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Regal Princess
Princess Cruises
Mar 12, 2028 - Mar 26, 2028 (14 Nights)
Miami • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Miami • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Philipsburg, St. Maarten • Miami
Average Starting Price
$1,443pp
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!

Wind Surf
Windstar Cruises
Dec 27, 2027 - Jan 9, 2028 (13 Nights)
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 • Road Bay, Anguilla • Gustavia, St. Barts • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Soper's Hole, Tortola • Philipsburg, St. Maarten
Average Starting Price
$3,760pp
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!

1% OFF
MSC World Europa
MSC Cruises
Nov 14, 2026 - Dec 12, 2026 (28 Nights)
Genoa (Portofino), Italy • Rome (Civitavecchia), Italy • La Spezia, Italy • Marseille (Provence), France • Barcelona, Spain • Arrecife (Lanzarote), Spain • Santa Cruz de Tenerife, Spain • Philipsburg, St. Maarten • St. Kitts • Kingstown, Saint Vincent Island, Saint Vincent • Bridgetown, Barbados • Grenada • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • St John's, Antigua • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique
Average Starting Price
$10,919pp
Jim's Onboard Credit
Star of the Seas
Royal Caribbean
Mar 19, 2028 - Mar 26, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,676pp
Jim's Onboard Credit

Jim's Ship Pick
This is the BEST ship I’ve EVER sailed on! It rarely felt crowded, the food was incredible, the shows were absolutely phenomenal, and there’s something for everyone!

Seabourn Ovation
Seabourn
Jan 22, 2028 - Jan 29, 2028 (7 Nights)
Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • Bridgetown, Barbados
Average Starting Price
$5,143pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Apr 15, 2028 - Apr 22, 2028 (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
$910pp
Jim's Onboard Credit
Harmony of the Seas
Royal Caribbean
Apr 15, 2028 - Apr 22, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,170pp
Jim's Onboard Credit
Enchanted Princess
Princess Cruises
Jan 23, 2029 - Feb 3, 2029 (11 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St. Lucia • Bridgetown, Barbados • St John's, Antigua • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,400pp
Jim's Onboard Credit
48% OFF
MSC Meraviglia
MSC Cruises
Dec 27, 2026 - Jan 10, 2027 (14 Nights)
Miami • Grand Turk • Ocean Cay • Nassau • Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami
Average Starting Price
$1,595pp
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!

Caribbean Princess
Princess Cruises
Feb 9, 2029 - Feb 20, 2029 (11 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Oranjestad, Aruba • Willemstad, Curacao • Fort Lauderdale
Average Starting Price
$1,093pp
Jim's Onboard Credit
Star Princess
Princess Cruises
Nov 11, 2028 - Nov 25, 2028 (14 Nights)
Fort Lauderdale • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$2,044pp
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!

49% OFF
MSC Opera
MSC Cruises
Sep 30, 2027 - Oct 14, 2027 (14 Nights)
Bridgetown, Barbados • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Tortola • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • Fort-De-France, Martinique • St John's, Antigua • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Bridgetown, Barbados
Average Starting Price
$1,378pp
Jim's Onboard Credit
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