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Valiant Lady
Virgin Voyages
Nov 7, 2026 - Nov 14, 2026 (7 Nights)
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
Average Starting Price
$1,043pp
Jim's Onboard Credit
Silver Ray
Silversea
Feb 26, 2027 - Mar 10, 2027 (12 Nights)
Bridgetown, Barbados • Bequia Island, Saint Vincent • Grenada • Fort-De-France, Martinique • Deshaies, Guadeloupe • Soufrier Bay, St. Lucia • St. Kitts • Philipsburg, St. Maarten • Gustavia, St. Barts • Road Bay, Anguilla • Miami
Average Starting Price
$6,500pp
Jim's Onboard Credit
MSC Magnifica
MSC Cruises
Mar 16, 2027 - May 5, 2027 (50 Nights)
Sydney, Australia • Noumea, New Caledonia • Luganville, Espirutu Santo • Apia, Samoa • International Dateline • Honolulu • Honolulu • Los Angeles • Cabo San Lucas • Puntarenas, Costa Rica • Balbao, Panama • Panama Canal, Panama • Panama Canal, Panama • La Romana, Dominican Republic • Tortola • Philipsburg, St. Maarten • Las Palmas (Gran Canaria), Spain • Ibiza, Spain • Naples, Italy • Rome (Civitavecchia), Italy
Average Starting Price
$7,189pp
Jim's Onboard Credit
46% OFF
MSC Meraviglia
MSC Cruises
Mar 7, 2027 - Mar 21, 2027 (14 Nights)
Miami • Grand Turk • Ocean Cay • Nassau • Miami • Philipsburg, St. Maarten • St John's, Antigua • St. Thomas • Nassau • Miami
Average Starting Price
$1,265pp
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!

Allure of the Seas
Royal Caribbean
Nov 22, 2026 - Nov 29, 2026 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$769pp
Jim's Onboard Credit
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
$14,070pp
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!

Brilliant Lady
Virgin Voyages
Jan 11, 2027 - Jan 21, 2027 (10 Nights)
Miami • Philipsburg, St. Maarten • Tortola • St. Croix • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Bimini • Miami
Average Starting Price
$990pp
Jim's Onboard Credit
Enchanted Princess
Princess Cruises
Mar 7, 2027 - Mar 17, 2027 (10 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Fort Lauderdale
Average Starting Price
$1,124pp
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!

Wind Surf
Windstar Cruises
Nov 5, 2027 - Nov 28, 2027 (23 Nights)
Lisbon, Portugal • Funchal, Portugal • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten • Gustavia, St. Barts • St John's, Antigua • Deshaies, Guadeloupe • Road Bay, Anguilla • Soper's Hole, Tortola • Great Harbor Jost Van Dyke, British Virgin Islands • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten
Average Starting Price
$4,813pp
Jim's Onboard Credit
EXPLORA II
Explora Journeys
Feb 17, 2028 - Feb 27, 2028 (10 Nights)
Manaus, Brazil • Parintins, Brazil • Alter Do Chao, Brazil • Macapa, , Brazil • Tobago • Castries, St. Lucia • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$6,715pp
Jim's Onboard Credit
49% OFF
MSC Opera
MSC Cruises
May 13, 2027 - May 27, 2027 (14 Nights)
Bridgetown, Barbados • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Tortola • 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 • Catalina Island, Dominican Republic • Bridgetown, Barbados
Average Starting Price
$1,748pp
Jim's Onboard Credit
Eurodam
Holland America Line
Dec 22, 2027 - Jan 2, 2028 (11 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Philipsburg, St. Maarten • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • Fort Lauderdale
Average Starting Price
$3,034pp
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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