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Pleasant Holidays Logo
Sandals Halcyon Beach Resort & Spa Hotel Rating: No Rating
Nights: 3
Dates: Oct 05, 2025 through Oct 08, 2025
This intimate 169-room beachfront resort is an island paradise for two. Overlooking a serene bay with pristine white-sand beach and emerald waters, and nestled amongst stunning tropical gardens, this resort showcases such exquisite natural beauty and warm laid-back energy that you'll have no choice but to have the time of your life.
from
$765.00
(USD)
Per Person
More Details Contact Us
Virgin Voyages Comedy Fest from Miami
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Virgin Voyages Comedy Fest from the UK
Departing on Aug 30, 2025 on the Scarlet Lady
Nights: 6
Dates: Aug 30, 2025 through Sep 05, 2025
Ship: Scarlet Lady
Get ready to laugh your aft off. There's nothing quite like a sunny European jaunt from the UK, and on this six-night voyage from Portsmouth to La Coruña, Bilbao, and Bordeaux, you'll be smiling at more than just the sunset.
from
$1,092.00
(USD)
Per Person
More Details Contact Us
Inside
$1,092.00
Cat: IZ
$182.00/Night
Outside
$1,194.00
Cat: VZ
$199.00/Night
Balcony
$1,434.00
Cat: TZ
$239.00/Night
Suite
$3,270.00
Cat: SS
$545.00/Night
San Juan Sunrises Dominican Dreams
Virgin Voyages Logo
Antiguan Elegance & Sunny St. Isles
Departing on Nov 28, 2026 on the Valiant Lady
Nights: 7
Dates: Nov 28, 2026 through Dec 05, 2026
Ship: Valiant Lady
This 7-night pre-holiday sailing departs San Juan, docking the next day on the colorful shores with picturesque waters of St. Thomas, US Virgin Islands. Next sail over to Tortola, followed by the bustling beach town of Basseterre, St. Kitts and Nevis. Next arrive in the epicenter of paradise, St. John's, Antigua, then over to St. Maarten, before returning to San Juan.
from
$1,253.00
(USD)
Per Person
More Details Contact Us
Inside
$1,253.00
Cat: IZ
$179.00/Night
Outside
$1,462.00
Cat: VZ
$208.86/Night
Balcony
$1,672.00
Cat: TZ
$238.86/Night
Suite
$4,304.00
Cat: SS
$614.86/Night
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Riu Palace Pacifico Hotel Rating: 4 stars
Nights: 3
Dates: Oct 05, 2025 through Oct 08, 2025
This exclusive beachfront hotel has over 400 rooms equipped with a host of amenities to ensure you have a comfortable and relaxing stay.
from
$310.00
(USD)
Per Person
More Details Contact Us
French Daze Ibiza Nights
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Italian Vistas to Spanish Sunsets
Departing on Jun 21, 2026 on the Valiant Lady
Nights: 7
Dates: Jun 21, 2026 through Jun 28, 2026
Ship: Valiant Lady
This 7-night odyssey departs from Barcelona and spends a day sailing to Civitavecchia - the gateway to Rome. Next, you'll sail to La Spezia, a picturesque port city conveniently located near Italy's most beloved destinations: Pisa, Positano and Florence.
from
$1,393.00
(USD)
Per Person
More Details Contact Us
Inside
$1,393.00
Cat: IZ
$199.00/Night
Outside
$1,603.00
Cat: VZ
$229.00/Night
Balcony
$1,891.00
Cat: TL
$270.14/Night
Suite
$4,340.00
Cat: SS
$620.00/Night
Adriatic Sea and Greek Gems
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Corfu, Dubrovnik & More
Departing on May 24, 2026 on the Scarlet Lady
Nights: 7
Dates: May 24, 2026 through May 31, 2026
Ship: Scarlet Lady
This 7-night Greek and Croatian adventure starts in Athens before spending a day of at-sea luxury on the way to Kotor.
