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Holidaze and Nights 1
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Sunny Miles of Tropical Isles
Departing on Feb 28, 2026 on the Valiant Lady
Nights: 7
Dates: Feb 28, 2026 through Mar 07, 2026
Ship: Valiant Lady
Itinerary:
San Juan, Philipsburg, Sailing, Bridgetown, Castries, Fort-de-France, Basseterre, San Juan
This dreamy 7-night Caribbean adventure begins in San Juan and docks the following day in St. Maarten. After spending a day of self-care at sea you'll land in Barbados, followed by St. Lucia, and stylish Martinique before arriving in Basseterre, St. Kitts - a bustling beach town known for its sprawling white sand beaches and quaint Caribbean vibes before returning to San Juan.
from
$1,044.00
(USD)
Per Person
More Details Contact Us
Inside
$1,044.00
Cat: IZ
$149.14/Night
Outside
$1,254.00
Cat: VZ
$179.14/Night
Balcony
$1,464.00
Cat: TZ
$209.14/Night
Suite
$4,095.00
Cat: SS
$585.00/Night
San Juan Sunrises Dominican Dreams
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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
Itinerary:
San Juan, St. Thomas, Sailing, Tortola, Basseterre, St. John's, Philipsburg, St. Maarten, San Juan
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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Hotel Mousai Cancun Hotel Rating: 4.5 stars
Nights: 3
Dates: Oct 16, 2025 through Oct 19, 2025
Location(s):
Cancun
The adults-only Hotel Mousai Cancun is a bold, all-inclusive oceanfront resort. It features ultra-chic suites with sleek décor and modern amenities.
from
$645.67
(USD)
Per Person
More Details Contact Us
Amalfi Coast
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Amalfi Coast, Cannes & Ibiza
Departing on May 25, 2026 on the Valiant Lady
Nights: 6
Dates: May 25, 2026 through May 31, 2026
Ship: Valiant Lady
Itinerary:
Civitavecchia (Rome), Amalfi Coast (Salerno), Sailing, Cannes, Ibiza, Barcelona
Set sail on a glorious 6-night one-way voyage, beginning in Rome (via Civitavecchia) and ending in Barcelona. Experience the real dolce vita from the moment you breathe in the citrus-infused air of the Amalfi Coast in Salerno, step into the glamorous world of the jet set crowd in Cannes on the Côte d'Azur, and revel in Ibiza's blend of beaches and nightlife during a sensational overnight stay.
from
$1,659.00
(USD)
Per Person
More Details Contact Us
Inside
$1,659.00
Cat: IN
$276.50/Night
Outside
$1,693.00
Cat: VW
$282.17/Night
Balcony
$1,693.00
Cat: TL
$282.17/Night
Suite
$3,660.00
Cat: SS
$610.00/Night
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Atelier Playa Mujeres Hotel Rating: 4.5 stars
Nights: 3
Dates: Oct 16, 2025 through Oct 19, 2025
Location(s):
Isla Mujeres
This adults-only (16+ years) all-inclusive resort is conveniently located in the exclusive Playa Mujeres complex overlooking the cerulean waters of the Caribbean Sea.
from
$751.00
(USD)
Per Person
More Details Contact Us
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Riu Latino Hotel Rating: 3.5 stars
Nights: 3
Dates: Oct 16, 2025 through Oct 19, 2025
Location(s):
Cancun
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
$283.00
(USD)
Per Person
More Details Contact Us
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Sandals Royal Caribbean Resort & Private Island Hotel Rating: No Rating
Nights: 3
Dates: Oct 19, 2025 through Oct 22, 2025
Location(s):
Montego Bay
Nestled on the northern shores of Jamaica this resort is renowned for its exclusive refinements. Its Georgian-style Great House setting hosts the gracious British traditions of a bygone era.
from
$893.00
(USD)
Per Person
More Details Contact Us
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Live Aqua Beach Resort Punta Cana Hotel Rating: 4.5 stars
Nights: 3
Dates: Oct 19, 2025 through Oct 22, 2025
Location(s):
Punta Cana
Live a completely exclusive experience in the Uvero Alto district of Punta Cana. Your dream of paradise comes true in an exotic destination framed by virgin beaches, lush vegetation and unbeatable service.
