Currency, current value
$USD

Explore 406 cruise vacations

Showing Loading cruise vacations: All Destinations, June 2025 - October 2026
Departs Miami, Florida
UP TO $300 IN ONBOARD CREDIT
On Caribbean sailings 7 nights or longer
|
On top of 70% off 2nd Sailor + balcony upgrades

70% off 2nd Sailor + Free balcony upgrade ends in…

Loading
Showing 143 cruise vacations that match your search
Showing 143 cruise vacations that match your search
Sort price type, current value Price per Sailor per night
Sort options, current value Sails first

Fire & Sunset Soirées

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Sailor per night
Loading
4 nights
Valiant Lady, Scarlet Lady & Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2026Best Rate
Thu, Sep 24 - Mon, Sep 28
from (US$)
2025
Wed, Jul 09 - Sun, Jul 13
from (US$)
Only suites remaining
2025
Wed, Aug 06 - Sun, Aug 10
from (US$)
DEAL

Grand Cayman, Costa Maya & More

  • Miami, Florida
  • George Town, Grand Cayman
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
per Sailor per night
Loading
7 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea Terrace cabins from
per Sailor per night
Loading
Departing on:
2025
Sun, Jul 13 - Sun, Jul 20
from (US$)
DEAL

Grand Turk, Puerto Plata & More

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • Grand Turk, Turks and Caicos
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Sailor per night
Loading
7 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2025
Sun, Jul 20 - Sun, Jul 27
from (US$)

Riviera Maya

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Sailor per night
Loading
5 nights
Valiant Lady, Scarlet Lady & Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2025Best Rate
Sun, Nov 16 - Fri, Nov 21
from (US$)
2025
Sun, Jul 27 - Fri, Aug 01
from (US$)
2025
Sun, Aug 24 - Fri, Aug 29
from (US$)

Dominican Daze

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Sailor per night
Loading
5 nights
Valiant Lady, Scarlet Lady & Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2025Best Rate
Fri, Oct 10 - Wed, Oct 15
from (US$)
2025
Fri, Aug 01 - Wed, Aug 06
from (US$)
2025
Fri, Aug 15 - Wed, Aug 20
from (US$)

Virgin Voyages Comedy Fest from Miami

  • Miami, Florida
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
per Sailor per night
Loading
5 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea Terrace cabins from
per Sailor per night
Loading
Departing on:
2025
Sun, Aug 10 - Fri, Aug 15
from (US$)

Mayan Sol

  • Miami, Florida
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
per Sailor per night
Loading
5 nights
Valiant Lady & Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea View cabins from
per Sailor per night
Loading
Departing on:
2025Best Rate
Sun, Oct 05 - Fri, Oct 10
from (US$)
2025
Sun, Sep 07 - Fri, Sep 12
from (US$)
2026
Mon, Jun 22 - Sat, Jun 27
from (US$)
DEAL

Brilliant Lady Miami MerMaiden

  • Miami, Florida
  • Philipsburg, St. Maarten
  • Tortola, British Virgin Islands
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Sailor per night
Loading
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2025
Fri, Oct 17 - Sat, Oct 25
from (US$) Brilliant Lady's Inaugural Season

Riviera Maya: Halloween Edition

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
per Sailor per night
Loading
5 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea View cabins from
per Sailor per night
Loading
Departing on:
2025
Sun, Oct 19 - Fri, Oct 24
from (US$)

Dominican Daze: Halloween Edition

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
per Sailor per night
Loading
5 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea Terrace cabins from
per Sailor per night
Loading
Departing on:
2025
Fri, Oct 24 - Wed, Oct 29
from (US$)

Valiant's Haunted Halloween Soirée

  • Miami, Florida
  • Key West, Florida
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea Terrace cabins from
per Sailor per night
Loading
4 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea Terrace cabins from
per Sailor per night
Loading
Departing on:
2025
Wed, Oct 29 - Sun, Nov 02
from (US$)
DEAL

Honduras, Mexico & Bahamas

  • Miami, Florida
  • Roatán, Honduras
  • Costa Maya, Mexico
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
per Sailor per night
Loading
7 nights
Scarlet Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea View cabins from
per Sailor per night
Loading
Departing on:
2025
Fri, Oct 31 - Fri, Nov 07
from (US$)
DEAL

