Tailored Travel Club
✆: 916-532-4113
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US Virgin Islands

(20 offers included)
Departing on Nov 20, 2026 on the Valiant Lady
Nights: 8
Dates: Nov 20, 2026 through Nov 28, 2026
Ship: Valiant Lady
Itinerary:
San Juan, St. Thomas, Sailing, Willemstad, Oranjestad, Sailing, Basseterre, Philipsburg, St. Maarten, San Juan
This 8-night Thanksgiving sailing departs from San Juan, first docking at the stunning St. Thomas, U.S. Virgin Islands. After a day at sea, arrive in Willemstad, Curaçao's capital that combines European influences with Caribbean cultures (and vibrant architecture). Next, wake up in Aruba, followed by sailing to St. Kitts and Nevis, then on to St. Maarten, before returning to San Juan.
from
$1,112.00
(USD)
Per Person
Inside
$1,112.00
Cat: IZ
$139.00/Night
Outside
$1,352.00
Cat: VZ
$169.00/Night
Balcony
$1,592.00
Cat: TZ
$199.00/Night
Suite
$4,720.00
Cat: RZ
$590.00/Night
Eastern Caribbean, 12 Nights (Q533) Roundtrip from Miami, FL, USA
Departing on Jan 08, 2026 on the Queen Elizabeth
Nights: 12
Dates: Jan 08, 2026 through Jan 20, 2026
Itinerary:
Miami, FL, USA, St. Thomas, Virgin Islands, U.S.A., Antigua, St Lucia, Saint Lucia, Barbados, Barbados, St. Maarten, Netherlands Antilles, Tortola, B.V.I., Miami, FL, USA
Discover the many treasures of the Eastern Caribbean on this 12-night voyage. On sea days, enjoy time to relax and unwind, perhaps while soaking up the sunshine on Queen Elizabeth’s decks.
from
$1,199.00
(USD)
Per Person
Inside
$1,199.00
Cat: IE
$99.92/Night
Outside
$1,199.00
Cat: FC
$99.92/Night
Suite
$5,499.00
Cat: P2
$458.25/Night
Departing on Feb 27, 2026 on the Norwegian Joy
Nights: 7
Dates: Feb 27, 2026 through Mar 06, 2026
Itinerary:
Orlando-Beaches-Port Canaveral, Fl, PUERTO PLATA, DOMINICAN REPUBLIC, ST THOMAS, VI, San Juan, Pr, Great Stirrup Cay, Bahamas, Orlando-Beaches-Port Canaveral, Fl
Come aboard one of our most awarded ships, Norwegian Joy, and enjoy sunny days and relaxation in the tropics. In Puerto Plata, uncover the local history at the 16th century Fortaleza San Felipe or snorkel among colorful coral reefs off of Dorado Beach. Recline on a catamaran in St. Thomas while sailing to Turtle Cove to snorkel with green sea turtles.
from
$909.00
(USD)
Per Person
Inside
$909.00
Cat: IF
$129.86/Night
Outside
$1,079.00
Cat: OB
$154.14/Night
Balcony
$1,179.00
Cat: BF
$168.43/Night
Suite
$1,429.00
Cat: MC
$204.14/Night
Departing on Dec 20, 2026 on the Norwegian Prima
Nights: 7
Dates: Dec 20, 2026 through Dec 27, 2026
Itinerary:
San Juan, Pr, Oranjestad, Aruba, Willemstad, Netherland Antilles, ST THOMAS, VI, Tortola, British Virgin Islands, San Juan, Pr
Leave the Big Easy behind for this weeklong cruise in the Caribbean. Your first stop is Cozumel on the coast of Mexico’s beautiful Yucatán Peninsula. The day is yours to snorkel, dive fabulous reefs, explore the jungle in an ATV, relax poolside at a beach club, or visit an ancient Mayan temple. Experience sun, fun and sand in Harvest Caye, the premier resort-style destination in Belize - cool off with a drink at the swim-up bar.
