Callahan's Travel Company
✆: (314) 952-6678 | ✉:

US Virgin Islands

(20 offers included)
Dates: May 03, 2022 through Sep 26, 2027
Location(s):
St. Thomas
Enjoy duty-free shopping, breathtaking sights, and one of the world's best beaches on this combination tour around St. Thomas.
from
$99.00
(USD)
Per Person
Departing on Feb 15, 2026 on the Enchanted Princess
Nights: 20
Dates: Feb 15, 2026 through Mar 07, 2026
Itinerary:
Fort Lauderdale, Princess Cays, St Thomas, St Maarten, Antigua, St Kitts, Tortola, Fort Lauderdale, Princess Cays, St Thomas, Dominica, Barbados, Martinique, Antigua, Fort Lauderdale
from
$3,498.00
(USD)
Per Person
Inside
$3,498.00
Cat: IF
$174.90/Night
Balcony
$4,214.00
Cat: BW
$210.70/Night
Suite
$5,078.00
Cat: MF
$253.90/Night
Departing on Oct 26, 2025 on the Grand Princess
Nights: 14
Dates: Oct 26, 2025 through Nov 09, 2025
Itinerary:
San Juan, Tortola, St Kitts, Dominica, Grenada, Barbados, San Juan, Barbados, Dominica, Antigua, St Maarten, St Thomas, San Juan
from
$1,396.00
(USD)
Per Person
Inside
$1,396.00
Cat: IE
$99.71/Night
10-Day Eastern Caribbean with Tortola Roundtrip from Fort Lauderdale
Departing on Nov 07, 2025 on the Caribbean Princess
Nights: 10
Dates: Nov 07, 2025 through Nov 17, 2025
Itinerary:
Fort Lauderdale, Tortola, St Maarten, Antigua, St Kitts, St Thomas, Grand Turk, Fort Lauderdale
from
$1,059.00
(USD)
Per Person
Inside
$1,059.00
Cat: IF
$105.90/Night
Outside
$1,265.00
Cat: OZ
$126.50/Night
Balcony
$1,409.00
Cat: BF
$140.90/Night
Suite
$2,409.00
Cat: S7
$240.90/Night
Caribbean: Curacao & Aruba Roundtrip from San Juan, Pr
Departing on Jan 17, 2027 on the Norwegian Breakaway
Nights: 7
Dates: Jan 17, 2027 through Jan 24, 2027
Itinerary:
San Juan, Pr, PUNTA CANA (LA ROMANA), DOMINICAN REPUBLIC, Oranjestad, Aruba, Willemstad, Netherland Antilles, ST THOMAS, VI, Tortola, British Virgin Islands, San Juan, Pr
Depart from San Juan, a city alive with vibrant hues and island rhythms, on a 7-day journey through the Caribbean. In La Romana, Dominican Republic, exotic landscapes and hidden caverns await -walk the mesmerizing Cueva de las Maravillas or savor authentic Dominican flavors as music fills the air. Sail onward to Oranjestad, Aruba, where pastel facades meet crystal-blue waters. Stroll lively streets or explore rugged coastlines dotted with wind-swept cacti under sunlit skies.
from
$960.00
(USD)
Per Person
Inside
$960.00
Cat: IF
$137.14/Night
Outside
$1,160.00
Cat: OB
$165.71/Night
Balcony
$1,360.00
Cat: BF
$194.29/Night
Suite
$1,510.00
Cat: MB
$215.71/Night
12-Day Circle Caribbean Roundtrip from Fort Lauderdale
Departing on Dec 11, 2025 on the Caribbean Princess
Nights: 12
Dates: Dec 11, 2025 through Dec 23, 2025
Itinerary:
Fort Lauderdale, Aruba, Bonaire, Dominica, St Maarten, St Thomas, Antigua, Fort Lauderdale
from
$749.00
(USD)
Per Person
Inside
$749.00
Cat: IF
$62.42/Night
Outside
$779.00
Cat: OZ
$64.92/Night
Balcony
$1,089.00
Cat: BF
$90.75/Night
Suite
$1,299.00
Cat: ME
$108.25/Night
8-Day Eastern Caribbean with St. Thomas Roundtrip from Fort Lauderdale
Departing on Jan 03, 2026 on the Majestic Princess
Nights: 8
Dates: Jan 03, 2026 through Jan 11, 2026
Itinerary:
Fort Lauderdale, Amber Cove, San Juan, St Maarten, St Thomas, Fort Lauderdale
from
$866.00
(USD)
Per Person
Inside
$866.00
Cat: IF
$108.25/Night
Balcony
$1,378.00
Cat: BE
$172.25/Night
Suite
$1,416.00
Cat: MF
$177.00/Night
No Image Available
Nights: 11
Dates: Jan 12, 2027 through Jan 23, 2027
Itinerary:
Fort Lauderdale, St Maarten, Antigua, Roseau, Martinique, St Kitts, St Thomas, Relaxaway Half Moon Cay, Fort Lauderdale
from
$2,354.00
(USD)
Per Person
+ $150.00 taxes/fees
Inside
$2,354.00
Cat: N
$214.00/Night
Outside
$3,004.00
Cat: F
$273.09/Night
Balcony
$3,204.00
Cat: VH
$291.27/Night
Suite
$4,304.00
Cat: BC
$391.27/Night
Category N - Flash Special: Book by Sunday 09/28/2025
Departing on Feb 12, 2026 on the Brilliant Lady
Nights: 8
Dates: Feb 12, 2026 through Feb 20, 2026
Itinerary:
Miami, Puerto Plata, San Juan, St. Maarten, St. Croix, Miami
This 8-night voyage sails from Miami to the Dominican Republic, Puerto Rico, St. Maarten, and St. Croix, before returning to Miami.
