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Explore 390 cruise vacations

Showing ‌ cruise vacations: North America & Caribbean, March 2025 - August 2026

Departs Miami

Showing 146 cruise vacations that match your search

Riviera Maya

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

Insider cabins from

$1,340

per Cabin

‌

5 nights

Valiant Lady, Scarlet Lady & Resilient Lady

BOOK NOW

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,340

per Cabin

‌

Departing on:

2025Best Rate

Sun, Nov 30 - Fri, Dec 05

from (US$)$1,340

2025

Sun, Mar 23 - Fri, Mar 28

from (US$)$2,752

2025

Sun, Apr 06 - Fri, Apr 11

from (US$)$1,698

Dominican Daze

Miami, Florida • Puerto Plata • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,502

per Cabin

‌

5 nights

Valiant Lady, Scarlet Lady & Resilient Lady

BOOK NOW

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,502

per Cabin

‌

Departing on:

2025Best Rate

Fri, Dec 05 - Wed, Dec 10

from (US$)$1,502

2025

Fri, Mar 28 - Wed, Apr 02

from (US$)$1,890

2025

Fri, Apr 25 - Wed, Apr 30

from (US$)$1,988

Western Caribbean Charm

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

Insider cabins from

$2,100

per Cabin

‌

6 nights

Scarlet Lady & Resilient Lady

BOOK NOW

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,100

per Cabin

‌

Departing on:

2025Best Rate

Sun, Nov 09 - Sat, Nov 15

from (US$)$2,100

2025

Sun, Mar 30 - Sat, Apr 05

from (US$)$2,646

2025

Sun, Apr 13 - Sat, Apr 19

from (US$)$2,644

* Port changes in place on select sailings — see full cruise details

Fire & Sunset Soirées

Miami, Florida • Key West, Florida • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,272

per Cabin

‌

4 nights

Valiant Lady, Scarlet Lady & Resilient Lady

BOOK NOW

+ up to $50 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,272

per Cabin

‌

Departing on:

2026Best Rate

Wed, Jan 07 - Sun, Jan 11

from (US$)$1,272

2025

Wed, Apr 02 - Sun, Apr 06

from (US$)$1,962

2025

Wed, Apr 16 - Sun, Apr 20

from (US$)$1,996

Eastern Caribbean Antilles

Miami, Florida • Puerto Plata • San Juan • St. Croix • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,878

per Cabin

‌

8 nights

Scarlet Lady

BOOK NOW

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,878

per Cabin

‌

Departing on:

2025Best Rate

Sat, Apr 05 - Sun, Apr 13

from (US$)$2,878

2025

Sat, Apr 19 - Sun, Apr 27

from (US$)$3,038

Sunny Daze in Puerto Plata & Nassau

Miami, Florida • Puerto Plata • Nassau • Miami, Florida

Insider cabins from

$1,630

per Cabin

‌

5 nights

Valiant Lady

BOOK NOW

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,630

per Cabin

‌

Departing on:

2025

Fri, Apr 11 - Wed, Apr 16

from (US$)$1,630

Mayan Sol

Miami, Florida • Costa Maya • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,490

per Cabin

‌

5 nights

Valiant Lady & Resilient Lady

BOOK NOW

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,490

per Cabin

‌

Departing on:

2025Best Rate

Sun, Sep 07 - Fri, Sep 12

from (US$)$1,490

2025

Sun, May 18 - Fri, May 23

from (US$)$2,058

2025

Sun, Jun 15 - Fri, Jun 20

from (US$)$2,096

Grand Cayman, Costa Maya & More

Miami, Florida • George Town • Costa Maya • Beach Club at Bimini • Miami, Florida

Insider cabins from

$3,230

per Cabin

‌

7 nights

Valiant Lady

BOOK NOW

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,230

per Cabin

‌

Departing on:

2025

Sun, Jul 13 - Sun, Jul 20

from (US$)$3,230

Grand Turk, Puerto Plata & More

Miami, Florida • Puerto Plata • Grand Turk • Beach Club at Bimini • Miami, Florida

Insider cabins from

$3,504

per Cabin

‌

7 nights

Valiant Lady

BOOK NOW

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,504

per Cabin

‌

Departing on:

2025

Sun, Jul 20 - Sun, Jul 27

from (US$)$3,504

Virgin Voyages Comedy Fest from Miami

Miami, Florida • Costa Maya • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,100

per Cabin

‌

5 nights

Valiant Lady

BOOK NOW

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,100

per Cabin

‌

Departing on:

2025

Sun, Aug 10 - Fri, Aug 15

from (US$)$2,100

RED HOT

Brilliant Lady Miami MerMaiden

Miami, Florida • Philipsburg, St. Maarten • Tortola • Beach Club at Bimini • Miami, Florida

Insider cabins from

$3,200

per Cabin

‌

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,200

per Cabin

‌

Departing on:

2025

Fri, Oct 17 - Sat, Oct 25

from (US$)$3,200

Riviera Maya: Halloween Edition

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

Sea View cabins from

$2,000

per Cabin

‌

5 nights

Valiant Lady

BOOK NOW

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Sea View cabins from

$2,000

per Cabin

‌

Departing on:

2025

Sun, Oct 19 - Fri, Oct 24

from (US$)$2,000

Dominican Daze: Halloween Edition

Miami, Florida • Puerto Plata • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,802

per Cabin

‌

5 nights

Valiant Lady

BOOK NOW

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,802

per Cabin

‌

Departing on:

2025

Fri, Oct 24 - Wed, Oct 29

from (US$)$1,802

Honduras, Mexico & Bahamas

Miami, Florida • Roatán • Costa Maya • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,450

per Cabin

‌

7 nights

Scarlet Lady

BOOK NOW

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,450

per Cabin

‌

Departing on:

2025

Fri, Oct 31 - Fri, Nov 07

from (US$)$2,450

Western Caribbean: From Miami to Bimini

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

Insider cabins from

$2,170

per Cabin

‌

7 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,170

per Cabin

‌

Departing on:

2025

Sat, Nov 01 - Sat, Nov 08

from (US$)$2,170

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

Miami, Florida • Puerto Plata • Philipsburg, St. Maarten • Tortola • San Juan

Insider cabins from

$2,100

per Cabin

‌

6 nights

Valiant Lady

BOOK NOW

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,100

per Cabin

‌

Departing on:

2025

Sun, Nov 02 - Sat, Nov 08

from (US$)$2,100

Colorful Curaçao to the Charming Caymans

Miami, Florida • Oranjestad • Willemstad • Cartagena • Ocho Rios • George Town • Miami, Florida

Insider cabins from

$3,136

per Cabin

‌

12 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,136

per Cabin

‌

Departing on:

2025

Sat, Nov 08 - Thu, Nov 20

from (US$)$3,136

San Juan Sunrises & Dominican Dreams

Miami, Florida • San Juan • Puerto Plata • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,974

per Cabin

‌

7 nights

Resilient Lady

BOOK NOW

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,974

per Cabin

‌

Departing on:

2025Best Rate

Sat, Nov 15 - Sat, Nov 22

from (US$)$1,974

2026

Sat, Jan 31 - Sat, Feb 07

from (US$)$2,086

2026

Sat, Feb 28 - Sat, Mar 07

from (US$)$2,086

Sunny San Juan & Isles of Beach Miles

Miami, Florida • Puerto Plata • San Juan • Philipsburg, St. Maarten • St. Croix • Miami, Florida

Insider cabins from

$2,384

per Cabin

‌

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,384

per Cabin

‌

Departing on:

2026Best Rate

Thu, Feb 12 - Fri, Feb 20

from (US$)$2,384

2025

Thu, Nov 20 - Fri, Nov 28

from (US$)$2,402

Miami, Grand Turk (& back)

Miami, Florida • Grand Turk • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,592

per Cabin

‌

5 nights

Scarlet Lady & Resilient Lady

BOOK NOW

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,592

per Cabin

‌

Departing on:

2026Best Rate

Fri, Feb 27 - Wed, Mar 04

from (US$)$1,592

2025

Fri, Nov 21 - Wed, Nov 26

from (US$)$1,850

2025

Fri, Dec 19 - Wed, Dec 24

from (US$)$1,804

Cayman Coves & Jamaican Waterfalls

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

Insider cabins from

$1,948

per Cabin

‌

7 nights

Resilient Lady

BOOK NOW

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,948

per Cabin

‌

Departing on:

2026Best Rate

Sat, Jan 24 - Sat, Jan 31

from (US$)$1,948

2025

Sat, Nov 22 - Sat, Nov 29

from (US$)$2,242

2025

Sat, Dec 06 - Sat, Dec 13

from (US$)$2,100

Antigua Waves & Grand Turk Caves

Miami, Florida • Grand Turk • St. John's • Basseterre • San Juan • Miami, Florida

Insider cabins from

$2,322

per Cabin

‌

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,322

per Cabin

‌

Departing on:

2026Best Rate

Fri, Feb 20 - Sun, Mar 01

from (US$)$2,322

2025

Fri, Nov 28 - Sun, Dec 07

from (US$)$2,370

2026

Fri, Jan 23 - Sun, Feb 01

from (US$)$3,210

San Juan, Samaná & Bimini

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

Insider cabins from

$1,948

per Cabin

‌

7 nights

Resilient Lady

BOOK NOW

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,948

per Cabin

‌

Departing on:

2026Best Rate

Sat, Jan 17 - Sat, Jan 24

from (US$)$1,948

2025

Sat, Nov 29 - Sat, Dec 06

from (US$)$1,976

Aruban Sunsets & Calm Cayman Days

Miami, Florida • Oranjestad • Cartagena • Ocho Rios • George Town • Miami, Florida

Insider cabins from

$2,838

per Cabin

‌

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,838

per Cabin

‌

Departing on:

2026Best Rate

Sun, Mar 01 - Thu, Mar 12

from (US$)$2,838

2025

Sun, Dec 07 - Thu, Dec 18

from (US$)$2,868

Brilliant Caribbean Holidays

Miami, Florida • Grand Turk • Puerto Plata • San Juan • Samaná • Miami, Florida

Insider cabins from

$3,200

per Cabin

‌

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,200

per Cabin

‌

Departing on:

2025

Thu, Dec 18 - Fri, Dec 26

from (US$)$3,200

Scarlet Caribbean Holidays

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

Insider cabins from

$1,758

per Cabin

‌

4 nights

Scarlet Lady

BOOK NOW

+ up to $50 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,758

per Cabin

‌

Departing on:

2025

Wed, Dec 24 - Sun, Dec 28

from (US$)$1,758

Brilliant New Year's Ahoy!

Miami, Florida • Grand Turk • St. John's • Basseterre • San Juan • Miami, Florida

Insider cabins from

$4,650

per Cabin

‌

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$4,650

per Cabin

‌

Departing on:

2025

Fri, Dec 26 - Sun, Jan 04

from (US$)$4,650

Resilient New Year's Ahoy!

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

Insider cabins from

$3,780

per Cabin

‌

7 nights

Resilient Lady

BOOK NOW

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,780

per Cabin

‌

Departing on:

2025

Sat, Dec 27 - Sat, Jan 03

from (US$)$3,780

Scarlet New Year's Ahoy!

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

Insider cabins from

$2,920

per Cabin

‌

5 nights

Scarlet Lady

BOOK NOW

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,920

per Cabin

‌

Departing on:

2025

Sun, Dec 28 - Fri, Jan 02

from (US$)$2,920

Cozumel, Grand Cayman & Bimini

Miami, Florida • George Town • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,946

per Cabin

‌

7 nights

Resilient Lady

BOOK NOW

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,946

per Cabin

‌

Departing on:

2026

Sat, Jan 03 - Sat, Jan 10

from (US$)$1,946

Aruba, Bonaire, Colombia, Jamaica & More

Miami, Florida • Oranjestad • Kralendijk • Cartagena • Ocho Rios • George Town • Miami, Florida

Insider cabins from

$2,840

per Cabin

‌

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,840

per Cabin

‌

Departing on:

2026

Sun, Jan 04 - Thu, Jan 15

from (US$)$2,840

Cayman Isles & Jamaican Miles

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

Insider cabins from

$1,948

per Cabin

‌

7 nights

Resilient Lady

BOOK NOW

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,948

per Cabin

‌

Departing on:

2026Best Rate

Sat, Jan 10 - Sat, Jan 17

from (US$)$1,948

2026

Sat, Mar 07 - Sat, Mar 14

from (US$)$2,226

RED HOT

Grand Turk Tranquility & St. Croix Charm

Miami, Florida • Grand Turk • Puerto Plata • San Juan • St. Croix • Miami, Florida

