Carefree Vacations
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Special Interest - Adults Only

(50 offers included)
Caribbean
Virgin Voyages Logo
The Semi-Annual Sale: Rates from $99*
Dates: Apr 26, 2026 through Oct 31, 2027
Itinerary:
USA, Europe, Caribbean
For a limited time, our Semi-Annual Sale unlocks sailings from just $99 per Sailor per night across destinations worldwide.
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Take Your Sweetie To Tahiti
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Take Your Sweetie to Tahiti
Dates: Mar 02, 2026 through Dec 31, 2026
Itinerary:
Tahiti, Tuamotus, Cook Islands, Marquesas Islands
Limited-Time Offer: Enjoy $1,000 Shipboard Credit, Champagne & Chocolate Treat
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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
$695.00
(USD)
Per Person
More Details Contact Us
Inside
$695.00
Cat: IZ
$139.00/Night
Outside
$795.00
Cat: VZ
$159.00/Night
Balcony
$945.00
Cat: TZ
$189.00/Night
Suite
$7,225.00
Cat: SM
$1,445.00/Night
Amenity Departure Dates
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Grand Velas Boutique Hotel Los Cabos Hotel Rating: 5 stars
Nights: 3
Dates: through
Location(s):
San Jose del Cabo
The Grand Velas Boutique Hotel Los Cabos is a luxury all-inclusive, adults only experience. Located within the prestigious Tourist Corridor of Los Cabos, this property is close to several outdoor and water activities, as well as its neighboring sister property, The Grand Velas Los Cabos, to which guests will also have access.
from
$1,626.00
(USD)
Per Person
More Details Contact Us
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Sandals Barbados Hotel Rating: No Rating
Nights: 3
Dates: through
Location(s):
St. Lawrence
Located at the bottom of the famed St. Lawrence Gap. Sandals Barbados offers luxury with inventive accommodations spanning three unique villages, featuring everything from ocean views, Butler Elite service to private tranquility soaking tubs on most patios and terraces and world-class cuisine with international appeal, including a festive Indian cuisine restaurant.
from
$901.00
(USD)
Per Person
More Details Contact Us
Southern Caribbean Cruise
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Southern Caribbean Cruise
Departing on Jan 29, 2028 on the Scarlet Lady
Nights: 7
Dates: Jan 29, 2028 through Feb 05, 2028
Ship: Scarlet Lady
Itinerary:
San Juan, Philipsburg, Barbados, St. Lucia, Antigua, Tortola Island, San Juan
This 7-night voyage from San Juan sails to some of the Caribbean's most stunning islands, including Barbados, St. Lucia, and Tortola.
from
$763.00
(USD)
Per Person
+ $275.00 taxes/fees
More Details Contact Us
Inside
$763.00
Cat: IZ
$109.00/Night
Outside
$903.00
Cat: VZ
$129.00/Night
Balcony
$1,253.00
Cat: TZ
$179.00/Night
Suite
$3,850.00
Cat: SS
$550.00/Night
Offer Image
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Secrets Mirabel Cancun Resort & Spa Hotel Rating: 4 stars
Nights: 3
Dates: through
Location(s):
Cancun
Whisk away to luxury at the adults-only, oceanfront Secrets Mirabel Cancun Resort & Spa and enjoy Unlimited-Luxury® experiences.
from
$365.67
(USD)
Per Person
More Details Contact Us
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Sandals Regency La Toc Hotel Rating: No Rating
Nights: 3
Dates: through
Location(s):
Castries
Set amidst 210 lush acres on a half-mile crescent shaped beach, this spectacular 331-room resort offers a 9-hole golf course, eight restaurants and eight bars.
from
$750.00
(USD)
Per Person
More Details Contact Us
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Shore Excursions Group Logo
Luxe Wine Tasting And Panoramic Split For Adults Only
Dates: Jan 09, 2025 through Apr 23, 2028
Location(s):
Split
Discover Croatia's rich flavors and breathtaking sights on our exclusive, adult-only tour. Starting at your cruise port, we embark on an enchanting drive to the picturesque town of Kastel, filled with panoramic views of Split.
from
$305.00
(USD)
Per Person
More Details Contact Us
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Paradisus La Perla Adults Only - Riviera Maya Hotel Rating: 4.5 stars
Nights: 3
Dates: through
Location(s):
Playa Del Carmen
Discover indulgent luxury on a private bay at this adults-only, all-inclusive resort. A preserved mangrove and ecosystem surround this lovely resort.
