Explore 399 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

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

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

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

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

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

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

Sat, Jan 17 - Sat, Jan 24

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

2026Best Rate

Sat, Nov 29 - Sat, Dec 06

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

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

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

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

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

Colorful Curaçao to the Charming Caymans

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

Insider cabins from

per Sailor per night

12 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

Sat, Nov 08 - Thu, Nov 20

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

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

Sun, Mar 01 - Thu, Mar 12

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Sailor per night

Departing on:

2026Best Rate

Sun, Dec 07 - Thu, Dec 18

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

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

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

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

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

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

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