Special Interest - Adults Only

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

$1,043.00

(USD)

Per Person

+ $0.00 taxes/fees

More Details Contact Us

Inside

$1,043.00

Cat: IZ

$149.00/Night

Outside

$1,253.00

Cat: VZ

$179.00/Night

Balcony

$1,463.00

Cat: TZ

$209.00/Night

Suite

$4,053.00

Cat: SS

$579.00/Night

80% Off 2nd Sailor Plus Up To $300 in free drinks

Valiant New Year's Ahoy!

Departing on Dec 27, 2025 on the Valiant Lady

Nights: 7

Dates: Dec 27, 2025 through Jan 03, 2026

Ship: Valiant Lady

Itinerary:

San Juan, Philipsburg, 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.

from

$1,884.00

(USD)

Per Person

+ $0.00 taxes/fees

More Details Contact Us

Inside

$1,884.00

Cat: IZ

$269.14/Night

Outside

$2,094.00

Cat: VZ

$299.14/Night

Balcony

$2,304.00

Cat: TZ

$329.14/Night

Suite

$5,777.00

Cat: SS

$825.29/Night

80% Off 2nd Sailor Plus Up To $300 in free drinks

Portsmouth to Ireland, Scotland & More

Departing on Aug 17, 2025 on the Scarlet Lady

Nights: 13

Dates: Aug 17, 2025 through Aug 30, 2025

Ship: Scarlet Lady

Itinerary:

Portsmouth, Amsterdam, Zeebrugge (Bruges), Sailing, Kirkwall, Stornoway, Sailing, Greenock, Belfast, Sailing...

This 13-night dreamy voyage sails from Portsmouth and first docks in the capital of art and architecture, Amsterdam for two days of excitement and exploration before hitting Bruges, Belgium. You'll then spend a day sailing to Kirkwall, then Stornoway, Scotland.

from

$2,068.00

(USD)

Per Person

+ $0.00 taxes/fees

More Details Contact Us

Inside

$2,068.00

Cat: IZ

$159.08/Night

Outside

$2,458.00

Cat: VZ

$189.08/Night

Balcony

$2,848.00

Cat: TZ

$219.08/Night

Suite

$6,825.00

Cat: SS

$525.00/Night

80% Off 2nd Sailor Plus Up To $300 in free drinks

Spanish & Italian Hot Spots

Departing on Jul 06, 2025 on the Scarlet Lady

Nights: 7

Dates: Jul 06, 2025 through Jul 13, 2025

Ship: Scarlet Lady

Itinerary:

Civitavecchia (Rome), Naples, Palermo, Sicily, Sailing, Marina di Carrara, Ajaccio, Corsica, Sailing, Barcelona

This 7-night sojourn leaves from the iconic city of Rome before hitting Naples, arguably one of the most idyllic Mediterranean stops to indulge in mouthwatering cuisine while appreciating the otherworldly views. Next, you'll make your way to Palermo before spending a day at sea on your way to Marina di Carrara and one day sailing to Ajaccio before returning to Barcelona.

from

$1,324.00

(USD)

Per Person

+ $0.00 taxes/fees

More Details Contact Us

Inside

N/A

Outside

$1,324.00

Cat: VZ

$189.14/Night

Balcony

$1,393.00

Cat: TZ

$199.00/Night

Suite

$4,165.00

Cat: RZ

$595.00/Night

80% Off 2nd Sailor Plus Up To $300 in free drinks

Scarlet New Year's Ahoy!