from
$1,345.00
(USD)
Per Person
More Details Contact Us
Inside
$1,345.00
Cat: IZ
$192.14/Night
Outside
$1,533.00
Cat: VZ
$219.00/Night
Balcony
$1,743.00
Cat: TZ
$249.00/Night
Suite
$3,940.00
Cat: RZ
$562.86/Night
St. Lucia
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St. Lucia, Barbados & More
Departing on Feb 07, 2026 on the Valiant Lady
Nights: 7
Dates: Feb 07, 2026 through Feb 14, 2026
Ship: Valiant Lady
This 7-night winter escape departs from San Juan and docks the next day at the glowing lagoons and sprawling beaches of St. Maarten, followed by the bright green rainforests and unique shops of St. Kitts. Next, wake up to the breathtaking waterfalls and intricate coral reefs of St. Lucia, followed by Barbados. Finally, spend a day on board sailing to St. Thomas before returning to San Juan.
from
$1,183.00
(USD)
Per Person
More Details Contact Us
Outside
$1,183.00
Cat: VZ
$169.00/Night
Balcony
$1,324.00
Cat: TZ
$189.14/Night
Suite
$3,885.00
Cat: SS
$555.00/Night
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Ladera Resort Hotel Rating: 4.5 stars
Nights: 3
Dates: Oct 05, 2025 through Oct 08, 2025
Once part of Rabot Estate, one of Soufrière's oldest cocoa plantations, this authentic and luxurious open-air hotel is surrounded by a lush hillside of mango trees.
from
$1,305.00
(USD)
Per Person
More Details Contact Us
Bimini Beach Club
Virgin Voyages Logo
Fire and Sunset Soirées
Departing on Aug 20, 2025 on the Valiant Lady
Nights: 4
Dates: Aug 20, 2025 through Aug 24, 2025
Ship: Valiant Lady
Cruise from vibrant Miami to Nassau for a day spent splashing around in the cerulean waters or exploring the lively downtown scene. Afterwards, you'll head to our private Beach Club experience in Bimini, Bahamas.
from
$797.00
(USD)
Per Person
More Details Contact Us
Outside
$797.00
Cat: VZ
$199.25/Night
Balcony
$877.00
Cat: TZ
$219.25/Night
Suite
$2,196.00
Cat: RZ
$549.00/Night
Amenity Departure Dates
Puerto Plata
Virgin Voyages Logo
Tortola, Charleston, Newport & More
Departing on Mar 28, 2026 on the Valiant Lady
Nights: 9
Dates: Mar 28, 2026 through Apr 06, 2026
Ship: Valiant Lady
This 9-night one-way adventure departs from San Juan arriving the next day in Tortola. Then, spend a day at sea headed to Puerto Plata, DR, followed by two days sailing to a big city with even bigger Southern charm, Charleston, SC. From there, you'll spend the next day sailing to the classic architecture and quintessentially New England city Newport, Rhode Island before finally arriving in NYC.
from
$1,071.00
(USD)
Per Person
More Details Contact Us
Inside
$1,071.00
Cat: IZ
$119.00/Night
Outside
$1,251.00
Cat: VZ
$139.00/Night
Balcony
$1,611.00
Cat: TZ
$179.00/Night
Suite
$4,160.00
Cat: SS
$462.22/Night
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Haven Riviera Cancun Resort & Spa Hotel Rating: 4.5 stars
Nights: 3
Dates: Oct 05, 2025 through Oct 08, 2025
Haven Riviera Cancun, recognized by Preferred Hotels & Resorts LVX Collection, is an oceanfront sanctuary of luxury and sophistication.
from
$381.33
(USD)
Per Person
More Details Contact Us
Bimini 2
Virgin Voyages Logo
Fire and Sunset Soirees
Departing on Mar 04, 2026 on the Scarlet Lady
Nights: 4
Dates: Mar 04, 2026 through Mar 08, 2026
Ship: Scarlet Lady
Cruise from vibrant Miami to Nassau for a day spent splashing around in the cerulean waters or exploring the lively downtown scene. Afterwards, you'll head to our private Beach Club experience in Bimini, Bahamas.
