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Emerald Princess
Princess Cruises
Feb 25, 2028 - Mar 3, 2028 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados
Average Starting Price
$1,804pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Feb 13, 2028 - Feb 20, 2028 (7 Nights)
Philipsburg, St. Maarten • St John's, Antigua • 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 • Gustavia, St. Barts • Philipsburg, St. Maarten
Average Starting Price
$2,483pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Nov 22, 2026 - Dec 6, 2026 (14 Nights)
Fort Lauderdale • Celebration Key • Grand Turk • Nassau • Fort Lauderdale • Philipsburg, St. Maarten • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale
Average Starting Price
$1,160pp
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!

Seabourn Ovation
Seabourn
Feb 26, 2028 - Mar 4, 2028 (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
$5,368pp
Jim's Onboard Credit
46% OFF
MSC Opera
MSC Cruises
Jun 28, 2027 - Jul 12, 2027 (14 Nights)
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 • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Tortola • La Romana, Dominican Republic
Average Starting Price
$3,779pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Mar 10, 2028 - Mar 17, 2028 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados
Average Starting Price
$2,229pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Feb 27, 2027 - Mar 13, 2027 (14 Nights)
Philipsburg, St. Maarten • 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 • Gustavia, St. Barts • Road Bay, Anguilla • Falmouth (English Harbour), Antigua & Barbuda • Philipsburg, St. Maarten • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten
Average Starting Price
$5,300pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Mar 11, 2029 - Mar 19, 2029 (8 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale
Average Starting Price
$1,125pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Mar 11, 2028 - Mar 18, 2028 (7 Nights)
Bridgetown, Barbados • Rodney Bay, Saint Lucia • Little Bay, Montserrat • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten
Average Starting Price
$5,668pp
Jim's Onboard Credit
49% OFF
MSC Opera
MSC Cruises
Oct 28, 2027 - Nov 11, 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
$1,468pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Feb 6, 2028 - Feb 13, 2028 (7 Nights)
Philipsburg, St. Maarten • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten
Average Starting Price
$2,537pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Mar 5, 2029 - Mar 19, 2029 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Grand Turk • Amber Cove, Dominican Republic • Fort Lauderdale • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale
Average Starting Price
$1,974pp
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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