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Crown Princess
Princess Cruises
Feb 28, 2027 - Mar 14, 2027 (14 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Martinique • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,296pp
Jim's Onboard Credit
29% OFF
Seven Seas Prestige
Regent Seven Seas Cruises
Dec 20, 2028 - Dec 30, 2028 (10 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Gustavia, St. Barts • Tortola • Miami
Average Starting Price
$7,399pp
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!

Hero of the Seas
Royal Caribbean
Nov 6, 2027 - Nov 13, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$1,817pp
Jim's Onboard Credit
Star of the Seas
Royal Caribbean
Sep 5, 2027 - Sep 12, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,460pp
Jim's Onboard Credit

Jim's Ship Pick
This is the BEST ship I’ve EVER sailed on! It rarely felt crowded, the food was incredible, the shows were absolutely phenomenal, and there’s something for everyone!

Grandeur of the Seas
Royal Caribbean
Sep 4, 2027 - Sep 11, 2027 (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
$705pp
Jim's Onboard Credit
Norwegian Aqua
Norwegian Cruise Line
May 30, 2027 - Jun 6, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$1,379pp
Jim's Onboard Credit
Harmony of the Seas
Royal Caribbean
May 15, 2027 - May 22, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$911pp
Jim's Onboard Credit
FREE Specialty Dining Meal
35% OFF
Carnival Vista
Carnival Cruise Line
Jun 19, 2027 - Jun 26, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Celebration Key • Fun Day at Sea • San Juan, Puerto Rico • St. Thomas • Fun Day at Sea • Fun Day at Sea • Port Canaveral (Orlando), Florida
Average Starting Price
$964pp
Jim's Onboard Credit
EXPLORA II
Explora Journeys
Mar 5, 2028 - Mar 12, 2028 (7 Nights)
Miami • Road Bay, Anguilla • St. Thomas • St. John's • St. John • San Juan, Puerto Rico
Average Starting Price
$3,915pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Mar 28, 2027 - Apr 4, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Thomas • St. Lucia • Oranjestad, Aruba • San Juan, Puerto Rico
Average Starting Price
$1,059pp
Jim's Onboard Credit
57% OFF
Carnival Venezia
Carnival Cruise Line
Feb 7, 2027 - Feb 14, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Celebration Key • Fun Day at Sea • San Juan, Puerto Rico • St. Thomas • Fun Day at Sea • Fun Day at Sea • Port Canaveral (Orlando), Florida
Average Starting Price
$428pp
Jim's Onboard Credit
Disney Treasure
Disney Cruise Line
May 8, 2027 - May 15, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Tortola • St. Thomas • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida
Average Starting Price
$2,442pp
Jim's Onboard Credit
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