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Star Legend
Windstar Cruises
Feb 21, 2028 - Mar 13, 2028 (21 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 • Funchal, Portugal • Casablanca, Morocco • Lisbon, Portugal
Average Starting Price
$4,271pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Dec 5, 2026 - Dec 12, 2026 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,169pp
Jim's Onboard Credit
Caribbean Princess
Princess Cruises
Nov 18, 2028 - Nov 26, 2028 (8 Nights)
Fort Lauderdale • Grand Turk • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • San Juan, Puerto Rico
Average Starting Price
$875pp
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!

Valiant Lady
Virgin Voyages
Dec 26, 2026 - Jan 2, 2027 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Fort-De-France, Martinique • Bridgetown, Barbados • Castries, St. Lucia • St John's, Antigua • San Juan, Puerto Rico
Average Starting Price
$1,533pp
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!

Carnival Magic
Carnival Cruise Line
Nov 28, 2026 - Dec 6, 2026 (8 Nights)
Miami • Relaxaway Half Moon Cay • Fun Day at Sea • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Fun Day at Sea • Fun Day at Sea • Miami
Average Starting Price
$528pp
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!

EXPLORA I
Explora Journeys
Dec 13, 2026 - Dec 27, 2026 (14 Nights)
Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • Philipsburg, St. Maarten • San Juan, Puerto Rico • Basseterre, St. Kitts and Nevis • Tortola • Gustavia, St. Barts • Gustavia, St. Barts • Road Bay, Anguilla • Miami
Average Starting Price
$8,090pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Jan 16, 2028 - Jan 23, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Bridgetown, Barbados • St. Lucia • San Juan, Puerto Rico
Average Starting Price
$679pp
Jim's Onboard Credit
Azamara Quest
Azamara
Nov 14, 2027 - Nov 28, 2027 (14 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St John's, Antigua • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados
Average Starting Price
$4,019pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Jan 23, 2028 - Jan 30, 2028 (7 Nights)
San Juan, Puerto Rico • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • Fort-De-France, Martinique • St John's, Antigua • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$836pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Jan 13, 2027 - Jan 21, 2027 (8 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Terre de Haut, Guadeloupe • Grenada • Castries, St. Lucia • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$5,550pp
Jim's Onboard Credit
47% OFF
MSC World America
MSC Cruises
Jul 24, 2027 - Aug 7, 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
$2,371pp
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
Oct 2, 2027 - Oct 9, 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
$704pp
Jim's Onboard Credit
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