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Virgin Islands Cruises Starting In October 2026 and 2027

If you're looking at joining a cruise to Virgin Islands in October 2026 or 2027, we have 20 unique cruise itineraries and 396 departures available, operated by five of the world's leading cruise lines departing in October.
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20 Cruises (396 Cruise Departures)
8 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Harmony of the Seas
Departures: Aug 2026 to Nov 2026
Visit: USA, Virgin Islands, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$811
Oceanview
$1,081
Balcony
$1,064
Suite
$2,430
From
US$811
Save 485
Per Person
View Trip
8 Day Eastern Caribbean From Miami To Miami with Norwegian Cruise Line
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Norwegian Cruise Line
Ships: Norwegian Aqua, Norwegian Aura, Norwegian Luna
Departures: Feb 2026 to Mar 2028
Visit: USA, Dominican Republic, Virgin Islands, Bahamas
Exclusive Savings
Inside
$929
Oceanview
$1,039
Balcony
$1,299
Suite
$1,799
From
US$929
Save 60
Per Person
View Trip
8 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Star Of The Seas
Departures: May 2026 to Oct 2026
Visit: USA, Bahamas, Virgin Islands, Saint Kitts and Nevis
Exclusive Savings
Inside
$1,347
Oceanview
$1,487
Balcony
$1,699
Suite
$3,330
From
US$1,347
Save 935
Per Person
View Trip
8 Day Perfect Day Cococay & East Carib with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Icon Of The Seas
Departures: Feb 2026 to Jul 2027
Visit: USA, Saint Martin, Virgin Islands, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$1,394
Oceanview
$1,438
Balcony
$1,666
Suite
$2,852
From
US$1,394
Save 1,136
Per Person
View Trip
8 Day Tortola, St. Kitts & Puerto Plata with Celebrity Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departures: Jul 2026 to Oct 2026
Visit: USA, Dominican Republic, Virgin Islands, Saint Kitts and Nevis
Exclusive Savings
Inside
$935
Oceanview
$1,049
Balcony
$1,201
Suite
$3,421
From
US$1,103
Save 479
Per Person
View Trip
8 Day Tortola, St. Maarten & Puerto Plata with Celebrity Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Celebrity Cruises
Ship: Celebrity Beyond
Departures: May 2026 to Oct 2026
Visit: USA, Dominican Republic, Virgin Islands, Saint Martin
Exclusive Savings
Inside
$838
Oceanview
$1,013
Balcony
$1,169
Suite
$2,983
From
US$984
Save 437
Per Person
View Trip
8 Day Great Stirrup Cay & Dominican Republic with Norwegian Cruise Line
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Norwegian Cruise Line
Ships: Norwegian Aqua, Norwegian Epic (+4 more), Norwegian Escape, Norwegian Getaway, Norwegian Joy, Norwegian Prima
Departures: Feb 2026 to Mar 2028
Visit: USA, Dominican Republic, Virgin Islands, Bahamas
Inside
$699
Oceanview
$869
Balcony
$979
Suite
$1,059
From
US$699
Per Person
View Trip
8 Day St. Thomas & St. Maarten Cruise with Celebrity Cruises
Cruise
 (1)

