Explore 419 cruise vacations

Showing cruise vacations: All Destinations, September 2025 - October 2025

2 Sailors , 1 Cabin

Insider

Select Caribbean sailings from $109 pp/pn

Greek Island Glow

Athens (Piraeus)
Santorini, Greece
Rhodes, Greece
Bodrum, Turkey
Mykonos, Greece
Athens (Piraeus)

Insider cabins from

$3,766~~$5,468~~

per Cabin

7 nights

Resilient Lady

+ Instant Savings

70% off a second Sailor

Insider cabins from

$3,766~~$5,468~~

per Cabin

Departing on:

Sun, Oct 12 - Sun, Oct 19

from (US$)$3,766

Sun, Sep 14 - Sun, Sep 21

from (US$)$3,850

Fall Colors: Coastal Northeast & Canada

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

Insider cabins from

$2,544~~$3,616~~

per Cabin

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ Instant Savings

70% off a second Sailor

Insider cabins from

$2,544~~$3,616~~

per Cabin

Departing on:

Mon, Sep 15 - Tue, Sep 23

from (US$)$2,544

70% off a 2nd Sailor + up to $500 off

Savings on new Brilliant Lady voyages, Europe, Caribbean and more through 2027.

Mayan Sol

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

Insider cabins from

$1,290~~$1,714~~

per Cabin

5 nights

Valiant Lady

+ Instant Savings

70% off a second Sailor

Insider cabins from

$1,290~~$1,714~~

per Cabin

Departing on:

Sun, Oct 05 - Fri, Oct 10

from (US$)$1,290

Italy to France & Spain

Rome (Civitavecchia)
Cagliari, Sardinia, Italy
Tuscany/Cinque Terre (Marina di Carrara), Italy
Ajaccio, Corsica, France
Cannes, France
Valencia, Spain
Barcelona

Insider cabins from

$3,510~~$5,200~~

per Cabin

9 nights

Scarlet Lady

+ Instant Savings

70% off a second Sailor

Insider cabins from

$3,510~~$5,200~~

per Cabin

Departing on:

Tue, Oct 07 - Thu, Oct 16

from (US$)$3,510

Brilliant Lady Miami MerMaiden

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

Insider cabins from

$2,384~~$3,436~~

per Cabin

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ Instant Savings

70% off a second Sailor

Insider cabins from

$2,384~~$3,436~~

per Cabin

Departing on:

Fri, Oct 17 - Sat, Oct 25

from (US$)$2,384

Riviera Maya: Halloween Edition

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

Insider cabins from

$1,290~~$1,704~~

per Cabin

5 nights

Valiant Lady

+ Instant Savings

70% off a second Sailor

Insider cabins from

$1,290~~$1,704~~

per Cabin

Departing on:

Sun, Oct 19 - Fri, Oct 24

from (US$)$1,290

★

EXTRA SAVINGS

Scarlet's Haunted Halloween Soirée

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

Insider cabins from

$1,514

per Cabin

7 nights

Scarlet Lady

+ Instant Savings

70% off a second Sailor

Insider cabins from

$1,514

per Cabin

Departing on:

Fri, Oct 31 - Fri, Nov 07

from (US$)$1,514