A Virgin Celebration Voyage (Lisbon)

  • Lisbon
  • Porto (Leixões), Portugal
  • La Coruña, Spain
  • Portsmouth
RockStar Quarters suites from
per Cabin
Loading
5 nights
Scarlet Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
RockStar Quarters suites from
per Cabin
Loading
Departing on:
2025
Tue, Jul 22 - Sun, Jul 27
from (US$)
Only suites remaining

Corfu, Dubrovnik & More

  • Athens (Piraeus)
  • Kotor, Montenegro
  • Dubrovnik, Croatia
  • Corfu, Greece
  • Mykonos, Greece
  • Athens (Piraeus)
Sea View cabins from
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025Best Rate
Sun, Sep 07 - Sun, Sep 14
from (US$)
2025
Sun, Jul 27 - Sun, Aug 03
from (US$)
Only suites remaining

England to Iceland & Norway

  • Portsmouth
  • Amsterdam, Netherlands
  • Bergen, Norway
  • Lerwick/Shetland, Scotland
  • Akureyri, Iceland
  • Ísafjörður, Iceland
  • Reykjavik, Iceland
  • Reykjavik
Mega RockStar Quarters suites from
per Cabin
10 nights
Scarlet Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Mega RockStar Quarters suites from
per Cabin
Departing on:
2025
Sun, Jul 27 - Wed, Aug 06
from (US$)
Only suites remaining

Riviera Maya

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
Loading
5 nights
Valiant Lady & Scarlet Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025Best Rate
Sun, Dec 14 - Fri, Dec 19
from (US$)
2025
Sun, Jul 27 - Fri, Aug 01
from (US$)
Only suites remaining
2025
Sun, Aug 24 - Fri, Aug 29
from (US$)

Fire & Sunset Soirées

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
Loading
4 nights
Valiant Lady & Scarlet Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025Best Rate
Wed, Dec 10 - Sun, Dec 14
from (US$)
2025
Wed, Aug 06 - Sun, Aug 10
from (US$)
2025
Wed, Aug 20 - Sun, Aug 24
from (US$)

Reykjavik to Amsterdam & Portsmouth

  • Reykjavik
  • Reykjavik, Iceland
  • Ísafjörður, Iceland
  • Akureyri, Iceland
  • Lerwick/Shetland, Scotland
  • Amsterdam, Netherlands
  • Portsmouth
Insider cabins from
per Cabin
Loading
11 nights
Scarlet Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Wed, Aug 06 - Sun, Aug 17
from (US$)

Istanbul, Santorini & More

  • Athens (Piraeus)
  • Istanbul, Turkey
  • Ephesus (Kuşadasi), Turkey
  • Mykonos, Greece
  • Rhodes, Greece
  • Santorini, Greece
  • Chania (Souda Bay), Crete, Greece
  • Athens (Piraeus)
Sea View cabins from
per Cabin
Loading
11 nights
Resilient Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025Best Rate
Sun, Aug 10 - Thu, Aug 21
from (US$)
2025
Sun, Sep 21 - Thu, Oct 02
from (US$)

Virgin Voyages Comedy Fest from Miami

  • Miami, Florida
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
per Cabin
Loading
5 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025
Sun, Aug 10 - Fri, Aug 15
from (US$)

Dominican Daze

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
per Cabin
Loading
5 nights
Valiant Lady & Scarlet Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025Best Rate
Fri, Oct 10 - Wed, Oct 15
from (US$)
2025
Fri, Aug 15 - Wed, Aug 20
from (US$)
2025
Fri, Aug 29 - Wed, Sep 03
from (US$)

Portsmouth to Ireland, Scotland & More

  • Portsmouth
  • Amsterdam, Netherlands
  • Bruges/Zeebruge (Brussels), Belgium
  • Kirkwall, Scotland
  • Stornoway, Isle of Lewis, Scotland
  • Glasgow (Greenock), Scotland
  • Belfast, Northern Ireland
  • Dublin, Ireland
  • Portsmouth
Insider cabins from
per Cabin
Loading
13 nights
Scarlet Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Sun, Aug 17 - Sat, Aug 30
from (US$)