Insider cabins from

$3,222

per Cabin

‌

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,222

per Cabin

‌

Departing on:

2026

Thu, Jan 15 - Fri, Jan 23

from (US$)$3,222

Magnetic Miami to Gorgeous George Town

Miami, Florida • Willemstad • Oranjestad • Cartagena • Ocho Rios • George Town • Miami, Florida

Insider cabins from

$2,840

per Cabin

‌

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,840

per Cabin

‌

Departing on:

2026

Sun, Feb 01 - Thu, Feb 12

from (US$)$2,840

Gorgeous Antigua, St. Kitts & Bimini

Miami, Florida • Puerto Plata • St. John's • Basseterre • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,322

per Cabin

‌

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,322

per Cabin

‌

Departing on:

2026

Thu, Mar 12 - Sat, Mar 21

from (US$)$2,322

Costa Mayan Caves & Honduran Waves

Miami, Florida • Costa Maya • Roatán • Cozumel (Playa del Carmen) • Miami, Florida

Insider cabins from

$2,006

per Cabin

‌

6 nights

Resilient Lady

BOOK NOW

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,006

per Cabin

‌

Departing on:

2026

Sat, Mar 14 - Fri, Mar 20

from (US$)$2,006

RED HOT

Puerto Rican Nights & St. Croix Delights

Miami, Florida • Puerto Plata • San Juan • St. Croix • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,544

per Cabin

‌

8 nights

Resilient Lady

BOOK NOW

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,544

per Cabin

‌

Departing on:

2026

Fri, Mar 20 - Sat, Mar 28

from (US$)$2,544

Panama Canal & Pacific Wonders

Miami, Florida • Cartagena • Colón • Panama Canal (Cruising) • Puntarenas • Puerto Quetzal • Cabo San Lucas • Los Angeles, California

Insider cabins from

$6,686

per Cabin

‌

16 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$6,686

per Cabin

‌

Departing on:

2026

Sat, Mar 21 - Mon, Apr 06

from (US$)$6,686

Puerto Plata, San Juan & Tortola

Miami, Florida • Puerto Plata • San Juan • Tortola • Miami, Florida

Insider cabins from

$2,228

per Cabin

‌

7 nights

Scarlet Lady

BOOK NOW

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,228

per Cabin

‌

Departing on:

2026

Sun, Apr 19 - Sun, Apr 26

from (US$)$2,228

‌

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Showing 146 cruise vacations that match your search

Riviera Maya

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

Insider cabins from

$1,340

per Cabin

‌

5 nights

Valiant Lady, Scarlet Lady & Resilient Lady

BOOK NOW

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,340

per Cabin

‌

Departing on:

2025Best Rate

Sun, Nov 30 - Fri, Dec 05

from (US$)$1,340

2025

Sun, Mar 23 - Fri, Mar 28

from (US$)$2,752

2025

Sun, Apr 06 - Fri, Apr 11

from (US$)$1,698

Dominican Daze

Miami, Florida • Puerto Plata • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,502

per Cabin

‌

5 nights

Valiant Lady, Scarlet Lady & Resilient Lady

BOOK NOW

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,502

per Cabin

‌

Departing on:

2025Best Rate

Fri, Dec 05 - Wed, Dec 10

from (US$)$1,502

2025

Fri, Mar 28 - Wed, Apr 02

from (US$)$1,890

2025

Fri, Apr 25 - Wed, Apr 30

from (US$)$1,988

Western Caribbean Charm

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

Insider cabins from

$2,100

per Cabin

‌

6 nights

Scarlet Lady & Resilient Lady

BOOK NOW

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,100

per Cabin

‌

Departing on:

2025Best Rate

Sun, Nov 09 - Sat, Nov 15

from (US$)$2,100

2025

Sun, Mar 30 - Sat, Apr 05

from (US$)$2,646

2025

Sun, Apr 13 - Sat, Apr 19

from (US$)$2,644

* Port changes in place on select sailings — see full cruise details

Fire & Sunset Soirées

Miami, Florida • Key West, Florida • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,272

per Cabin

‌

4 nights

Valiant Lady, Scarlet Lady & Resilient Lady

BOOK NOW

+ up to $50 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,272

per Cabin

‌

Departing on:

2026Best Rate

Wed, Jan 07 - Sun, Jan 11

from (US$)$1,272

2025

Wed, Apr 02 - Sun, Apr 06

from (US$)$1,962

2025

Wed, Apr 16 - Sun, Apr 20

from (US$)$1,996

Eastern Caribbean Antilles

Miami, Florida • Puerto Plata • San Juan • St. Croix • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,878

per Cabin

‌

8 nights

Scarlet Lady

BOOK NOW

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,878

per Cabin

‌

Departing on:

2025Best Rate

Sat, Apr 05 - Sun, Apr 13

from (US$)$2,878

2025

Sat, Apr 19 - Sun, Apr 27

from (US$)$3,038

Sunny Daze in Puerto Plata & Nassau

Miami, Florida • Puerto Plata • Nassau • Miami, Florida

Insider cabins from

$1,630

per Cabin

‌

5 nights

Valiant Lady

BOOK NOW

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,630

per Cabin

‌

Departing on:

2025

Fri, Apr 11 - Wed, Apr 16

from (US$)$1,630

Mayan Sol

Miami, Florida • Costa Maya • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,490

per Cabin

‌

5 nights

Valiant Lady & Resilient Lady

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+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,490

per Cabin

‌

Departing on:

2025Best Rate

Sun, Sep 07 - Fri, Sep 12

from (US$)$1,490

2025

Sun, May 18 - Fri, May 23

from (US$)$2,058

2025

Sun, Jun 15 - Fri, Jun 20

from (US$)$2,096

Grand Cayman, Costa Maya & More

Miami, Florida • George Town • Costa Maya • Beach Club at Bimini • Miami, Florida

Insider cabins from

$3,230

per Cabin

‌

7 nights

Valiant Lady

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+ up to $200 in drinks — on us

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Insider cabins from

$3,230

per Cabin

‌

Departing on:

2025

Sun, Jul 13 - Sun, Jul 20

from (US$)$3,230

Grand Turk, Puerto Plata & More

Miami, Florida • Puerto Plata • Grand Turk • Beach Club at Bimini • Miami, Florida

Insider cabins from

$3,504

per Cabin

‌

7 nights

Valiant Lady

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+ up to $200 in drinks — on us

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Insider cabins from

$3,504

per Cabin

‌

Departing on:

2025

Sun, Jul 20 - Sun, Jul 27

from (US$)$3,504

Virgin Voyages Comedy Fest from Miami

Miami, Florida • Costa Maya • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,100

per Cabin

‌

5 nights

Valiant Lady

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+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,100

per Cabin

‌

Departing on:

2025

Sun, Aug 10 - Fri, Aug 15

from (US$)$2,100

RED HOT

Brilliant Lady Miami MerMaiden

Miami, Florida • Philipsburg, St. Maarten • Tortola • Beach Club at Bimini • Miami, Florida

Insider cabins from

$3,200

per Cabin

‌

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

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+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,200

per Cabin

‌

Departing on:

2025

Fri, Oct 17 - Sat, Oct 25

from (US$)$3,200

Riviera Maya: Halloween Edition

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

Sea View cabins from

$2,000

per Cabin

‌

5 nights

Valiant Lady

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+ up to $100 in drinks — on us

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Sea View cabins from

$2,000

per Cabin

‌

Departing on:

2025

Sun, Oct 19 - Fri, Oct 24

from (US$)$2,000

Dominican Daze: Halloween Edition

Miami, Florida • Puerto Plata • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,802

per Cabin

‌

5 nights

Valiant Lady

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+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,802

per Cabin

‌

Departing on:

2025

Fri, Oct 24 - Wed, Oct 29

from (US$)$1,802

Honduras, Mexico & Bahamas

Miami, Florida • Roatán • Costa Maya • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,450

per Cabin

‌

7 nights

Scarlet Lady

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+ up to $200 in drinks — on us

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Insider cabins from

$2,450

per Cabin

‌

Departing on:

2025

Fri, Oct 31 - Fri, Nov 07

from (US$)$2,450

Western Caribbean: From Miami to Bimini

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

Insider cabins from

$2,170

per Cabin

‌

7 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

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+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,170

per Cabin

‌

Departing on:

2025

Sat, Nov 01 - Sat, Nov 08

from (US$)$2,170

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

Miami, Florida • Puerto Plata • Philipsburg, St. Maarten • Tortola • San Juan

Insider cabins from

$2,100

per Cabin

‌

6 nights

Valiant Lady

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+ up to $100 in drinks — on us

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Insider cabins from

$2,100

per Cabin

‌

Departing on:

2025

Sun, Nov 02 - Sat, Nov 08

from (US$)$2,100

Colorful Curaçao to the Charming Caymans

Miami, Florida • Oranjestad • Willemstad • Cartagena • Ocho Rios • George Town • Miami, Florida

Insider cabins from

$3,136

per Cabin

‌

12 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

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+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,136

per Cabin

‌

Departing on:

2025

Sat, Nov 08 - Thu, Nov 20

from (US$)$3,136

San Juan Sunrises & Dominican Dreams

Miami, Florida • San Juan • Puerto Plata • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,974

per Cabin

‌

7 nights

Resilient Lady

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+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,974

per Cabin

‌

Departing on:

2025Best Rate

Sat, Nov 15 - Sat, Nov 22

from (US$)$1,974

2026

Sat, Jan 31 - Sat, Feb 07

from (US$)$2,086

2026

Sat, Feb 28 - Sat, Mar 07

from (US$)$2,086

Sunny San Juan & Isles of Beach Miles

Miami, Florida • Puerto Plata • San Juan • Philipsburg, St. Maarten • St. Croix • Miami, Florida

Insider cabins from

$2,384

per Cabin

‌

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

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+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,384

per Cabin

‌

Departing on:

2026Best Rate

Thu, Feb 12 - Fri, Feb 20

from (US$)$2,384

2025

Thu, Nov 20 - Fri, Nov 28

from (US$)$2,402

Miami, Grand Turk (& back)

Miami, Florida • Grand Turk • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,592

per Cabin

‌

5 nights

Scarlet Lady & Resilient Lady

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+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,592

per Cabin

‌

Departing on:

2026Best Rate

Fri, Feb 27 - Wed, Mar 04

from (US$)$1,592

2025

Fri, Nov 21 - Wed, Nov 26

from (US$)$1,850

2025

Fri, Dec 19 - Wed, Dec 24

from (US$)$1,804

Cayman Coves & Jamaican Waterfalls

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

Insider cabins from

$1,948

per Cabin

‌

7 nights

Resilient Lady

BOOK NOW

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,948

per Cabin

‌

Departing on:

2026Best Rate

Sat, Jan 24 - Sat, Jan 31

from (US$)$1,948

2025

Sat, Nov 22 - Sat, Nov 29

from (US$)$2,242

2025

Sat, Dec 06 - Sat, Dec 13

from (US$)$2,100

Antigua Waves & Grand Turk Caves

Miami, Florida • Grand Turk • St. John's • Basseterre • San Juan • Miami, Florida

Insider cabins from

$2,322

per Cabin

‌

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

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+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,322

per Cabin

‌

Departing on:

2026Best Rate

Fri, Feb 20 - Sun, Mar 01

from (US$)$2,322

2025

Fri, Nov 28 - Sun, Dec 07

from (US$)$2,370

2026

Fri, Jan 23 - Sun, Feb 01

from (US$)$3,210

San Juan, Samaná & Bimini

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

Insider cabins from

$1,948

per Cabin

‌

7 nights

Resilient Lady

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+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,948

per Cabin

‌

Departing on:

2026Best Rate

Sat, Jan 17 - Sat, Jan 24

from (US$)$1,948

2025

Sat, Nov 29 - Sat, Dec 06

from (US$)$1,976

Aruban Sunsets & Calm Cayman Days

Miami, Florida • Oranjestad • Cartagena • Ocho Rios • George Town • Miami, Florida

Insider cabins from

$2,838

per Cabin

‌

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

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+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,838

per Cabin

‌

Departing on:

2026Best Rate

Sun, Mar 01 - Thu, Mar 12

from (US$)$2,838

2025

Sun, Dec 07 - Thu, Dec 18

from (US$)$2,868

Brilliant Caribbean Holidays

Miami, Florida • Grand Turk • Puerto Plata • San Juan • Samaná • Miami, Florida

Insider cabins from

$3,200

per Cabin

‌

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,200

per Cabin

‌

Departing on:

2025

Thu, Dec 18 - Fri, Dec 26

from (US$)$3,200

Scarlet Caribbean Holidays

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

Insider cabins from

$1,758

per Cabin

‌

4 nights

Scarlet Lady

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+ up to $50 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,758

per Cabin

‌

Departing on:

2025

Wed, Dec 24 - Sun, Dec 28

from (US$)$1,758

Brilliant New Year's Ahoy!