from
$1,709.00
(USD)
Per Person
Inside
$1,709.00
Cat: IF
$244.14/Night
Outside
$1,959.00
Cat: OB
$279.86/Night
Balcony
$2,029.00
Cat: BF
$289.86/Night
Suite
$3,139.00
Cat: MB
$448.43/Night
Departing on Dec 23, 2026 on the Norwegian Jewel
Nights: 12
Dates: Dec 23, 2026 through Jan 04, 2027
Itinerary:
Miami, Fl, Great Stirrup Cay, Bahamas, CABO ROJO, DOMINICAN REPUBLIC, Oranjestad, Aruba, Willemstad, Netherland Antilles, PHILIPSBURG ST MAARTEN, NETHERLAND ANTILLES, ST THOMAS, VI, Tortola, British Virgin Islands, PUERTO PLATA, DOMINICAN REPUBLIC, Miami, Fl
Unveil the vibrant beauty of the Caribbean on a sun-soaked 12-day vacation. Grab a frozen drink and lounge in your private beachfront cabana on Great Stirrup Cay, our tropical paradise that’s just for you. In Oranjestad, Aruba, embrace European-Caribbean charm along vibrant avenues or seek out the calm of secluded coves. Stroll the colorful streets of Willemstad, Curacao, admiring Dutch-inspired architecture and lively markets brimming with local treasures.
from
$1,729.00
(USD)
Per Person
Inside
$1,729.00
Cat: IF
$144.08/Night
Outside
$1,919.00
Cat: OK
$159.92/Night
Balcony
$2,949.00
Cat: BF
$245.75/Night
Suite
$3,209.00
Cat: MA
$267.42/Night
Departing on Dec 28, 2026 on the Azamara Journey
Nights: 17
Dates: Dec 28, 2026 through Jan 14, 2027
Itinerary:
Bridgetown, Oranjestad, Willemstad, Castries, Charlestown, Nevis, Frederiksted, Saint Croix, San Juan, Virgin Gorda, Gustavia, Philipsburg, St. John's, Antigua, Basseterre, St.Kitts, Road Town, Tortola, Miami, Florida
from
$4,689.00
(USD)
Per Person
Inside
$4,689.00
Cat: 09
$275.82/Night
Outside
$4,829.00
Cat: 08
$284.06/Night
Balcony
$6,759.00
Cat: V3
$397.59/Night
Suite
$9,419.00
Cat: N2
$554.06/Night
Departing on Jan 05, 2026 on the Norwegian Getaway
Nights: 10
Dates: Jan 05, 2026 through Jan 15, 2026
Itinerary:
Miami, Fl, PUERTO PLATA, DOMINICAN REPUBLIC, ST THOMAS, VI, ST JOHNS ANTIGUA, PHILIPSBURG ST MAARTEN, NETHERLAND ANTILLES, Basseterre, Saint Kitts - Nevis, San Juan, Pr, Great Stirrup Cay, Bahamas, Miami, Fl
Turn up the chill this winter island-hopping the best of The Caribbean. In Puerto Plata, uncover the local history at the 16th century Fortaleza San Felipe or embark on an off-roading adventure through lush jungle to swim in cascading mountain pools. Then snorkel among colorful tropical fish and green sea turtles in St. Thomas at Turtle Cove. Shake things up in San Juan on a guided tour that includes custom cocktails, culinary treats and historic sites.
from
$719.00
(USD)
Per Person
Inside
$719.00
Cat: IF
$71.90/Night
Balcony
$1,029.00
Cat: BA
$102.90/Night
Departing on Mar 29, 2026 on the Caribbean Princess
Nights: 20
Dates: Mar 29, 2026 through Apr 18, 2026
Itinerary:
Fort Lauderdale, Princess Cays, San Juan, St Kitts, St Lucia, Martinique, Antigua, Fort Lauderdale, Princess Cays, St Thomas, St Maarten, Antigua, St Kitts, Tortola, Fort Lauderdale
from
$1,785.00
(USD)
Per Person
Inside
$1,785.00
Cat: IF
$89.25/Night
Outside
$2,265.00
Cat: OZ
$113.25/Night
Balcony
$3,805.00
Cat: BF
$190.25/Night
Suite
$4,955.00
Cat: ME
$247.75/Night
Caribbean Yachting Hideaways San Juan to St John's
Departing on Jan 31, 2026 on the Emerald Azzurra
Nights: 7
Dates: Jan 31, 2026 through Feb 07, 2026
Itinerary:
San Juan, Puerto Rico, Culebra 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, Antigua and Barbuda
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
$5,945.00
(USD)
Per Person
