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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 387 departures available, operated by five of the world's leading cruise lines departing in October.
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20 Cruises (387 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
Exclusive Savings
Inside
$832
Oceanview
$1,022
Balcony
$1,004
Suite
$3,436
From
US$1,238
Save 50
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
$1,294
Oceanview
$1,376
Balcony
$1,662
Suite
$3,379
From
US$1,294
Save 955
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: Mar 2026 to Mar 2028
Visit: USA, Dominican Republic, Virgin Islands, Bahamas
Inside
$729
Oceanview
$929
Balcony
$1,029
Suite
$1,249
From
US$729
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
$1,582
Oceanview
$1,725
Balcony
$1,804
Suite
$2,770
From
US$1,582
Save 927
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: Mar 2026 to Mar 2028
Visit: USA, Dominican Republic, Virgin Islands, Bahamas
Exclusive Savings
Inside
$889
Oceanview
$989
Balcony
$1,359
Suite
$1,749
From
US$889
Save 63
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 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
$733
Oceanview
$955
Balcony
$1,135
Suite
$3,007
From
US$868
Save 526
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
$3,130
From
US$1,440
Save 1,028
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
$2,550
From
US$997
Save 683
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: Mar 2026 to Jul 2027
Visit: USA, Saint Martin, Virgin Islands, Bahamas
Bonus Onboard Credit
Exclusive Savings
Inside
$1,433
Oceanview
$1,484
Balcony
$1,664
Suite
$2,750
From
US$1,433
Save 1,111
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
$909
Oceanview
$1,017
Balcony
$1,104
Suite
$3,171
From
US$1,081
Save 527
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
$791
Oceanview
$949
Balcony
$1,306
Suite
$2,485
From
US$791
Save 551
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: Mar 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
$2,175
From
US$916
Save 1,666
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
$766
Balcony
$1,248
Suite
$1,473
From
US$689
Save 568
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
$3,590
From
US$1,163
Save 367
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
$507
Oceanview
$516
Balcony
$1,124
Suite
$1,265
From
US$507
Save 393
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
$1,549
Oceanview
$2,079
Balcony
$2,606
Suite
$4,514
From
US$1,549
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
Exclusive Savings
Inside
$629
Oceanview
$789
Balcony
$1,229
Suite
$1,869
From
US$629
Save 59
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
Inside
$629
Oceanview
$789
Balcony
$1,229
Suite
$1,869
From
US$629
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
Inside
$559
Oceanview
$789
Balcony
$1,229
Suite
$1,869
From
US$559
Per Person
View Trip
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