Virgin Voyages Comedy Fest from the UK

  • Portsmouth
  • La Coruña, Spain
  • Bilbao, Spain
  • Bordeaux (Le Verdon), France
  • Portsmouth
Insider cabins from
per Cabin
Loading
6 nights
Scarlet Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Sat, Aug 30 - Fri, Sep 05
from (US$)

Brilliant Lady New York MerMaiden

  • New York City, New York
  • Royal Naval Dockyard, Bermuda
  • New York City, New York
Sea Terrace cabins from
per Cabin
Loading
5 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea Terrace cabins from
per Cabin
Loading
Departing on:
2025
Fri, Sep 05 - Wed, Sep 10
from (US$) Brilliant Lady's Inaugural Season

Portsmouth to Amsterdam & Bordeaux

  • Portsmouth
  • Amsterdam, Netherlands
  • Bruges/Zeebruge (Brussels), Belgium
  • Bordeaux (Le Verdon), France
  • Portsmouth
Sea View cabins from
per Cabin
Loading
7 nights
Scarlet Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025
Fri, Sep 05 - Fri, Sep 12
from (US$)

Mayan Sol

  • Miami, Florida
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
Loading
5 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025Best Rate
Sun, Oct 05 - Fri, Oct 10
from (US$)
2025
Sun, Sep 07 - Fri, Sep 12
from (US$)

The Big Apple to Bermuda

  • New York City, New York
  • Royal Naval Dockyard, Bermuda
  • New York City, New York
Insider cabins from
per Cabin
Loading
5 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Wed, Sep 10 - Mon, Sep 15
from (US$) Brilliant Lady's Inaugural Season

Portsmouth to Lisbon, Casablanca & Spain

  • Portsmouth
  • La Coruña, Spain
  • Lisbon, Portugal
  • Casablanca, Morocco
  • Málaga, Spain
  • Ibiza, Spain
  • Barcelona
Sea Terrace cabins from
per Cabin
Loading
13 nights
Scarlet Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea Terrace cabins from
per Cabin
Loading
Departing on:
2025
Fri, Sep 12 - Thu, Sep 25
from (US$)

Fall Colors: Coastal Northeast & Canada

  • New York City, New York
  • Boston, Massachusetts
  • Eastport, Maine
  • Saint John, New Brunswick
  • Halifax, Nova Scotia
  • New York City, New York
Sea View cabins from
per Cabin
Loading
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025
Mon, Sep 15 - Tue, Sep 23
from (US$) Brilliant Lady's Inaugural Season

Autumn Leaves: New York to Quebec

  • New York City, New York
  • Boston, Massachusetts
  • Eastport, Maine
  • Saint John, New Brunswick
  • Halifax, Nova Scotia
  • Quebec City, Quebec
Sea View cabins from
per Cabin
Loading
10 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025
Tue, Sep 23 - Fri, Oct 03
from (US$) Brilliant Lady's Inaugural Season

Barcelona to Cannes, Rome & Tuscany

  • Barcelona
  • Ibiza, Spain
  • Palma de Mallorca, Spain
  • Cannes, France
  • Ajaccio, Corsica, France
  • Cagliari, Sardinia, Italy
  • Florence/Pisa (Livorno), Italy
  • Pompeii/Capri (Naples), Italy
  • Rome (Civitavecchia)
Sea View cabins from
per Cabin
Loading
12 nights
Scarlet Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025
Thu, Sep 25 - Tue, Oct 07
from (US$)
DEAL

Starry Nights in Greece & Croatia

  • Athens (Piraeus)
  • Santorini, Greece
  • Bodrum, Turkey
  • Mykonos, Greece
  • Dubrovnik, Croatia
  • Kotor, Montenegro
  • Corfu, Greece
  • Athens (Piraeus)
Sea Terrace cabins from
per Cabin
Loading
10 nights
Resilient Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea Terrace cabins from
per Cabin
Loading
Departing on:
2025
Thu, Oct 02 - Sun, Oct 12
from (US$)

Fall Leaves to Miami Scenes

  • Quebec City, Quebec
  • Halifax, Nova Scotia
  • Saint John, New Brunswick
  • Eastport, Maine
  • Boston, Massachusetts
  • Charleston, South Carolina
  • Miami, Florida
Insider cabins from
per Cabin
Loading
13 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Fri, Oct 03 - Thu, Oct 16
from (US$) Brilliant Lady's Inaugural Season