from
$346.00
(USD)
Per Person
More Details Contact Us
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Dominican Daze
Departing on Sep 26, 2025 on the Valiant Lady
Nights: 5
Dates: Sep 26, 2025 through Oct 01, 2025
Ship: Valiant Lady
Itinerary:
Miami, Sailing, Puerto Plata, Sailing, Beach Club at Bimini, Miami
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.
from
$895.00
(USD)
Per Person
More Details Contact Us
Outside
$895.00
Cat: VZ
$179.00/Night
Balcony
$1,046.00
Cat: TZ
$209.20/Night
Suite
$2,345.00
Cat: RZ
$469.00/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
Itinerary:
Seattle, Washington, Inside Passage (Cruising), Alaska, Ketchikan, Alaska, Sitka, Alaska, Tracy Arm Fjord (Cruising), Alaska, Prince Rupert, Sailing, Seattle, Washington
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
$5,695.00
Cat: SAB
$813.57/Night
Cartagena
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Picturesque Panama Canal Collective
Departing on Oct 29, 2026 on the Brilliant Lady
Nights: 17
Dates: Oct 29, 2026 through Nov 15, 2026
Itinerary:
Los Angeles, California, Sailing, Cabo San Lucas, Sailing, Puerto Quetzal, Sailing, Puntarenas, Sailing, Panama City, Panama Canal (Cruising), Cartagena, Sailing, Miami
This paramount Panamanian voyage sails 2 days from LA before arriving in idyllic Cabo, then sails 3 days to the natural wonders of Puerto Quetzal, Guatemala & 1 more day to the verdant jungles of Puntarenas, Costa Rica followed by a sea day to Panama City. Next, sail the Panama Canal's breathtaking vistas before arriving in Cartagena, Colombia for 2 days. Finally, sail 2 days returning to Miami.
from
$2,704.00
(USD)
Per Person
More Details Contact Us
Inside
$2,704.00
Cat: IZ
$159.06/Night
Outside
$3,213.00
Cat: VZ
$189.00/Night
Balcony
$3,724.00
Cat: TZ
$219.06/Night
Suite
$10,670.00
Cat: SS
$627.65/Night
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Hideaway at Royalton Saint Lucia, An Autograph Collection All-Inclusive Hotel Rating: 4.5 stars
Nights: 3
Dates: Oct 19, 2025 through Oct 22, 2025
Location(s):
Gros Islet
This luxurious adults-only resort offers a one-of-a-kind experience with anticipatory service, elegantly styled rooms and exceptional amenities.
from
$579.33
(USD)
Per Person
More Details Contact Us
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Kimpton Mas Olas Hotel Rating: 4 stars
Nights: 3
Dates: Oct 19, 2025 through Oct 22, 2025
Location(s):
Baja
Kimpton Mas Olas Resort and Spa is beautifully located beachfront in Baja, where you can journey to where your mind opens, your body heals, and your soul revives.
from
$799.33
(USD)
Per Person
More Details Contact Us
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Pueblo Bonito Pacifica Golf and Spa Resort Hotel Rating: 4 stars
Nights: 3
Dates: Oct 19, 2025 through Oct 22, 2025
Location(s):
Cabo San Lucas
This resort offers Luxury without Limitations, a deluxe all-inclusive plan providing gourmet a la carte dining, enhanced guest services, golf green fees, clubs, equipment, and carts and a wide range of amenities.
from
$350.33
(USD)
Per Person
More Details Contact Us
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Fire & Sunset Soirées
Departing on Jan 07, 2027 on the Brilliant Lady
Nights: 4
Dates: Jan 07, 2027 through Jan 11, 2027
Itinerary:
Miami, Florida, Key West, Florida, Sailing, Beach Club at Bimini, Miami, Florida
Cruise from vibrant Miami to Key West 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
$636.00
(USD)
Per Person
More Details Contact Us
Inside
$636.00
Cat: IZ
$159.00/Night
Outside
$716.00
Cat: VZ
$179.00/Night
Balcony
$837.00
Cat: TZ
$209.25/Night
Suite
$2,090.00
Cat: SS
$522.50/Night
Riviera Maya 1
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Riviera Maya
Departing on May 11, 2026 on the Resilient Lady
Nights: 5
Dates: May 11, 2026 through May 16, 2026
Itinerary:
Miami, Sailing, Cozumel (Playa del Carmen), Sailing, Beach Club at Bimini, Miami
The Riviera Maya is a dreamer's gateway to Cozumel (Playa del Carmen) and Tulum. Arriving from Miami and departing late with an additional day and night spent at The Beach Club at Bimini, you'll have plenty of time to see each port from every sun and moonlit angle.
