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Viking Sea
Viking
Jan 19, 2029 - Jan 29, 2029 (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
$4,999pp
Jim's Onboard Credit
Grandeur of the Seas
Royal Caribbean
Nov 6, 2027 - Nov 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
$798pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Mar 13, 2027 - Mar 27, 2027 (14 Nights)
Philipsburg, St. Maarten • Falmouth (English Harbour), Antigua & Barbuda • 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 • 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
$6,420pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Mar 12, 2028 - Mar 26, 2028 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,908pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Apr 2, 2028 - Apr 16, 2028 (14 Nights)
Miami • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Miami • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Miami
Average Starting Price
$1,788pp
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!

Seabourn Ovation
Seabourn
Feb 27, 2027 - Mar 13, 2027 (14 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 • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • Bridgetown, Barbados
Average Starting Price
$10,018pp
Jim's Onboard Credit
Star of the Seas
Royal Caribbean
Jan 10, 2027 - Jan 17, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,453pp
Jim's Onboard Credit
FREE Specialty Dining Meal

Jim's Ship Pick
This is the BEST ship I’ve EVER sailed on! It rarely felt crowded, the food was incredible, the shows were absolutely phenomenal, and there’s something for everyone!

Rhapsody of the Seas
Royal Caribbean
Jan 9, 2027 - Jan 16, 2027 (7 Nights)
San Juan, Puerto Rico • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Fort-De-France, Martinique • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$526pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Caribbean Princess
Princess Cruises
Jan 26, 2029 - Feb 2, 2029 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Dominica • Bridgetown, Barbados
Average Starting Price
$905pp
Jim's Onboard Credit
Enchanted Princess
Princess Cruises
Dec 3, 2028 - Dec 13, 2028 (10 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St John's, Antigua • St. Lucia • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,100pp
Jim's Onboard Credit
Harmony of the Seas
Royal Caribbean
Nov 28, 2026 - Dec 5, 2026 (7 Nights)
Port Canaveral (Orlando), Florida • Philipsburg, St. Maarten • San Juan, Puerto Rico • Perfect Day Cococay • Port Canaveral (Orlando), Florida
Average Starting Price
$691pp
Jim's Onboard Credit
48% OFF
MSC Meraviglia
MSC Cruises
Dec 13, 2026 - Dec 27, 2026 (14 Nights)
Miami • Grand Turk • Ocean Cay • Nassau • Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami
Average Starting Price
$1,505pp
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!

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