from
$455.67
(USD)
Per Person
More Details Contact Us
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Marival Armony Luxury Resort & World Spa Hotel Rating: 4 stars
Nights: 3
Dates: through
Location(s):
Punta Mita
Discover the perfect balance between luxury and nature ("armony") at the brand new all-inclusive Marival® Armony Luxury Resort & Suites.
from
$458.00
(USD)
Per Person
More Details Contact Us
Amalfi Coast, Cannes & Ibiza
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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
$738.00
(USD)
Per Person
More Details Contact Us
Inside
$738.00
Cat: IZ
$123.00/Night
Outside
$918.00
Cat: VZ
$153.00/Night
Balcony
$1,038.00
Cat: TZ
$173.00/Night
Palma de Mallorca
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Spanish Serenity to French Daydreams
Departing on Jun 14, 2026 on the Valiant Lady
Nights: 7
Dates: Jun 14, 2026 through Jun 21, 2026
Ship: Valiant Lady
Itinerary:
Barcelona, Valencia, Palma de Mallorca, Sailing, Cannes, Ibiza, Barcelona
This 7-night sultry sojourn departs from Barcelona and arrives first in Valencia, followed by a day at sea sailing to Palma de Mallorca. Next, spend a day sailing to Cannes, where you'll experience the unparalleled luxury of the French Riviera before spending two nights basking in the sun & dancing under the moon in Ibiza before finally returning to Barcelona.
from
$723.00
(USD)
Per Person
More Details Contact Us
Inside
$723.00
Cat: IZ
$103.29/Night
Outside
$863.00
Cat: VZ
$123.29/Night
Balcony
$1,073.00
Cat: TZ
$153.29/Night
Suite
$3,213.00
Cat: RZ
$459.00/Night
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Wyndham Alltra Playa del Carmen Adults Only All Inclusive Hotel Rating: 3.5 stars
Nights: 3
Dates: through
Location(s):
Playa Del Carmen
In the heart of the Riviera Maya, Wyndham Alltra Playa del Carmen provides guests with a sun-kissed beach backdrop to relish unexpected delights, enjoy genuine hospitality, and explore the region's vibrant city center, just steps away.
from
$358.67
(USD)
Per Person
More Details Contact Us
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Secrets Akumal Riviera Maya Hotel Rating: 4.5 stars
Nights: 3
Dates: through
Location(s):
Akumal
Ideally located in the heart of the Riviera Maya along the white-sand beaches and calm, clear waters of Akumal, this stunning resort offers adults a charming, picturesque escape complete with an exceptional luxury experience.
from
$568.67
(USD)
Per Person
More Details Contact Us
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Bahia Principe Luxury Sian Kaan Hotel Rating: 4 stars
Nights: 3
Dates: through
Location(s):
Riviera Maya
Sian Ka'an: the origin of the sky, as referred to by the ancient Mayan. This is the best way to describe the Caribbean celestial soul where its minimalist decoration reach perfection in the jungle effervescence of the Riviera Maya and the iridescent waters that bathe it.
from
$268.00
(USD)
Per Person
More Details Contact Us
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Secrets St. Lucia Resort & Spa Hotel Rating: 4.5 stars
Nights: 3
Dates: through
Location(s):
Saint Lucia
Boasting a beachfront location and panoramic views, Secrets St. Lucia Resort & Spa offers a luxury retreat with world-class amenities.
from
$862.67
(USD)
Per Person
More Details Contact Us
Western Caribbean & Bimini Beach Club
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Western Caribbean & Bimini Beach Club
Departing on Jan 09, 2028 on the Resilient Lady
Nights: 7
Dates: Jan 09, 2028 through Jan 16, 2028
Itinerary:
Miami, Key West, Ocho Rios, George Town, Bimini Islands, Miami
This 7-night voyage departs from Miami, beginning with the laid-back charm of Key West before a relaxing day at sea leads you to the lush beauty of Ocho Rios and the turquoise waters of George Town.