from
$946.00
(USD)
Per Person
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
$2,825.00
Cat: SS
$565.00/Night
Tortola
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Saint Isles & The Greater Antilles
Departing on Feb 20, 2027 on the Valiant Lady
Nights: 7
Dates: Feb 20, 2027 through Feb 27, 2027
Ship: Valiant Lady
Itinerary:
San Juan, Tortola, Sailing, Castries, Bridgetown, Roseau, Philipsburg, San Juan
This 7-night sojourn departs from San Juan and arrives the next day in Tortola on the British Virgin Islands. After a day at sea you'll arrive amongst the waterfalls and lagoons of Castries, St. Lucia followed by the beguiling beaches of Bridgetown, Barbados. Next, arrive on the shores of Roseau, Dominica then Phillipsburg, on the beloved Dutch side of St. Maarten before returning to San Juan.
from
$1,254.00
(USD)
Per Person
More Details Contact Us
Inside
$1,254.00
Cat: IZ
$179.14/Night
Outside
$1,464.00
Cat: VZ
$209.14/Night
Balcony
$1,673.00
Cat: TZ
$239.00/Night
Suite
$4,340.00
Cat: SS
$620.00/Night
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Divine Cave Experience Hotel Rating: No Rating
Nights: 3
Dates: Oct 19, 2025 through Oct 22, 2025
Location(s):
Santorini
Staying at the Divine Cave Experience allows you to feel submerged in luxury and serenity. The heavenly hotel features 10 cave suites that have been designed to elevate the senses, and all of them have miraculous views of the Aegean and the world-famous Caldera.
from
$466.33
(USD)
Per Person
More Details Contact Us
Bimini Beach Club
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Cozumel, Grand Cayman & Bimini
Departing on Jan 03, 2026 on the Resilient Lady
Nights: 7
Dates: Jan 03, 2026 through Jan 10, 2026
Itinerary:
Miami, Florida, Sailing, George Town, Sailing, Cozumel (Playa del Carmen), Sailing, Beach Club at Bimini, Miami, Florida
This 7-night Western Caribbean getaway sets sail from Miami and spends a day at sea on your way to George Town, Grand Cayman. From there you'll spend a day sailing to Cozumel, a colorful capital city offering outdoor adventure, beautiful views and excitement at every turn.
from
$833.00
(USD)
Per Person
More Details Contact Us
Inside
$833.00
Cat: IZ
$119.00/Night
Outside
$1,184.00
Cat: VZ
$169.14/Night
Balcony
$1,253.00
Cat: TZ
$179.00/Night
Suite
$3,525.00
Cat: SS
$503.57/Night
Amenity Departure Dates
Brilliant New Years Ahoy
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Brilliant New Year's Ahoy!
Departing on Dec 26, 2025 on the Brilliant Lady
Nights: 9
Dates: Dec 26, 2025 through Jan 04, 2026
Itinerary:
Miami, Florida, Sailing, Grand Turk, Sailing, St. John's, Basseterre, San Juan, Sailing, Miami, Florida
Ring in the new year in style by cruising the Caribbean on this 9-night round-trip, sailing from Miami to Grand Turk, Antigua, St. Kitts & Nevis, and San Juan. Make sure to spend time on St. Kitts' beautiful beaches, like Cockleshell Bay and Frigate Bay.
from
$2,241.00
(USD)
Per Person
More Details Contact Us
Inside
$2,241.00
Cat: IZ
$249.00/Night
Outside
$2,602.00
Cat: VZ
$289.11/Night
Balcony
$2,871.00
Cat: TZ
$319.00/Night
Suite
$8,055.00
Cat: SAP
$895.00/Night
Amenity Departure Dates
Glorious Greek Isles to Spanish Sunsets
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Istanbul Delights & Santorini Dreams
Departing on Jun 24, 2026 on the Scarlet Lady
Nights: 11
Dates: Jun 24, 2026 through Jul 05, 2026
Ship: Scarlet Lady
Itinerary:
Piraeus (Athens), Sailing, Istanbul, Sailing, Kusadasi (Ephesus), Mykonos, Rhodes, Santorini, Chania, Crete, Sailing, Piraeus (Athens)
This 11-night sailing from Athens visits Istanbul, Kusadasi, Mykonos, Rhodes, Santorini, and Crete. You'll spend the week marveling at the serene architecture of the Greek Isles, and basking in the Santorini sunshine.
