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Cruise Dates

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October 2026

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Norwegian Bliss

Norwegian Cruise Line

Dec 11, 2026 - Dec 23, 2026 (12 Nights)

Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Tortola • Philipsburg, St. Maarten • St. Thomas • Manhattan

Average Starting Price

Jan 9, 2028 - Jan 23, 2028 (14 Nights)

Miami • St. Kitts • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Miami • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Miami

Average Starting Price

$1,088pp

Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

Emerald Princess

Princess Cruises

Jan 2, 2028 - Jan 16, 2028 (14 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Jan 25, 2027 - Feb 5, 2027 (11 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Fort Lauderdale

Average Starting Price

Nov 26, 2028 - Dec 3, 2028 (7 Nights)

San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

53% OFF

Jul 26, 2027 - Aug 2, 2027 (7 Nights)

La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • Fort-De-France, Martinique • St John's, Antigua • La Romana, Dominican Republic

Average Starting Price

Aug 21, 2027 - Aug 28, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Dec 28, 2026 - Jan 7, 2027 (10 Nights)

Miami • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • Tortola • St John's, Antigua • Bimini • Miami

Average Starting Price

$1,390pp

Jim's Onboard Credit

Phyllis' Holiday Pick
Best time of the year to cruise! I love spending the holidays cruising with my family! The ships are beautifully decorated, and ringing in New Year’s Eve at sea is an experience I’ll never forget!

Wind Surf

Windstar Cruises

Nov 28, 2027 - Dec 5, 2027 (7 Nights)

Philipsburg, St. Maarten • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten

Average Starting Price

45% OFF

Feb 21, 2027 - Mar 7, 2027 (14 Nights)

Miami • Nassau • Ocean Cay • Grand Turk • Miami • Philipsburg, St. Maarten • St John's, Antigua • St. Thomas • Amber Cove, Dominican Republic • Miami

Average Starting Price

$1,155pp

Jim's Onboard Credit

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!

45% OFF