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Explore 413 cruise vacations

Showing cruise vacations: All Destinations, November 2025 - November 2027

Quick find:

CA$50 - CA$200 Sailor per night

Last chance: 80% off 2nd Sailor + Free Drinks

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

CA$142~~CA$209~~

per Sailor per night

12 nights

Valiant Lady

+ up to $400 free drinks

80% off second Sailor

Insider cabins from

CA$142~~CA$209~~

per Sailor per night

Departing on:

Mon, Oct 19 - Sat, Oct 31

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

CA$145~~CA$221~~

per Sailor per night

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$145~~CA$221~~

per Sailor per night

Departing on:

Sat, Nov 22 - Sat, Nov 29

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

CA$145~~CA$220~~

per Sailor per night

9 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$145~~CA$220~~

per Sailor per night

Departing on:

Sat, Mar 28 - Mon, Apr 06

Transatlantic Miami to Morocco & Spain

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

Insider cabins from

CA$151~~CA$239~~

per Sailor per night

14 nights

Scarlet Lady

+ up to $400 free drinks

80% off second Sailor

Insider cabins from

CA$151~~CA$239~~

per Sailor per night

Departing on:

Sat, Apr 24 - Sat, May 08

Spain & Morocco Transatlantic

Miami, Florida
Santa Cruz de Tenerife, Spain
Tangier, Morocco
Málaga, Spain
Barcelona

Insider cabins from

CA$151~~CA$235~~

per Sailor per night

14 nights

Resilient Lady

+ up to $400 free drinks

80% off second Sailor

Insider cabins from

CA$151~~CA$235~~

per Sailor per night

Departing on:

Sun, May 02 - Sun, May 16

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

CA$157~~CA$239~~

per Sailor per night

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$157~~CA$239~~

per Sailor per night

Departing on:

Fri, Nov 28 - Sun, Dec 07

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

CA$157~~CA$241~~

per Sailor per night

6 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$157~~CA$241~~

per Sailor per night

Departing on:

Sat, Nov 29 - Fri, Dec 05

Virgin Island Views & Saint Isle Blues

San Juan, Puerto Rico
Tortola, British Virgin Islands
Bridgetown, Barbados
Kingstown, St. Vincent
Basseterre, St. Kitts and Nevis
St. Croix, U.S. Virgin Islands
San Juan, Puerto Rico

Insider cabins from

CA$157~~CA$244~~

per Sailor per night

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$157~~CA$244~~

per Sailor per night

Departing on:

Sat, Jan 10 - Sat, Jan 17

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

CA$157~~CA$243~~

per Sailor per night

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$157~~CA$243~~

per Sailor per night

Departing on:

Sat, Mar 07 - Sat, Mar 14

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

CA$157~~CA$240~~

per Sailor per night

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$157~~CA$240~~

per Sailor per night

Departing on:

Sat, Jan 31 - Sat, Feb 07

Eastern Caribbean & Bimini Beach Club

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

Insider cabins from

CA$157~~CA$233~~

per Sailor per night

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$157~~CA$233~~

per Sailor per night

Departing on:

Sat, Jan 17 - Sat, Jan 24

Sat, Nov 29 - Sat, Dec 06

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

CA$157~~CA$232~~

per Sailor per night

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$157~~CA$232~~

per Sailor per night

Departing on:

Sat, Jan 31 - Sat, Feb 07

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

CA$157~~CA$243~~

per Sailor per night

8 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$157~~CA$243~~

per Sailor per night

Departing on:

Fri, Dec 05 - Sat, Dec 13

Cayman Isles & Jamaican Miles

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

Insider cabins from

CA$157~~CA$230~~

per Sailor per night

7 nights

Resilient Lady & Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$157~~CA$230~~

per Sailor per night

Departing on:

Sat, Jan 10 - Sat, Jan 17

Thu, Apr 15 - Thu, Apr 22

Cayman Coves & Jamaican Waterfalls

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

Insider cabins from

CA$157~~CA$230~~

per Sailor per night

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$157~~CA$230~~

per Sailor per night

Departing on:

Sat, Jan 24 - Sat, Jan 31

Sat, Dec 06 - Sat, Dec 13

Sat, Feb 21 - Sat, Feb 28

Riviera Maya

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

Insider cabins from

CA$171~~CA$235~~

per Sailor per night

5 nights

Scarlet Lady

+ up to $100 free drinks

80% off second Sailor

Insider cabins from

CA$171~~CA$235~~

per Sailor per night

Departing on:

Sun, Dec 14 - Fri, Dec 19

Sun, Jan 25 - Fri, Jan 30

Sun, Jan 11 - Fri, Jan 16

Miami, Grand Turk (& back)

Miami, Florida
Grand Turk, Turks and Caicos
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

CA$171~~CA$249~~

per Sailor per night

5 nights

Scarlet Lady

+ up to $100 free drinks

80% off second Sailor

Insider cabins from

CA$171~~CA$249~~

per Sailor per night

Departing on:

Sun, Nov 30 - Fri, Dec 05

Eastern Caribbean Antilles

Miami, Florida
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

CA$171~~CA$257~~

per Sailor per night

8 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$171~~CA$257~~

per Sailor per night

Departing on:

Sat, Dec 05 - Sun, Dec 13

Aruban Sunsets & Calm Cayman Days

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

Insider cabins from

CA$171~~CA$265~~

per Sailor per night

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $400 free drinks

80% off second Sailor

Insider cabins from

CA$171~~CA$265~~

per Sailor per night

Departing on:

Sun, Dec 07 - Thu, Dec 18

Sun, Mar 01 - Thu, Mar 12

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

CA$171~~CA$267~~

per Sailor per night

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$171~~CA$267~~

per Sailor per night

Departing on:

Sat, Feb 14 - Sat, Feb 21

Barbados, Antigua, BVI & More

San Juan, Puerto Rico
Tortola, British Virgin Islands
Bridgetown, Barbados
Fort-de-France, Martinique
St. John's, Antigua
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

CA$171~~CA$266~~

per Sailor per night

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$171~~CA$266~~

per Sailor per night

Departing on:

Sat, Jan 24 - Sat, Jan 31

Aruba, Bonaire, Colombia, Jamaica & More

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

Insider cabins from

CA$171~~CA$264~~

per Sailor per night

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $400 free drinks

80% off second Sailor

Insider cabins from

CA$171~~CA$264~~

per Sailor per night

Departing on:

Sun, Jan 04 - Thu, Jan 15

Magnetic Miami to Gorgeous George Town

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

Insider cabins from

CA$171~~CA$264~~

per Sailor per night

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $400 free drinks

80% off second Sailor

Insider cabins from

CA$171~~CA$264~~

per Sailor per night

Departing on:

Sun, Feb 01 - Thu, Feb 12

Western Caribbean & Bimini Beach Club

Miami, Florida
Costa Maya, Mexico
Roatán, Honduras
Belize City, Belize
Cozumel, Mexico
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

CA$171~~CA$249~~

per Sailor per night

8 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$171~~CA$249~~

per Sailor per night

Departing on:

Sat, Jan 16 - Sun, Jan 24

Sat, Mar 13 - Sun, Mar 21

Sunny Miles of Tropical Isles

San Juan, Puerto Rico
Philipsburg, St. Maarten
Bridgetown, Barbados
Castries, St. Lucia
Fort-de-France, Martinique
Basseterre, St. Kitts and Nevis
San Juan, Puerto Rico

Insider cabins from

CA$171~~CA$267~~

per Sailor per night

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$171~~CA$267~~

per Sailor per night

Departing on:

Sat, Feb 28 - Sat, Mar 07

Sat, Dec 12 - Sat, Dec 19

Sat, Jan 16 - Sat, Jan 23

Eastern Caribbean & Bimini Beach Club

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

Insider cabins from

CA$171~~CA$255~~

per Sailor per night

8 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$171~~CA$255~~

per Sailor per night

Departing on:

Sat, Jan 30 - Sun, Feb 07

Spanish Isles & Transatlantic Miles

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

Insider cabins from

CA$171~~CA$276~~

per Sailor per night

14 nights

Scarlet Lady

+ up to $400 free drinks

80% off second Sailor

Insider cabins from

CA$171~~CA$276~~

per Sailor per night

Departing on:

Sun, Oct 11 - Sun, Oct 25

Bermuda Beauty to East Coast Elegance

New York City, New York
Royal Naval Dockyard, Bermuda
Nassau, Bahamas
Charleston, South Carolina
New York City, New York

Insider cabins from

CA$173~~CA$254~~

per Sailor per night

9 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$173~~CA$254~~

per Sailor per night

Departing on:

Thu, Apr 16 - Sat, Apr 25

St. Lucia, St. Maarten, Barbados & More

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

Insider cabins from

CA$185~~CA$289~~

per Sailor per night

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$185~~CA$289~~

per Sailor per night

Departing on:

Sat, Dec 13 - Sat, Dec 20

Sunny San Juan & Isles of Beach Miles

Miami, Florida
Puerto Plata, Dominican Republic
San Juan, Puerto Rico
Philipsburg, St. Maarten
St. Croix, U.S. Virgin Islands
Miami, Florida

Insider cabins from

CA$185~~CA$286~~

per Sailor per night

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$185~~CA$286~~

per Sailor per night

Departing on:

Thu, Nov 20 - Fri, Nov 28

San Juan Sunrises & Dominican Dreams

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

Insider cabins from

CA$185~~CA$279~~

per Sailor per night

7 nights

Resilient Lady & Scarlet Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$185~~CA$279~~

per Sailor per night

Departing on:

Sat, Mar 28 - Sat, Apr 04

Sun, Jan 03 - Sun, Jan 10

Sat, Apr 17 - Sat, Apr 24

Western Caribbean & Bimini Beach Club

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

Insider cabins from

CA$185~~CA$271~~

per Sailor per night

6 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$185~~CA$271~~

per Sailor per night

Departing on:

Sun, Nov 29 - Sat, Dec 05

Sun, Dec 13 - Sat, Dec 19

Sun, Jan 10 - Sat, Jan 16

Western Caribbean & Bimini Beach Club

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

Insider cabins from

CA$185~~CA$268~~

per Sailor per night

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$185~~CA$268~~

per Sailor per night

Departing on:

Sun, Feb 28 - Sun, Mar 07

Sun, Feb 07 - Sun, Feb 14

Sun, Apr 11 - Sun, Apr 18

Sunsets in the Lesser Antilles

San Juan, Puerto Rico
Oranjestad, Aruba
Willemstad, Curaçao
Fort-de-France, Martinique
Basseterre, St. Kitts and Nevis
San Juan, Puerto Rico

Insider cabins from

CA$185~~CA$289~~

per Sailor per night

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$185~~CA$289~~

per Sailor per night

Departing on:

Sat, Dec 05 - Sat, Dec 12

Sat, Jan 09 - Sat, Jan 16

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

CA$185~~CA$276~~

per Sailor per night

10 nights

Brilliant Lady

+ up to $400 free drinks

80% off second Sailor

Insider cabins from

CA$185~~CA$276~~

per Sailor per night

Departing on:

Mon, Jan 25 - Thu, Feb 04

Mon, Feb 22 - Thu, Mar 04

Cayman Coves & Jamaican Waterfalls

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

Insider cabins from

CA$185~~CA$277~~

per Sailor per night

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$185~~CA$277~~

per Sailor per night

Departing on:

Sat, Feb 07 - Sat, Feb 14

Sat, Dec 13 - Sat, Dec 20

Captivating Costa Maya & Cozumel Charm

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

Insider cabins from

CA$185~~CA$268~~

per Sailor per night

6 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$185~~CA$268~~

per Sailor per night

Departing on:

Mon, Nov 16 - Sun, Nov 22

Hollywood Sunsets & Mexican Horizons

Los Angeles, California
Cabo San Lucas, Mexico
Mazatlán, Mexico
Puerto Vallarta, Mexico
Los Angeles, California

Insider cabins from

CA$185~~CA$277~~

per Sailor per night

7 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$185~~CA$277~~

per Sailor per night

Departing on:

Sat, Sep 18 - Sat, Sep 25

Sat, Sep 25 - Sat, Oct 02

Sat, Oct 02 - Sat, Oct 09

St. Kitts, Barbados, Martinique & More

San Juan, Puerto Rico
Basseterre, St. Kitts and Nevis
Bridgetown, Barbados
Fort-de-France, Martinique
St. John's, Antigua
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

CA$185~~CA$291~~

per Sailor per night

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$185~~CA$291~~

per Sailor per night

Departing on:

Sat, Jan 17 - Sat, Jan 24

Western Caribbean & Bimini Beach Club

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

Insider cabins from

CA$192~~CA$280~~

per Sailor per night

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$192~~CA$280~~

per Sailor per night

Departing on:

Sun, Apr 04 - Sun, Apr 11

November Nights in the Eastern Caribbean

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

Insider cabins from

CA$192~~CA$292~~

per Sailor per night

8 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$192~~CA$292~~

per Sailor per night

Departing on:

Sun, Nov 08 - Mon, Nov 16

Coastal Pacific: From LA to Vancouver

Los Angeles, California
San Diego, California
San Francisco, California
Astoria, Oregon
Victoria, British Columbia
Vancouver, British Columbia

Insider cabins from

CA$194~~CA$288~~

per Sailor per night

9 nights

Brilliant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$194~~CA$288~~

per Sailor per night

Departing on:

Sun, May 02 - Tue, May 11

Cozumel, Grand Cayman & Bimini

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

Insider cabins from

CA$194~~CA$284~~

per Sailor per night

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$194~~CA$284~~

per Sailor per night

Departing on:

Sat, Jan 03 - Sat, Jan 10

Antigua, Martinique, & Barbados & More

San Juan, Puerto Rico
Philipsburg, St. Maarten
Bridgetown, Barbados
Fort-de-France, Martinique
St. John's, Antigua
Tortola, British Virgin Islands
San Juan, Puerto Rico

Insider cabins from

CA$199~~CA$313~~

per Sailor per night

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$199~~CA$313~~

per Sailor per night

Departing on:

Sat, Feb 21 - Sat, Feb 28

Dominican Daze

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

Insider cabins from

CA$199~~CA$285~~

per Sailor per night

5 nights

Valiant Lady & Resilient Lady

+ up to $100 free drinks

80% off second Sailor

Insider cabins from

CA$199~~CA$285~~

per Sailor per night

Departing on:

Mon, Oct 11 - Sat, Oct 16

Mon, Oct 25 - Sat, Oct 30

Mon, Sep 28 - Sat, Oct 03

San Juan & St. Isles: Valentine’s Voyage

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

CA$199~~CA$298~~

per Sailor per night

10 nights

Brilliant Lady

+ up to $400 free drinks

80% off second Sailor

Insider cabins from

CA$199~~CA$298~~

per Sailor per night

Departing on:

Mon, Feb 08 - Thu, Feb 18

Puerto Rico to Aruba, Bonaire & More

San Juan, Puerto Rico
Oranjestad, Aruba
Willemstad, Curaçao
Kralendijk, Bonaire
Fort-de-France, Martinique
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

CA$199~~CA$303~~

per Sailor per night

8 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$199~~CA$303~~

per Sailor per night

Departing on:

Fri, Jan 29 - Sat, Feb 06

Valiant Caribbean Holidays

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

Insider cabins from

CA$199~~CA$312~~

per Sailor per night

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$199~~CA$312~~

per Sailor per night

Departing on:

Sat, Dec 20 - Sat, Dec 27

Fire & Sunset Soirées

Miami, Florida
Key West, Florida
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

CA$199~~CA$282~~

per Sailor per night

4 nights

Scarlet Lady & Valiant Lady

+ up to $100 free drinks

80% off second Sailor

Insider cabins from

CA$199~~CA$282~~

per Sailor per night

Departing on:

Wed, Dec 10 - Sun, Dec 14

Thu, Oct 21 - Mon, Oct 25

Wed, Jan 07 - Sun, Jan 11

Picturesque Panama Canal Collective

Los Angeles, California
Cabo San Lucas, Mexico
Puerto Quetzal, Guatemala
Puntarenas, Costa Rica
Panama City, Panama
Panama Canal (Cruising), Panama
Cartagena, Colombia
Miami, Florida

Insider cabins from

CA$199~~CA$289~~

per Sailor per night

17 nights

Brilliant Lady

+ up to $400 free drinks

80% off second Sailor

Insider cabins from

CA$199~~CA$289~~

per Sailor per night

Departing on:

Thu, Oct 29 - Sun, Nov 15

Eastern Caribbean & Bimini Beach Club

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

Insider cabins from

CA$199~~CA$304~~

per Sailor per night

8 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$199~~CA$304~~

per Sailor per night

Departing on:

Sat, Mar 27 - Sun, Apr 04

Eastern Caribbean Cruise

Miami, Florida
Grand Turk, Turks and Caicos
Samaná, Dominican Republic
Puerto Plata, Dominican Republic
Miami, Florida

Insider cabins from

CA$199~~CA$305~~

per Sailor per night

6 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$199~~CA$305~~

per Sailor per night

Departing on:

Sun, Mar 21 - Sat, Mar 27

Thanksgiving: St. Isles, Aruba & Curaçao

San Juan, Puerto Rico
Charlotte Amalie, St. Thomas
Willemstad, Curaçao
Oranjestad, Aruba
Basseterre, St. Kitts and Nevis
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

CA$199~~CA$312~~

per Sailor per night

8 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$199~~CA$312~~

per Sailor per night

Departing on:

Fri, Nov 20 - Sat, Nov 28

Caribbean East: Virgin & Saint Isles

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

Insider cabins from

CA$199~~CA$285~~

per Sailor per night

6 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$199~~CA$285~~

per Sailor per night

Departing on:

Sat, Jan 23 - Fri, Jan 29

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

CA$200~~CA$307~~

per Sailor per night

9 nights

Brilliant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$200~~CA$307~~

per Sailor per night

Departing on:

Mon, Dec 14 - Wed, Dec 23

Resilient Valentine's Voyage

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

Insider cabins from

CA$200~~CA$301~~

per Sailor per night

7 nights

Resilient Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$200~~CA$301~~

per Sailor per night

Departing on:

Sat, Feb 14 - Sat, Feb 21

Saint (Isles) & Seas of the Caribbean

San Juan, Puerto Rico
Tortola, British Virgin Islands
Bridgetown, Barbados
Castries, St. Lucia
St. John's, Antigua
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

CA$200~~CA$299~~

per Sailor per night

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$200~~CA$299~~

per Sailor per night

Departing on:

Sat, Jan 02 - Sat, Jan 09

LA Lights & Vancouver Vistas

Los Angeles, California
Catalina Island, California
San Francisco, California
Astoria, Oregon
Victoria, British Columbia
Vancouver, British Columbia

Insider cabins from

CA$200~~CA$300~~

per Sailor per night

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$200~~CA$300~~

per Sailor per night

Departing on:

Sun, May 03 - Mon, May 11

Antiguan Elegance & Sunny St. Isles

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

Insider cabins from

CA$200~~CA$305~~

per Sailor per night

7 nights

Valiant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$200~~CA$305~~

per Sailor per night

Departing on:

Sat, Nov 28 - Sat, Dec 05

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

CA$200~~CA$309~~

per Sailor per night

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$200~~CA$309~~

per Sailor per night

Departing on:

Thu, Mar 12 - Sat, Mar 21

Mexican Riviera Halloween Cruise

Los Angeles, California
Cabo San Lucas, Mexico
Puerto Vallarta, Mexico
Mazatlán, Mexico
Los Angeles, California

Insider cabins from

CA$200~~CA$304~~

per Sailor per night

7 nights

Brilliant Lady

+ up to $300 free drinks

80% off second Sailor

Insider cabins from

CA$200~~CA$304~~

per Sailor per night

Departing on:

Sat, Oct 17 - Sat, Oct 24