from
$2,091.00
(USD)
Per Person
More Details Contact Us
Inside
$2,091.00
Cat: IN
$190.09/Night
Outside
$2,531.00
Cat: VW
$230.09/Night
Balcony
$2,531.00
Cat: TL
$230.09/Night
Suite
$5,505.00
Cat: RZ
$500.45/Night
Puerto Rican Daze and Caribbean Nights Fort de France
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Lesser Antilles: Valentine's Day
Departing on Feb 13, 2027 on the Valiant Lady
Nights: 7
Dates: Feb 13, 2027 through Feb 20, 2027
Ship: Valiant Lady
Itinerary:
San Juan, Sailing, Oranjestad, Willemstad, Sailing, Fort-de-France, Basseterre, San Juan
This Valentine's Day sojourn departs from San Juan and provides a day of on-board luxury while sailing to your first stop, Oranjestad, Aruba. From there you'll dock in the warm waters of Willemstad, before spending another day sailing to Fort-de-France in magical Martinique, followed by the bustling beach town with beguiling beaches, Basseterre, St. Kitts & Nevis, before returning to San Juan.
from
$1,322.00
(USD)
Per Person
More Details Contact Us
Inside
$1,322.00
Cat: IZ
$188.86/Night
Outside
$1,532.00
Cat: VZ
$218.86/Night
Balcony
$1,742.00
Cat: TZ
$248.86/Night
Suite
$4,339.00
Cat: SS
$619.86/Night
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Inside Passage Alaska & Canadian Coasts
Departing on Jun 11, 2026 on the Brilliant Lady
Nights: 12
Dates: Jun 11, 2026 through Jun 23, 2026
Itinerary:
Seattle, Washington, Inside Passage (Cruising), Alaska, Ketchikan, Alaska, Sitka, Alaska, Hubbard Glacier (Cruising), Alaska, Skagway, Alaska, Icy Strait Point, Alaska, Haines, Alaska, Sailing, Prince Rupert, Sailing, Victoria, Seattle, Washington
This 12-night icy Pacific journey departs from Seattle and cruises up the picturesque Inside Passage to Ketchikan, followed by awe-inspiring Sitka, Alaska. Next, sail past the Hubbard Glacier on your way to Skagway, Icy Strait Point and Haines, followed by a day sailing to Prince Rupert, BC.
from
$2,748.00
(USD)
Per Person
More Details Contact Us
Inside
$2,748.00
Cat: IZ
$229.00/Night
Outside
$3,108.00
Cat: VZ
$259.00/Night
Balcony
$3,589.00
Cat: TZ
$299.08/Night
Suite
$8,100.00
Cat: SS
$675.00/Night
New Year''s Ahoy 2
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Valiant New Year's Ahoy!
Departing on Dec 26, 2026 on the Valiant Lady
Nights: 7
Dates: Dec 26, 2026 through Jan 02, 2027
Ship: Valiant Lady
Itinerary:
San Juan, Philipsburg, St. Maarten, Basseterre, Castries, Bridgetown, Sailing, St. Croix, San Juan
This 7-night sunny adventure departs from San Juan before docking the next day in Phillipsburg, St. Maarten followed by Basseterre, St. Kitts - home to some of the world's best beaches and dreamiest vacay-vibes. The next day you'll hit Castries, St. Lucia before Bridgetown, Barbados. Then spend a day relaxing on board headed to Frederiksted, St. Croix before returning to San Juan.
from
$2,162.00
(USD)
Per Person
More Details Contact Us
Inside
$2,162.00
Cat: IZ
$308.86/Night
Outside
$2,372.00
Cat: VZ
$338.86/Night
Balcony
$2,582.00
Cat: TZ
$368.86/Night
Suite
$4,829.00
Cat: SS
$689.86/Night
Caribbean Breeze Haunted Seas
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Miami to Grand Turk: Halloween Edition
Departing on Oct 25, 2026 on the Scarlet Lady
Nights: 6
Dates: Oct 25, 2026 through Oct 31, 2026
Ship: Scarlet Lady
Itinerary:
Miami, Florida, Sailing, Grand Turk, Puerto Plata, Sailing, Beach Club at Bimini, Miami, Florida
This 6-night sojourn starts in Miami and spends a day sailing to the beach-ladened city of Grand Turk, followed by a day of outdoor adventure, self-care, or utter relaxation on the beaches of Puerto Plata. Spend one more day at sea sailing to Bimini, home of our famous Beach Club at Bimini, where you can sunbathe, swim in the enormous pool, and sip perfect cocktails before returning to Miami.
