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Cruise Dates

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October 2026

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56% OFF

Margaritaville at Sea Beachcomber

Margaritaville at Sea

Jan 16, 2027 - Jan 23, 2027 (7 Nights)

Miami • St. Thomas • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami

Average Starting Price

$569pp

Jim's Onboard Credit

Norwegian Epic

Norwegian Cruise Line

Jan 7, 2028 - Jan 14, 2028 (7 Nights)

Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida

Average Starting Price

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

Miami • Philipsburg, St. Maarten • St. Thomas • Puerto Plata, Dominican Republic • Miami

Average Starting Price

Dec 23, 2027 - Jan 6, 2028 (14 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Grand Turk • Amber Cove, Dominican Republic • Nassau • Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • San Juan, Puerto Rico • Grand Turk • Fort Lauderdale

Average Starting Price

$3,944pp

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!

Norwegian Bliss

Norwegian Cruise Line

Jan 15, 2028 - Jan 26, 2028 (11 Nights)

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

Average Starting Price

Jan 16, 2028 - Jan 30, 2028 (14 Nights)

Miami • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Miami • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Miami

Average Starting Price

$1,138pp

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!

Rotterdam

Holland America Line

Jan 8, 2028 - Jan 22, 2028 (14 Nights)

Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • Grand Turk • Nassau • Fort Lauderdale

Average Starting Price

$3,229pp

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!

EXPLORA I

Explora Journeys

Dec 27, 2026 - Jan 11, 2027 (15 Nights)

Miami • Puerto Plata, Dominican Republic • Catalina Island, Dominican Republic • St. John • New Year Fireworks SJU • New Year Fireworks SJU • Great Harbor Jost Van Dyke, British Virgin Islands • Basseterre, St. Kitts and Nevis • St. Thomas • San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • Little Bay, Montserrat • Tortola • Miami

Average Starting Price

$15,520pp

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!

Allura

Oceania Cruises

Jan 27, 2027 - Feb 5, 2027 (9 Nights)

Miami • St. Thomas • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • Tortola • Miami

Average Starting Price

46% OFF

Mar 13, 2027 - Mar 27, 2027 (14 Nights)

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

Average Starting Price

$1,345pp

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!