Departing on Dec 28, 2025 on the Scarlet Lady

Nights: 5

Dates: Dec 28, 2025 through Jan 02, 2026

Ship: Scarlet Lady

Itinerary:

Miami, Sailing, Cozumel (Playa del Carmen), Sailing, Beach Club at Bimini, Miami

Ring in the new year cruising the Caribbean on a 5-night sailing to Cozumel (Playa del Carmen) and Tulum. Arriving early and departing late from Mexico - and with a day and sunset spent at The Beach Club at Bimini - you'll have plenty of time to ramp up the adventure and wind down to chill while seeing each port from every sun and moonlit angle.

from

$1,460.00

(USD)

Per Person

+ $0.00 taxes/fees

More Details Contact Us

Inside

$1,460.00

Cat: IZ

$292.00/Night

Outside

$1,745.00

Cat: VZ

$349.00/Night

Balcony

$1,964.00

Cat: TZ

$392.80/Night

Suite

$3,399.00

Cat: SS

$679.80/Night

80% Off 2nd Sailor Plus Up To $300 in free drinks

Western Caribbean Charm

Departing on Apr 27, 2025 on the Scarlet Lady

Nights: 6

Dates: Apr 27, 2025 through May 03, 2025

Ship: Scarlet Lady

Itinerary:

Miami, Florida, Sailing, Roatán, Costa Maya, Sailing, Beach Club at Bimini, Miami, Florida

Cruise through the Caribbean on a six-night sailing featuring a full day of unrivaled experiences in Costa Maya, Mexico, and another in Roatán, Honduras. With 2 days at sea to indulge in the good life on board, you'll also get to explore the rich history and turquoise waters of the Bahamas with a visit to the exclusive Beach Club at Bimini.

from

$1,075.00

(USD)

Per Person

+ $0.00 taxes/fees

More Details Contact Us

Inside

N/A

Outside

$1,075.00

Cat: VZ

$179.17/Night

Balcony

$1,255.00

Cat: TZ

$209.17/Night

Suite

$2,880.00

Cat: SS

$480.00/Night

Amenity Departure Dates

80% Off 2nd Sailor Plus Up To $300 in free drinks

Sandals Barbados Hotel Rating: No Rating

Nights: 3

Dates: Jun 22, 2025 through Jun 25, 2025

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

$1,062.67

(USD)

Per Person

More Details Contact Us

Miami to LA via Panama Canal

Departing on Mar 21, 2026 on the Brilliant Lady

Nights: 16

Dates: Mar 21, 2026 through Apr 06, 2026

Ship: Brilliant Lady

Itinerary:

Miami, Florida, Sailing, Cartagena, Colón, Panama Canal (Cruising), Sailing, Puntarenas, Sailing, Puerto Quetzal, Sailing...

This 16-night one-way truly is a once-in-a-lifetime odyssey. From Miami, you'll sail to Cartagena, followed by Colon, Panama. Marvel at the view (while being part of it) across the Panama Canal then onward to Guatemala's volcanic coast. Next, you'll sail to Cabo San Lucas (known for its endless activities) before arriving on the famed shores of Los Angeles.

from

$3,343.00

(USD)

Per Person

+ $0.00 taxes/fees

More Details Contact Us

Inside

$3,343.00

Cat: IZ

$208.94/Night

Outside

$3,823.00

Cat: VZ

$238.94/Night

Balcony

$4,303.00

Cat: TZ

$268.94/Night

Suite

N/A

80% Off 2nd Sailor Plus Up To $300 in free drinks

Breathless Cancun Soul Resort & Spa Hotel Rating: 4 stars

Nights: 3

Dates: Jun 22, 2025 through Jun 25, 2025

Location(s):

Cancun

Breathless® Cancun Soul Resort & Spa is located 25 minutes from Cancun International Airport (CUN) along the lively Cancun strip in the Hotel Zone.

from

$404.33

(USD)

Per Person

More Details Contact Us

Valiant Caribbean Holidays

Departing on Dec 19, 2026 on the Valiant Lady

Nights: 7

Dates: Dec 19, 2026 through Dec 26, 2026

Ship: Valiant Lady

Itinerary:

San Juan, Philipsburg, St. Maarten, Basseterre, St. John's, Castries, Sailing, Tortola, San Juan

This 7-night idyllic journey departs from San Juan and docks the next day in St. Maarten. From there you'll head to St. Kitts followed by St. Johns in Antigua - the quintessential paradise lover's paradise - where you'll discover the epitome of a tropical haven. From there you'll dock in St. Lucia, then spend a day sailing to the British Virgin Islands before finally returning to San Juan.

