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44% OFF
MSC Opera
MSC Cruises
Apr 30, 2027 - May 7, 2027 (7 Nights)
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
Average Starting Price
$1,937pp
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
Grandeur of the Seas
Royal Caribbean
Sep 18, 2027 - Sep 25, 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
$650pp
Jim's Onboard Credit
49% OFF
MSC World Europa
MSC Cruises
Apr 10, 2027 - Apr 24, 2027 (14 Nights)
Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • Santa Cruz de Tenerife, Spain • Barcelona, Spain
Average Starting Price
$829pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Jan 13, 2027 - Jan 21, 2027 (8 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Terre de Haut, Guadeloupe • Grenada • Castries, St. Lucia • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$5,920pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Nov 27, 2027 - Dec 4, 2027 (7 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Little Bay, Montserrat • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten
Average Starting Price
$4,768pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Jan 29, 2028 - Feb 5, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$731pp
Jim's Onboard Credit
Enchanted Princess
Princess Cruises
Jan 25, 2028 - Feb 5, 2028 (11 Nights)
Fort Lauderdale • St. Thomas • St. Kitts • St. Lucia • Bridgetown, Barbados • St John's, Antigua • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,244pp
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 • Scarborough (Tobago), Trinidad and Tobago • St. Lucia • Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$7,045pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Mar 20, 2028 - Apr 3, 2028 (14 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 • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico
Average Starting Price
$4,014pp
Jim's Onboard Credit
Scarlet Lady
Virgin Voyages
Jan 15, 2028 - Jan 22, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$833pp
Jim's Onboard Credit
Eurodam
Holland America Line
Jan 12, 2028 - Jan 22, 2028 (10 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$2,459pp
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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