Balcony
$5,945.00
Cat: A
$849.29/Night
14-Day Eastern/Western Caribbean Adventurer Roundtrip from Fort Lauderdale
Departing on Mar 08, 2026 on the Majestic Princess
Nights: 14
Dates: Mar 08, 2026 through Mar 22, 2026
Itinerary:
Fort Lauderdale, Princess Cays, San Juan, St Thomas, Fort Lauderdale, Cozumel, Roatan (Mahognay Bay), Belize City, Costa Maya (Mahahual), Fort Lauderdale
from
$1,698.00
(USD)
Per Person
Inside
$1,698.00
Cat: IF
$121.29/Night
Balcony
$2,319.00
Cat: BW
$165.64/Night
Suite
$2,868.00
Cat: MF
$204.86/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
$1,804.00
(USD)
Per Person
+ $245.00 taxes/fees
Inside
$1,804.00
Cat: N
$128.86/Night
Outside
$2,704.00
Cat: HH
$193.14/Night
Balcony
$2,704.00
Cat: VH
$193.14/Night
Suite
$4,704.00
Cat: SZ
$336.00/Night
Category N - Flash Special: Book by Sunday 12/28/2025
14-Day Eastern Caribbean: Bahamas & San Juan Roundtrip from Fort Lauderdale
Departing on Feb 07, 2027 on the Nieuw Statendam
Nights: 14
Dates: Feb 07, 2027 through Feb 21, 2027
Itinerary:
Fort Lauderdale, Nassau, Amber Cove, Grand Turk, Relaxaway Half Moon Cay, Fort Lauderdale, Grand Turk, San Juan, St Thomas, Relaxaway Half Moon Cay, Fort Lauderdale
from
$2,684.00
(USD)
Per Person
+ $230.00 taxes/fees
Inside
$2,684.00
Cat: N
$191.71/Night
Outside
$3,394.00
Cat: F
$242.43/Night
Balcony
$3,394.00
Cat: VH
$242.43/Night
Suite
$4,294.00
Cat: BC
$306.71/Night
Category N - Flash Special: Book by Sunday 12/28/2025
Departing on Feb 07, 2027 on the Norwegian Prima
Nights: 7
Dates: Feb 07, 2027 through Feb 14, 2027
Itinerary:
San Juan, Pr, PHILIPSBURG ST MAARTEN, NETHERLAND ANTILLES, Basseterre, Saint Kitts - Nevis, Bridgetown, Barbados, ST LUCIA, SAINT LUCIA, ST THOMAS, VI, Tortola, British Virgin Islands, San Juan, Pr
Leave the Big Easy behind for this weeklong cruise in the Caribbean. Your first stop is Cozumel on the coast of Mexico’s beautiful Yucatán Peninsula. The day is yours to snorkel, dive fabulous reefs, explore the jungle in an ATV, relax poolside at a beach club, or visit an ancient Mayan temple. Experience sun, fun and sand in Harvest Caye, the premier resort-style destination in Belize - cool off with a drink at the swim-up bar.
from
$1,299.00
(USD)
Per Person
Inside
$1,299.00
Cat: IF
$185.57/Night
Outside
$1,449.00
Cat: OB
$207.00/Night
Balcony
$1,819.00
Cat: BF
$259.86/Night
Suite
$2,409.00
Cat: MB
$344.14/Night
Departing on Aug 08, 2026 on the Regal Princess
Nights: 14
Dates: Aug 08, 2026 through Aug 22, 2026
Itinerary:
Fort Lauderdale, Cozumel, Belize City, Roatan (Mahognay Bay), Fort Lauderdale, Princess Cays, San Juan, St Thomas, Fort Lauderdale
from
$1,108.00
(USD)
Per Person
Inside
$1,108.00
Cat: IF
$79.14/Night
Balcony
$1,538.00
Cat: BW
$109.86/Night
Suite
$1,948.00
Cat: MF
$139.14/Night
Departing on Jan 03, 2027 on the Norwegian Prima
Nights: 7
Dates: Jan 03, 2027 through Jan 10, 2027
Itinerary:
San Juan, Pr, ST THOMAS, VI, Tortola, British Virgin Islands, Oranjestad, Aruba, Willemstad, Netherland Antilles, San Juan, Pr
Leave the Big Easy behind for this weeklong cruise in the Caribbean. Your first stop is Cozumel on the coast of Mexico’s beautiful Yucatán Peninsula. The day is yours to snorkel, dive fabulous reefs, explore the jungle in an ATV, relax poolside at a beach club, or visit an ancient Mayan temple. Experience sun, fun and sand in Harvest Caye, the premier resort-style destination in Belize - cool off with a drink at the swim-up bar.