from

$1,393.00

(USD)

Per Person

+ $130.00 taxes/fees

More Details Contact Us

Inside

$1,393.00

Cat: IZ

$199.00/Night

Outside

$1,603.00

Cat: VZ

$229.00/Night

Balcony

$1,813.00

Cat: TZ

$259.00/Night

Suite

$4,536.00

Cat: SS

$648.00/Night

80% Off 2nd Sailor Plus Up To $300 in free drinks

Fire & Sunset Soirées

Departing on Dec 10, 2026 on the Brilliant Lady

Nights: 4

Dates: Dec 10, 2026 through Dec 14, 2026

Ship: Brilliant 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

$676.00

(USD)

Per Person

+ $203.00 taxes/fees

More Details Contact Us

Inside

$676.00

Cat: IZ

$169.00/Night

Outside

$757.00

Cat: VZ

$189.25/Night

Balcony

$877.00

Cat: TZ

$219.25/Night

Suite

$2,160.00

Cat: SS

$540.00/Night

80% Off 2nd Sailor Plus Up To $300 in free drinks

Honduras, Mexico & Bahamas

Departing on Oct 31, 2025 on the Scarlet Lady

Nights: 7

Dates: Oct 31, 2025 through Nov 07, 2025

Ship: Scarlet Lady

Itinerary:

Miami, Sailing, Roatan, Costa Maya, Cozumel (Playa del Carmen), Sailing, Beach Club at Bimini, Miami

This 7-night sun-soaked sojourn sets sail from Miami kicking off with a day at sea before docking in Roatan - an idyllic start to a beach holiday escape.

from

$1,224.00

(USD)

Per Person

+ $0.00 taxes/fees

More Details Contact Us

Inside

$1,224.00

Cat: IN

$174.86/Night

Outside

$1,434.00

Cat: VW

$204.86/Night

Balcony

$1,574.00

Cat: TL

$224.86/Night

Suite

$3,254.00

Cat: SS

$464.86/Night

80% Off 2nd Sailor Plus Up To $300 in free drinks

Dominican Daze

Departing on Aug 31, 2026 on the Resilient Lady

Nights: 5

Dates: Aug 31, 2026 through Sep 05, 2026

Ship: Resilient 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. Add a full day and night spent at the exclusive Beach Club in Bimini, Bahamas.

from

$745.00

(USD)

Per Person

+ $0.00 taxes/fees

More Details Contact Us

Inside

$745.00

Cat: IZ

$149.00/Night

Outside

$845.00

Cat: VZ

$169.00/Night

Balcony

$995.00

Cat: TZ

$199.00/Night

Suite

$2,600.00

Cat: SS

$520.00/Night

80% Off 2nd Sailor Plus Up To $300 in free drinks

Breathless Montego Bay Resort & Spa Hotel Rating: 4 stars

Nights: 3

Dates: Jun 22, 2025 through Jun 25, 2025

Location(s):

Montego Bay

Surrounded by Montego Bay Marine Park, the all-inclusive Breathless® Montego Bay Resort & Spa offers an idyllic adults-only getaway.

from

$698.67

(USD)

Per Person

More Details Contact Us

Dominican Daze

Departing on Dec 05, 2025 on the Scarlet Lady

Nights: 5

Dates: Dec 05, 2025 through Dec 10, 2025

Ship: Scarlet Lady

Itinerary:

Miami, Puerto Plata, Bimini Islands, 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

+ $0.00 taxes/fees

More Details Contact Us

Inside

$745.00

Cat: IZ

$149.00/Night

Outside

$1,000.00

Cat: VW

$200.00/Night

Balcony

$1,126.00

Cat: TL

$225.20/Night

Suite

$2,185.00

Cat: RZ

$437.00/Night

80% Off 2nd Sailor Plus Up To $300 in free drinks

Riu Palace Kukulkan Hotel Rating: 4 stars

Nights: 3

Dates: Jun 22, 2025 through Jun 25, 2025

Location(s):