from
$833.00
(USD)
Per Person
+ $260.00 taxes/fees
More Details Contact Us
Inside
$833.00
Cat: IZ
$119.00/Night
Outside
$1,043.00
Cat: VZ
$149.00/Night
Balcony
$1,253.00
Cat: TZ
$179.00/Night
Suite
$3,500.00
Cat: SS
$500.00/Night
Offer Image
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Couples Sans Souci Hotel Rating: 4.5 stars
Nights: 3
Dates: through
Location(s):
Ocho Rios
Couples Sans Souci blends old world glamour with modern style. Tucked between into a hillside overlooking the Caribbean sea, this hidden beachfront gem exudes a sense of solitude and intimacy.
from
$508.67
(USD)
Per Person
More Details Contact Us
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Atelier Playa Mujeres Hotel Rating: 4.5 stars
Nights: 3
Dates: through
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
$745.67
(USD)
Per Person
More Details Contact Us
Eastern Caribbean & Bimini Beach Club
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Eastern Caribbean & Bimini Beach Club
Departing on Mar 11, 2028 on the Resilient Lady
Nights: 8
Dates: Mar 11, 2028 through Mar 19, 2028
Itinerary:
Miami, Puerto Plata, San Juan, St. Croix, Bimini Islands, Miami
This 8-night epic Caribbean sojourn departing from Miami spends a day sailing to your first respite, Puerto Plata.
from
$1,032.00
(USD)
Per Person
More Details Contact Us
Inside
$1,032.00
Cat: IZ
$129.00/Night
Outside
$1,272.00
Cat: VZ
$159.00/Night
Balcony
$1,512.00
Cat: TZ
$189.00/Night
Suite
$3,920.00
Cat: SS
$490.00/Night
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Secrets Riviera Cancun Resort & Spa Hotel Rating: 4.5 stars
Nights: 3
Dates: through
Location(s):
Puerto Morelos
Secrets® Riviera Cancun Resort & Spa is an all-suite luxury resort nestled between the Caribbean Sea and the Lagoon of Bahia Petempich.
from
$462.33
(USD)
Per Person
More Details Contact Us
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Temptation Cancun Resort Hotel Rating: 3.5 stars
Nights: 3
Dates: through
Location(s):
Cancun
A one-of-a-kind "playground for grown-ups," this chic, trendy, all-inclusive resort caters to the uninhibited traveler, who seeks adventurous daytime activities, trendy evening shows and performances, theme parties, fine dining, endless entertainment options, and first class accommodations.
from
$498.67
(USD)
Per Person
More Details Contact Us
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Alaska: Glaciers & More
Departing on Aug 12, 2027 on the Brilliant Lady
Nights: 12
Dates: Aug 12, 2027 through Aug 24, 2027
Itinerary:
Seattle, Inside Passage, Ketchikan, Sitka, Hubbard Glacier, Skagway, Haines, Juneau, Icy Strait, Victoria, Seattle
This 12-night adventure departs from Seattle, winding through the serene Inside Passage before reaching Ketchikan and the historic port of Sitka.
from
$1,902.00
(USD)
Per Person
More Details Contact Us
Inside
$1,902.00
Cat: IN
$158.50/Night
Outside
$2,029.00
Cat: VZ
$169.08/Night
Balcony
$2,748.00
Cat: TZ
$229.00/Night
Suite
$7,080.00
Cat: SS
$590.00/Night
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Myconian Naia - Preferred Hotels & Resorts Hotel Rating: 5 stars
Nights: 3
Dates: through
Location(s):
Mykonos
Perched atop a hill with expansive views of the island and cerulean waters of the Aegean, Myconian Naia - Preferred Hotels & Resorts sets a new standard for refined luxury.
from
$752.00
(USD)
Per Person
More Details Contact Us
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Panama Canal: LA to Miami Halloween
Departing on Oct 29, 2026 on the Brilliant Lady
Nights: 17
Dates: Oct 29, 2026 through Nov 15, 2026
Itinerary:
Los Angeles, Cabo San Lucas, Puerto Quetzal, Puntarenas, Panama City, Cartagena, 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.
