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Zuiderdam
Holland America Line
Dec 23, 2027 - Jan 6, 2028 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Grand Turk • Amber Cove, Dominican Republic • Nassau • Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • San Juan, Puerto Rico • Grand Turk • Fort Lauderdale
Average Starting Price
$3,944pp
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!

Rotterdam
Holland America Line
Jan 15, 2028 - Jan 29, 2028 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • Grand Turk • Nassau • Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$3,419pp
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!

31% OFF
Carnival Horizon
Carnival Cruise Line
Oct 14, 2028 - Oct 28, 2028 (14 Nights)
Galveston • Fun Day at Sea • Fun Day at Sea • Ocho Rios, Jamaica • Fun Day at Sea • Fun Day at Sea • Bridgetown, Barbados • St. Lucia • St. Kitts • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • Galveston
Average Starting Price
$1,360pp
Jim's Onboard Credit
Norwegian Getaway
Norwegian Cruise Line
Nov 16, 2026 - Nov 23, 2026 (7 Nights)
Port Canaveral (Orlando), Florida • Great Stirrup Cay • St. Thomas • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Port Canaveral (Orlando), Florida
Average Starting Price
$419pp
Jim's Onboard Credit
55% OFF
MSC Seaside
MSC Cruises
Dec 21, 2026 - Dec 28, 2026 (7 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami
Average Starting Price
$678pp
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!

Star Pride
Windstar Cruises
Nov 8, 2027 - Nov 22, 2027 (14 Nights)
San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • 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
$4,014pp
Jim's Onboard Credit
49% OFF
MSC World America
MSC Cruises
Jul 10, 2027 - Jul 24, 2027 (14 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami • Roatan, Honduras • Costa Maya • Cozumel • Ocean Cay • Miami
Average Starting Price
$2,411pp
Jim's Onboard Credit

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

Grandeur of the Seas
Royal Caribbean
May 15, 2027 - May 22, 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
$689pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Azamara Quest
Azamara
Nov 6, 2027 - Nov 21, 2027 (15 Nights)
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
$4,319pp
Jim's Onboard Credit
Norwegian Dawn
Norwegian Cruise Line
Jan 18, 2028 - Jan 28, 2028 (10 Nights)
Jacksonville • Grand Bahama Island • Puerto Plata, Dominican Republic • Samana, Dominican Republic • St. Thomas • Tortola • San Juan, Puerto Rico • Jacksonville
Average Starting Price
$989pp
Jim's Onboard Credit
EXPLORA IV
Explora Journeys
Dec 4, 2027 - Dec 13, 2027 (9 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. John • Gustavia, St. Barts • St. Thomas • Miami
Average Starting Price
$5,285pp
Jim's Onboard Credit
Volendam
Holland America Line
Dec 22, 2026 - Jan 5, 2027 (14 Nights)
Fort Lauderdale • Key West, Florida • Oranjestad, Aruba • Charlotteville, Tobago • Grenada • Bridgetown, Barbados • Castries, St. Lucia • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$2,664pp
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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