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Norwegian Pearl
Norwegian Cruise Line
Mar 2, 2027 - Mar 12, 2027 (10 Nights)
Philadelphia • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Tortola • Philadelphia
Average Starting Price
$889pp
Jim's Onboard Credit
Sirena
Oceania Cruises
Nov 21, 2027 - Dec 22, 2027 (31 Nights)
Miami • Cozumel • Santo Tomas de Castilla, Guatemala • Harvest Caye, Belize • Costa Maya • Miami • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • Castries, St. Lucia • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • Miami • Nassau • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Basseterre, St. Kitts and Nevis • St. Thomas • St John's, Antigua • Gustavia, St. Barts • Tortola • Miami
Average Starting Price
$8,649pp
Jim's Onboard Credit
22% OFF
Seven Seas Mariner
Regent Seven Seas Cruises
Mar 26, 2027 - Apr 10, 2027 (15 Nights)
Miami • Tortola • Gustavia, St. Barts • Fort-De-France, Martinique • Kingstown, Saint Vincent Island, Saint Vincent • Bridgetown, Barbados • Grenada • Willemstad, Curacao • Kralendijk, Bonaire • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$13,009pp
Jim's Onboard Credit
Grandeur of the Seas
Royal Caribbean
Aug 28, 2027 - Sep 4, 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
$648pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Nov 13, 2027 - Nov 20, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Lucia • Bridgetown, Barbados • St. Kitts • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,359pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Feb 27, 2027 - Mar 6, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$676pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Feb 20, 2027 - Feb 27, 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
$568pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Norwegian Aqua
Norwegian Cruise Line
Aug 22, 2027 - Aug 29, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$1,029pp
Jim's Onboard Credit
Nieuw Amsterdam
Holland America Line
Mar 12, 2027 - Mar 21, 2027 (9 Nights)
Fort Lauderdale • St John's, Antigua • St. Thomas • Tortola • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$1,834pp
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!

Marina
Oceania Cruises
Dec 27, 2027 - Jan 6, 2028 (10 Nights)
Miami • Nassau • San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • St. Thomas • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$3,499pp
Jim's Onboard Credit

Phyllis' Holiday Pick
Best time of the year to cruise! I love spending the holidays cruising with my family! The ships are beautifully decorated, and ringing in New Year’s Eve at sea is an experience I’ll never forget!

Vision of the Seas
Royal Caribbean
Feb 14, 2027 - Feb 21, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$521pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Norwegian Luna
Norwegian Cruise Line
Nov 7, 2027 - Nov 14, 2027 (7 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami
Average Starting Price
$929pp
Jim's Onboard Credit
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