Miami, Florida • Grand Turk • St. John's • Basseterre • San Juan • Miami, Florida

Insider cabins from

$4,650

per Cabin

‌

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$4,650

per Cabin

‌

Departing on:

2025

Fri, Dec 26 - Sun, Jan 04

from (US$)$4,650

Resilient New Year's Ahoy!

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

Insider cabins from

$3,780

per Cabin

‌

7 nights

Resilient Lady

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+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,780

per Cabin

‌

Departing on:

2025

Sat, Dec 27 - Sat, Jan 03

from (US$)$3,780

Scarlet New Year's Ahoy!

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

Insider cabins from

$2,920

per Cabin

‌

5 nights

Scarlet Lady

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+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,920

per Cabin

‌

Departing on:

2025

Sun, Dec 28 - Fri, Jan 02

from (US$)$2,920

Cozumel, Grand Cayman & Bimini

Miami, Florida • George Town • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,946

per Cabin

‌

7 nights

Resilient Lady

BOOK NOW

+ up to $200 in drinks — on us

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Insider cabins from

$1,946

per Cabin

‌

Departing on:

2026

Sat, Jan 03 - Sat, Jan 10

from (US$)$1,946

Aruba, Bonaire, Colombia, Jamaica & More

Miami, Florida • Oranjestad • Kralendijk • Cartagena • Ocho Rios • George Town • Miami, Florida

Insider cabins from

$2,840

per Cabin

‌

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

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+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,840

per Cabin

‌

Departing on:

2026

Sun, Jan 04 - Thu, Jan 15

from (US$)$2,840

Cayman Isles & Jamaican Miles

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

Insider cabins from

$1,948

per Cabin

‌

7 nights

Resilient Lady

BOOK NOW

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,948

per Cabin

‌

Departing on:

2026Best Rate

Sat, Jan 10 - Sat, Jan 17

from (US$)$1,948

2026

Sat, Mar 07 - Sat, Mar 14

from (US$)$2,226

RED HOT

Grand Turk Tranquility & St. Croix Charm

Miami, Florida • Grand Turk • Puerto Plata • San Juan • St. Croix • Miami, Florida

Insider cabins from

$3,222

per Cabin

‌

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

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+ up to $200 in drinks — on us

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Insider cabins from

$3,222

per Cabin

‌

Departing on:

2026

Thu, Jan 15 - Fri, Jan 23

from (US$)$3,222

Magnetic Miami to Gorgeous George Town

Miami, Florida • Willemstad • Oranjestad • Cartagena • Ocho Rios • George Town • Miami, Florida

Insider cabins from

$2,840

per Cabin

‌

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,840

per Cabin

‌

Departing on:

2026

Sun, Feb 01 - Thu, Feb 12

from (US$)$2,840

Gorgeous Antigua, St. Kitts & Bimini

Miami, Florida • Puerto Plata • St. John's • Basseterre • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,322

per Cabin

‌

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,322

per Cabin

‌

Departing on:

2026

Thu, Mar 12 - Sat, Mar 21

from (US$)$2,322

Costa Mayan Caves & Honduran Waves

Miami, Florida • Costa Maya • Roatán • Cozumel (Playa del Carmen) • Miami, Florida

Insider cabins from

$2,006

per Cabin

‌

6 nights

Resilient Lady

BOOK NOW

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,006

per Cabin

‌

Departing on:

2026

Sat, Mar 14 - Fri, Mar 20

from (US$)$2,006

RED HOT

Puerto Rican Nights & St. Croix Delights

Miami, Florida • Puerto Plata • San Juan • St. Croix • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,544

per Cabin

‌

8 nights

Resilient Lady

BOOK NOW

+ up to $200 in drinks — on us

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Insider cabins from

$2,544

per Cabin

‌

Departing on:

2026

Fri, Mar 20 - Sat, Mar 28

from (US$)$2,544

Panama Canal & Pacific Wonders

Miami, Florida • Cartagena • Colón • Panama Canal (Cruising) • Puntarenas • Puerto Quetzal • Cabo San Lucas • Los Angeles, California

Insider cabins from

$6,686

per Cabin

‌

16 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$6,686

per Cabin

‌

Departing on:

2026

Sat, Mar 21 - Mon, Apr 06

from (US$)$6,686

Puerto Plata, San Juan & Tortola

Miami, Florida • Puerto Plata • San Juan • Tortola • Miami, Florida

Insider cabins from

$2,228

per Cabin

‌

7 nights

Scarlet Lady

BOOK NOW

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,228

per Cabin

‌

Departing on:

2026

Sun, Apr 19 - Sun, Apr 26

from (US$)$2,228

Explore 390 cruise vacations

Riviera Maya

Dominican Daze

Western Caribbean Charm

Fire & Sunset Soirées

Eastern Caribbean Antilles

Sunny Daze in Puerto Plata & Nassau

Mayan Sol

Grand Cayman, Costa Maya & More

Grand Turk, Puerto Plata & More

Virgin Voyages Comedy Fest from Miami

Brilliant Lady Miami MerMaiden

Riviera Maya: Halloween Edition

Dominican Daze: Halloween Edition

Honduras, Mexico & Bahamas

Western Caribbean: From Miami to Bimini

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

Colorful Curaçao to the Charming Caymans

San Juan Sunrises & Dominican Dreams

Sunny San Juan & Isles of Beach Miles

Miami, Grand Turk (& back)

Cayman Coves & Jamaican Waterfalls

Antigua Waves & Grand Turk Caves

San Juan, Samaná & Bimini

Aruban Sunsets & Calm Cayman Days

Brilliant Caribbean Holidays

Scarlet Caribbean Holidays

Brilliant New Year's Ahoy!

Resilient New Year's Ahoy!

Scarlet New Year's Ahoy!

Cozumel, Grand Cayman & Bimini

Aruba, Bonaire, Colombia, Jamaica & More

Cayman Isles & Jamaican Miles

Grand Turk Tranquility & St. Croix Charm

Magnetic Miami to Gorgeous George Town

Gorgeous Antigua, St. Kitts & Bimini

Costa Mayan Caves & Honduran Waves

Puerto Rican Nights & St. Croix Delights

Panama Canal & Pacific Wonders

Puerto Plata, San Juan & Tortola

Riviera Maya

Dominican Daze

Western Caribbean Charm

Fire & Sunset Soirées

Eastern Caribbean Antilles

Sunny Daze in Puerto Plata & Nassau

Mayan Sol

Grand Cayman, Costa Maya & More

Grand Turk, Puerto Plata & More

Virgin Voyages Comedy Fest from Miami

Brilliant Lady Miami MerMaiden

Riviera Maya: Halloween Edition

Dominican Daze: Halloween Edition

Honduras, Mexico & Bahamas

Western Caribbean: From Miami to Bimini

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

Colorful Curaçao to the Charming Caymans

San Juan Sunrises & Dominican Dreams

Sunny San Juan & Isles of Beach Miles

Miami, Grand Turk (& back)

Cayman Coves & Jamaican Waterfalls

Antigua Waves & Grand Turk Caves

San Juan, Samaná & Bimini

Aruban Sunsets & Calm Cayman Days

Brilliant Caribbean Holidays

Scarlet Caribbean Holidays

Brilliant New Year's Ahoy!

Resilient New Year's Ahoy!

Scarlet New Year's Ahoy!

Cozumel, Grand Cayman & Bimini

Aruba, Bonaire, Colombia, Jamaica & More

Cayman Isles & Jamaican Miles

Grand Turk Tranquility & St. Croix Charm

Magnetic Miami to Gorgeous George Town

Gorgeous Antigua, St. Kitts & Bimini

Costa Mayan Caves & Honduran Waves

Puerto Rican Nights & St. Croix Delights

Panama Canal & Pacific Wonders

Puerto Plata, San Juan & Tortola

80% off your 2nd Sailor + free drinks