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Wind Surf
Windstar Cruises
Nov 28, 2027 - Dec 5, 2027 (7 Nights)
Philipsburg, St. Maarten • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten
Average Starting Price
$2,537pp
Jim's Onboard Credit
Seabourn Venture
Seabourn
Sep 17, 2027 - Oct 10, 2027 (23 Nights)
Kangerlussuaq, Greenland • Nuuk (Godthaab), Greenland • Pangnirtung, Nunavut • Evergreen Island • Lady Franklin Island, Canada • Monumental Island (Nunavut), Canada • Lower Savage Islands, Canada • Praslin • Nachvak Fiord, Torngat Mts, Canada • Ramah Bay • Robben Island, South Africa • Hebron, Canada • Nain, Canada • Indian Harbour, Newfoundland • Battle Harbour, Labrador • L'Anse aux Meadows, Newfoundland • Halifax, Nova Scotia • St. Kitts • Little Bay, Montserrat • Rodney Bay, Saint Lucia • Bridgetown, Barbados
Average Starting Price
$25,819pp
Jim's Onboard Credit
Sky Princess
Princess Cruises
Feb 20, 2028 - Mar 5, 2028 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • Cozumel • Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Fort Lauderdale
Average Starting Price
$1,168pp
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!

49% OFF
MSC World Asia
MSC Cruises
Nov 19, 2027 - Nov 30, 2027 (11 Nights)
Bridgetown, Barbados • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • St John's, Antigua • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Bridgetown, Barbados
Average Starting Price
$1,569pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Feb 6, 2027 - Feb 13, 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
$608pp
Jim's Onboard Credit
FREE Specialty Dining Meal
40% OFF
Marina
Oceania Cruises
Dec 10, 2026 - Dec 22, 2026 (12 Nights)
Miami • St. Thomas • Gustavia, St. Barts • St John's, Antigua • Fort-De-France, Martinique • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Tortola • Miami
Average Starting Price
$2,640pp
Jim's Onboard Credit
EXPLORA IV
Explora Journeys
Apr 29, 2028 - May 6, 2028 (7 Nights)
San Juan, Puerto Rico • St. John • Pointe-à-Pitre, Guadeloupe • St. Kitts • Marigot Bay, St. Martin, French West Indies • Miami
Average Starting Price
$3,755pp
Jim's Onboard Credit
Norwegian Bliss
Norwegian Cruise Line
Feb 1, 2027 - Feb 13, 2027 (12 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Tortola • St. Kitts • Philipsburg, St. Maarten • Manhattan
Average Starting Price
$1,119pp
Jim's Onboard Credit
Zaandam
Holland America Line
Feb 13, 2027 - Mar 14, 2027 (29 Nights)
Buenos Aires, Argentina • Buenos Aires, Argentina • Santos (Sao Paulo), Brazil • Ilha Grande, Brazil • Rio de Janeiro, Brazil • Rio de Janeiro, Brazil • Salvador da Bahia, Brazil • Recife, Brazil • Fortaleza, Brazil • Icoaraci (Belem), Brazil • Crossing the Equator • Devil's Island, France • Bridgetown, Barbados • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico • Fort Lauderdale
Average Starting Price
$6,114pp
Jim's Onboard Credit
Eurodam
Holland America Line
Feb 12, 2028 - Feb 23, 2028 (11 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$2,854pp
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!

Celebrity Beyond
Celebrity Cruises
Jan 3, 2027 - Jan 10, 2027 (7 Nights)
Fort Lauderdale • Puerto Plata, Dominican Republic • St. Thomas • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$1,034pp
Jim's Onboard Credit
Seabourn Quest
Seabourn
Dec 6, 2026 - Dec 20, 2026 (14 Nights)
Miami • San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Terre de Haut, Guadeloupe • Little Bay, Montserrat • Road Bay, Anguilla • Great Harbor Jost Van Dyke, British Virgin Islands • Miami
Average Starting Price
$7,153pp
Jim's Onboard Credit
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