Explore 409 cruise vacations

Showing 0 cruise vacations: All Destinations, July 2025 - April 2026
UP TO $300 IN ONBOARD CREDIT
On Caribbean sailings 7 nights or longer
|
On top of 70% off 2nd Sailor + balcony upgrades
Showing 91 cruise vacations that match your search
Showing 91 cruise vacations that match your search
Loading
Loading

Fire & Sunset Soirées

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
per Cabin
Loading
4 nights
Valiant Lady & Scarlet Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025Best Rate
Wed, Dec 10 - Sun, Dec 14
from (US$)
2025
Wed, Jul 09 - Sun, Jul 13
from (US$)
2025
Wed, Aug 06 - Sun, Aug 10
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 View cabins from
per Cabin
Loading
10 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025Best Rate
Thu, Jul 10 - Sun, Jul 20
from (US$)
2025
Thu, Oct 02 - Sun, Oct 12
from (US$)
DEAL

Grand Cayman, Costa Maya & More

  • Miami, Florida
  • George Town, Grand Cayman
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Sun, Jul 13 - Sun, Jul 20
from (US$)
DEAL

Grand Turk, Puerto Plata & More

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

Corfu, Dubrovnik & More

  • Athens (Piraeus)
  • Kotor, Montenegro
  • Dubrovnik, Croatia
  • Corfu, Greece
  • Mykonos, Greece
  • Athens (Piraeus)
Insider cabins from
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025Best Rate
Sun, Jul 27 - Sun, Aug 03
from (US$)
2025
Sun, Sep 07 - Sun, Sep 14
from (US$)

England to Iceland & Norway

  • Portsmouth
  • Amsterdam, Netherlands
  • Bergen, Norway
  • Lerwick/Shetland, Scotland
  • Akureyri, Iceland
  • Ísafjörður, Iceland
  • Reykjavik, Iceland
  • Reykjavik
Sea Terrace cabins from
per Cabin
Loading
10 nights
Scarlet Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea Terrace cabins from
per Cabin
Loading
Departing on:
2025
Sun, Jul 27 - Wed, Aug 06
from (US$)

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
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025Best Rate
Sun, Nov 16 - Fri, Nov 21
from (US$)
2025
Sun, Jul 27 - Fri, Aug 01
from (US$)
2025
Sun, Aug 24 - Fri, Aug 29
from (US$)

Dominican Daze

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
Loading
5 nights
Valiant Lady & Scarlet Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025Best Rate
Fri, Nov 07 - Wed, Nov 12
from (US$)
2025
Fri, Aug 01 - Wed, Aug 06
from (US$)
2025
Fri, Aug 15 - Wed, Aug 20
from (US$)

Greek Island Glow

  • Athens (Piraeus)
  • Santorini, Greece
  • Rhodes, Greece
  • Bodrum, Turkey
  • Mykonos, Greece
  • Athens (Piraeus)
Insider cabins from
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025Best Rate
Sun, Oct 12 - Sun, Oct 19
from (US$)
2025
Sun, Aug 03 - Sun, Aug 10
from (US$)
2025
Sun, Aug 31 - Sun, Sep 07
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
+ free balcony upgrade
SWING INTO SUMMER: 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
+ free balcony upgrade
SWING INTO SUMMER: 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
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025
Sun, Aug 10 - Fri, Aug 15
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
Sea View cabins from
per Cabin
Loading
13 nights
Scarlet Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea View 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
Sea Terrace cabins from
per Cabin
Loading
6 nights
Scarlet Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea Terrace cabins from
per Cabin
Loading
Departing on:
2025
Sat, Aug 30 - Fri, Sep 05
from (US$)

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
+ free balcony upgrade
SWING INTO SUMMER: 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
Sea View cabins from
per Cabin
Loading
5 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025Best Rate
Sun, Sep 07 - Fri, Sep 12
from (US$)
2025
Sun, Oct 05 - Fri, Oct 10
from (US$)

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
+ free balcony upgrade
SWING INTO SUMMER: 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
Insider cabins from
per Cabin
Loading
13 nights
Scarlet Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider 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
Insider cabins from
per Cabin
Loading
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider 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 Terrace cabins from
per Cabin
Loading
10 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea Terrace 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
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025
Thu, Sep 25 - Tue, Oct 07
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
+ free balcony upgrade
SWING INTO SUMMER: 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
Insider cabins from
per Cabin
Loading
9 nights
Scarlet Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider 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
+ free balcony upgrade
SWING INTO SUMMER: 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
+ free balcony upgrade
SWING INTO SUMMER: 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