Cancun

The beachfront Riu Palace Kukulkan is an adults-only hotel exclusive to people over 18. It is situated in front of Cancun's shopping center, "La Isla," and features a variety of restaurants, bars and nightclubs.

from

$404.67

(USD)

Per Person

More Details Contact Us

Fire and Sunset Soirees

Departing on Jan 07, 2026 on the Scarlet Lady

Nights: 4

Dates: Jan 07, 2026 through Jan 11, 2026

Ship: Scarlet Lady

Itinerary:

Miami, Nassau, Beach Club at Bimini, Sailing, 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

$636.00

(USD)

Per Person

+ $0.00 taxes/fees

More Details Contact Us

Inside

$636.00

Cat: IZ

$159.00/Night

Outside

$717.00

Cat: VZ

$179.25/Night

Balcony

$837.00

Cat: TZ

$209.25/Night

Suite

$1,781.00

Cat: RZ

$445.25/Night

80% Off 2nd Sailor Plus Up To $300 in free drinks

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

Itinerary:

Portsmouth, Sailing, La Coruña, Bilbao, Le Verdon, Sailing, Portsmouth

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

$1,256.00

(USD)

Per Person

+ $0.00 taxes/fees

More Details Contact Us

Inside

$1,256.00

Cat: IN

$209.33/Night

Outside

$1,436.00

Cat: VW

$239.33/Night

Balcony

$1,616.00

Cat: TL

$269.33/Night

Suite

$3,180.00

Cat: SS

$530.00/Night

80% Off 2nd Sailor Plus Up To $300 in free drinks

Sandals Ochi Beach Resort Hotel Rating: No Rating

Nights: 3

Dates: Jun 22, 2025 through Jun 25, 2025

Location(s):

Ocho Rios

Nestled between luxuriant hillside gardens and the glistening turquoise waters of the Caribbean, this modern-day Garden of Eden features villa suites with private pools.

from

$579.33

(USD)

Per Person

More Details Contact Us

Saint (Isles) & Seas of the Caribbean

Departing on Mar 21, 2026 on the Valiant Lady

Nights: 7

Dates: Mar 21, 2026 through Mar 28, 2026

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

$1,114.00

(USD)

Per Person

+ $0.00 taxes/fees

More Details Contact Us

Inside

$1,114.00

Cat: IZ

$159.14/Night

Outside

$1,324.00

Cat: VZ

$189.14/Night

Balcony

$1,534.00

Cat: TZ

$219.14/Night

Suite

$3,745.00

Cat: SS

$535.00/Night

80% Off 2nd Sailor Plus Up To $300 in free drinks

Secrets St. James Montego Bay Hotel Rating: 4.5 stars

Nights: 3

Dates: Jun 22, 2025 through Jun 25, 2025

Location(s):

Montego Bay

Tucked away on a half-mile stretch of paradise, where the turquoise waters lap against sugar-white sand, there is Secrets® St.

from

$585.67

(USD)

Per Person

More Details Contact Us

Riu Reggae Hotel Rating: 4 stars

Nights: 3

Dates: Jun 22, 2025 through Jun 25, 2025

Location(s):

Montego Bay

Ideally located on the beach and surrounded by incredible nature, the Riu Reggae is a new all-inclusive, adults-only hotel.

from

$446.33

(USD)

Per Person

More Details Contact Us

Resilient New Year's Ahoy!

Departing on Dec 27, 2026 on the Resilient Lady

Nights: 7

Dates: Dec 27, 2026 through Jan 03, 2027

Ship: Resilient Lady

Itinerary:

Miami, Florida, Sailing, Ocho Rios, Sailing, George Town, Sailing, Beach Club at Bimini, Miami, Florida

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

$5,600.00

Cat: SS

$800.00/Night

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

Ship: Brilliant Lady

Itinerary:

Miami, Florida, Sailing, Oranjestad, Willemstad, Sailing, Cartagena, Sailing, Ocho Rios, George Town, Sailing...

