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Star Pride
Windstar Cruises
Nov 22, 2026 - Nov 29, 2026 (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
$2,691pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Apr 2, 2028 - Apr 16, 2028 (14 Nights)
Miami • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Miami • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Miami
Average Starting Price
$1,763pp
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!

Vision of the Seas
Royal Caribbean
Jan 3, 2027 - Jan 10, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Roseau, Dominica • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$728pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Mar 26, 2027 - Apr 4, 2027 (9 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • Philipsburg, St. Maarten • Oranjestad, Aruba • Willemstad, Curacao • Fort Lauderdale
Average Starting Price
$2,299pp
Jim's Onboard Credit
Sky Princess
Princess Cruises
Nov 26, 2028 - Dec 10, 2028 (14 Nights)
Fort Lauderdale • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Fort Lauderdale
Average Starting Price
$1,484pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Jan 9, 2027 - Jan 16, 2027 (7 Nights)
San Juan, Puerto Rico • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Fort-De-France, Martinique • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$548pp
Jim's Onboard Credit
Caribbean Princess
Princess Cruises
Dec 15, 2028 - Dec 22, 2028 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • St. Kitts • Martinique • Grenada • Bridgetown, Barbados
Average Starting Price
$775pp
Jim's Onboard Credit
Star Princess
Princess Cruises
Oct 28, 2028 - Nov 11, 2028 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Fort Lauderdale
Average Starting Price
$2,054pp
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!

Sun Princess
Princess Cruises
Jan 12, 2029 - Jan 19, 2029 (7 Nights)
Port Canaveral (Orlando), Florida • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Port Canaveral (Orlando), Florida
Average Starting Price
$1,025pp
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!

Norwegian Prima
Norwegian Cruise Line
Mar 25, 2028 - Apr 1, 2028 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • St. Lucia • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,259pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Dec 28, 2026 - Jan 13, 2027 (16 Nights)
San Juan, Puerto Rico • St John's, Antigua • Pointe-à-Pitre, Guadeloupe • St. John • New Year Fireworks SJU • New Year Fireworks SJU • Samana, Dominican Republic • Puerto Plata, Dominican Republic • Miami • St. John • Gustavia, St. Barts • St John's, Antigua • Tortola • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$14,960pp
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!

Emerald Princess
Princess Cruises
Feb 27, 2028 - Mar 5, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$764pp
Jim's Onboard Credit
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