Italy to France & Spain

  • Rome (Civitavecchia)
  • Cagliari, Sardinia, Italy
  • Tuscany/Cinque Terre (Marina di Carrara), Italy
  • Ajaccio, Corsica, France
  • Cannes, France
  • Valencia, Spain
  • Barcelona
Sea View cabins from
per Cabin
Loading
9 nights
Scarlet Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025
Tue, Oct 07 - Thu, Oct 16
from (US$)

Scarlet's Haunted Halloween Soirée

  • Barcelona
  • Palma de Mallorca, Spain
  • Casablanca, Morocco
  • Funchal, Madeira, Portugal
  • Santa Cruz de Tenerife, Spain
  • Miami, Florida
Insider cabins from
per Cabin
Loading
15 nights
Scarlet Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Thu, Oct 16 - Fri, Oct 31
from (US$)
DEAL

Brilliant Lady Miami MerMaiden

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
Loading
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Fri, Oct 17 - Sat, Oct 25
from (US$) Brilliant Lady's Inaugural Season

Mykonos Moons to Spanish Sunrises

  • Athens (Piraeus)
  • Mykonos, Greece
  • Catania, Sicily, Italy
  • Palma de Mallorca, Spain
  • Valencia, Spain
  • Barcelona
Insider cabins from
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Sun, Oct 19 - Sun, Oct 26
from (US$)

Riviera Maya: Halloween Edition

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
per Cabin
Loading
5 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025
Sun, Oct 19 - Fri, Oct 24
from (US$)

Dominican Daze: Halloween Edition

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

Resilient's Haunted Halloween Soirée

  • Barcelona
  • Valencia, Spain
  • Casablanca, Morocco
  • Las Palmas de Gran Canaria, Spain
  • Miami, Florida
Sea View cabins from
per Cabin
Loading
14 nights
Resilient Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025
Sun, Oct 26 - Sun, Nov 09
from (US$)

Valiant's Haunted Halloween Soirée

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
per Cabin
Loading
4 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea Terrace cabins from
per Cabin
Loading
Departing on:
2025
Wed, Oct 29 - Sun, Nov 02
from (US$)
DEAL

Honduras, Mexico & Bahamas

  • Miami, Florida
  • Roatán, Honduras
  • Costa Maya, Mexico
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
Loading
7 nights
Scarlet Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Fri, Oct 31 - Fri, Nov 07
from (US$)
DEAL

Western Caribbean: From Miami to Bimini

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
Loading
7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Sat, Nov 01 - Sat, Nov 08
from (US$) Brilliant Lady's Inaugural Season

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
Loading
6 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Sun, Nov 02 - Sat, Nov 08
from (US$)
DEAL

Colorful Curaçao to the Charming Caymans

  • Miami, Florida
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Insider cabins from
per Cabin
Loading
12 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Sat, Nov 08 - Thu, Nov 20
from (US$) Brilliant Lady's Inaugural Season
DEAL

Saint (Isles) & Seas of the Caribbean

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Bridgetown, Barbados
  • Castries, St. Lucia
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Sea View cabins from
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025
Sat, Nov 08 - Sat, Nov 15
from (US$)

Western Caribbean Charm

  • Miami, Florida
  • Costa Maya, Mexico
  • Roatán, Honduras
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
Loading
6 nights
Resilient Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Sun, Nov 09 - Sat, Nov 15
from (US$)
DEAL

San Juan Sunrises & Dominican Dreams

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025
Sat, Nov 15 - Sat, Nov 22
from (US$)
DEAL

Sunny Miles of Tropical Isles

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Bridgetown, Barbados
  • Castries, St. Lucia
  • Fort-de-France, Martinique
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
Sea View cabins from
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025
Sat, Nov 15 - Sat, Nov 22
from (US$)
DEAL

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
Loading
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Thu, Nov 20 - Fri, Nov 28
from (US$) Brilliant Lady's Inaugural Season

Miami, Grand Turk (& back)