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Celebrity Cruises
Ship: Celebrity Apex
Departures: Oct 2027 to Apr 2028
Visit: USA, Dominican Republic, Virgin Islands, Saint Martin
Exclusive Savings
Inside
$911
Oceanview
$1,011
Balcony
$1,136
Suite
$2,661
From
US$1,073
Save 482
Per Person
View Trip
8 Day Perfect Day Cococay & East Carib with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ships: Harmony of the Seas, Star Of The Seas, Utopia of the Seas
Departures: Feb 2026 to Apr 2028
Visit: USA, Bahamas, Virgin Islands, Saint Martin
Bonus Onboard Credit
Exclusive Savings
Inside
$916
Oceanview
$1,067
Balcony
$1,096
Suite
$2,125
From
US$916
Save 1,585
Per Person
View Trip
8 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Icon Of The Seas
Departures: Jun 2026 to Oct 2026
Visit: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,492
Oceanview
$1,615
Balcony
$1,685
Suite
$2,910
From
US$1,492
Save 888
Per Person
View Trip
9 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Adventure of the Seas
Departures: Sep 2026 to Oct 2026
Visit: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$777
Oceanview
$1,087
Balcony
$1,380
Suite
$2,185
From
US$777
Save 481
Per Person
View Trip
8 Day Perfect Day Cococay & East Carib with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Harmony of the Seas
Departures: Aug 2027 to Oct 2027
Visit: USA, Saint Martin, Virgin Islands, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$997
Oceanview
$1,157
Balcony
$1,187
Suite
$2,297
From
US$997
Save 677
Per Person
View Trip
8 Day Perfect Day Cococay & East Carib with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Star Of The Seas
Departures: May 2027 to Oct 2027
Visit: USA, Bahamas, Dominican Republic, Virgin Islands
Bonus Onboard Credit
Exclusive Savings
Inside
$1,440
Oceanview
$1,560
Balcony
$1,680
Suite
$3,243
From
US$1,440
Save 1,028
Per Person
View Trip
8 Day South Caribbean with MSC Cruises
Cruise

8 Days (7 Nights) La Romana to La Romana
Cruise Line: MSC Cruises
Ship: MSC Opera
Departures: Nov 2026 to Nov 2027
Visit: Dominican Republic, Barbados, Martinique, Guadeloupe, Virgin Islands
Bonus Onboard Credit
Inside
$619
Oceanview
$789
Balcony
$1,229
Suite
$1,848
From
US$619
Per Person
View Trip
8 Day South Caribbean with MSC Cruises
Cruise

8 Days (7 Nights) La Romana to La Romana
Cruise Line: MSC Cruises
Ship: MSC Opera
Departures: Apr 2027 to Nov 2027
Visit: Dominican Republic, Virgin Islands, Saint Martin, Martinique, Antigua and Barbuda
Bonus Onboard Credit
Inside
$629
Oceanview
$789
Balcony
$1,229
Suite
$1,869
From
US$629
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ships: Grandeur of the Seas, Rhapsody of the Seas
Departures: May 2027 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Bonus Onboard Credit
Exclusive Savings
Inside
$689
Oceanview
$769
Balcony
$1,248
Suite
$1,423
From
US$689
Save 568
Per Person
View Trip
8 Day South Caribbean with MSC Cruises
Cruise

8 Days (7 Nights) Fort-de-France to Fort-de-France
Cruise Line: MSC Cruises
Ship: MSC Opera
Departures: Apr 2027 to Oct 2027
Visit: Martinique, Guadeloupe, Virgin Islands, Dominican Republic, Saint Martin
Bonus Onboard Credit
Inside
$629
Oceanview
$789
Balcony
$1,229
Suite
$1,839
From
US$629
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departures: Sep 2026 to Oct 2026
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
$530
Oceanview
$570
Balcony
$1,293
Suite
$1,367
From
US$530
Save 340
Per Person
View Trip
10 Day Bermuda & Caribbean Cruise: New York, Bermuda & St. Marteen with Azamara Cruises
Cruise
 (3)

10 Days (9 Nights) New York to San Juan
Cruise Line: Azamara Cruises
Ships: Azamara Journey, Azamara Quest
Departures: Oct 2026 to Oct 2027
Visit: USA, Bermuda, Saint Martin, Virgin Islands, Puerto Rico
Azamara Always Included
Inside
$1,789
Oceanview
$2,059
Balcony
$2,499
Suite
$4,342
From
US$1,789
Per Person
View Trip
10 Day Boston To San Juan Cruise with Celebrity Cruises
Cruise

10 Days (9 Nights) Boston to San Juan
Cruise Line: Celebrity Cruises
Ship: Celebrity Summit
Departure: 20 October 2027
Visit: USA, Dominican Republic, Virgin Islands, Antigua and Barbuda, Puerto Rico
Exclusive Savings
Inside
$1,004
Oceanview
$1,054
Balcony
$1,229
Suite
$3,591
From
US$1,163
Save 367
Per Person
View Trip
Results: 20 results

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