Explore 398 cruise vacations

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

Fri, Oct 03 - Thu, Oct 16

Spanish Isles & Transatlantic Miles

Barcelona
Casablanca, Morocco
Las Palmas de Gran Canaria, Spain
Santa Cruz de Tenerife, Spain
Miami, Florida

Insider cabins from

per Sailor per night

14 nights

Scarlet Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

Sun, Oct 11 - Sun, Oct 25

Resilient's Haunted Halloween Soirée

Barcelona
Valencia, Spain
Casablanca, Morocco
Las Palmas de Gran Canaria, Spain
Miami, Florida

Sea View cabins from

per Sailor per night

14 nights

Resilient Lady

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

per Sailor per night

Departing on:

Sun, Oct 26 - Sun, Nov 09

Scarlet's Haunted Halloween Soirée

Barcelona
Palma de Mallorca, Spain
Casablanca, Morocco
Funchal, Madeira, Portugal
Santa Cruz de Tenerife, Spain
Miami, Florida

Insider cabins from

per Sailor per night

15 nights

Scarlet Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

Thu, Oct 16 - Fri, Oct 31

DEAL

Cayman Coves & Jamaican Waterfalls

Miami, Florida
Ocho Rios, Jamaica
George Town, Grand Cayman
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

per Sailor per night

7 nights

Resilient Lady

Sat, Dec 06 - Sat, Dec 13

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

2025Best Rate

Sat, Dec 13 - Sat, Dec 20

Sat, Jan 24 - Sat, Jan 31

Transatlantic to Spain & Morocco

Miami, Florida
Las Palmas de Gran Canaria, Spain
Casablanca, Morocco
Alicante, Spain
Barcelona

Sea View cabins from

per Sailor per night

14 nights

Scarlet Lady

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

per Sailor per night

Departing on:

Sun, Apr 26 - Sun, May 10

One-way to SJ: DR, St. Maarten & BVI

Miami, Florida
Puerto Plata, Dominican Republic
Philipsburg, St. Maarten
Tortola, British Virgin Islands
San Juan, Puerto Rico

Insider cabins from

per Sailor per night

6 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

Sun, Nov 02 - Sat, Nov 08

DEAL

Cayman Isles & Jamaican Miles

Miami, Florida
George Town, Grand Cayman
Ocho Rios, Jamaica
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

per Sailor per night

7 nights

Resilient Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

Sat, Jan 10 - Sat, Jan 17

DEAL

Cozumel, Grand Cayman & Bimini

Miami, Florida
George Town, Grand Cayman
Cozumel, Mexico
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

per Sailor per night

7 nights

Resilient Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

Sat, Jan 03 - Sat, Jan 10

DEAL

San Juan Sunrises & Dominican Dreams

Miami, Florida
Puerto Plata, Dominican Republic
San Juan, Puerto Rico
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

per Sailor per night

7 nights

Resilient Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

Sat, Jan 31 - Sat, Feb 07

Sat, Feb 28 - Sat, Mar 07

DEAL

Quaint Castries to Elegant Antigua

San Juan, Puerto Rico
Basseterre, St. Kitts and Nevis
Castries, St. Lucia
Fort-de-France, Martinique
St. John's, Antigua
Tortola, British Virgin Islands
San Juan, Puerto Rico

Insider cabins from

per Sailor per night

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

Sat, Mar 07 - Sat, Mar 14

Tortola, Charleston, Newport & More

San Juan, Puerto Rico
Tortola, British Virgin Islands
Puerto Plata, Dominican Republic
Charleston, South Carolina
Newport, Rhode Island
New York City, New York

Insider cabins from

per Sailor per night

9 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

Sat, Mar 28 - Mon, Apr 06

DEAL

San Juan, Samaná & Bimini

Miami, Florida
San Juan, Puerto Rico
Samaná, Dominican Republic
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

per Sailor per night

7 nights

Resilient Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

Sat, Jan 17 - Sat, Jan 24

Sat, Nov 29 - Sat, Dec 06

Riviera Maya

Miami, Florida
Cozumel, Mexico
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

per Sailor per night

5 nights

Scarlet Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

Sun, Dec 14 - Fri, Dec 19

DEAL

Antigua Waves & Grand Turk Caves

Miami, Florida
Grand Turk, Turks and Caicos
St. John's, Antigua
Basseterre, St. Kitts and Nevis
San Juan, Puerto Rico
Miami, Florida

Insider cabins from

per Sailor per night

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

Fri, Nov 28 - Sun, Dec 07

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

2025Best Rate

Fri, Feb 20 - Sun, Mar 01

DEAL

St. Lucia, Barbados & More

San Juan, Puerto Rico
Philipsburg, St. Maarten
Basseterre, St. Kitts and Nevis
Castries, St. Lucia
Bridgetown, Barbados
Charlotte Amalie, St. Thomas
San Juan, Puerto Rico