from
$1,051.00
(USD)
Per Person
More Details Contact Us
Inside
$1,051.00
Cat: IN
$175.17/Night
Outside
$1,380.00
Cat: VW
$230.00/Night
Balcony
$1,380.00
Cat: TL
$230.00/Night
Suite
$3,390.00
Cat: SS
$565.00/Night
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Ladera Resort Hotel Rating: 4.5 stars
Nights: 3
Dates: Oct 19, 2025 through Oct 22, 2025
Location(s):
St. Lucia
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
$1,120.67
(USD)
Per Person
More Details Contact Us
Riviera Maya 3
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Riviera Maya: Halloween Edition
Departing on Oct 19, 2025 on the Valiant Lady
Nights: 5
Dates: Oct 19, 2025 through Oct 24, 2025
Ship: Valiant Lady
Itinerary:
Miami, Sailing, Cozumel (Playa del Carmen), Sailing, Beach Club at Bimini, Miami
The Riviera Maya is a dreamer's gateway to Cozumel (Playa del Carmen) and Tulum. Arriving from Miami and departing late with an additional day and night spent at The Beach Club at Bimini, you'll have plenty of time to see each port from every sun and moonlit angle.
from
$845.00
(USD)
Per Person
More Details Contact Us
Outside
$845.00
Cat: VZ
$169.00/Night
Balcony
$996.00
Cat: TZ
$199.20/Night
Suite
$2,595.00
Cat: RZ
$519.00/Night
Amenity Departure Dates
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Hollywood Sunsets & Mexican Horizons
Departing on Sep 19, 2026 on the Brilliant Lady
Nights: 7
Dates: Sep 19, 2026 through Sep 26, 2026
Itinerary:
Los Angeles, Cabo San Lucas, Mazatlan, Puerto Vallarta, Los Angeles
This 7-night journey departs from Los Angeles, starting with a full day of self-care and soaking up the sun while sailing to Cabo San Lucas. The next day you'll arrive in Mazatlan followed by Puerto Vallarta, a regular on many "World's Best" lists due to its splendid beaches and world-renowned food and drink scene. After, you'll have two more days to relax on the ship before returning to LA.
from
$1,044.00
(USD)
Per Person
More Details Contact Us
Inside
$1,044.00
Cat: IZ
$149.14/Night
Outside
$1,254.00
Cat: VZ
$179.14/Night
Balcony
$1,464.00
Cat: TZ
$209.14/Night
Suite
$3,728.00
Cat: SS
$532.57/Night
Virgin Voyages Comedy Fest from Miami
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Virgin Voyages Comedy Fest from Miami
Departing on Aug 10, 2025 on the Valiant Lady
Nights: 5
Dates: Aug 10, 2025 through Aug 15, 2025
Ship: Valiant Lady
Itinerary:
Miami, Sailing, Cozumel (Playa del Carmen), Sailing, Beach Club at Bimini, Miami
Get ready to laugh your aft off. This is more than just a cruise, it's a comedy fest at sea. Smile at more than just the sunset as you sail from Miami to the shores of the Yucatán Peninsula.
from
$1,276.00
(USD)
Per Person
More Details Contact Us
Balcony
$1,276.00
Cat: TR
$255.20/Night
Suite
$2,554.00
Cat: RZ
$510.80/Night
Amenity Departure Dates
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Pleasant Holidays Logo
Romer House Waikiki Hotel Rating: 3.5 stars
Nights: 3
Dates: Oct 19, 2025 through Oct 22, 2025
Location(s):
Honolulu, Oahu
The Romer House Waikiki is a modern surf lodge located in the heart of Waikiki and a short walk from the beach.
from
$226.67
(USD)
Per Person
More Details Contact Us
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Sandals Dunn's River Hotel Rating: No Rating
Nights: 3
Dates: Oct 19, 2025 through Oct 22, 2025
Location(s):
Ocho Rios
The completely reimagined Sandals Dunn's River is where nature and luxury go hand in hand. Ideally located on the stunning north coast of Jamaica, here you will find rivers meandering through forests and cascading waterfalls.
