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Hero of the Seas
Royal Caribbean
Mar 11, 2028 - Mar 18, 2028 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$2,047pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Dec 19, 2027 - Jan 3, 2028 (15 Nights)
Philipsburg, St. Maarten • St John's, Antigua • Gustavia, St. Barts • Road Bay, Anguilla • Soper's Hole, Tortola • Great Harbor Jost Van Dyke, British Virgin Islands • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Charlestown, Nevis • Philipsburg, St. Maarten • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten
Average Starting Price
$4,545pp
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!

Rhapsody of the Seas
Royal Caribbean
Feb 26, 2028 - Mar 4, 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
$906pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Mar 20, 2027 - Apr 8, 2027 (19 Nights)
Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • Bridgetown, Barbados • Castries, St. Lucia • Funchal, Portugal • Portimão, Portugal • Lisbon, Portugal
Average Starting Price
$10,898pp
Jim's Onboard Credit
45% OFF
MSC Meraviglia
MSC Cruises
Jan 30, 2027 - Feb 13, 2027 (14 Nights)
Miami • Nassau • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Miami • Grand Turk • Ocean Cay • Nassau • Miami
Average Starting Price
$1,105pp
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!

Star Pride
Windstar Cruises
Nov 22, 2026 - Dec 6, 2026 (14 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 • St. John • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$5,204pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Jan 17, 2027 - Jan 31, 2027 (14 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Martinique • Grenada • St. Lucia • 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
$1,636pp
Jim's Onboard Credit
Scarlet Lady
Virgin Voyages
Mar 4, 2028 - Mar 11, 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
$973pp
Jim's Onboard Credit
Enchanted Princess
Princess Cruises
Jan 6, 2027 - Jan 16, 2027 (10 Nights)
Fort Lauderdale • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St John's, Antigua • Philipsburg, St. Maarten • St. Kitts • Fort Lauderdale
Average Starting Price
$1,489pp
Jim's Onboard Credit
29% OFF
MSC World Europa
MSC Cruises
Feb 23, 2027 - Mar 9, 2027 (14 Nights)
Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • St John's, Antigua • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Bridgetown, Barbados
Average Starting Price
$1,918pp
Jim's Onboard Credit
49% OFF
MSC World Asia
MSC Cruises
Jan 16, 2028 - Jan 23, 2028 (7 Nights)
Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe
Average Starting Price
$859pp
Jim's Onboard Credit
53% OFF
Carnival Magic
Carnival Cruise Line
Dec 18, 2026 - Dec 26, 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
$586pp
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!

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