from
$716.00
(USD)
Per Person
More Details Contact Us
Inside
$716.00
Cat: IZ
$179.00/Night
Outside
$796.00
Cat: VZ
$199.00/Night
Balcony
$917.00
Cat: TZ
$229.25/Night
Suite
$2,250.00
Cat: SS
$562.50/Night
Greek Island Glow
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Greek Island Glow
Departing on Jul 20, 2025 on the Resilient Lady
Nights: 7
Dates: Jul 20, 2025 through Jul 27, 2025
Sail from Athens to the most idyllic Greek Isles in the Med - like Santorini, Rhodes, and Bodrum (Turkey). With an overnight in the glamorous hot spot of Mykonos, you can immerse yourself in the quiet charm of the island and attend those world-famous beach club parties.
from
$1,330.00
(USD)
Per Person
More Details Contact Us
Inside
$1,330.00
Cat: I4
$190.00/Night
Outside
$1,891.00
Cat: VW
$270.14/Night
Suite
$5,415.00
Cat: SB
$773.57/Night
Ibiza
Virgin Voyages Logo
Rome, Florence, Corsica & Ibiza
Departing on Jul 24, 2026 on the Scarlet Lady
Nights: 9
Dates: Jul 24, 2026 through Aug 02, 2026
Ship: Scarlet Lady
This 9-night getaway departs from Barcelona to Palma de Mallorca before spending a luxurious day at sea sailing to Cannes, Rome, and followed by Livorno - the gateway to Florence and Pisa.
from
$1,611.00
(USD)
Per Person
+ $227.00 taxes/fees
More Details Contact Us
Inside
$1,611.00
Cat: IZ
$179.00/Night
Outside
$1,882.00
Cat: VZ
$209.11/Night
Balcony
$2,151.00
Cat: TZ
$239.00/Night
Suite
$5,015.00
Cat: SS
$557.22/Night
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Riu Palace Antillas Hotel Rating: 4 stars
Nights: 3
Dates: Oct 05, 2025 through Oct 08, 2025
The Hotel Riu Palace Antillas is located on the shores of Palm Beach, Aruba. This adults-only hotel offers the ideal place to relax and enjoy the sun, both at the wonderful swimming pool and on the golden sands of Palm Beach.
from
$729.00
(USD)
Per Person
More Details Contact Us
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Sandals Royal Bahamian Spa Resort & Offshore Island Hotel Rating: No Rating
Nights: 3
Dates: Oct 05, 2025 through Oct 08, 2025
This award-winning resort is the premier destination for people in love who demand only the very best.
from
$810.67
(USD)
Per Person
More Details Contact Us
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Secrets Papagayo Costa Rica Hotel Rating: 4 stars
Nights: 3
Dates: Oct 05, 2025 through Oct 08, 2025
Perfectly situated on a serene beachfront and surrounded by lush tropical gardens, Secrets® Papagayo Costa Rica offers an Unlimited-Luxury® experience in one of the most romantic and intimate settings imaginable.
from
$417.00
(USD)
Per Person
More Details Contact Us
Spanish Isles Rome Cannes
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Spanish Isles, Rome & Cannes
Departing on May 31, 2026 on the Valiant Lady
Nights: 7
Dates: May 31, 2026 through Jun 07, 2026
Ship: Valiant Lady
The allure of the Med will pull you in from the moment you sail away from - and return to - Barcelona. In Palma de Mallorca, uncork Iberia's best flavors on a trip to the Mallorcan countryside, explore the eternal landmarks of Rome (via Civitavecchia), immerse yourself in peak coastal chic in glamorous Cannes, and indulge in Ibiza's famed nightlife during an unforgettable overnight stay.
from
$1,505.00
(USD)
Per Person
More Details Contact Us
Inside
$1,505.00
Cat: IN
$215.00/Night
Outside
$1,890.00
Cat: VW
$270.00/Night
Balcony
$1,890.00
Cat: TL
$270.00/Night
Suite
$4,575.00
Cat: SS
$653.57/Night
WYNN LAS VEGAS
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Exclusive up to $200 resort credit + Free room upgrade at Wynn Las Vegas
Dates: Jul 02, 2025 through Nov 30, 2025
Exclusive up to $200 resort credit + Free room upgrade at Wynn Las Vegas
More Details Contact Us
George Town
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Cayman Isles & Bimini Beach Miles
Departing on Jun 13, 2026 on the Resilient Lady
Nights: 5
Dates: Jun 13, 2026 through Jun 18, 2026
This 5-night Caribbean escape departs from the vibrant lights of Miami, offering a day of onboard luxury en route to your first destination: George Town, Grand Cayman. Here, you can swim with stingrays, bask in the sun, and savor authentic Caribbean cuisine. Afterward, enjoy another relaxing day at sea as you sail to the Beach Club at Bimini, before returning to Miami.