from
$922.67
(USD)
Per Person
More Details Contact Us
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Catalonia Royal Tulum Hotel Rating: 3.5 stars
Nights: 3
Dates: Oct 16, 2025 through Oct 19, 2025
Location(s):
Riviera Maya
The adults-only Catalonia Royal Tulum is an all-inclusive paradise located in Xpu-Ha, Riviera Maya, one of the most beautiful beaches in the Caribbean.
from
$269.33
(USD)
Per Person
More Details Contact Us
Holidaze and Nights 1
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Brilliant Caribbean Holidays
Departing on Dec 18, 2025 on the Brilliant Lady
Nights: 8
Dates: Dec 18, 2025 through Dec 26, 2025
Itinerary:
Miami, Florida, Sailing, Grand Turk, Puerto Plata, San Juan, Samaná, Sailing, Miami, Florida
What better way to get in the holiday spirit than with this 8-night round-trip voyage sailing from Miami to Grand Turk, the Dominican Republic, and Puerto Rico. In Puerto Plata, ditch the snow for pristine beaches, like Playa Dorada and Playa Sousa, and visit natural wonders like the spectacular Damajaqua Cascades and Las Cuevas de Cabarete caves.
from
$1,352.00
(USD)
Per Person
More Details Contact Us
Inside
$1,352.00
Cat: IZ
$169.00/Night
Outside
$1,593.00
Cat: VZ
$199.13/Night
Balcony
$1,673.00
Cat: TZ
$209.13/Night
Suite
$4,360.00
Cat: SS
$545.00/Night
Amenity Departure Dates
Aruban Sunsets and Calm Canyon Days
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Aruban Sunsets & Calm Cayman Days
Departing on Mar 01, 2026 on the Brilliant Lady
Nights: 11
Dates: Mar 01, 2026 through Mar 12, 2026
Itinerary:
Miami, Florida, Sailing, Oranjestad, Sailing, Cartagena, Sailing, Ocho Rios, George Town, Sailing, Miami, Florida
This 11-night voyage from Miami stops in Aruba, Colombia, Jamaica, and the Cayman Islands. Perhaps the most exciting part of the trip is your visit to South America. Cartagena is known for its colorful colonial architecture, walled 16th century Old Town, narrow stone walkways, and white sand beaches.
from
$1,419.00
(USD)
Per Person
More Details Contact Us
Inside
$1,419.00
Cat: IZ
$129.00/Night
Outside
$1,750.00
Cat: VZ
$159.09/Night
Balcony
$2,080.00
Cat: TZ
$189.09/Night
Suite
$4,975.00
Cat: SS
$452.27/Night
Amenity Departure Dates
New Year''s Ahoy 3
Virgin Voyages Logo
Saint (Isles) & Seas of the Caribbean
Departing on Jan 02, 2027 on the Valiant Lady
Nights: 7
Dates: Jan 02, 2027 through Jan 09, 2027
Ship: Valiant Lady
Itinerary:
San Juan, Tortola, Sailing, Bridgetown, Castries, St. John's, Philipsburg, San Juan
Set out from San Juan on this epic 7-night voyage to some of the Caribbean's most beautiful islands. Start in Road Town, the capital of Tortola in the British Virgin Islands, where you can visit local rum distilleries, or relax at Cane Garden Bay Beach. Then complete your whirlwind Caribbean tour by heading to Barbados, St. Lucia, Antigua, and St. Maarten.