Insider cabins from

per Sailor per night

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

Sat, Feb 07 - Sat, Feb 14

Valiant Valentine's Voyage

San Juan, Puerto Rico
Oranjestad, Aruba
Willemstad, Curaçao
St. Croix, U.S. Virgin Islands
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

per Sailor per night

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

Sat, Feb 14 - Sat, Feb 21

Portsmouth to Ireland, Scotland & More

Portsmouth
Amsterdam, Netherlands
Bruges/Zeebruge (Brussels), Belgium
Kirkwall, Scotland
Stornoway, Isle of Lewis, Scotland
Glasgow (Greenock), Scotland
Belfast, Northern Ireland
Dublin, Ireland
Portsmouth

Insider cabins from

per Sailor per night

13 nights

Scarlet Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

Sun, Aug 17 - Sat, Aug 30

DEAL

Aruban Sunsets & Calm Cayman Days

Miami, Florida
Oranjestad, Aruba
Cartagena, Colombia
Ocho Rios, Jamaica
George Town, Grand Cayman
Miami, Florida

Insider cabins from

per Sailor per night

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

Sun, Mar 01 - Thu, Mar 12

Sun, Dec 07 - Thu, Dec 18

San Juan to Barbados & the St. Isles

San Juan, Puerto Rico
Philipsburg, St. Maarten
Basseterre, St. Kitts and Nevis
Roseau, Dominica
Bridgetown, Barbados
San Juan, Puerto Rico

Insider cabins from

per Sailor per night

6 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

Sat, Nov 29 - Fri, Dec 05

DEAL

Antigua & the St. Isles

San Juan, Puerto Rico
Philipsburg, St. Maarten
Basseterre, St. Kitts and Nevis
St. John's, Antigua
Castries, St. Lucia
Charlotte Amalie, St. Thomas
San Juan, Puerto Rico

Insider cabins from

per Sailor per night

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

Sat, Jan 31 - Sat, Feb 07

NY to San Juan: Bermuda & Caribbean

New York City, New York
Royal Naval Dockyard, Bermuda
The Beach Club at Bimini, Bahamas
St. Croix, U.S. Virgin Islands
Philipsburg, St. Maarten
Tortola, British Virgin Islands
San Juan, Puerto Rico

Insider cabins from

per Sailor per night

12 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

Mon, Oct 19 - Sat, Oct 31

DEAL

Red Hot Sailing Club Voyage

Miami, Florida
Puerto Plata, Dominican Republic
St. John's, Antigua
Basseterre, St. Kitts and Nevis
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

per Sailor per night

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

Thu, Mar 12 - Sat, Mar 21

DEAL

Nicky Jam x Virgin Voyages

San Juan, Puerto Rico
Willemstad, Curaçao
Oranjestad, Aruba
Roseau, Dominica
St. John's, Antigua
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

per Sailor per night

8 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

Fri, Dec 05 - Sat, Dec 13

DEAL

Pre-Holiday Caribbean Getaway

Miami, Florida
Philipsburg, St. Maarten
Tortola, British Virgin Islands
San Juan, Puerto Rico
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

per Sailor per night

9 nights

Brilliant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

Mon, Dec 14 - Wed, Dec 23

DEAL

Thanksgiving in the Lesser Antilles

San Juan, Puerto Rico
Tortola, British Virgin Islands
Basseterre, St. Kitts and Nevis
St. John's, Antigua
Castries, St. Lucia
Charlotte Amalie, St. Thomas
San Juan, Puerto Rico

Insider cabins from

per Sailor per night

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

Sat, Nov 22 - Sat, Nov 29

DEAL

St. Isles & Sun-soaked Seas

Miami, Florida
Philipsburg, St. Maarten
Tortola, British Virgin Islands
Basseterre, St. Kitts and Nevis
St. John's, Antigua
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

per Sailor per night

10 nights

Brilliant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

Sun, Nov 15 - Wed, Nov 25

Mon, Jan 25 - Thu, Feb 04

2027

DEAL

St. Maarten, Tortola, San Juan & more

Miami, Florida
Philipsburg, St. Maarten
Tortola, British Virgin Islands
St. Croix, U.S. Virgin Islands
San Juan, Puerto Rico
Puerto Plata, Dominican Republic
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

per Sailor per night

10 nights

Brilliant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

Mon, Nov 30 - Thu, Dec 10

Mon, Jan 11 - Thu, Jan 21

2027

Autumn Leaves: New York to Quebec

New York City, New York
Boston, Massachusetts
Eastport, Maine
Saint John, New Brunswick
Halifax, Nova Scotia
Quebec City, Quebec

Sea View cabins from

per Sailor per night

10 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

per Sailor per night

Departing on:

Tue, Sep 23 - Fri, Oct 03

Grand Turk, Puerto Plata & Bimini

Miami, Florida
The Beach Club at Bimini, Bahamas
Puerto Plata, Dominican Republic
Grand Turk, Turks and Caicos
Miami, Florida

Insider cabins from

per Sailor per night

6 nights

Brilliant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

Mon, Jan 26 - Sun, Feb 01

Reykjavik to Amsterdam & Portsmouth

Reykjavik
Reykjavik, Iceland
Ísafjörður, Iceland
Akureyri, Iceland
Lerwick/Shetland, Scotland
Amsterdam, Netherlands
Portsmouth

Sea View cabins from

per Sailor per night

11 nights

Scarlet Lady

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

per Sailor per night

Departing on:

Wed, Aug 06 - Sun, Aug 17