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Viking Sky
Viking
Nov 14, 2028 - Nov 24, 2028 (10 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico
Average Starting Price
$3,799pp
Jim's Onboard Credit
Seabourn Venture
Seabourn
Sep 16, 2027 - Nov 19, 2027 (64 Nights)
Reykjavik, Iceland • 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 • Port of Spain, Trinidad • Devil's Island, France • Crossing the Equator • Fortaleza, Brazil • Natal, Brazil • Salvador, Brazil • Armacao dos Buzios, Brazil • Parati • Rio de Janeiro, Brazil • Camboriu, Brazil • Montevideo, Uruguay • The Seabourn Falkland Island Experience • The Seabourn Falkland Island Experience • Port Stanley, Falkland Islands • The Seabourn South Georgia Experience • The Seabourn South Georgia Experience • The Seabourn South Georgia Experience • The Seabourn Antarctic Experience • The Seabourn Antarctic Experience • The Seabourn Antarctic Experience • The Seabourn Antarctic Experience • The Seabourn Antarctic Experience • Ushuaia, Argentina • Ushuaia, Argentina
Average Starting Price
$49,569pp
Jim's Onboard Credit
49% OFF
MSC World Asia
MSC Cruises
Nov 20, 2027 - Nov 27, 2027 (7 Nights)
Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • St John's, Antigua • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique
Average Starting Price
$999pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Nov 29, 2026 - Dec 13, 2026 (14 Nights)
San Juan, Puerto Rico • St. John • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Deshaies, Guadeloupe • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico
Average Starting Price
$7,584pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Mar 11, 2028 - Mar 18, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico
Average Starting Price
$831pp
Jim's Onboard Credit
Seabourn Quest
Seabourn
Nov 22, 2026 - Dec 6, 2026 (14 Nights)
Miami • San Juan, Puerto Rico • Road Bay, Anguilla • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Little Bay, Montserrat • Terre de Haut, Guadeloupe • Virgin Gorda, British Virgin Islands • Great Harbor Jost Van Dyke, British Virgin Islands • Miami
Average Starting Price
$7,153pp
Jim's Onboard Credit
Eurodam
Holland America Line
Mar 15, 2028 - Apr 1, 2028 (17 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 • Grand Turk • Amber Cove, Dominican Republic • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$4,239pp
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 Opera
MSC Cruises
Dec 13, 2027 - Dec 27, 2027 (14 Nights)
La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • La Romana, Dominican Republic
Average Starting Price
$2,002pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Feb 21, 2027 - Feb 28, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • St. Lucia • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,099pp
Jim's Onboard Credit
Star Legend
Windstar Cruises
Feb 14, 2028 - Feb 21, 2028 (7 Nights)
San Juan, Puerto Rico • St. John • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • 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
Norwegian Bliss
Norwegian Cruise Line
Jan 4, 2027 - Jan 16, 2027 (12 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Tortola • Philipsburg, St. Maarten • St. Thomas • Manhattan
Average Starting Price
$1,669pp
Jim's Onboard Credit
31% OFF
Seven Seas Grandeur
Regent Seven Seas Cruises
Jan 25, 2028 - Feb 4, 2028 (10 Nights)
Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Castries, St. Lucia • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • St John's, Antigua • Roseau, Dominica • Bridgetown, Barbados
Average Starting Price
$6,599pp
Jim's Onboard Credit
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