from
$1,272.00
(USD)
Per Person
Inside
$1,272.00
Cat: IZ
$159.00/Night
Outside
$1,593.00
Cat: VZ
$199.13/Night
Balcony
$2,081.00
Cat: TR
$260.13/Night
Suite
$4,200.00
Cat: SS
$525.00/Night
West Indies Explorer Roundtrip from San Juan
Departing on Jan 27, 2028 on the Viking Sea
Nights: 10
Dates: Jan 27, 2028 through Feb 06, 2028
Ship: Viking Sea
Itinerary:
San Juan, Tortola (Road Town), St. Kitts (Basseterre), Castries, Bridgetown, Roseau, Antigua (St. John’s), Philipsburg, St. Thomas (Charlotte Amalie), San Juan
Set sail on a roundtrip voyage from San Juan to explore the colorful Caribbean. Start deep in the heart of this tropical paradise and avoid the long sea days associated with most Caribbean cruises-allowing you to visit more ports and spend more time discovering rich island cultures. Immerse yourself in the British, French and Dutch cultures of the Lesser Antilles as you cruise azure waters from Tortola and St. Lucia to Dominica, St. Martin and St. Thomas.
from
$4,299.00
(USD)
Per Person
Balcony
$4,299.00
Cat: V2
$429.90/Night
Suite
$6,999.00
Cat: PS3
$699.90/Night
Departing on Jan 03, 2026 on the Emerald Azzurra
Nights: 14
Dates: Jan 03, 2026 through Jan 17, 2026
Itinerary:
San Juan, Puerto Rico, Culebra Island & Vieques Island, Puerto Rico, St. John, U.S. Virgin Islands, Jost Van Dyke, British Virgin Islands, Philipsburg, Sint Maarten, Gustavia, Saint Barthélemy, Little Bay, Montserrat, St John's, Antigua, Barbuda, Antigua and Barbuda, Îles des Saintes, Guadeloupe, Deshaies, Guadeloupe, Gustavia, Saint Barthélemy, Virgin Gorda, British Virgin Islands, Norman Island, British Virgin Islands, San Juan, Puerto Rico
Embark on an unforgettable Caribbean voyage exploring pristine beaches and coral reefs, island-hopping through diverse cultures, where the warmth of the locals will enhance your luxury yacht adventure.
from
$15,360.00
(USD)
Per Person
Balcony
$15,360.00
Cat: A
$1,097.14/Night
Departing on Nov 09, 2025 on the Grand Princess
Nights: 14
Dates: Nov 09, 2025 through Nov 23, 2025
Itinerary:
San Juan, St Maarten, Dominica, Barbados, Grenada, St Kitts, San Juan, St Maarten, Dominica, Barbados, Antigua, St Thomas, San Juan
from
$1,355.00
(USD)
Per Person
Inside
$1,355.00
Cat: IC
$96.79/Night
Outside
$1,222.00
Cat: OZ
$87.29/Night
Departing on Dec 28, 2025 on the Grand Princess
Nights: 14
Dates: Dec 28, 2025 through Jan 11, 2026
Itinerary:
San Juan, St Thomas, St Maarten, Antigua, St Vincent, Barbados, San Juan, St Thomas, St Kitts, St Lucia, Grenada, Barbados, San Juan
from
$2,214.00
(USD)
Per Person
Inside
$2,214.00
Cat: IE
$158.14/Night
Outside
$2,174.00
Cat: OZ
$155.29/Night
Balcony
$3,809.00
Cat: B2
$272.07/Night
Departing on Dec 28, 2026 on the Azamara Journey
Nights: 8
Dates: Dec 28, 2026 through Jan 05, 2027
Itinerary:
Bridgetown, Oranjestad, Willemstad, Castries, Charlestown, Nevis, Frederiksted, Saint Croix, San Juan
from
$2,109.00
(USD)
Per Person
Inside
$2,109.00
Cat: Z
$263.63/Night
Outside
$2,669.00
Cat: Y
$333.63/Night
Balcony
$3,579.00
Cat: X
$447.38/Night
Suite
$5,489.00
Cat: W
$686.13/Night
West Indies Island Hopping San Juan to San Juan
Departing on Dec 27, 2027 on the Emerald Kaia
Nights: 7
Dates: Dec 27, 2027 through Jan 03, 2028
Ship: Emerald Kaia
Itinerary:
San Juan, Puerto Rico, St. John, U.S. Virgin Islands, Philipsburg, Sint Maarten, St. John’s, Antigua, Antigua and Barbuda, South Friars Bay, St. Kitts, Norman Island, British Virgin Islands, Virgin Gorda, British Virgin Islands, San Juan, Puerto Rico
Uncover remote beaches, vibrant towns, and crystal-clear waters from San Juan to Saint Barthélemy and explore the diverse cultures and natural wonders of Puerto Rico, the U.S. and British Virgin Islands.