from
$1,182.00
(USD)
Per Person
More Details Contact Us
Inside
$1,182.00
Cat: IZ
$168.86/Night
Outside
$1,392.00
Cat: VZ
$198.86/Night
Balcony
$1,602.00
Cat: TZ
$228.86/Night
Suite
$4,374.00
Cat: SS
$624.86/Night
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
Itinerary:
Miami, Key West, Bimini Islands, Miami
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
$801.00
(USD)
Per Person
More Details Contact Us
Inside
$801.00
Cat: IN
$200.25/Night
Outside
$981.00
Cat: VW
$245.25/Night
Balcony
$877.00
Cat: TZ
$219.25/Night
Suite
$1,996.00
Cat: RZ
$499.00/Night
Amenity Departure Dates
Bimini 1
Virgin Voyages Logo
Scarlet Caribbean Holidays
Departing on Dec 21, 2026 on the Scarlet Lady
Nights: 5
Dates: Dec 21, 2026 through Dec 26, 2026
Ship: Scarlet Lady
Itinerary:
Miami, Florida, Sailing, Cozumel (Playa Del Carmen), Sailing, Beach Club at Bimini, Miami, Florida
This 5-night Holiday excursion departs from Miami and spends a day sailing to the most quintessential location for a "holiday in the sun," Cozumel, Mexico. After basking on the white-sand beaches and exploring the miles-long Meso-American barrier reef, you'll spend a day of self-care on board sailing to our private Beach Club at Bimini before returning to your final destination of Miami.
from
$996.00
(USD)
Per Person
More Details Contact Us
Inside
$996.00
Cat: IZ
$199.20/Night
Outside
$1,096.00
Cat: VZ
$219.20/Night
Balcony
$1,245.00
Cat: TZ
$249.00/Night
Suite
$3,200.00
Cat: SS
$640.00/Night
Offer Image
Pleasant Holidays Logo
Alila Napa Valley - Adults Only Hotel Rating: 5 stars
Nights: 3
Dates: Oct 19, 2025 through Oct 22, 2025
Location(s):
St. Helena
Whisk away to the lavish Alila Napa Valley Hotel & Spa and experience luxury at its finest. This adult-only oasis is filled with mesmerizing views and rustic charm.
from
$1,295.33
(USD)
Per Person
More Details Contact Us
Caribbean Breeze Haunted Seas
Virgin Voyages Logo
Valiant's Haunted Halloween Soirée
Departing on Oct 31, 2026 on the Valiant Lady
Nights: 7
Dates: Oct 31, 2026 through Nov 07, 2026
Ship: Valiant Lady
Itinerary:
San Juan, Willemstad, Oranjestad, Fort-de-France, Basseterre, San Juan
This spooky season sailing spends a day sailing from San Juan to Willemstad, nestled onto the picturesque shores of Curaçao, followed by the iridescent turquoise waters of nearby Oranjestad, Aruba. From there, you'll sail another day to Fort-de-France, Martinique followed by Basseterre, St. Kitts and Nevis, where you'll be greeted by warm locals & white sand beaches before returning to San Juan.
from
$1,254.00
(USD)
Per Person
More Details Contact Us
Inside
$1,254.00
Cat: IZ
$179.14/Night
Outside
$1,464.00
Cat: VZ
$209.14/Night
Balcony
$1,673.00
Cat: TZ
$239.00/Night
Suite
$4,305.00
Cat: SS
$615.00/Night
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
Itinerary:
San Juan, Tortola, Sailing, Puerto Plata, Sailing, Charleston, South Carolina, Sailing, Newport, Rhode Island, New York City, New York
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
Offer Image
Pleasant Holidays Logo
Secrets Cap Cana Resort & Spa Hotel Rating: 4.5 stars
Nights: 3
Dates: Oct 19, 2025 through Oct 22, 2025
Location(s):
Punta Cana
This gorgeous resort in Cap Cana is just steps from the sugar-sand Juanillo Beach and crystal blue waters.
from
$519.33
(USD)
Per Person
More Details Contact Us
Quaint Castries to Elegant Antigua
Virgin Voyages Logo
Quaint Castries to Elegant Antigua
Departing on Mar 07, 2026 on the Valiant Lady
Nights: 7
Dates: Mar 07, 2026 through Mar 14, 2026
Ship: Valiant Lady
Itinerary:
San Juan, Basseterre, Sailing, Castries, Fort-de-France, St. John's, Tortola, San Juan
This 7-night voyage starts in San Juan and makes its first stop in St. Kitts before sailing to St. Lucia's tropical capital, Castries, then the stylish French isle of Martinique. Next, you'll experience the epitome of beach luxury in St. Johns, Antigua, followed by Tortola - arguably the most thrilling of the British Virgin Islands to soak up the sun before returning to San Juan.
