Showing cruise vacations: All Destinations, September 2026 - December 2026

Quick find:

Sails Valiant Lady

Save up to $1,000 in Instant Savings

Showing 15 cruise vacations that match your search

New England & Canada Cruise

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

Insider cabins from

$1,192~~$1,647~~

per Sailor

8 nights

Valiant Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$1,192~~$1,647~~

per Sailor

Departing on:

Sat, Sep 19 - Sun, Sep 27

from (US$)$1,192

Bermuda Overnight Cruise

New York City, New York
Royal Naval Dockyard, Bermuda
New York City, New York

RockStar Quarters suites from

$2,495

per Sailor

5 nights

Valiant Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

RockStar Quarters suites from

$2,495

per Sailor

Departing on:

Sun, Sep 27 - Fri, Oct 02

from (US$)$2,495

Only suites remaining

YOUR FARE JUST GOT LIGHTER

UP TO $1,000 INSTANT SAVINGS

Plus 70% off your second Sailor across all inventory.

Stuff at Sea

New York City, New York
Royal Naval Dockyard, Bermuda
New York City, New York

Mega RockStar Quarters suites from

$3,495

per Sailor

5 nights

Valiant Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Mega RockStar Quarters suites from

$3,495

per Sailor

Departing on:

Fri, Oct 02 - Wed, Oct 07

from (US$)$3,495

Only suites remaining

Bermuda Overnight Cruise

New York City, New York
Royal Naval Dockyard, Bermuda
New York City, New York

Insider cabins from

$813~~$1,091~~

per Sailor

6 nights

Valiant Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$813~~$1,091~~

per Sailor

Departing on:

Tue, Oct 13 - Mon, Oct 19

Wed, Oct 07 - Tue, Oct 13

from (US$)$4,260

Only suites remaining

Bermuda & Caribbean: NYC to San Juan

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

$1,188~~$1,626~~

per Sailor

12 nights

Valiant Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$1,188~~$1,626~~

per Sailor

Departing on:

Mon, Oct 19 - Sat, Oct 31

from (US$)$1,188

Southern Caribbean Halloween Cruise

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

Sea View cabins from

$1,113~~$1,636~~

per Sailor

7 nights

Valiant Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Sea View cabins from

$1,113~~$1,636~~

per Sailor

Departing on:

Sat, Oct 31 - Sat, Nov 07

from (US$)$1,113

Southern Caribbean Cruise

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

$973~~$1,415~~

per Sailor

7 nights

Valiant Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$973~~$1,415~~

per Sailor

Departing on:

Sat, Dec 12 - Sat, Dec 19

Sat, Nov 07 - Sat, Nov 14

from (US$)$1,669

Southern Caribbean Cruise

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

Insider cabins from

$894~~$1,300~~

per Sailor

6 nights

Valiant Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$894~~$1,300~~

per Sailor

Departing on:

Sat, Nov 14 - Fri, Nov 20

Southern Caribbean Cruise

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

$1,112~~$1,621~~

per Sailor

8 nights

Valiant Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$1,112~~$1,621~~

per Sailor

Departing on:

Fri, Nov 20 - Sat, Nov 28

from (US$)$1,112

Southern Caribbean Cruise

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

$903~~$1,303~~

per Sailor

7 nights

Valiant Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$903~~$1,303~~

per Sailor

Departing on:

Sat, Nov 28 - Sat, Dec 05

Southern Caribbean & Aruban Nights

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

Insider cabins from

$903~~$1,313~~

per Sailor

7 nights

Valiant Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$903~~$1,313~~

per Sailor

Departing on:

Sat, Dec 05 - Sat, Dec 12

Southern Caribbean Holiday Cruise

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

Insider cabins from

$973~~$1,421~~

per Sailor

7 nights

Valiant Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$973~~$1,421~~

per Sailor

Departing on:

Sat, Dec 19 - Sat, Dec 26

Southern Caribbean New Year's Cruise

San Juan, Puerto Rico
Philipsburg, St. Maarten
Fort-de-France, Martinique
Bridgetown, Barbados
Castries, St. Lucia
St. John's, Antigua
San Juan, Puerto Rico

Insider cabins from

$1,603~~$2,382~~

per Sailor

7 nights

Valiant Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$1,603~~$2,382~~

per Sailor

Departing on:

Sat, Dec 26 - Sat, Jan 02

from (US$)$1,603

Average starting price per Sailor (incl. taxes & fees)