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Brilliant Lady
Virgin Voyages
Nov 15, 2026 - Nov 25, 2026 (10 Nights)
Miami • Philipsburg, St. Maarten • Tortola • Basseterre, St. Kitts and Nevis • St John's, Antigua • Bimini • Miami
Average Starting Price
$1,800pp
Jim's Onboard Credit
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
Seabourn Ovation
Seabourn
Nov 27, 2027 - Dec 4, 2027 (7 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Little Bay, Montserrat • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten
Average Starting Price
$4,768pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Jan 29, 2028 - Feb 5, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$843pp
Jim's Onboard Credit
Enchanted Princess
Princess Cruises
Jan 25, 2028 - Feb 5, 2028 (11 Nights)
Fort Lauderdale • St. Thomas • St. Kitts • St. Lucia • Bridgetown, Barbados • St John's, Antigua • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,244pp
Jim's Onboard Credit
Sun Princess
Princess Cruises
Dec 19, 2028 - Dec 29, 2028 (10 Nights)
Port Canaveral (Orlando), Florida • Celebration Key • St. Kitts • Bridgetown, Barbados • St. Lucia • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$2,450pp
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!

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
EXPLORA II
Explora Journeys
Feb 17, 2028 - Feb 27, 2028 (10 Nights)
Manaus, Brazil • Parintins, Brazil • Alter Do Chao, Brazil • Macapa, , Brazil • Scarborough (Tobago), Trinidad and Tobago • St. Lucia • Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$7,045pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Mar 20, 2028 - Apr 3, 2028 (14 Nights)
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 • 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
$4,014pp
Jim's Onboard Credit
Scarlet Lady
Virgin Voyages
Jan 15, 2028 - Jan 22, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$833pp
Jim's Onboard Credit
Eurodam
Holland America Line
Jan 12, 2028 - Jan 22, 2028 (10 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$2,459pp
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!

Vision of the Seas
Royal Caribbean
Feb 20, 2028 - Feb 27, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Oranjestad, Aruba • Willemstad, Curacao • San Juan, Puerto Rico
Average Starting Price
$781pp
Jim's Onboard Credit
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