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Port: Philipsburg, St. Maarten×
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Azamara Quest
Azamara
Nov 28, 2027 - Dec 5, 2027 (7 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,769pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Feb 20, 2027 - Mar 6, 2027 (14 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale • Celebration Key • Grand Turk • Nassau • Fort Lauderdale
Average Starting Price
$1,451pp
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!

Celebrity Ascent
Celebrity Cruises
Dec 4, 2026 - Dec 14, 2026 (10 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • Castries, St. Lucia • Grenada • Bridgetown, Barbados • St John's, Antigua • Fort Lauderdale
Average Starting Price
$1,394pp
Jim's Onboard Credit
Viking Sea
Viking
Dec 30, 2028 - Jan 9, 2029 (10 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico
Average Starting Price
$4,499pp
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!

Wind Surf
Windstar Cruises
Dec 19, 2027 - Dec 27, 2027 (8 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
Average Starting Price
$3,028pp
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!

Hero of the Seas
Royal Caribbean
Mar 25, 2028 - Apr 1, 2028 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$2,048pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Mar 11, 2028 - Mar 18, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico
Average Starting Price
$831pp
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
$11,298pp
Jim's Onboard Credit
Azamara Journey
Azamara
Nov 28, 2026 - Dec 5, 2026 (7 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • Gustavia, St. Barts • San Juan, Puerto Rico
Average Starting Price
$3,899pp
Jim's Onboard Credit
Scarlet Lady
Virgin Voyages
Mar 18, 2028 - Mar 25, 2028 (7 Nights)
San Juan, Puerto Rico • Oranjestad, Aruba • Castries, St. Lucia • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$973pp
Jim's Onboard Credit
46% OFF
MSC Meraviglia
MSC Cruises
Jan 16, 2027 - Jan 30, 2027 (14 Nights)
Miami • Philipsburg, St. Maarten • St John's, Antigua • St. Thomas • Puerto Plata, Dominican Republic • Miami • Nassau • Ocean Cay • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$1,175pp
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
$1,569pp
Jim's Onboard Credit
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