from
$995.00
(USD)
Per Person
More Details Contact Us
Inside
$995.00
Cat: IZ
$199.00/Night
Outside
$1,096.00
Cat: VZ
$219.20/Night
Balcony
$1,376.00
Cat: TL
$275.20/Night
Suite
$3,200.00
Cat: SS
$640.00/Night
Caribbean Breeze Haunted Seas
Virgin Voyages Logo
Scarlet's Haunted Halloween Soiree
Departing on Oct 31, 2026 on the Scarlet Lady
Nights: 5
Dates: Oct 31, 2026 through Nov 05, 2026
Ship: Scarlet Lady
This 5-night excursion departs Miami and allows for a day of self-care, spooky surprises and on-board luxury while sailing to one of the most popular destinations for beach-goers and water-adventurer's alike: Cozumel. From there spend a day recuperating with a cocktail on the sun deck headed to our private beach club on the picturesque island of Bimini before returning the following day to Miami.
from
$845.00
(USD)
Per Person
More Details Contact Us
Inside
$845.00
Cat: IZ
$169.00/Night
Outside
$945.00
Cat: VZ
$189.00/Night
Balcony
$1,095.00
Cat: TZ
$219.00/Night
Suite
$2,925.00
Cat: SS
$585.00/Night
Costa Mayan Caves & Honduran Waves
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Costa Mayan Caves & Honduran Waves
Departing on Mar 14, 2026 on the Resilient Lady
Nights: 6
Dates: Mar 14, 2026 through Mar 20, 2026
This 6-night Caribbean getaway departs Miami and provides a day of sun and self-care at sea while sailing to your first stop, Roatán, a tropical Honduran island that sports the second largest great barrier reef in the world, sprawling rainforests, cascading waterfalls and lush lagoons.
from
$1,014.00
(USD)
Per Person
+ $245.00 taxes/fees
More Details Contact Us
Inside
$1,014.00
Cat: IZ
$169.00/Night
Outside
$1,194.00
Cat: VZ
$199.00/Night
Balcony
$1,375.00
Cat: TZ
$229.17/Night
Suite
$3,540.00
Cat: SS
$590.00/Night
Cayman Coves Jamaican Waterfalls George Town
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Cayman Coves & Jamaican Waterfalls
Departing on Jan 24, 2026 on the Resilient Lady
Nights: 7
Dates: Jan 24, 2026 through Jan 31, 2026
This 7-night Western Caribbean adventure sets sail from Miami and spends a day at sea on your way to a nature lover's haven: Ocho Rios, Jamaica. From there you'll spend a day sailing to George Town, Grand Cayman, a colorful capital city offering outdoor adventure, beautiful views and excitement at every turn.
from
$973.00
(USD)
Per Person
More Details Contact Us
Inside
$973.00
Cat: IZ
$139.00/Night
Outside
$1,183.00
Cat: VZ
$169.00/Night
Balcony
$1,393.00
Cat: TZ
$199.00/Night
Suite
$3,595.00
Cat: SS
$513.57/Night
Miami to the Cayman Islands Cartagena
Virgin Voyages Logo
Aruba, Bonaire, Colombia, Jamaica & More
Departing on Jan 04, 2026 on the Brilliant Lady
Nights: 11
Dates: Jan 04, 2026 through Jan 15, 2026
Embark on an 11-night round-trip voyage from Miami, with stops in Aruba, Bonaire, Colombia, Jamaica, and the Cayman Islands. Make the most of your time in South America by exploring Cartagena's colorful colonial architecture, walled 16th century Old Town, narrow stone walkways, and white sand beaches.
