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46% OFF
Carnival Venezia
Carnival Cruise Line
Dec 13, 2026 - Dec 20, 2026 (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
$595pp
Jim's Onboard Credit
33% OFF
Seven Seas Splendor
Regent Seven Seas Cruises
Dec 6, 2027 - Dec 20, 2027 (14 Nights)
Barcelona, Spain • Arrecife (Lanzarote), Spain • Santa Cruz de Tenerife, Spain • San Juan, Puerto Rico • Miami
Average Starting Price
$7,199pp
Jim's Onboard Credit
Independence of the Seas
Royal Caribbean
Jan 10, 2028 - Jan 19, 2028 (9 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Oranjestad, Aruba • Willemstad, Curacao • Miami
Average Starting Price
$995pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Jan 15, 2028 - Jan 22, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico
Average Starting Price
$757pp
Jim's Onboard Credit
47% OFF
MSC World America
MSC Cruises
Sep 4, 2027 - Sep 11, 2027 (7 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami
Average Starting Price
$784pp
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
Sep 18, 2027 - Sep 25, 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
$650pp
Jim's Onboard Credit
Eurodam
Holland America Line
Nov 28, 2026 - Dec 12, 2026 (14 Nights)
Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Cozumel • Fort Lauderdale
Average Starting Price
$2,204pp
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!

5% OFF
Nieuw Amsterdam
Holland America Line
Dec 11, 2026 - Dec 20, 2026 (9 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Tortola • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$829pp
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!

Zuiderdam
Holland America Line
Dec 19, 2026 - Jan 2, 2027 (14 Nights)
Miami • Amber Cove, Dominican Republic • Grand Turk • Relaxaway Half Moon Cay • Key West, Florida • Miami • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Miami
Average Starting Price
$2,389pp
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
Feb 5, 2028 - Feb 19, 2028 (14 Nights)
Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale • Nassau • Amber Cove, Dominican Republic • Grand Turk • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$3,459pp
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!

Star Pride
Windstar Cruises
Nov 22, 2027 - Nov 29, 2027 (7 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
Average Starting Price
$2,411pp
Jim's Onboard Credit
Scarlet Lady
Virgin Voyages
Jan 8, 2028 - Jan 15, 2028 (7 Nights)
San Juan, Puerto Rico • Oranjestad, Aruba • Willemstad, Curacao • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$833pp
Jim's Onboard Credit
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