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Wind Surf
Windstar Cruises
Feb 27, 2028 - Mar 12, 2028 (14 Nights)
Philipsburg, St. Maarten • Falmouth (English Harbour), Antigua & Barbuda • 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 • Gustavia, St. Barts • 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
$4,250pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Dec 19, 2026 - Jan 2, 2027 (14 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 • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • Bridgetown, Barbados
Average Starting Price
$8,718pp
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!

49% OFF
MSC Opera
MSC Cruises
Nov 29, 2027 - Dec 6, 2027 (7 Nights)
La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • La Romana, Dominican Republic
Average Starting Price
$649pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Mar 11, 2029 - Mar 25, 2029 (14 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale
Average Starting Price
$1,974pp
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
Feb 6, 2027 - Feb 20, 2027 (14 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 • Falmouth (English Harbour), Antigua & Barbuda • 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 • Gustavia, St. Barts • Philipsburg, St. Maarten
Average Starting Price
$7,330pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Mar 3, 2029 - Mar 10, 2029 (7 Nights)
Philipsburg, St. Maarten • St. Kitts • Saint Barthelemy, Gustavia • Castries, St. Lucia • Terre de Haut, Guadeloupe • Grenada • Bridgetown, Barbados
Average Starting Price
$5,343pp
Jim's Onboard Credit
49% OFF
MSC Opera
MSC Cruises
Apr 15, 2027 - Apr 29, 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
$1,858pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Nov 28, 2026 - Dec 6, 2026 (8 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale
Average Starting Price
$509pp
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!

Wind Surf
Windstar Cruises
Mar 12, 2028 - Apr 3, 2028 (22 Nights)
Philipsburg, St. Maarten • St John's, Antigua • 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 • Gustavia, St. Barts • Philipsburg, St. Maarten • Horta (Azores), Portugal • Ponta Delgada (Azores), Portugal • Lisbon, Portugal
Average Starting Price
$4,388pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Feb 24, 2029 - Mar 3, 2029 (7 Nights)
Bridgetown, Barbados • Bequia Island, Saint Vincent • Trois Ilets, Martinique • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten
Average Starting Price
$5,168pp
Jim's Onboard Credit
49% OFF
MSC Opera
MSC Cruises
Dec 6, 2027 - Dec 20, 2027 (14 Nights)
La Romana, Dominican Republic • Catalina Island, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • La Romana, Dominican Republic
Average Starting Price
$1,458pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Dec 26, 2026 - Jan 3, 2027 (8 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • Grand Turk • Fort Lauderdale
Average Starting Price
$1,229pp
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!

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