from
$1,420.00
(USD)
Per Person
More Details Contact Us
Inside
$1,420.00
Cat: IZ
$129.09/Night
Outside
$1,749.00
Cat: VZ
$159.00/Night
Balcony
$2,079.00
Cat: TZ
$189.00/Night
Suite
$5,280.00
Cat: SS
$480.00/Night
Amenity Departure Dates
Barbados Antigua BVI More
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Barbados, Antigua, BVI & More
Departing on Jan 24, 2026 on the Valiant Lady
Nights: 7
Dates: Jan 24, 2026 through Jan 31, 2026
Ship: Valiant Lady
This 7-night Caribbean journey starts in San Juan, stopping for a full day in Tortola on the British Virgin Islands. After, you'll island hop between Barbados and magnetic Martinique before arriving at the epitome of a Caribbean paradise - St. Johns on the island of Antigua. Next, you'll sail to St. Maarten, a tiny island bursting with beauty, before returning to San Juan.
from
$1,506.00
(USD)
Per Person
More Details Contact Us
Outside
$1,506.00
Cat: VW
$215.14/Night
Balcony
$1,506.00
Cat: TL
$215.14/Night
Suite
$3,710.00
Cat: SS
$530.00/Night
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Riu Latino Hotel Rating: 3.5 stars
Nights: 3
Dates: Oct 05, 2025 through Oct 08, 2025
This modern adults-only hotel lies directly on the beachfront of Costa Mujeres. Riu Latino is located near the town of Cancún, from which guests can find excellent connections to the archaeological sites that reflect the Mayan culture.
from
$258.00
(USD)
Per Person
More Details Contact Us
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Brilliant Lady LA MerMaiden
Departing on Apr 07, 2026 on the Brilliant Lady
Nights: 5
Dates: Apr 07, 2026 through Apr 12, 2026
This 5-night round trip MerMaiden sails from one of the most dreamed about cities in the world - Los Angeles. View the iconic Hollywood sign on a gorgeous hike, or soak up the scene in funky Venice Beach before sailing to Santa Barbara.
from
$895.00
(USD)
Per Person
More Details Contact Us
Inside
$895.00
Cat: IZ
$179.00/Night
Outside
$1,045.00
Cat: VZ
$209.00/Night
Balcony
$1,195.00
Cat: TZ
$239.00/Night
Suite
$4,005.00
Cat: SS
$801.00/Night
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Sun Palace Hotel Rating: 4 stars
Nights: 3
Dates: Oct 05, 2025 through Oct 08, 2025
Bask in luxury at the adults-only Sun Palace ideally located in Cancun's Hotel Zone. Let the pampering begin in your lavish, amenity-rich room or suite.
from
$488.33
(USD)
Per Person
More Details Contact Us
Casa Velas Hotel Boutique
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Exclusive room savings + Guaranteed room upgrade + Free golf + More at Casa Velas Hotel Boutique
Dates: Jul 02, 2025 through Jan 31, 2026
Exclusive room savings + Guaranteed room upgrade + Free golf + More.
More Details Contact Us
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Riu Palace Las Americas Hotel Rating: 4 stars
Nights: 3
Dates: Oct 05, 2025 through Oct 08, 2025
This stunning 24-hour all-inclusive resort includes 372 guest rooms located on a dazzling stretch of white-sand beach framed by tropical trees and crystal-clear turquoise waters.
from
$331.67
(USD)
Per Person
More Details Contact Us
San Juan Sunrises Dominican Dreams
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San Juan Sunrises & Dominican Dreams
Departing on Mar 28, 2026 on the Resilient Lady
Nights: 7
Dates: Mar 28, 2026 through Apr 04, 2026
This 7-night Eastern Caribbean adventure departs from Miami and spends two days sailing to sunny San Juan, Puerto Rico. Here you can immerse yourself in the enchanting culture, white sand beaches and lush rainforests before arriving the next day in Puerto Plata.
from
$1,043.00
(USD)
Per Person
More Details Contact Us
Inside
$1,043.00
Cat: IZ
$149.00/Night
Outside
$1,323.00
Cat: VZ
$189.00/Night
Balcony
$1,464.00
Cat: TZ
$209.14/Night
Suite
$3,980.00
Cat: SS
$568.57/Night
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Casa Chameleon at Las Catalinas Hotel Rating: 5 stars
Nights: 3
Dates: Oct 05, 2025 through Oct 08, 2025
Perched high on a hilltop above the town of Las Catalinas on Costa Rica's pristine Guanacaste peninsula, Casa Chameleon at Las Catalinas promises an idyllic getaway.