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
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025
Sun, Oct 19 - Fri, Oct 24
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
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Fri, Oct 31 - Fri, Nov 07
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
Loading
6 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Sun, Nov 02 - Sat, Nov 08
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
Insider cabins from
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025Best Rate
Sat, Nov 15 - Sat, Nov 22
from (US$)
2026
Sat, Mar 28 - Sat, Apr 04
from (US$)
2026
Sat, Apr 18 - Sat, Apr 25
from (US$)

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
+ free balcony upgrade
SWING INTO SUMMER: 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
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025Best Rate
Sat, Dec 13 - Sat, Dec 20
from (US$)
2025
Sat, Nov 22 - Sat, Nov 29
from (US$)
2025
Sat, Dec 06 - Sat, Dec 13
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
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025
Sat, Nov 22 - Sat, Nov 29
from (US$)

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
Sea View cabins from
per Cabin
Loading
6 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea View 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
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2025Best Rate
Sat, Nov 29 - Sat, Dec 06
from (US$)
2026
Sat, Jan 17 - Sat, Jan 24
from (US$)
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
+ free balcony upgrade
SWING INTO SUMMER: 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
+ free balcony upgrade
SWING INTO SUMMER: 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

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
+ free balcony upgrade
SWING INTO SUMMER: 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
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider 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
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2025
Wed, Dec 24 - Sun, Dec 28
from (US$)
DEAL

Aruban Sights & Antiguan Nights

  • San Juan, Puerto Rico
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2026
Sat, Jan 03 - Sat, Jan 10
from (US$)
DEAL

Cozumel, Grand Cayman & Bimini

  • Miami, Florida
  • George Town, Grand Cayman
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2026
Sat, Jan 03 - Sat, Jan 10
from (US$)
DEAL

Cayman Isles & Jamaican Miles

  • Miami, Florida
  • George Town, Grand Cayman
  • Ocho Rios, Jamaica
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Cabin
Loading
7 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2026Best Rate
Sat, Jan 10 - Sat, Jan 17
from (US$)
2026
Sat, Mar 07 - Sat, Mar 14
from (US$)
DEAL

Virgin Island Views & Saint Isle Blues

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Bridgetown, Barbados
  • Kingstown, St. Vincent
  • Basseterre, St. Kitts and Nevis
  • St. Croix, U.S. Virgin Islands
  • San Juan, Puerto Rico
Insider cabins from
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2026
Sat, Jan 10 - Sat, Jan 17
from (US$)
DEAL

St. Kitts, Barbados, Martinique & More

  • San Juan, Puerto Rico
  • Basseterre, St. Kitts and Nevis
  • Bridgetown, Barbados
  • Fort-de-France, Martinique
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2026
Sat, Jan 17 - Sat, Jan 24
from (US$)
DEAL

Antigua & the St. Isles

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • 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
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2026
Sat, Jan 31 - Sat, Feb 07
from (US$)
DEAL

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
Loading
7 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2026Best Rate
Sat, Jan 31 - Sat, Feb 07
from (US$)
2026
Sat, Feb 28 - Sat, Mar 07
from (US$)
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
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2026
Sat, Feb 07 - Sat, Feb 14
from (US$)
DEAL

St. Lucia, Barbados & More

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts and Nevis
  • Castries, St. Lucia
  • Bridgetown, Barbados
  • Charlotte Amalie, St. Thomas
  • San Juan, Puerto Rico
Sea View cabins from
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
2026
Sat, Feb 07 - Sat, Feb 14
from (US$)
DEAL

Aruba, Curaçao and the St. Isles

  • San Juan, Puerto Rico
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • St. Croix, U.S. Virgin Islands
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2026
Sat, Feb 14 - Sat, Feb 21
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
Insider cabins from
per Cabin
Loading
7 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2026
Sat, Feb 28 - Sat, Mar 07
from (US$)
DEAL

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
Loading
8 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
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
Loading
9 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2026
Sat, Mar 28 - Mon, Apr 06
from (US$)
DEAL

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
Loading
7 nights
Scarlet Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
2026
Sun, Apr 19 - Sun, Apr 26
from (US$)
Average starting price per cabin (incl. taxes & fees)