from
$1,683.00
(USD)
Per Person
More Details Contact Us
Inside
$1,683.00
Cat: IZ
$99.00/Night
Outside
$2,023.00
Cat: VZ
$119.00/Night
Balcony
$2,193.00
Cat: TZ
$129.00/Night
Suite
$9,503.00
Cat: RZ
$559.00/Night
Bimini Beach Club Cruise
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Bimini Beach Club Cruise
Departing on Jan 04, 2028 on the Brilliant Lady
Nights: 3
Dates: Jan 04, 2028 through Jan 07, 2028
Itinerary:
Miami, Bimini Islands, Miami
This 3-night voyage departs from vibrant Miami and spends a day sailing to the serene shores of Bimini, where you can relax at the exclusive Beach Club at Bimini, bask in the sun, and enjoy crafted cocktails before returning to your final destination of Miami.
from
$357.00
(USD)
Per Person
More Details Contact Us
Inside
$357.00
Cat: IZ
$119.00/Night
Outside
$417.00
Cat: VZ
$139.00/Night
Balcony
$507.00
Cat: TZ
$169.00/Night
Suite
$1,850.00
Cat: SS
$616.67/Night
Offer Image
Virgin Voyages Logo
Alaska: Inside Passage & Glacial Fjords
Departing on Jun 04, 2026 on the Brilliant Lady
Nights: 7
Dates: Jun 04, 2026 through Jun 11, 2026
Itinerary:
Seattle, Ketchikan, Sitka, Prince Rupert, Seattle
This 7-night odyssey departs from Seattle and cruises up the picturesque Inside Passage to Ketchikan, a quaint village nestled amongst the Tongass National Forest.
from
$1,114.00
(USD)
Per Person
More Details Contact Us
Inside
$1,114.00
Cat: IZ
$159.14/Night
Outside
$1,393.00
Cat: VZ
$199.00/Night
Balcony
$1,813.00
Cat: TZ
$259.00/Night
Suite
$7,133.00
Cat: MZ
$1,019.00/Night
Offer Image
Pleasant Holidays Logo
Live Aqua Beach Resort Cancun Hotel Rating: 4.5 stars
Nights: 3
Dates: through
Location(s):
Cancun
This adults-only, all-inclusive resort is set beachfront in the lively Cancun. Accommodations include 371 contemporary rooms and suites.
from
$502.33
(USD)
Per Person
More Details Contact Us
Key West & Bimini New Year's Cruise
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Key West & Bimini New Year's Cruise
Departing on Dec 30, 2027 on the Valiant Lady
Nights: 4
Dates: Dec 30, 2027 through Jan 03, 2028
Ship: Valiant Lady
Itinerary:
Miami, Key West, Bimini Islands, Miami
This New Year's getaway departs from Miami, with your first stop in vibrant Key West.
from
$956.00
(USD)
Per Person
+ $206.00 taxes/fees
More Details Contact Us
Inside
$956.00
Cat: IZ
$239.00/Night
Outside
$1,076.00
Cat: VZ
$269.00/Night
Balcony
$1,236.00
Cat: TZ
$309.00/Night
Suite
$2,900.00
Cat: SS
$725.00/Night
Western Caribbean & Bimini Beach Club
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Western Caribbean & Bimini Beach Club
Departing on Dec 13, 2026 on the Resilient Lady
Nights: 6
Dates: Dec 13, 2026 through Dec 19, 2026
Itinerary:
Miami, Bimini Islands, Ocho Rios, George Town, Miami
This 6-night voyage departs from Miami, sailing first to the Beach Club at Bimini for a day of sun and celebration before a relaxing day at sea.
from
$774.00
(USD)
Per Person
More Details Contact Us
Inside
$774.00
Cat: IZ
$129.00/Night
Outside
$834.00
Cat: VZ
$139.00/Night
Balcony
$1,014.00
Cat: TZ
$169.00/Night
Suite
$2,454.00
Cat: RZ
$409.00/Night
Offer Image
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Couples Tower Isle Hotel Rating: 4.5 stars
Nights: 3
Dates: through
Location(s):
Ocho Rios
Blending breezy island-chic with Jamaica's flair for elegance and sophistication, Couples Tower Isle is Couples' flagship retreat on the lush coastline of Ocho Rios.
from
$395.33
(USD)
Per Person
More Details Contact Us
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Pacific Coastal: Vancouver to LA
Departing on Sep 10, 2027 on the Brilliant Lady
Nights: 8
Dates: Sep 10, 2027 through Sep 18, 2027
Itinerary:
Vancouver, San Francisco, Santa Barbara, Catalina Island, San Diego, Los Angeles
This 8-night voyage departs from Vancouver, British Columbia late in the evening affording you the opportunity to explore this storied city.
