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Rhapsody of the Seas
Royal Caribbean
Dec 19, 2026 - Dec 26, 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
$1,172pp
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!

Crown Princess
Princess Cruises
Feb 26, 2027 - Mar 5, 2027 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • Philipsburg, St. Maarten • Martinique • Dominica • Grenada • Bridgetown, Barbados
Average Starting Price
$1,559pp
Jim's Onboard Credit
47% OFF
MSC World America
MSC Cruises
Nov 20, 2027 - Dec 4, 2027 (14 Nights)
Miami • Roatan, Honduras • Costa Maya • Cozumel • Ocean Cay • Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami
Average Starting Price
$1,711pp
Jim's Onboard Credit

Jim Sr's Ship Pick
This ship never felt crowded - and the Pizza & Burger spot was a total win!

Norwegian Prima
Norwegian Cruise Line
Apr 22, 2028 - Apr 29, 2028 (7 Nights)
San Juan, Puerto Rico • Cabo Rojo, Dominican Republic • Falmouth, Jamaica • George Town, Cayman Islands • Cozumel • Galveston
Average Starting Price
$899pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Apr 16, 2028 - Apr 23, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Willemstad, Curacao • Oranjestad, Aruba • San Juan, Puerto Rico
Average Starting Price
$872pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Jan 22, 2029 - Feb 5, 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
$1,874pp
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!

Sky Princess
Princess Cruises
Mar 4, 2029 - Mar 11, 2029 (7 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale
Average Starting Price
$975pp
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!

Caribbean Princess
Princess Cruises
Feb 2, 2029 - Feb 9, 2029 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados
Average Starting Price
$945pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Mar 21, 2027 - Apr 5, 2027 (15 Nights)
Bridgetown, Barbados • Grenada • Castries, St. Lucia • Fort-De-France, Martinique • Gustavia, St. Barts • Gustavia, St. Barts • Virgin Gorda, British Virgin Islands • Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • Tortola • San Juan, Puerto Rico
Average Starting Price
$14,105pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Feb 19, 2027 - Feb 26, 2027 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados
Average Starting Price
$1,669pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Nov 22, 2026 - Nov 29, 2026 (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
$1,179pp
Jim's Onboard Credit
46% OFF
MSC World America
MSC Cruises
Nov 27, 2027 - Dec 4, 2027 (7 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami
Average Starting Price
$814pp
Jim's Onboard Credit

Jim Sr's Ship Pick
This ship never felt crowded - and the Pizza & Burger spot was a total win!

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