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

$1,568.00

(USD)

Per Person

+ $0.00 taxes/fees

More Details Contact Us

Inside

$1,568.00

Cat: IZ

$130.67/Night

Outside

$1,928.00

Cat: VZ

$160.67/Night

Balcony

$2,288.00

Cat: TZ

$190.67/Night

Suite

$5,480.00

Cat: SS

$456.67/Night

Amenity Departure Dates

80% Off 2nd Sailor Plus Up To $300 in free drinks

Sandals Royal Bahamian Spa Resort & Offshore Island Hotel Rating: No Rating

Nights: 3

Dates: Jun 22, 2025 through Jun 25, 2025

Location(s):

Nassau

This award-winning resort is the premier destination for people in love who demand only the very best.

from

$1,111.67

(USD)

Per Person

More Details Contact Us

Miami, Grand Turk (& back)

Departing on Oct 03, 2026 on the Resilient Lady

Nights: 5

Dates: Oct 03, 2026 through Oct 08, 2026

Ship: Resilient Lady

Itinerary:

Miami, Sailing, Grand Turk, Sailing, Beach Club at Bimini, Miami

Miami, Grand Turk (& back) sails to the snow-white shores of the Grand Turk for plenty of time to lay by the beach and explore the city streets. Add a full day spent at the exclusive Beach Club in Bimini, Bahamas.

from

$796.00

(USD)

Per Person

+ $0.00 taxes/fees

More Details Contact Us

Inside

$796.00

Cat: IZ

$159.20/Night

Outside

$895.00

Cat: VZ

$179.00/Night

Balcony

$1,045.00

Cat: TZ

$209.00/Night

Suite

$2,725.00

Cat: SS

$545.00/Night

80% Off 2nd Sailor Plus Up To $300 in free drinks

Grand Velas Boutique Hotel Los Cabos Hotel Rating: 5 stars

Nights: 3

Dates: Jun 22, 2025 through Jun 25, 2025

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

$1,382.67

(USD)

Per Person

More Details Contact Us

TRS Coral Hotel Hotel Rating: 4.5 stars

Nights: 3

Dates: Jun 22, 2025 through Jun 25, 2025

Location(s):

Cancun

The TRS Coral Hotel is Cancun's newest Adults Only All-Inclusive resort. Located on sandy, white shores lapped by aquamarine water, the resort is a heavenly Caribbean hideaway.

from

$597.33

(USD)

Per Person

More Details Contact Us

Secrets Royal Beach Punta Cana Hotel Rating: 4 stars

Nights: 3

Dates: Jun 22, 2025 through Jun 25, 2025

Location(s):

Punta Cana

Located on over 700 yards of a palm-studded white sand beach along the majestic turquoise Caribbean Sea, Secrets® Royal Beach Punta Cana offers adults a serene seaside getaway in paradise.

from

$518.00

(USD)

Per Person

More Details Contact Us

Ladera Resort Hotel Rating: 4.5 stars

Nights: 3

Dates: Jun 22, 2025 through Jun 25, 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

Cayman Coves & Jamaican Waterfalls

Departing on Jan 24, 2026 on the Resilient Lady

Nights: 7

Dates: Jan 24, 2026 through Jan 31, 2026

Ship: Resilient Lady

Itinerary:

Miami, Florida, Sailing, Ocho Rios, Sailing, George Town, Sailing, Beach Club at Bimini, Miami, Florida

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

$974.00

(USD)

Per Person

+ $0.00 taxes/fees

More Details Contact Us

Inside

$974.00

Cat: IZ

$139.14/Night

Outside

$1,184.00

Cat: VZ

$169.14/Night

Balcony

$1,394.00

Cat: TZ

$199.14/Night

Suite

$3,395.00

Cat: SS

$485.00/Night

80% Off 2nd Sailor Plus Up To $300 in free drinks

Le Blanc Spa Resort Hotel Rating: 5 stars

Nights: 3

Dates: Jun 22, 2025 through Jun 25, 2025

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

$901.33

(USD)

Per Person

More Details Contact Us

Catalonia Royal Tulum Hotel Rating: 3.5 stars

Nights: 3

Dates: Jun 22, 2025 through Jun 25, 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

