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Norwegian Prima
Norwegian Cruise Line
Mar 11, 2028 - Mar 18, 2028 (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
$1,239pp
Jim's Onboard Credit
Viking Sea
Viking
Jan 29, 2029 - Feb 8, 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
Emerald Princess
Princess Cruises
Mar 12, 2028 - Mar 19, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$934pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Mar 26, 2028 - Apr 2, 2028 (7 Nights)
San Juan, Puerto Rico • Bridgetown, Barbados • Grenada • Castries, St. Lucia • St John's, Antigua • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$773pp
Jim's Onboard Credit
Norwegian Aura
Norwegian Cruise Line
Jul 8, 2028 - Jul 15, 2028 (7 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami
Average Starting Price
$1,599pp
Jim's Onboard Credit
Disney Treasure
Disney Cruise Line
Mar 25, 2028 - Apr 1, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • St. Thomas • Tortola • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida
Average Starting Price
$2,789pp
Jim's Onboard Credit
Caribbean Princess
Princess Cruises
Dec 15, 2028 - Dec 22, 2028 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • St. Kitts • Martinique • Grenada • Bridgetown, Barbados
Average Starting Price
$775pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Feb 19, 2029 - Mar 5, 2029 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • Grand Turk • 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!

Norwegian Aqua
Norwegian Cruise Line
Dec 13, 2026 - Dec 20, 2026 (7 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami
Average Starting Price
$559pp
Jim's Onboard Credit
Norwegian Escape
Norwegian Cruise Line
Apr 30, 2028 - May 7, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$1,149pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Nov 21, 2026 - Nov 28, 2026 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico
Average Starting Price
$918pp
Jim's Onboard Credit
Harmony of the Seas
Royal Caribbean
Nov 14, 2026 - Nov 21, 2026 (7 Nights)
Port Canaveral (Orlando), Florida • St. Thomas • Perfect Day Cococay • Nassau • Port Canaveral (Orlando), Florida
Average Starting Price
$691pp
Jim's Onboard Credit
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