Western Caribbean: From Miami to Bimini

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Sailor per night
Loading
7 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2025
Sat, Nov 01 - Sat, Nov 08
from (US$) Brilliant Lady's Inaugural Season

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
Loading
6 nights
Valiant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2025
Sun, Nov 02 - Sat, Nov 08
from (US$)
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
Loading
12 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2025
Sat, Nov 08 - Thu, Nov 20
from (US$) Brilliant Lady's Inaugural Season

Western Caribbean Charm

  • Miami, Florida
  • Costa Maya, Mexico
  • Roatán, Honduras
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Sailor per night
Loading
6 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2025
Sun, Nov 09 - Sat, Nov 15
from (US$)
DEAL

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
per Sailor per night
Loading
7 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2026Best Rate
Sat, Mar 28 - Sat, Apr 04
from (US$)
2025
Sat, Nov 15 - Sat, Nov 22
from (US$)
2026
Sat, Apr 18 - Sat, Apr 25
from (US$)
DEAL

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
per Sailor per night
Loading
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2025Best Rate
Thu, Nov 20 - Fri, Nov 28
from (US$) Brilliant Lady's Inaugural Season
2026
Thu, Feb 12 - Fri, Feb 20
from (US$) Brilliant Lady's Inaugural Season

Miami, Grand Turk (& back)

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Sailor per night
Loading
5 nights
Scarlet Lady & Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2026Best Rate
Sat, Sep 19 - Thu, Sep 24
from (US$)
2025
Fri, Nov 21 - Wed, Nov 26
from (US$)
2025
Sun, Nov 30 - Fri, Dec 05
from (US$)
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
Loading
7 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2026Best Rate
Sat, Jan 24 - Sat, Jan 31
from (US$)
2025
Sat, Nov 22 - Sat, Nov 29
from (US$)
2025
Sat, Dec 06 - Sat, Dec 13
from (US$)
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
Loading
9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2026Best Rate
Fri, Feb 20 - Sun, Mar 01
from (US$) Brilliant Lady's Inaugural Season
2025
Fri, Nov 28 - Sun, Dec 07
from (US$) Brilliant Lady's Inaugural Season
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
Loading
7 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2025Best Rate
Sat, Nov 29 - Sat, Dec 06
from (US$)
2026
Sat, Jan 17 - Sat, Jan 24
from (US$)
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
Loading
11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2025Best Rate
Sun, Dec 07 - Thu, Dec 18
from (US$) Brilliant Lady's Inaugural Season
2026
Sun, Mar 01 - Thu, Mar 12
from (US$) Brilliant Lady's Inaugural Season
DEAL

Brilliant Caribbean Holidays

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Samaná, Dominican Republic
  • Miami, Florida
Insider cabins from
per Sailor per night
Loading
8 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2025
Thu, Dec 18 - Fri, Dec 26
from (US$) Brilliant Lady's Inaugural Season
DEAL

Resilient Caribbean Holidays

  • Miami, Florida
  • San Juan, Puerto Rico
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Sailor per night
Loading
7 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2025
Sat, Dec 20 - Sat, Dec 27
from (US$)

Scarlet Caribbean Holidays

  • Miami, Florida
  • Nassau, Bahamas
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
per Sailor per night
Loading
4 nights
Scarlet Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea View cabins from
per Sailor per night
Loading
Departing on:
2025
Wed, Dec 24 - Sun, Dec 28
from (US$)
DEAL

Brilliant New Year's Ahoy!

  • 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
Loading
9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2025
Fri, Dec 26 - Sun, Jan 04
from (US$) Brilliant Lady's Inaugural Season
DEAL

Resilient New Year's Ahoy!

  • Miami, Florida
  • Ocho Rios, Jamaica
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Sailor per night
Loading
7 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2025
Sat, Dec 27 - Sat, Jan 03
from (US$)

Scarlet New Year's Ahoy!