$320.67

(USD)

Per Person

More Details Contact Us

San Juan, Samana & Bimini

Departing on Jan 17, 2026 on the Resilient Lady

Nights: 7

Dates: Jan 17, 2026 through Jan 24, 2026

Ship: Resilient Lady

Itinerary:

Miami, Florida, Sailing, San Juan, Samaná, Sailing, Beach Club at Bimini, Miami, Florida

This 7-night sun-drenched Miami sojourn spends two days sailing to your first destination, the beachy respite of San Juan. Next, call in Samaná, a small coastal city that's the gateway to the beauty of the Dominican Republic and all it has to offer, including 5-star golfing, stunning beaches, eclectic shopping and so much more. Lastly, spend a day sailing to Bimini before returning to Miami.

from

$974.00

(USD)

Per Person

+ $0.00 taxes/fees

More Details Contact Us

Inside

$974.00

Cat: IZ

$139.14/Night

Outside

$1,184.00

Cat: VZ

$169.14/Night

Balcony

$1,394.00

Cat: TZ

$199.14/Night

Suite

$3,500.00

Cat: SS

$500.00/Night

80% Off 2nd Sailor Plus Up To $300 in free drinks

Western Caribbean: From Miami to Bimini

Departing on Nov 01, 2025 on the Brilliant Lady

Nights: 7

Dates: Nov 01, 2025 through Nov 08, 2025

Ship: Brilliant Lady

Itinerary:

Miami, Florida, Sailing, Ocho Rios, Sailing, George Town, Sailing, Beach Club at Bimini, Miami, Florida

This 7-night voyage from Miami brings you to Jamaica, the Cayman Islands, and our exclusive Bahamian beach club in Bimini. One of the trip's highlights is undoubtedly George Town on Grand Cayman.

from

$1,268.00

(USD)

Per Person

+ $0.00 taxes/fees

More Details Contact Us

Inside

$1,268.00

Cat: IN

$181.14/Night

Outside

$1,295.00

Cat: VZ

$185.00/Night

Balcony

$1,505.00

Cat: TZ

$215.00/Night

Suite

$3,612.00

Cat: SS

$516.00/Night

Amenity Departure Dates

80% Off 2nd Sailor Plus Up To $300 in free drinks

Corfu, Dubrovnik & More

Departing on Jun 15, 2025 on the Resilient Lady

Nights: 7

Dates: Jun 15, 2025 through Jun 22, 2025

Ship: Resilient Lady

Itinerary:

Piraeus (Athens), Sailing, Kotor, Dubrovnik, Corfu, Sailing, Mykonos, Piraeus (Athens)

This 7-night Greek and Croatian adventure starts in Athens before spending a day of at-sea luxury on the way to Kotor. The next day touch down in dazzling Dubrovnik to pursue the Balkan adventure of your fantasies, then dip your toes in the sand in Corfu and spend one more day at sea on your way to making your mark and soaking up the unparalleled rays of sun in Mykonos before returning to Athens.

from

$1,485.00

(USD)

Per Person

+ $0.00 taxes/fees

More Details Contact Us

Inside

N/A

Outside

$1,485.00

Cat: VZ

$212.14/Night

Balcony

$1,695.00

Cat: TZ

$242.14/Night

Suite

$5,586.00

Cat: SAP

$798.00/Night

80% Off 2nd Sailor Plus Up To $300 in free drinks

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

$995.00

(USD)

Per Person

+ $249.00 taxes/fees

More Details Contact Us

Inside

$995.00

Cat: IZ

$199.00/Night

Outside

$1,095.00

Cat: VZ

$219.00/Night

Balcony

$1,245.00

Cat: TZ

$249.00/Night

Suite

$3,375.00

Cat: SS

$675.00/Night

80% Off 2nd Sailor Plus Up To $300 in free drinks

Ocean Riviera Paradise El Beso Hotel Rating: 4 stars

Nights: 3

Dates: Jun 22, 2025 through Jun 25, 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