from
$873.00
(USD)
Per Person
+ $338.00 taxes/fees
More Details Contact Us
Inside
$873.00
Cat: IZ
$109.13/Night
Outside
$1,033.00
Cat: VZ
$129.13/Night
Balcony
$1,193.00
Cat: TZ
$149.13/Night
Suite
$4,800.00
Cat: SS
$600.00/Night
Southern Caribbean Cruise
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Southern Caribbean Cruise
Departing on Nov 27, 2027 on the Scarlet Lady
Nights: 7
Dates: Nov 27, 2027 through Dec 04, 2027
Ship: Scarlet Lady
Itinerary:
San Juan, St. Thomas, Tortola Island, St. Kitts, Antigua, 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.
from
$763.00
(USD)
Per Person
+ $229.00 taxes/fees
More Details Contact Us
Inside
$763.00
Cat: IZ
$109.00/Night
Outside
$903.00
Cat: VZ
$129.00/Night
Balcony
$1,237.00
Cat: TL
$176.71/Night
Suite
$3,850.00
Cat: SS
$550.00/Night
Le Blanc Spa Resort
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Le Blanc Spa Resort Hotel Rating: 5 stars
Nights: 3
Dates: through
Location(s):
Cancun
The height of all-inclusive luxury is just above sea level at Le Blanc Spa Resort Cancun, a AAA Five-Diamond adults-only oasis.
from
$697.67
(USD)
Per Person
More Details Contact Us
Italy to France & Spain Rome Image
Virgin Voyages Logo
Total Eclipse of the (Med)
Departing on Aug 10, 2026 on the Scarlet Lady
Nights: 12
Dates: Aug 10, 2026 through Aug 22, 2026
Ship: Scarlet Lady
Itinerary:
Barcelona, Palma de Mallorca, Sailing, Ibiza, Sailing, Cannes, Ajaccio, Corsica, La Spezia, Sailing, Amalfi Coast (Salerno), Catania, Sicily, Sailing, Civitavecchia (Rome)
This 12-night one-way voyage from Barcelona to Rome brings you to Mallorca, Ibiza, Cannes, Corsica, La Spezia, the Amalfi Coast, and Sicily. One minute you'll be partying it up in Ibiza, the next you'll be living the glamorous Hollywood lifestyle in Cannes, or walking in the footsteps of emperors in Rome - all under the magical, mysterious glow of the epic solar eclipse.
from
$2,433.00
(USD)
Per Person
More Details Contact Us
Inside
$2,433.00
Cat: IZ
$202.75/Night
Outside
$2,673.00
Cat: VZ
$222.75/Night
Balcony
$2,913.00
Cat: TZ
$242.75/Night
Suite
$8,160.00
Cat: SS
$680.00/Night
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
$1,089.00
(USD)
Per Person
More Details Contact Us
Inside
$1,089.00
Cat: IZ
$99.00/Night
Outside
$1,309.00
Cat: VZ
$119.00/Night
Balcony
$1,639.00
Cat: TZ
$149.00/Night
Suite
$4,287.00
Cat: RZ
$389.73/Night
Amenity Departure Dates
Offer Image
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New York to Bermuda (& Back)
Departing on Oct 07, 2026 on the Valiant Lady
Nights: 6
Dates: Oct 07, 2026 through Oct 13, 2026
Ship: Valiant Lady
Itinerary:
New York City, Bermuda, New York City
This 6-night escape departs from New York, giving you two blissful days at sea to unwind before arriving at the pink sand shores of Bermuda.
from
$594.00
(USD)
Per Person
More Details Contact Us
Inside
$594.00
Cat: IZ
$99.00/Night
Outside
$774.00
Cat: VZ
$129.00/Night
Balcony
$894.00
Cat: TZ
$149.00/Night
Suite
$3,150.00
Cat: SS
$525.00/Night
Southern Caribbean Cruise
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Southern Caribbean Cruise
Departing on Jan 02, 2028 on the Scarlet Lady
Nights: 6
Dates: Jan 02, 2028 through Jan 08, 2028
Ship: Scarlet Lady
Itinerary:
San Juan, Tortola Island, St. Kitts, Antigua, St. Lucia, San Juan
This 6-night voyage departs from San Juan, arriving the next day in Tortola, British Virgin Islands.