from
$645.67
(USD)
Per Person
More Details Contact Us
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Le Blanc Spa Resort Los Cabos Hotel Rating: 5 stars
Nights: 3
Dates: Oct 05, 2025 through Oct 08, 2025
Nestled among the sun-kissed beaches of the Baja Peninsula, Le Blanc Spa Resort Los Cabos beckons you with the perfect balance of natural beauty and pampering service.
from
$1,011.00
(USD)
Per Person
More Details Contact Us
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Breathless Riviera Cancun Resort & Spa Hotel Rating: 4 stars
Nights: 3
Dates: Oct 05, 2025 through Oct 08, 2025
Treat yourself to this vibrant oceanside getaway where nearly everything is included with Unlimited Luxury®, which redefines the all-inclusive experience.
from
$338.00
(USD)
Per Person
More Details Contact Us
Puerto Plata
Virgin Voyages Logo
Sunny San Juan & Isles of Beach Miles
Departing on Nov 20, 2025 on the Brilliant Lady
Nights: 8
Dates: Nov 20, 2025 through Nov 28, 2025
This 8-night voyage sails from Miami to the Dominican Republic, Puerto Rico, St. Maarten, and St. Croix, before returning to Miami. You'll also have a couple sea days to really explore the ship.
from
$1,193.00
(USD)
Per Person
More Details Contact Us
Inside
$1,193.00
Cat: IZ
$149.13/Night
Outside
$1,433.00
Cat: VZ
$179.13/Night
Balcony
$1,672.00
Cat: TZ
$209.00/Night
Suite
$4,040.00
Cat: SS
$505.00/Night
Amenity Departure Dates
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Brilliant Lady Seattle MerMaiden
Departing on May 21, 2026 on the Brilliant Lady
Nights: 7
Dates: May 21, 2026 through May 28, 2026
This 7-night MerMaiden voyage from Seattle spends a day sailing to Ketchikan, Alaska, a quaint village located amongst the Tongass National Forest. From there we'll dock in verdant Sitka followed by a day voyaging up the impressive Tracy Arm Fjord (Cruising). Next, we'll sail to Prince Rupert, BC before spending a final day sailing back to Seattle.
from
$1,813.00
(USD)
Per Person
More Details Contact Us
Inside
$1,813.00
Cat: IZ
$259.00/Night
Outside
$2,023.00
Cat: VZ
$289.00/Night
Balcony
$2,233.00
Cat: TZ
$319.00/Night
Suite
$6,696.00
Cat: SCP
$956.57/Night
Valiant New Year''s Ahoy 2025
Virgin Voyages Logo
Resilient New Year's Ahoy!
Departing on Dec 27, 2026 on the Resilient Lady
Nights: 7
Dates: Dec 27, 2026 through Jan 03, 2027
Usher in the new year on this 7-night Western Caribbean adventure. Set sail from Miami and spend a day at sea on your way to a nature lover's haven: Ocho Rios, Jamaica. From there you'll spend a day sailing to George Town, Grand Cayman, a colorful capital city offering outdoor adventure and beautiful views. From there spend a day sailing to the Beach Club at Bimini before returning to Miami.
from
$1,953.00
(USD)
Per Person
+ $229.00 taxes/fees
More Details Contact Us
Inside
$1,953.00
Cat: IZ
$279.00/Night
Outside
$2,163.00
Cat: VZ
$309.00/Night
Balcony
$2,373.00
Cat: TZ
$339.00/Night
Suite
$5,800.00
Cat: SS
$828.57/Night
Bimini 1
Virgin Voyages Logo
Jamaican Waves & Bimini Breeze
Departing on Feb 15, 2027 on the Scarlet Lady
Nights: 5
Dates: Feb 15, 2027 through Feb 20, 2027
Ship: Scarlet Lady
This 5-night Caribbean getaway departs from the beaches of Miami, offering a full day of onboard luxury and five-star entertainment over to Ocho Rios, a waterfall-ladened oasis on the white sand shores of Jamaica. From there, spend a day savoring the Michelin chef-curated menus onboard headed to the Beach Club at Bimini, before returning to Miami.