$316.33

(USD)

Per Person

More Details Contact Us

Mayan Sol

Departing on Sep 07, 2025 on the Valiant Lady

Nights: 5

Dates: Sep 07, 2025 through Sep 12, 2025

Ship: Valiant Lady

Itinerary:

Miami, Sailing, Costa Maya, Sailing, Beach Club at Bimini, Miami

Sail from Miami to the shores of the Yucatán Peninsula, with a day spent at The Beach Club in Bimini, Bahamas - complete with a bonfire party under the stars. Arriving in Costa Maya, you'll have plenty of time to relax by the beach and explore the ancient ruins.

from

$745.00

(USD)

Per Person

+ $0.00 taxes/fees

More Details Contact Us

Inside

$745.00

Cat: IZ

$149.00/Night

Outside

$846.00

Cat: VZ

$169.20/Night

Balcony

$996.00

Cat: TZ

$199.20/Night

Suite

$2,699.00

Cat: SS

$539.80/Night

Amenity Departure Dates

80% Off 2nd Sailor Plus Up To $300 in free drinks

Cayman Isles & Jamaican Miles

Departing on Jan 10, 2026 on the Resilient Lady

Nights: 7

Dates: Jan 10, 2026 through Jan 17, 2026

Ship: Resilient Lady

Itinerary:

Miami, Florida, Sailing, George Town, Sailing, Ocho Rios, Sailing, Beach Club at Bimini, Miami, Florida

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

$974.00

(USD)

Per Person

+ $0.00 taxes/fees

More Details Contact Us

Inside

$974.00

Cat: IZ

$139.14/Night

Outside

$1,184.00

Cat: VZ

$169.14/Night

Balcony

$1,394.00

Cat: TZ

$199.14/Night

Suite

$3,465.00

Cat: SS

$495.00/Night

80% Off 2nd Sailor Plus Up To $300 in free drinks

Catalonia Royal La Romana Adults Only Hotel Rating: 4.5 stars

Nights: 3

Dates: Jun 22, 2025 through Jun 25, 2025

Location(s):

Dominicus

Enjoy tranquil vibes and luxurious accommodations at the all-inclusive Catalonia Royal La Romana Adults Only hotel.

from

$372.00

(USD)

Per Person

More Details Contact Us

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

$1,050.00

(USD)

Per Person

+ $0.00 taxes/fees

More Details Contact Us

Inside

$1,050.00

Cat: IN

$210.00/Night

Outside

$1,095.00

Cat: VZ

$219.00/Night

Balcony

$1,146.00

Cat: TZ

$229.20/Night

Suite

$3,245.00

Cat: SS

$649.00/Night

Amenity Departure Dates

80% Off 2nd Sailor Plus Up To $300 in free drinks

El Dorado Royale, a Spa Resort Hotel Rating: 4 stars

Nights: 3

Dates: Jun 22, 2025 through Jun 25, 2025

Location(s):

Riviera Maya

El Dorado Royale, awarded 4 Diamonds by AAA for its high-quality services, is Mexico's premier adults-only beachfront resort, where couples, weddings, and honeymoons enjoy a unique experience.

from

$588.00

(USD)

Per Person

More Details Contact Us

Mykonos Moons to Spanish Sunrises

Departing on Oct 04, 2026 on the Scarlet Lady

Nights: 7

Dates: Oct 04, 2026 through Oct 11, 2026

Ship: Scarlet Lady

Itinerary:

Piraeus (Athens), Mykonos, Sailing, Catania, Sicily, Sailing, Palma de Mallorca, Valencia, Barcelona

This 7-night Mediterranean voyage begins in Athens and docks the following day in mystical Mykonos. From there spend a day sailing to picturesque Catania, an ancient city on the Ionian Sea that radiates Sicilian vibes through and through. F

from

$1,184.00

(USD)

