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Cruise Dates

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October 2026

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Valiant Lady

Virgin Voyages

Jan 23, 2027 - Jan 29, 2027 (6 Nights)

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

Average Starting Price

Jan 17, 2027 - Jan 24, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • St John's, Antigua • Fort-De-France, Martinique • Kingstown, Saint Vincent Island, Saint Vincent • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico

Average Starting Price

$571pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Brilliant Lady

Virgin Voyages

Feb 8, 2027 - Feb 18, 2027 (10 Nights)

Miami • Philipsburg, St. Maarten • Tortola • St. Croix • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Bimini • Miami

Average Starting Price

Jan 29, 2027 - Feb 7, 2027 (9 Nights)

Fort Lauderdale • St John's, Antigua • St. Thomas • Tortola • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$1,834pp

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!

Rhapsody of the Seas

Royal Caribbean

Jan 23, 2027 - Jan 30, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico

Average Starting Price

$532pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Vista

Oceania Cruises

Mar 20, 2029 - Mar 31, 2029 (11 Nights)

Miami • San Juan, Puerto Rico • St John's, Antigua • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • Tortola • Miami

Average Starting Price

Dec 12, 2027 - Dec 19, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • St. Kitts • Martinique • Dominica • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Dec 12, 2027 - Dec 27, 2027 (15 Nights)

Miami • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Miami • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • Tortola • Miami

Average Starting Price

$1,403pp

Jim's Onboard Credit

Norwegian Epic

Norwegian Cruise Line

Dec 24, 2027 - Dec 31, 2027 (7 Nights)

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

Average Starting Price

$1,239pp

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!

9% OFF

Crystal Serenity

Crystal Cruises

Feb 12, 2028 - Feb 19, 2028 (7 Nights)

Fort Lauderdale • Tortola • Gustavia, St. Barts • Roseau, Dominica • St. Kitts • San Juan, Puerto Rico

Average Starting Price

$3,560pp

Jim's Onboard Credit

Norwegian Aura

Norwegian Cruise Line

Jul 17, 2027 - Jul 24, 2027 (7 Nights)

Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami

Average Starting Price

$1,349pp

Jim's Onboard Credit

Norwegian Bliss

Norwegian Cruise Line

Jan 3, 2028 - Jan 15, 2028 (12 Nights)

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

Average Starting Price

$1,419pp

Jim's Onboard Credit

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