from
$845.00
(USD)
Per Person
+ $273.00 taxes/fees
More Details Contact Us
Inside
$845.00
Cat: IZ
$169.00/Night
Outside
$946.00
Cat: VZ
$189.20/Night
Balcony
$1,096.00
Cat: TZ
$219.20/Night
Suite
$2,575.00
Cat: SS
$515.00/Night
Holidaze and Nights 1
Virgin Voyages Logo
Resilient Caribbean Holidays
Departing on Dec 20, 2025 on the Resilient Lady
Nights: 7
Dates: Dec 20, 2025 through Dec 27, 2025
This 7-night holiday adventure departs from Miami and spends two days sailing to sunny San Juan, Puerto Rico. Shake off those winter blues and immerse yourself in the enchanting culture, white sand beaches and verdant rainforests before arriving the next day in Puerto Plata.
from
$1,183.00
(USD)
Per Person
More Details Contact Us
Inside
$1,183.00
Cat: IZ
$169.00/Night
Outside
$1,534.00
Cat: VZ
$219.14/Night
Balcony
$1,744.00
Cat: TZ
$249.14/Night
Suite
$4,155.00
Cat: SS
$593.57/Night
Italy to France & Spain Rome Image
Virgin Voyages Logo
Sicily, Naples, Cannes & More
Departing on Aug 22, 2026 on the Scarlet Lady
Nights: 9
Dates: Aug 22, 2026 through Aug 31, 2026
Ship: Scarlet Lady
This 9-night epic adventure sails from Civitavecchia, the gateway to Rome and all its landmarks. The following day we'll arrive in Catania, followed by Naples, then Ajaccio. Next we'll arrive at every seasoned traveler (and celebrity)'s favorite vacation respite, Cannes. Next we'll dock in Livorno, located in Italy's Tuscany region and a stone's throw to Florence and Pisa before returning to Rome.
from
$1,639.00
(USD)
Per Person
More Details Contact Us
Inside
$1,639.00
Cat: IZ
$182.11/Night
Outside
$1,882.00
Cat: VZ
$209.11/Night
Balcony
$2,151.00
Cat: TZ
$239.00/Night
Suite
$4,973.00
Cat: RZ
$552.56/Night
George Town
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Cayman Isles & Jamaican Miles
Departing on Apr 15, 2027 on the Valiant Lady
Nights: 7
Dates: Apr 15, 2027 through Apr 22, 2027
Ship: Valiant Lady
This 7-night Eastern Caribbean getaway departs from Miami and spends a day sailing to your first stop, George Town, Grand Cayman. Spend the day here swimming with stingrays, soaking up the culture (and the sun), and witnessing ocean wildlife through a glass bottom boat. From there, spend a day sailing to Ocho Rios followed by one more headed to the beach club at Bimini before returning to Miami.
from
$1,113.00
(USD)
Per Person
+ $303.00 taxes/fees
More Details Contact Us
Inside
$1,113.00
Cat: IZ
$159.00/Night
Outside
$1,254.00
Cat: VZ
$179.14/Night
Balcony
$1,464.00
Cat: TZ
$209.14/Night
Suite
$4,225.00
Cat: SS
$603.57/Night
Offer Image
Pleasant Holidays Logo
Secrets The Vine Cancun Hotel Rating: 4.5 stars
Nights: 3
Dates: Oct 05, 2025 through Oct 08, 2025
A location full of beauty all its own, Secrets® The Vine Cancun is situated by the Caribbean Sea and Laguna Nichupte with ocean views as far as the eye can see.