Per Person

+ $0.00 taxes/fees

More Details Contact Us

Inside

$1,184.00

Cat: IZ

$169.14/Night

Outside

$1,394.00

Cat: VZ

$199.14/Night

Balcony

$1,604.00

Cat: TZ

$229.14/Night

Suite

$4,095.00

Cat: SS

$585.00/Night

80% Off 2nd Sailor Plus Up To $300 in free drinks

Couples Negril Hotel Rating: 4.5 stars

Nights: 3

Dates: Jun 22, 2025 through Jun 25, 2025

Location(s):

Negril

Couples Negril is a lively, low-key 18-acre beachfront playground offering a peerless selection of all-inclusive experiences designed to awaken your spirit of adventure.

from

$535.00

(USD)

Per Person

More Details Contact Us

Scarlet Caribbean Holidays

Departing on Dec 24, 2025 on the Scarlet Lady

Nights: 4

Dates: Dec 24, 2025 through Dec 28, 2025

Ship: Scarlet Lady

Itinerary:

Miami, Florida, Sailing, Nassau, Beach Club at Bimini, Miami, Florida

On this four-night voyage decked with festive surprises, you'll rock around the sun-drenched city of Nassau and even get the (sandy) white Christmas of your dreams at our private beach club experience in Bimini.

from

$880.00

(USD)

Per Person

+ $0.00 taxes/fees

More Details Contact Us

Inside

$880.00

Cat: IN

$220.00/Night

Outside

$1,000.00

Cat: VW

$250.00/Night

Balcony

$1,101.00

Cat: TL

$275.25/Night

Suite

$2,360.00

Cat: SS

$590.00/Night

80% Off 2nd Sailor Plus Up To $300 in free drinks

Brilliant Caribbean Holidays

Departing on Dec 18, 2025 on the Brilliant Lady

Nights: 8

Dates: Dec 18, 2025 through Dec 26, 2025

Ship: Brilliant Lady

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

$1,600.00

(USD)

Per Person

+ $0.00 taxes/fees

More Details Contact Us

Inside

$1,600.00

Cat: IZ

$200.00/Night

Outside

$1,840.00

Cat: VZ

$230.00/Night

Balcony

$2,080.00

Cat: TZ

$260.00/Night

Suite

$4,167.00

Cat: SS

$520.88/Night

Amenity Departure Dates

80% Off 2nd Sailor Plus Up To $300 in free drinks

Riu Palace Jamaica - Exclusive up to 61% off rooms

Dates: Mar 19, 2025 through Dec 23, 2025

Location(s):

Montego Bay

Riu Palace Jamaica - Exclusive up to 61% off rooms

More Details Contact Us

Viceroy Riviera Maya Hotel Rating: 5 stars

Nights: 3

Dates: Jun 22, 2025 through Jun 25, 2025

Location(s):

Playa Del Carmen

This beachfront resort refuge is situated on seven miles of white-sand beach and nestled in the tropical forest.

from

$913.00

(USD)

Per Person

More Details Contact Us

Puerto Rican Daze and Caribbean Nights Fort de France

Puerto Rico to Aruba, Bonaire & More

Departing on Jan 29, 2027 on the Valiant Lady

Nights: 8

Dates: Jan 29, 2027 through Feb 06, 2027

Ship: Valiant Lady

Itinerary:

San Juan, Sailing, Oranjestad, Willemstad, Kralendijk, Sailing, Fort-de-France, Philipsburg, St. Maarten, San Juan

This 8-night San Juan voyage spends a day sailing to your first stop, Oranjestad, Aruba - the happiest island in all of the Caribbean. Next, wake up in Willemstad, Curaçao, where European influences blend seamlessly with white-sand beaches. Continue to Kralendijk, Bonaire, followed by a day of luxury sailing to Martinique, then St. Maarten, before returning to San Juan.

from

$1,312.00

(USD)

Per Person

+ $223.00 taxes/fees

More Details Contact Us

Inside

$1,312.00

Cat: IZ

$164.00/Night

Outside

$1,552.00

Cat: VZ

$194.00/Night

Balcony

$1,792.00

Cat: TZ

$224.00/Night

Suite

$4,640.00

Cat: SS

$580.00/Night