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Sea View cabins from
per Sailor per night
Loading
5 nights
Scarlet Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea View cabins from
per Sailor per night
Loading
Departing on:
2025
Sun, Dec 28 - Fri, Jan 02
from (US$)
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
Loading
7 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2026
Sat, Jan 03 - Sat, Jan 10
from (US$)
DEAL

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
per Sailor per night
Loading
11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2026
Sun, Jan 04 - Thu, Jan 15
from (US$) Brilliant Lady's Inaugural Season
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
Loading
7 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2026Best Rate
Sat, Jan 10 - Sat, Jan 17
from (US$)
2026
Sat, Mar 07 - Sat, Mar 14
from (US$)

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
Loading
6 nights
Brilliant Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2026
Mon, Jan 26 - Sun, Feb 01
from (US$)
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
Loading
7 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2026Best Rate
Sat, Jan 31 - Sat, Feb 07
from (US$)
2026
Sat, Feb 28 - Sat, Mar 07
from (US$)
DEAL

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
per Sailor per night
Loading
11 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2026
Sun, Feb 01 - Thu, Feb 12
from (US$) Brilliant Lady's Inaugural Season
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
Loading
7 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2026
Sat, Feb 07 - Sat, Feb 14
from (US$)
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
Loading
9 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2026
Thu, Mar 12 - Sat, Mar 21
from (US$) Brilliant Lady's Inaugural Season

Costa Mayan Caves & Honduran Waves

  • Miami, Florida
  • Roatán, Honduras
  • Costa Maya, Mexico
  • Cozumel, Mexico
  • Miami, Florida
Insider cabins from
per Sailor per night
Loading
6 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2026
Sat, Mar 14 - Fri, Mar 20
from (US$)
DEAL

Puerto Rican Nights & St. Croix Delights

  • 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
per Sailor per night
Loading
8 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2026
Fri, Mar 20 - Sat, Mar 28
from (US$)

Panama Canal & Pacific Wonders

  • Miami, Florida
  • Cartagena, Colombia
  • Colón, Panama
  • Panama Canal (Cruising), Panama
  • Puntarenas, Costa Rica
  • Puerto Quetzal, Guatemala
  • Cabo San Lucas, Mexico
  • Los Angeles, California
Insider cabins from
per Sailor per night
Loading
16 nights
Brilliant Lady
Brilliant Lady's Inaugural Season
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2026
Sat, Mar 21 - Mon, Apr 06
from (US$) Brilliant Lady's Inaugural Season
DEAL

Puerto Plata, San Juan & Tortola

  • Miami, Florida
  • Puerto Plata, Dominican Republic
  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Miami, Florida
Insider cabins from
per Sailor per night
Loading
7 nights
Scarlet Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2026
Sun, Apr 19 - Sun, Apr 26
from (US$)

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
Loading
14 nights
Scarlet Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Sea View cabins from
per Sailor per night
Loading
Departing on:
2026
Sun, Apr 26 - Sun, May 10
from (US$)

Cayman Isles & Bimini Beach Miles

  • Miami, Florida
  • George Town, Grand Cayman
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Sailor per night
Loading
5 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2026Best Rate
Sat, Jun 13 - Thu, Jun 18
from (US$)
2026
Mon, Jun 08 - Sat, Jun 13
from (US$)

Miami to Grand Turk: Halloween Edition

  • Miami, Florida
  • Grand Turk, Turks and Caicos
  • Puerto Plata, Dominican Republic
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Sailor per night
Loading
6 nights
Scarlet Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2026
Sun, Oct 25 - Sat, Oct 31
from (US$)

Mexico & Bimini: Halloween Edition

  • Miami, Florida
  • Cozumel, Mexico
  • Costa Maya, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Sailor per night
Loading
6 nights
Resilient Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2026
Mon, Oct 26 - Sun, Nov 01
from (US$)

Scarlet's Haunted Halloween Soirée

  • Miami, Florida
  • Cozumel, Mexico
  • The Beach Club at Bimini, Bahamas
  • Miami, Florida
Insider cabins from
per Sailor per night
Loading
5 nights
Scarlet Lady
BOOK NOW
+ free balcony upgrade
SWING INTO SUMMER: 70% off 2nd Sailor
Insider cabins from
per Sailor per night
Loading
Departing on:
2026
Sat, Oct 31 - Thu, Nov 05
from (US$)
Average starting price per Sailor per night (incl. taxes & fees)