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Port: Philipsburg, St. Maarten×
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Wind Surf
Windstar Cruises
Mar 6, 2027 - Mar 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
$5,720pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Dec 31, 2027 - Jan 7, 2028 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • St John's, Antigua • St. Lucia • Bridgetown, Barbados
Average Starting Price
$1,964pp
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!

Regal Princess
Princess Cruises
Feb 5, 2029 - Feb 19, 2029 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • 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!

Seabourn Ovation
Seabourn
Feb 20, 2027 - Feb 27, 2027 (7 Nights)
Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • Bridgetown, Barbados
Average Starting Price
$5,848pp
Jim's Onboard Credit
38% OFF
MSC Opera
MSC Cruises
Aug 20, 2027 - Aug 27, 2027 (7 Nights)
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
Average Starting Price
$1,167pp
Jim's Onboard Credit
48% OFF
MSC World Europa
MSC Cruises
Nov 14, 2026 - Dec 5, 2026 (21 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
Average Starting Price
$1,039pp
Jim's Onboard Credit
49% OFF
MSC World Asia
MSC Cruises
Apr 22, 2028 - May 6, 2028 (14 Nights)
Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • Santa Cruz de Tenerife, Spain • Barcelona, Spain • Marseille (Provence), France
Average Starting Price
$898pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Jan 23, 2028 - Feb 6, 2028 (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
$3,830pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Jan 15, 2027 - Jan 22, 2027 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • Philipsburg, St. Maarten • Martinique • Grenada • St. Lucia • Bridgetown, Barbados
Average Starting Price
$1,489pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Dec 11, 2028 - Dec 28, 2028 (17 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale • St. Kitts • Martinique • Dominica • St John's, Antigua • Philipsburg, St. Maarten • Celebration Key • Fort Lauderdale
Average Starting Price
$2,824pp
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!

Emerald Princess
Princess Cruises
Jan 14, 2028 - Jan 20, 2028 (6 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Bridgetown, Barbados
Average Starting Price
$1,554pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Feb 19, 2028 - Feb 26, 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
$5,343pp
Jim's Onboard Credit
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