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Port: San Juan, Puerto Rico×
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Rhapsody of the Seas
Royal Caribbean
Apr 1, 2028 - Apr 8, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$817pp
Jim's Onboard Credit
26% OFF
Carnival Vista
Carnival Cruise Line
Nov 14, 2026 - Nov 22, 2026 (8 Nights)
Port Canaveral (Orlando), Florida • Fun Day at Sea • Fun Day at Sea • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fun Day at Sea • Celebration Key • Port Canaveral (Orlando), Florida
Average Starting Price
$378pp
Jim's Onboard Credit
Star Princess
Princess Cruises
Nov 4, 2028 - Nov 18, 2028 (14 Nights)
Fort Lauderdale • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Fort Lauderdale • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Fort Lauderdale
Average Starting Price
$2,094pp
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!

52% OFF
MSC World America
MSC Cruises
Dec 26, 2026 - Jan 2, 2027 (7 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami
Average Starting Price
$1,414pp
Jim's Onboard Credit

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

Crown Princess
Princess Cruises
Dec 27, 2026 - Jan 10, 2027 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,938pp
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!

Enchanted Princess
Princess Cruises
Feb 13, 2029 - Feb 24, 2029 (11 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St John's, Antigua • Bridgetown, Barbados • St. Lucia • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,500pp
Jim's Onboard Credit
EXPLORA II
Explora Journeys
Feb 17, 2028 - Feb 27, 2028 (10 Nights)
Manaus, Brazil • Parintins, Brazil • Alter Do Chao, Brazil • Macapa, , Brazil • Tobago • Castries, St. Lucia • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$6,850pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Mar 4, 2028 - Mar 11, 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
Sun Princess
Princess Cruises
Jan 19, 2029 - Jan 26, 2029 (7 Nights)
Port Canaveral (Orlando), Florida • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Port Canaveral (Orlando), Florida
Average Starting Price
$925pp
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!

Scarlet Lady
Virgin Voyages
Apr 22, 2028 - May 4, 2028 (12 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Funchal, Portugal • Tangier, Morocco • Barcelona, Spain
Average Starting Price
$1,428pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Jan 30, 2028 - Feb 13, 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
$1,323pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Dec 28, 2026 - Jan 5, 2027 (8 Nights)
San Juan, Puerto Rico • St John's, Antigua • Pointe-à-Pitre, Guadeloupe • St. John • New Year Fireworks SJU • New Year Fireworks SJU • Samana, Dominican Republic • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$6,710pp
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!

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