from
$6,495.00
(USD)
Per Person
Outside
$6,495.00
Cat: D
$927.86/Night
Suite
$8,320.00
Cat: B
$1,188.57/Night
Departing on Mar 07, 2026 on the Enchanted Princess
Nights: 20
Dates: Mar 07, 2026 through Mar 27, 2026
Itinerary:
Fort Lauderdale, Princess Cays, St Thomas, Antigua, St Maarten, St Kitts, Tortola, Fort Lauderdale, Princess Cays, St Thomas, Dominica, Barbados, Martinique, Antigua, Fort Lauderdale
from
$3,198.00
(USD)
Per Person
Inside
$3,198.00
Cat: IF
$159.90/Night
Balcony
$3,782.00
Cat: BW
$189.10/Night
Suite
$4,338.00
Cat: MF
$216.90/Night
14-Day Southern Caribbean Adventurer Roundtrip from San Juan
Departing on Feb 28, 2027 on the Crown Princess
Nights: 14
Dates: Feb 28, 2027 through Mar 14, 2027
Itinerary:
San Juan, St Thomas, St Kitts, Dominica, Grenada, Barbados, San Juan, St Thomas, St Maarten, Antigua, St Lucia, Barbados, San Juan
from
$1,954.00
(USD)
Per Person
Inside
$1,954.00
Cat: IF
$139.57/Night
Outside
$2,246.00
Cat: OZ
$160.43/Night
Balcony
$2,879.00
Cat: BF
$205.64/Night
Suite
$3,554.00
Cat: ME
$253.86/Night
9-Day Eastern Caribbean with St. Thomas Roundtrip from Port Canaveral (Orlando)
Departing on Nov 20, 2026 on the Sky Princess
Nights: 9
Dates: Nov 20, 2026 through Nov 29, 2026
Ship: Sky Princess
Itinerary:
Port Canaveral (Orlando), Grand Turk, Amber Cove, San Juan, St Thomas, Princess Cays, Port Canaveral (Orlando)
from
$903.00
(USD)
Per Person
Inside
$903.00
Cat: IF
$100.33/Night
Balcony
$1,291.00
Cat: BW
$143.44/Night
Suite
$1,663.00
Cat: MF
$184.78/Night
West Indies Explorer Roundtrip from San Juan
Departing on Nov 25, 2026 on the Viking Sea
Nights: 10
Dates: Nov 25, 2026 through Dec 05, 2026
Ship: Viking Sea
Itinerary:
San Juan, Tortola (Road Town), St. Kitts (Basseterre), Castries, Bridgetown, Roseau, Antigua (St. John’s), Philipsburg, St. Thomas (Charlotte Amalie), San Juan
Set sail on a roundtrip voyage from San Juan to explore the colorful Caribbean. Start deep in the heart of this tropical paradise and avoid the long sea days associated with most Caribbean cruises-allowing you to visit more ports and spend more time discovering rich island cultures. Immerse yourself in the British, French and Dutch cultures of the Lesser Antilles as you cruise azure waters from Tortola and St. Lucia to Dominica, St. Martin and St. Thomas.
from
$3,599.00
(USD)
Per Person
Balcony
$3,599.00
Cat: V1
$359.90/Night
Suite
$5,999.00
Cat: PS3
$599.90/Night
Departing on Dec 05, 2026 on the Zuiderdam
Nights: 14
Dates: Dec 05, 2026 through Dec 19, 2026
Ship: Zuiderdam
Itinerary:
Miami, Grand Turk, San Juan, St Thomas, Relaxaway Half Moon Cay, Miami, Relaxaway Half Moon Cay, Ocho Rios, Grand Cayman, Cozumel, Miami
from
$2,454.00
(USD)
Per Person
+ $245.00 taxes/fees
Inside
$2,454.00
Cat: N
$175.29/Night
Outside
$2,854.00
Cat: HH
$203.86/Night
Balcony
$3,204.00
Cat: VH
$228.86/Night
Suite
$5,104.00
Cat: SZ
$364.57/Night
Category N - Flash Special: Book by Sunday 09/28/2025