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Regal Princess
Princess Cruises
Jan 23, 2028 - Feb 6, 2028 (14 Nights)
Miami • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Miami • St. Kitts • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Miami
Average Starting Price
$1,108pp
Jim's Onboard Credit
Grandeur of the Seas
Royal Caribbean
Sep 11, 2027 - Sep 18, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico
Average Starting Price
$609pp
Jim's Onboard Credit
Celebrity Apex
Celebrity Cruises
Feb 13, 2027 - Feb 20, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Basseterre, St. Kitts and Nevis • Port Canaveral (Orlando), Florida
Average Starting Price
$1,375pp
Jim's Onboard Credit
Silver Dawn
Silversea
Jan 15, 2028 - Jan 25, 2028 (10 Nights)
San Juan, Puerto Rico • Great Harbor Jost Van Dyke, British Virgin Islands • Gustavia, St. Barts • St. Kitts • Fort-De-France, Martinique • Grenada • Canouan, Saint Vincent and the Grenadines • Castries, St. Lucia • St John's, Antigua • St. John • San Juan, Puerto Rico
Average Starting Price
$4,500pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Feb 14, 2027 - Feb 21, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$558pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Seabourn Venture
Seabourn
Oct 1, 2027 - Nov 19, 2027 (49 Nights)
Halifax, Nova Scotia • St. Kitts • Little Bay, Montserrat • Rodney Bay, Saint Lucia • Bridgetown, Barbados • Port of Spain, Trinidad • Devil's Island, France • Crossing the Equator • Fortaleza, Brazil • Natal, Brazil • Salvador, Brazil • Armacao dos Buzios, Brazil • Parati • Rio de Janeiro, Brazil • Camboriu, Brazil • Montevideo, Uruguay • The Seabourn Falkland Island Experience • The Seabourn Falkland Island Experience • Port Stanley, Falkland Islands • The Seabourn South Georgia Experience • The Seabourn South Georgia Experience • The Seabourn South Georgia Experience • The Seabourn Antarctic Experience • The Seabourn Antarctic Experience • The Seabourn Antarctic Experience • The Seabourn Antarctic Experience • The Seabourn Antarctic Experience • Ushuaia, Argentina • Ushuaia, Argentina
Average Starting Price
$40,069pp
Jim's Onboard Credit
Rotterdam
Holland America Line
Feb 13, 2027 - Mar 6, 2027 (21 Nights)
Fort Lauderdale • Key West, Florida • George Town, Cayman Islands • Ocho Rios, Jamaica • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$4,109pp
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!

9% OFF
Crystal Grace
Crystal Cruises
Jan 3, 2029 - Jan 19, 2029 (16 Nights)
Fort Lauderdale • Grand Turk • Samana, Dominican Republic • Great Harbor Jost Van Dyke, British Virgin Islands • St John's, Antigua • St. Kitts • Gustavia, St. Barts • San Juan, Puerto Rico • Gustavia, St. Barts • St. Kitts • St John's, Antigua • Great Harbor Jost Van Dyke, British Virgin Islands • Samana, Dominican Republic • Grand Turk • Fort Lauderdale
Average Starting Price
$9,080pp
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!

29% OFF
Seven Seas Mariner
Regent Seven Seas Cruises
Nov 17, 2028 - Nov 29, 2028 (12 Nights)
Miami • St. Thomas • Gustavia, St. Barts • St John's, Antigua • Pointe-à-Pitre, Guadeloupe • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Tortola • Miami
Average Starting Price
$7,399pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Dec 4, 2027 - Dec 11, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • St. Lucia • St. Thomas • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$1,309pp
Jim's Onboard Credit
Silver Nova
Silversea
Feb 11, 2028 - Feb 22, 2028 (11 Nights)
Miami • San Juan, Puerto Rico • Soper's Hole, Tortola • St. Kitts • St John's, Antigua • Gustavia, St. Barts • St. John • Miami
Average Starting Price
$6,300pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Feb 14, 2027 - Feb 28, 2027 (14 Nights)
San Juan, Puerto Rico • St. Thomas • St. Kitts • 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
$1,428pp
Jim's Onboard Credit
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