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Emerald Princess
Princess Cruises
Dec 26, 2027 - Jan 9, 2028 (14 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,613pp
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!

Norwegian Viva
Norwegian Cruise Line
Nov 1, 2027 - Nov 15, 2027 (14 Nights)
Lisbon, Portugal • Las Palmas (Gran Canaria), Spain • Mindelo, Cape Verde • Tortola • Great Stirrup Cay • Miami
Average Starting Price
$1,639pp
Jim's Onboard Credit
Norwegian Aura
Norwegian Cruise Line
Aug 21, 2027 - Aug 28, 2027 (7 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami
Average Starting Price
$1,099pp
Jim's Onboard Credit
Valiant Lady
Virgin Voyages
Nov 14, 2026 - Nov 20, 2026 (6 Nights)
San Juan, Puerto Rico • Tortola • St John's, Antigua • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$774pp
Jim's Onboard Credit
Norwegian Epic
Norwegian Cruise Line
Jan 14, 2028 - Jan 21, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Nassau • Port Canaveral (Orlando), Florida
Average Starting Price
$839pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Nov 28, 2026 - Dec 5, 2026 (7 Nights)
San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$973pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Dec 26, 2026 - Jan 2, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,258pp
Jim's Onboard Credit
FREE Specialty Dining Meal

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!

Vision of the Seas
Royal Caribbean
Dec 6, 2026 - Dec 13, 2026 (7 Nights)
San Juan, Puerto Rico • Tortola • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$718pp
Jim's Onboard Credit
FREE Specialty Dining Meal
48% OFF
MSC Opera
MSC Cruises
Jun 21, 2027 - Jun 28, 2027 (7 Nights)
La Romana, Dominican Republic • Catalina Island, Dominican Republic • Bridgetown, Barbados • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Tortola • La Romana, Dominican Republic
Average Starting Price
$784pp
Jim's Onboard Credit
Brilliant Lady
Virgin Voyages
Nov 15, 2026 - Nov 25, 2026 (10 Nights)
Miami • Philipsburg, St. Maarten • Tortola • Basseterre, St. Kitts and Nevis • St John's, Antigua • Bimini • Miami
Average Starting Price
$5,900pp
Jim's Onboard Credit
Norwegian Bliss
Norwegian Cruise Line
Jan 26, 2028 - Feb 7, 2028 (12 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Tortola • St. Thomas • St. Kitts • Philipsburg, St. Maarten • Manhattan
Average Starting Price
$1,529pp
Jim's Onboard Credit
Nieuw Amsterdam
Holland America Line
Dec 11, 2026 - Dec 27, 2026 (16 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Tortola • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Grand Turk • Amber Cove, Dominican Republic • Key West, Florida • Fort Lauderdale
Average Starting Price
$2,439pp
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!

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