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71% OFF
MSC Poesia
MSC Cruises
Nov 12, 2026 - Nov 22, 2026 (10 Nights)
Miami • St. Thomas • St. Kitts • Philipsburg, St. Maarten • St John's, Antigua • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$498pp
Jim's Onboard Credit
Jewel of the Seas
Royal Caribbean
Dec 7, 2026 - Dec 16, 2026 (9 Nights)
Tampa • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Puerto Plata, Dominican Republic • Tampa
Average Starting Price
$961pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Azamara Quest
Azamara
Oct 28, 2027 - Nov 21, 2027 (24 Nights)
New York, New York • Hamilton, Bermuda • Hamilton, Bermuda • Hamilton, Bermuda • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St. Thomas • St John's, Antigua • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico
Average Starting Price
$6,129pp
Jim's Onboard Credit
Enchanted Princess
Princess Cruises
Jan 4, 2028 - Jan 15, 2028 (11 Nights)
Fort Lauderdale • St. Thomas • St. Kitts • St. Lucia • Bridgetown, Barbados • St John's, Antigua • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,084pp
Jim's Onboard Credit
Celebrity Reflection
Celebrity Cruises
Dec 28, 2026 - Jan 4, 2027 (7 Nights)
Fort Lauderdale • Puerto Plata, Dominican Republic • St. Thomas • St John's, Antigua • Fort Lauderdale
Average Starting Price
$1,870pp
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!

31% OFF
Carnival Horizon
Carnival Cruise Line
Jan 6, 2029 - Jan 20, 2029 (14 Nights)
Galveston • Fun Day at Sea • Fun Day at Sea • Ocho Rios, Jamaica • Fun Day at Sea • St. Croix • Philipsburg, St. Maarten • St. Kitts • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • Galveston
Average Starting Price
$1,335pp
Jim's Onboard Credit
Coral Princess
Princess Cruises
Nov 8, 2026 - Nov 18, 2026 (10 Nights)
Fort Lauderdale • St John's, Antigua • Philipsburg, St. Maarten • Dominica • St. Kitts • St. Thomas • Fort Lauderdale
Average Starting Price
$739pp
Jim's Onboard Credit
Norwegian Breakaway
Norwegian Cruise Line
Nov 8, 2026 - Nov 22, 2026 (14 Nights)
Boston • St. Thomas • St. Lucia • Grenada • Willemstad, Curacao • Oranjestad, Aruba • George Town, Cayman Islands • New Orleans
Average Starting Price
$949pp
Jim's Onboard Credit
Oasis of the Seas
Royal Caribbean
Dec 28, 2026 - Jan 4, 2027 (7 Nights)
Fort Lauderdale • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,698pp
Jim's Onboard Credit
FREE Specialty Dining Meal

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!

28% OFF
Carnival Pride
Carnival Cruise Line
Jan 9, 2028 - Jan 23, 2028 (14 Nights)
Baltimore • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • St. Thomas • Philipsburg, St. Maarten • Dominica • St. Lucia • Bridgetown, Barbados • St John's, Antigua • Tortola • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • Baltimore
Average Starting Price
$1,506pp
Jim's Onboard Credit
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
Hero of the Seas
Royal Caribbean
Sep 11, 2027 - Sep 18, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$1,527pp
Jim's Onboard Credit
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