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Grandeur of the Seas
Royal Caribbean
Apr 24, 2027 - May 1, 2027 (7 Nights)
Colon, Panama • Kingstown, Saint Vincent Island, Saint Vincent • Castries, St. Lucia • St John's, Antigua • Tortola • San Juan, Puerto Rico
Average Starting Price
$845pp
Jim's Onboard Credit
FREE Specialty Dining Meal
55% OFF
MSC World America
MSC Cruises
Jan 23, 2027 - Jan 30, 2027 (7 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami
Average Starting Price
$566pp
Jim's Onboard Credit

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

Regal Princess
Princess Cruises
Nov 27, 2028 - Dec 11, 2028 (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
$1,524pp
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!

Viking Sea
Viking
Nov 16, 2027 - Nov 27, 2027 (11 Nights)
Lisbon, Portugal • Sail the North Atlantic Ocean • Funchal, Portugal • Santa Cruz de Tenerife, Spain • Santa Cruz de la Palma, Spain • Sail the North Atlantic Ocean • Sail the North Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • San Juan, Puerto Rico
Average Starting Price
$2,899pp
Jim's Onboard Credit
Sky Princess
Princess Cruises
Nov 29, 2026 - Dec 7, 2026 (8 Nights)
Port Canaveral (Orlando), Florida • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Grand Turk • Port Canaveral (Orlando), Florida
Average Starting Price
$872pp
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
Jan 19, 2029 - Jan 26, 2029 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados
Average Starting Price
$895pp
Jim's Onboard Credit
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
Norwegian Prima
Norwegian Cruise Line
Dec 13, 2026 - Dec 20, 2026 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Kitts • Bridgetown, Barbados • St. Lucia • Tortola • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$839pp
Jim's Onboard Credit
48% OFF
MSC World America
MSC Cruises
Apr 8, 2028 - Apr 22, 2028 (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
$2,631pp
Jim's Onboard Credit

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

Regal Princess
Princess Cruises
Feb 25, 2029 - Mar 5, 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
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!

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