from
$1,609.00
(USD)
Per Person
Inside
$1,609.00
Cat: IF
$229.86/Night
Outside
$1,669.00
Cat: OB
$238.43/Night
Balcony
$1,769.00
Cat: BF
$252.71/Night
Suite
$2,219.00
Cat: MB
$317.00/Night
7-Day Eastern Caribbean with St. Thomas Roundtrip from Fort Lauderdale
Departing on Mar 08, 2026 on the Majestic Princess
Nights: 7
Dates: Mar 08, 2026 through Mar 15, 2026
Itinerary:
Fort Lauderdale, Princess Cays, San Juan, St Thomas, Fort Lauderdale
from
$749.00
(USD)
Per Person
Inside
$749.00
Cat: IF
$107.00/Night
Balcony
$999.00
Cat: BW
$142.71/Night
Suite
$1,219.00
Cat: MF
$174.14/Night
Departing on Jan 03, 2027 on the Nieuw Statendam
Nights: 14
Dates: Jan 03, 2027 through Jan 17, 2027
Itinerary:
Fort Lauderdale, Grand Turk, San Juan, St Thomas, Relaxaway Half Moon Cay, Fort Lauderdale, Relaxaway Half Moon Cay, Ocho Rios, Grand Cayman, Cozumel, Fort Lauderdale
from
$2,299.00
(USD)
Per Person
+ $255.00 taxes/fees
Inside
$2,299.00
Cat: N
$164.21/Night
Outside
$3,109.00
Cat: F
$222.07/Night
Balcony
$3,109.00
Cat: VH
$222.07/Night
Suite
$4,009.00
Cat: BC
$286.36/Night
Category N - Flash Special: Book by Sunday 12/28/2025
14-Day Southern Caribbean Adventurer Roundtrip from San Juan
Departing on Jan 24, 2027 on the Crown Princess
Nights: 14
Dates: Jan 24, 2027 through Feb 07, 2027
Itinerary:
San Juan, St Thomas, St Maarten, Antigua, St Lucia, Barbados, San Juan, St Thomas, St Kitts, Dominica, Grenada, Barbados, San Juan
from
$2,156.00
(USD)
Per Person
Inside
$2,156.00
Cat: IF
$154.00/Night
Outside
$2,375.00
Cat: OZ
$169.64/Night
Balcony
$2,756.00
Cat: BF
$196.86/Night
Suite
$3,566.00
Cat: ME
$254.71/Night
Departing on Oct 19, 2026 on the Valiant Lady
Nights: 12
Dates: Oct 19, 2026 through Oct 31, 2026
Ship: Valiant Lady
Itinerary:
New York City, Bermuda, Bimini Islands, St. Croix, Philipsburg, Tortola Island, San Juan
This 12-night one-way escape departs NYC, sailing to Bermuda for two full days before heading to our exclusive Beach Club at Bimini. Then, explore St. Croix's verdant rainforests, the stunning beaches of St. Maarten, and the wondrous beauty overlooking the peaks of Tortola, before ending your journey in the vibrant streets of San Juan.
from
$1,188.00
(USD)
Per Person
Inside
$1,188.00
Cat: IZ
$99.00/Night
Outside
$1,548.00
Cat: VZ
$129.00/Night
Balcony
$1,908.00
Cat: TZ
$159.00/Night
Suite
$6,300.00
Cat: SS
$525.00/Night
Transatlantic: Bahamas & Spain Barcelona, Spain to Orlando-Beaches-Port Canaveral, Fl
Departing on Nov 01, 2026 on the Norwegian Epic
Nights: 14
Dates: Nov 01, 2026 through Nov 15, 2026
Itinerary:
Barcelona, Spain, CADIZ SEVILLE, SPAIN, Santa Cruz De Tenerife, Spain, ST THOMAS, VI, Great Stirrup Cay, Bahamas, Orlando-Beaches-Port Canaveral, Fl
Explore breathtaking views on your transatlantic cruise aboard the newly refurbished Norwegian Epic. Savor a day touring Cádiz with a visit to the bustling Mercado Central de Abastos – a covered market boasting more than 150 stalls selling fresh seafood and delicious local cuisine – and recline on one of the town’s many beautiful beaches. Visit Casablanca’s central market, a massive kaleidoscope of colors, and see the modernist landmark of the Hassan II Mosque.
from
$1,069.00
(USD)
Per Person
Inside
$1,069.00
Cat: IF
$76.36/Night
Balcony
$1,689.00
Cat: BF
$120.64/Night
Suite
$1,909.00
Cat: MC
$136.36/Night