from
$834.00
(USD)
Per Person
More Details Contact Us
Inside
$834.00
Cat: IZ
$119.14/Night
Outside
$1,113.00
Cat: VZ
$159.00/Night
Balcony
$1,323.00
Cat: TZ
$189.00/Night
Suite
$3,675.00
Cat: SS
$525.00/Night
Offer Image
Pleasant Holidays Logo
Ocean Riviera Paradise El Beso Hotel Rating: 4 stars
Nights: 3
Dates: Oct 16, 2025 through Oct 19, 2025
Location(s):
Playa Del Carmen
The Ocean Riviera Paradise El Beso is an exclusive adults-only area of the Ocean Riviera Paradise, perfect for a romantic getaway or a gathering of friends.
from
$292.00
(USD)
Per Person
More Details Contact Us
Dominican Daze 2
Virgin Voyages Logo
Dominican Daze
Departing on Sep 28, 2026 on the Resilient Lady
Nights: 5
Dates: Sep 28, 2026 through Oct 03, 2026
Itinerary:
Miami, Sailing, Puerto Plata, Sailing, Beach Club at Bimini, Miami
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
$745.00
(USD)
Per Person
More Details Contact Us
Inside
$745.00
Cat: IZ
$149.00/Night
Outside
$845.00
Cat: VZ
$169.00/Night
Balcony
$996.00
Cat: TZ
$199.20/Night
Suite
$2,700.00
Cat: SS
$540.00/Night
San Juan Sunrises Dominican Dreams
Virgin Voyages Logo
San Juan Sunrises & Dominican Dreams
Departing on Jan 31, 2026 on the Resilient Lady
Nights: 7
Dates: Jan 31, 2026 through Feb 07, 2026
Itinerary:
Miami, Sailing, San Juan, Puerto Plata, Sailing, Beach Club at Bimini, Miami
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
$833.00
(USD)
Per Person
More Details Contact Us
Inside
$833.00
Cat: IZ
$119.00/Night
Outside
$1,113.00
Cat: VZ
$159.00/Night
Balcony
$1,323.00
Cat: TZ
$189.00/Night
Suite
$3,283.00
Cat: RZ
$469.00/Night
Offer Image
Pleasant Holidays Logo
Hilton Playa del Carmen Hotel Rating: 4.5 stars
Nights: 3
Dates: Oct 16, 2025 through Oct 19, 2025
Location(s):
Playa Del Carmen
This luxurious all-inclusive resort offers adults an outstanding beachfront location in Playa del Carmen.
from
$356.00
(USD)
Per Person
More Details Contact Us
French Daze Ibiza Nights
Virgin Voyages Logo
Portsmouth to Lisbon, Casablanca & Spain
Departing on Sep 12, 2025 on the Scarlet Lady
Nights: 13
Dates: Sep 12, 2025 through Sep 25, 2025
Ship: Scarlet Lady
Itinerary:
Portsmouth, Sailing, La Coruna, Lisbon, Sailing, Casablanca, Sailing, Malaga, Sailing, Ibiza, Barcelona
This 13-night impressive excursion departs from Portsmouth and spends two days sailing to La Coruña. Then spend two days in Lisbon before heading to Casablanca.
from
$2,197.00
(USD)
Per Person
More Details Contact Us
Outside
$2,405.00
Cat: VW
$185.00/Night
Balcony
$2,197.00
Cat: TZ
$169.00/Night
Suite
$5,717.00
Cat: RZ
$439.77/Night
Bimini 1
Virgin Voyages Logo
Fire and Sunset Soirees
Departing on Nov 05, 2026 on the Scarlet Lady
Nights: 4
Dates: Nov 05, 2026 through Nov 09, 2026
Ship: Scarlet Lady
Itinerary:
Miami, Florida, Key West, Florida, Sailing, Beach Club at Bimini, Miami, Florida
Cruise from vibrant Miami to Key West 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
$697.00
(USD)
Per Person
More Details Contact Us
Inside
$697.00
Cat: IZ
$174.25/Night
Outside
$776.00
Cat: VZ
$194.00/Night
Balcony
$897.00
Cat: TZ
$224.25/Night
Suite
$2,090.00
Cat: SS
$522.50/Night
Offer Image
Pleasant Holidays Logo
Barcelo Maya Riviera Hotel Rating: 4.5 stars
Nights: 3
Dates: Oct 16, 2025 through Oct 19, 2025
Location(s):
Solidaridad
Surrounded by sea and nature is Barcelo Maya Riviera - Adults Only, a 1.2-mile beachfront all-inclusive hotel.
from
$358.67
(USD)
Per Person
More Details Contact Us
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