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Norwegian Bliss
Norwegian Cruise Line
Nov 9, 2026 - Nov 21, 2026 (12 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Tortola • Philipsburg, St. Maarten • St. Thomas • Manhattan
Average Starting Price
$1,219pp
Jim's Onboard Credit
Harmony of the Seas
Royal Caribbean
Dec 23, 2026 - Dec 30, 2026 (7 Nights)
Port Canaveral (Orlando), Florida • Philipsburg, St. Maarten • San Juan, Puerto Rico • Perfect Day Cococay • Port Canaveral (Orlando), Florida
Average Starting Price
$2,023pp
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!

60% OFF
Margaritaville at Sea Beachcomber
Margaritaville at Sea
Jan 9, 2027 - Jan 16, 2027 (7 Nights)
Miami • St. Thomas • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$899pp
Jim's Onboard Credit
Seabourn Pursuit
Seabourn
Sep 24, 2028 - Oct 2, 2028 (8 Nights)
Halifax, Nova Scotia • Hamilton, Bermuda • San Juan, Puerto Rico • Oranjestad, Aruba
Average Starting Price
$5,088pp
Jim's Onboard Credit
Silver Nova
Silversea
Dec 21, 2026 - Dec 29, 2026 (8 Nights)
Bridgetown, Barbados • Soufrier Bay, St. Lucia • Bequia Island, Saint Vincent • Grenada • Fort-De-France, Martinique • St. Kitts • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$4,200pp
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!

EXPLORA III
Explora Journeys
Jan 21, 2027 - Feb 5, 2027 (15 Nights)
Miami • St. Thomas • Road Bay, Anguilla • St. Pierre • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • San Juan, Puerto Rico • Tortola • St John's, Antigua • Providenciales, Turks and Caicos Islands • Key West, Florida • Miami
Average Starting Price
$9,635pp
Jim's Onboard Credit
Viking Sea
Viking
Jan 15, 2027 - Jan 25, 2027 (10 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico
Average Starting Price
$6,799pp
Jim's Onboard Credit
56% OFF
MSC World America
MSC Cruises
May 8, 2027 - May 22, 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
$1,341pp
Jim's Onboard Credit

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

Sky Princess
Princess Cruises
Feb 21, 2027 - Mar 1, 2027 (8 Nights)
Port Canaveral (Orlando), Florida • Nassau • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Grand Turk • Port Canaveral (Orlando), Florida
Average Starting Price
$1,199pp
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!

Star Pride
Windstar Cruises
Mar 20, 2028 - Mar 27, 2028 (7 Nights)
San Juan, Puerto Rico • St. John • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$2,443pp
Jim's Onboard Credit
Grandeur of the Seas
Royal Caribbean
May 1, 2027 - May 8, 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
$656pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Regal Princess
Princess Cruises
Jan 30, 2028 - Feb 6, 2028 (7 Nights)
Miami • St. Kitts • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Miami
Average Starting Price
$539pp
Jim's Onboard Credit
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