from
$654.00
(USD)
Per Person
More Details Contact Us
Inside
$654.00
Cat: IZ
$109.00/Night
Outside
$774.00
Cat: VZ
$129.00/Night
Balcony
$1,074.00
Cat: TZ
$179.00/Night
Suite
$3,300.00
Cat: SS
$550.00/Night
Greece, Turkey & Mykonos Overnight
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Greek Isles & Mykonos Overnight
Departing on Aug 01, 2027 on the Scarlet Lady
Nights: 7
Dates: Aug 01, 2027 through Aug 08, 2027
Ship: Scarlet Lady
Itinerary:
Athens, Bodrum, Rhodes Island, Mykonos, Santorini, Athens
Sail from Athens to the most idyllic Greek Isles in the Med - like Bodrum (Turkey), Rhodes, and Santorini.
from
$1,323.00
(USD)
Per Person
+ $342.00 taxes/fees
More Details Contact Us
Inside
$1,323.00
Cat: IZ
$189.00/Night
Outside
$1,533.00
Cat: VZ
$219.00/Night
Balcony
$1,674.00
Cat: TZ
$239.14/Night
Suite
$4,620.00
Cat: SS
$660.00/Night
Offer Image
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The House by Elegant Hotels Hotel Rating: 4.5 stars
Nights: 3
Dates: through
Location(s):
St. James
Overlooking the Caribbean Sea, this award-winning adults-only retreat is designed with romance in mind.
from
$902.33
(USD)
Per Person
More Details Contact Us
Greek Isle Days & Istanbul Nights
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Greek Isle Days & Istanbul Nights
Departing on Jul 21, 2027 on the Scarlet Lady
Nights: 11
Dates: Jul 21, 2027 through Aug 01, 2027
Ship: Scarlet Lady
Itinerary:
Athens, Chania, Rhodes Island, Mykonos, Ephesus, Istanbul, Santorini, Athens
Depart from Athens, arriving the next day in charming Chania, followed by a day of meandering the streets of Rhodes, then mystical Mykonos.
from
$2,080.00
(USD)
Per Person
More Details Contact Us
Inside
$2,080.00
Cat: IZ
$189.09/Night
Outside
$2,299.00
Cat: VZ
$209.00/Night
Balcony
$2,629.00
Cat: TZ
$239.00/Night
Suite
$7,150.00
Cat: SS
$650.00/Night
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Pleasant Holidays Logo
Barcelo Maya Riviera Hotel Rating: 4.5 stars
Nights: 3
Dates: through
Location(s):
Solidaridad
Surrounded by sea and nature is Barcelo Maya Riviera - Adults Only, a 1.2-mile beachfront all-inclusive hotel.
from
$395.00
(USD)
Per Person
More Details Contact Us
Mayan Sol 1
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Mayan Sol
Departing on Jun 22, 2026 on the Resilient Lady
Nights: 5
Dates: Jun 22, 2026 through Jun 27, 2026
Itinerary:
Miami, Florida, Sailing, Costa Maya, Sailing, Beach Club at Bimini, Miami, Florida
Sail from Miami to the shores of the Yucatán Peninsula, with a day spent at The Beach Club in Bimini, Bahamas. Arriving in Costa Maya, you'll have plenty of time to relax by the beach and explore the ancient ruins.
from
$795.00
(USD)
Per Person
More Details Contact Us
Inside
$795.00
Cat: IZ
$159.00/Night
Outside
$895.00
Cat: VZ
$179.00/Night
Balcony
$995.00
Cat: TZ
$199.00/Night
Suite
$2,345.00
Cat: RZ
$469.00/Night
Amenity Departure Dates
Caribbean Breeze Haunted Seas
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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
Itinerary:
Miami, Florida, Sailing, Cozumel (Playa del Carmen), Sailing, Beach Club at Bimini, Miami, Florida
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
$747.00
(USD)
Per Person
More Details Contact Us
Inside
$747.00
Cat: IN
$149.40/Night
Outside
$845.00
Cat: VZ
$169.00/Night
Balcony
$945.00
Cat: TZ
$189.00/Night
Suite
$2,445.00
Cat: RZ
$489.00/Night
Amenity Departure Dates
Holidaze and Nights 1
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Sunny Miles of Tropical Isles
Departing on Jan 16, 2027 on the Valiant Lady
Nights: 7
Dates: Jan 16, 2027 through Jan 23, 2027
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
$1,043.00
(USD)
Per Person
More Details Contact Us
Inside
$1,043.00
Cat: IZ
$149.00/Night
Outside
$1,113.00
Cat: VZ
$159.00/Night
Balcony
$1,323.00
Cat: TZ
$189.00/Night
Suite
$2,863.00
Cat: RZ
$409.00/Night
Amenity Departure Dates
Western Caribbean & Bimini Beach Club
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Western Caribbean & Bimini Beach Club
Departing on Jan 23, 2028 on the Resilient Lady
Nights: 6
Dates: Jan 23, 2028 through Jan 29, 2028
Itinerary:
Miami, Ocho Rios, George Town, Bimini Islands, Miami
This 6-night Western Caribbean adventure sets sail from Miami and spends one day at sea on your way to a nature lover's haven: Ocho Rios, Jamaica.