from
$374.67
(USD)
Per Person
More Details Contact Us
San Juan Sunrises Dominican Dreams
Virgin Voyages Logo
Thanksgiving: St. Isles, Aruba & Curacao
Departing on Nov 20, 2026 on the Valiant Lady
Nights: 8
Dates: Nov 20, 2026 through Nov 28, 2026
Ship: Valiant Lady
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
$1,513.00
(USD)
Per Person
More Details Contact Us
Inside
$1,513.00
Cat: IZ
$189.13/Night
Outside
$1,752.00
Cat: VZ
$219.00/Night
Balcony
$1,992.00
Cat: TZ
$249.00/Night
Suite
$4,920.00
Cat: SS
$615.00/Night
Italy to France & Spain Rome Image
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Italy to France & Spain
Departing on Oct 07, 2025 on the Scarlet Lady
Nights: 9
Dates: Oct 07, 2025 through Oct 16, 2025
Ship: Scarlet Lady
Our final 9-night Mediterranean voyage of the season departs from the pulse of Italian culture and cuisine – Rome, and spends a day sailing to Cagliari, then another day to Marina di Carrara, then France’s iconic Ajaccio and Cannes. Then, spend another day achieving the pinnacle of self-care at sea sailing to Valencia before arriving at your final destination of Barcelona.
from
$1,765.00
(USD)
Per Person
More Details Contact Us
Inside
$1,765.00
Cat: IN
$196.11/Night
Outside
$1,791.00
Cat: VZ
$199.00/Night
Balcony
$2,062.00
Cat: TZ
$229.11/Night
Suite
$4,725.00
Cat: SS
$525.00/Night
Offer Image
Pleasant Holidays Logo
Casa Velas Puerto Vallarta Hotel Rating: 4 stars
Nights: 3
Dates: Oct 05, 2025 through Oct 08, 2025
Casa Velas is a boutique hotel nestled on the rolling greens of the Marina Vallarta Golf Course in Puerto Vallarta.
from
$549.00
(USD)
Per Person
More Details Contact Us
Secrets Papagayo Costa Rica
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Exclusive free breakfast in bed with mimosas + Welcome amenity + More at Secrets Papagayo Costa Rica
Dates: Jul 02, 2025 through Jan 31, 2026
Exclusive free breakfast in bed with mimosas + Welcome amenity + Access to Jacuzzi & sauna.
More Details Contact Us
Dominican Daze 1
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Dominican Daze
Departing on Nov 25, 2026 on the Brilliant Lady
Nights: 5
Dates: Nov 25, 2026 through Nov 30, 2026
Dominican Daze sails to the snow-white shores of the Dominican Republic from Miami, for plenty of time to lay by the beach and explore the city streets. Add a full day and night spent at the exclusive Beach Club in Bimini, Bahamas.
from
$946.00
(USD)
Per Person
+ $182.00 taxes/fees
More Details Contact Us
Inside
$946.00
Cat: IZ
$189.20/Night
Outside
$1,046.00
Cat: VZ
$209.20/Night
Balcony
$1,195.00
Cat: TZ
$239.00/Night
Suite
$2,575.00
Cat: SS
$515.00/Night
Offer Image
Pleasant Holidays Logo
Marquis Los Cabos All Inclusive Resort & Spa Hotel Rating: 4.5 stars
Nights: 3
Dates: Oct 05, 2025 through Oct 08, 2025
Marquis Los Cabos emerges as an all-inclusive enclave where attention to detail and passion for service and excellence is a must, and the spirit of Mexico infuses every piece of the adults-only haven.
from
$581.33
(USD)
Per Person
More Details Contact Us
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Riu Montego Bay Hotel Rating: 4 stars
Nights: 3
Dates: Oct 05, 2025 through Oct 08, 2025
Located in the northwest of the island and directly on the beach of Mahoe Bay, this completely renovated Adults Only - All Inclusive resort offers 826-rooms and a wide range of services for guests' convenience and enjoyment.
from
$334.67
(USD)
Per Person
More Details Contact Us
Cartagena
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Colorful Curacao to the Charming Caymans
Departing on Nov 08, 2025 on the Brilliant Lady
Nights: 12
Dates: Nov 08, 2025 through Nov 20, 2025
This 12-night voyage from Miami stops in Aruba, Curacao, Colombia, Jamaica, and the Cayman Islands. Perhaps the most exciting part of the trip is spending a night in Cartagena, Colombia.
from
$1,909.00
(USD)
Per Person
More Details Contact Us
Outside
$1,909.00
Cat: VZ
$159.08/Night
Balcony
$2,269.00
Cat: TZ
$189.08/Night
Suite
$5,760.00
Cat: SS
$480.00/Night
Amenity Departure Dates