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
per Cabin
Loading
5 nights
Scarlet Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025Best Rate
Sun, Nov 30 - Fri, Dec 05
from (US$)
2025
Fri, Nov 21 - Wed, Nov 26
from (US$)
2025
Fri, Dec 19 - Wed, Dec 24
from (US$)
DEAL

Cayman Coves & Jamaican Waterfalls

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025Best Rate
Sat, Dec 06 - Sat, Dec 13
from (US$)
2025
Sat, Nov 22 - Sat, Nov 29
from (US$)
2025
Sat, Dec 13 - Sat, Dec 20
from (US$)
DEAL

Thanksgiving in the Lesser Antilles

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Basseterre, St. Kitts and Nevis
  • St. John's, Antigua
  • Castries, St. Lucia
  • Charlotte Amalie, St. Thomas
  • San Juan, Puerto Rico
Insider cabins from
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Sat, Nov 22 - Sat, Nov 29
from (US$)
DEAL

Antigua Waves & Grand Turk Caves

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • St. John's, Antigua
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
  • Miami, Florida
Insider cabins from
per Cabin
Loading
9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Fri, Nov 28 - Sun, Dec 07
from (US$) Brilliant Lady's Inaugural Season

San Juan to Barbados & the St. Isles

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • Roseau, Dominica
  • Bridgetown, Barbados
  • San Juan, Puerto Rico
Insider cabins from
per Cabin
Loading
6 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Sat, Nov 29 - Fri, Dec 05
from (US$)
DEAL

San Juan, Samaná & Bimini

  • Miami, Florida
  • San Juan, Puerto Rico
  • Samaná, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Sat, Nov 29 - Sat, Dec 06
from (US$)
DEAL

Nicky Jam x Virgin Voyages

  • San Juan, Puerto Rico
  • Willemstad, Curaçao
  • Oranjestad, Aruba
  • Roseau, Dominica
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
per Cabin
Loading
8 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Fri, Dec 05 - Sat, Dec 13
from (US$)
DEAL

Aruban Sunsets & Calm Cayman Days

  • Miami, Florida
  • Oranjestad, Aruba
  • Cartagena, Colombia
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • Miami, Florida
Insider cabins from
per Cabin
Loading
11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Sun, Dec 07 - Thu, Dec 18
from (US$) Brilliant Lady's Inaugural Season
DEAL

St. Lucia, St. Maarten, Barbados & More

  • San Juan, Puerto Rico
  • Basseterre, St. Kitts and Nevis
  • Castries, St. Lucia
  • Roseau, Dominica
  • Bridgetown, Barbados
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Sea View cabins from
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025
Sat, Dec 13 - Sat, Dec 20
from (US$)
DEAL

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
Loading
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Thu, Dec 18 - Fri, Dec 26
from (US$) Brilliant Lady's Inaugural Season
DEAL

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
Loading
7 nights
Resilient Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from (US$)
DEAL

Valiant Caribbean Holidays

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • St. John's, Antigua
  • Castries, St. Lucia
  • Tortola, British Virgin Islands
  • San Juan, Puerto Rico
Sea View cabins from
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from (US$)

Scarlet Caribbean Holidays

  • Miami, Florida
  • Nassau, Bahamas
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
per Cabin
Loading
4 nights
Scarlet Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025
Wed, Dec 24 - Sun, Dec 28
from (US$)
DEAL

Brilliant New Year's Ahoy!

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • St. John's, Antigua
  • Basseterre, St. Kitts and Nevis
  • San Juan, Puerto Rico
  • Miami, Florida
Insider cabins from
per Cabin
Loading
9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Fri, Dec 26 - Sun, Jan 04
from (US$) Brilliant Lady's Inaugural Season
DEAL

Resilient New Year's Ahoy!

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from (US$)
DEAL

Valiant New Year’s Ahoy!

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • Castries, St. Lucia
  • Bridgetown, Barbados
  • St. Croix, U.S. Virgin Islands
  • San Juan, Puerto Rico
Insider cabins from
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from (US$)

Scarlet New Year's Ahoy!

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
per Cabin
Loading
5 nights
Scarlet Lady
BOOK NOW
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025
Sun, Dec 28 - Fri, Jan 02
from (US$)
Average starting price per cabin (incl. taxes & fees)