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Resilient Lady
Virgin Voyages
Feb 26, 2028 - Mar 5, 2028 (8 Nights)
Miami • Philipsburg, St. Maarten • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Bimini • Miami
Average Starting Price
$1,112pp
Jim's Onboard Credit
Majestic Princess
Princess Cruises
Nov 19, 2026 - Dec 22, 2026 (33 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St. Lucia • Bridgetown, Barbados • Fortaleza, Brazil • Rio de Janeiro, Brazil • Montevideo, Uruguay • Buenos Aires, Argentina • Buenos Aires, Argentina • Buenos Aires, Argentina • Montevideo, Uruguay • Puerto Madryn, Argentina • Falkland Islands • Cape Horn, Chile • Ushuaia, Argentina • Beagle Channel, Argentina • Punta Arenas, Chile • Puerto Montt, Chile • Valparaíso, Chile
Average Starting Price
$3,671pp
Jim's Onboard Credit
Adventure of the Seas
Royal Caribbean
Nov 7, 2026 - Nov 15, 2026 (8 Nights)
Fort Lauderdale • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • San Juan, Puerto Rico • Grand Turk • Fort Lauderdale
Average Starting Price
$407pp
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!

Norwegian Pearl
Norwegian Cruise Line
Jan 15, 2028 - Jan 27, 2028 (12 Nights)
Philadelphia • Philipsburg, St. Maarten • St. Lucia • Bridgetown, Barbados • St John's, Antigua • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Philadelphia
Average Starting Price
$989pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Nov 1, 2027 - Nov 8, 2027 (7 Nights)
San Juan, Puerto Rico • St. John • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$2,443pp
Jim's Onboard Credit
Sonata
Oceania Cruises
Jan 11, 2029 - Jan 23, 2029 (12 Nights)
Miami • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Pointe-à-Pitre, Guadeloupe • Basseterre, St. Kitts and Nevis • Tortola • Miami
Average Starting Price
$6,199pp
Jim's Onboard Credit
Grandeur of the Seas
Royal Caribbean
May 15, 2027 - May 22, 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
$689pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Azamara Quest
Azamara
Nov 6, 2027 - Nov 21, 2027 (15 Nights)
San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St. Thomas • St John's, Antigua • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico
Average Starting Price
$4,319pp
Jim's Onboard Credit
Rotterdam
Holland America Line
Feb 23, 2027 - Mar 6, 2027 (11 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$2,269pp
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!

Nieuw Amsterdam
Holland America Line
Nov 20, 2026 - Dec 11, 2026 (21 Nights)
Fort Lauderdale • Kralendijk, Bonaire • Willemstad, Curacao • Willemstad, Curacao • Relaxaway Half Moon Cay • Fort Lauderdale • Philipsburg, St. Maarten • Fort-De-France, Martinique • Bridgetown, Barbados • Scarborough (Tobago), Trinidad and Tobago • Castries, St. Lucia • St. Kitts • Key West, Florida • Fort Lauderdale
Average Starting Price
$3,199pp
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!

Allure of the Seas
Royal Caribbean
Feb 28, 2027 - Mar 7, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$977pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Harmony of the Seas
Royal Caribbean
May 15, 2027 - May 22, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$911pp
Jim's Onboard Credit
FREE Specialty Dining Meal
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