from
$714.00
(USD)
Per Person
More Details Contact Us
Inside
$714.00
Cat: IZ
$119.00/Night
Outside
$894.00
Cat: VZ
$149.00/Night
Balcony
$1,074.00
Cat: TZ
$179.00/Night
Suite
$3,000.00
Cat: SS
$500.00/Night
Brilliant New Years Ahoy
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Brilliant New Year's Ahoy!
Departing on Dec 28, 2026 on the Brilliant Lady
Nights: 10
Dates: Dec 28, 2026 through Jan 07, 2027
Itinerary:
Miami, Florida, Sailing, Philipsburg, St. Maarten, Basseterre, Tortola, St. John's, Sailing, Beach Club at Bimini, Miami, Florida
Depart Miami and sail 2 days to the bounding beaches (& beach bars) of Philipsburg, Saint Maarten. The next day ring in the New Year surrounded by the iridescent waters and flawless vibes of Basseterre, St. Kitts, followed by Tortola, British Virgin Islands then the world-renowned paradise oasis of St. John's, Antigua. Sail 2 more days to the private Beach Club at Bimini before returning to Miami.
from
$2,387.00
(USD)
Per Person
More Details Contact Us
Inside
$2,387.00
Cat: IN
$238.70/Night
Outside
$2,490.00
Cat: VZ
$249.00/Night
Balcony
$2,791.00
Cat: TZ
$279.10/Night
Suite
$5,942.00
Cat: RZ
$594.20/Night
Med Coastal Medley: Athens to Barcelona
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Med Coastal Medley: Athens to Barcelona
Departing on Oct 24, 2027 on the Scarlet Lady
Nights: 7
Dates: Oct 24, 2027 through Oct 31, 2027
Ship: Scarlet Lady
Itinerary:
Athens, Mykonos, Salerno, Cannes, Barcelona
Set sail from Athens to your first stop in the sun-soaked charm and blue-door dotted wonder of Mykonos.
from
$1,253.00
(USD)
Per Person
More Details Contact Us
Inside
$1,253.00
Cat: IZ
$179.00/Night
Outside
$1,394.00
Cat: VZ
$199.14/Night
Balcony
$1,604.00
Cat: TZ
$229.14/Night
Suite
$4,620.00
Cat: SS
$660.00/Night
Starry Nights in Greece & Croatia
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Starry Nights in Greece & Croatia
Departing on Jun 14, 2026 on the Scarlet Lady
Nights: 10
Dates: Jun 14, 2026 through Jun 24, 2026
Ship: Scarlet Lady
Itinerary:
Athens, Santorini, Bodrum, Mykonos, Dubrovnik, Kotor, Corfu, Athens
Our 10-night sailing from Athens is the dreamiest voyage for any explorer - whether snapping photos in breathtaking Santorini, snorkeling the blue-green waters of Dubrovnik, cocktail-ladened merriment at a world-renowned beach club in Mykonos, or experiencing beguiling Bodrum - where dazzling waters are perfectly paired with unbelievable views and world-class cuisine.
from
$1,190.00
(USD)
Per Person
More Details Contact Us
Inside
$1,190.00
Cat: IZ
$119.00/Night
Outside
$1,490.00
Cat: VZ
$149.00/Night
Balcony
$1,690.00
Cat: TZ
$169.00/Night
Suite
$5,690.00
Cat: RZ
$569.00/Night