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Seabourn Ovation
Seabourn
Mar 13, 2027 - Mar 20, 2027 (7 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
Average Starting Price
$6,173pp
Jim's Onboard Credit
Crystal Serenity
Crystal Cruises
Nov 8, 2026 - Nov 23, 2026 (15 Nights)
Lisbon, Portugal • Funchal, Portugal • Ponta Delgada (Azores), Portugal • Horta (Azores), Portugal • St John's, Antigua • Tortola • San Juan, Puerto Rico • Fort Lauderdale
Average Starting Price
$7,800pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Jan 23, 2027 - Jan 30, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico
Average Starting Price
$547pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Azamara Quest
Azamara
Jul 29, 2027 - Sep 10, 2027 (43 Nights)
Copenhagen, Denmark • Visby (Gotland), Sweden • Stockholm, Sweden • Stockholm, Sweden • Turku, Finland • Helsinki, Finland • Tallinn, Estonia • Riga, Latvia • Klaipeda, Lithuania • Gdynia, Poland • Bornholm, Denmark • Wismar, Germany • Kiel Canal, Germany • Portsmouth, England • Falmouth, England • Dublin, Ireland • Belfast, Northern Ireland • Faroe Islands (Torshavn), Denmark • Runavik (Faroe Islands), Denmark • Eskifjordur, Iceland • Hosavik, Iceland • Akureyri, Iceland • Isafjoerdur, Iceland • Reykjanes, Iceland • Reykjavik, Iceland • Reykjavik, Iceland • Prince Christian Sound, Greenland • Qaqortoq (Julianehåb), Greenland • Nanortalik, Greenland • St John's, Newfoundland • St John's, Newfoundland • Halifax, Nova Scotia • Lunenburg, Canada • Portland, Maine • Boston • Cape Cod Canal, Massachusetts • Newport, Rhode Island • New York, New York
Average Starting Price
$19,829pp
Jim's Onboard Credit
49% OFF
MSC World Asia
MSC Cruises
Dec 28, 2027 - Jan 11, 2028 (14 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Grenada • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Roseau, Dominica • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Bridgetown, Barbados
Average Starting Price
$2,739pp
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!

31% OFF
MSC World Europa
MSC Cruises
Feb 27, 2027 - Mar 6, 2027 (7 Nights)
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
$959pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Feb 13, 2028 - Feb 20, 2028 (7 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
Average Starting Price
$2,448pp
Jim's Onboard Credit
Enchanted Princess
Princess Cruises
Feb 3, 2029 - Feb 13, 2029 (10 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St. Lucia • St John's, Antigua • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,150pp
Jim's Onboard Credit
EXPLORA I
Explora Journeys
Nov 12, 2026 - Nov 17, 2026 (5 Nights)
St John's, Antigua • Road Bay, Anguilla • San Juan, Puerto Rico • Miami
Average Starting Price
$2,600pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Dec 19, 2026 - Dec 27, 2026 (8 Nights)
Fort Lauderdale • Oranjestad, Aruba • Willemstad, Curacao • St John's, Antigua • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$699pp
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!

Silver Spirit
Silversea
Feb 17, 2028 - Feb 29, 2028 (12 Nights)
Bridgetown, Barbados • Bequia Island, Saint Vincent • Castries, St. Lucia • Oranjestad, Aruba • Kralendijk, Bonaire • Willemstad, Curacao • Gustavia, St. Barts • St John's, Antigua • Fort-De-France, Martinique • Grenada • Bridgetown, Barbados
Average Starting Price
$4,500pp
Jim's Onboard Credit
33% OFF
Seven Seas Grandeur
Regent Seven Seas Cruises
Feb 4, 2028 - Feb 14, 2028 (10 Nights)
Bridgetown, Barbados • Willemstad, Curacao • Oranjestad, Aruba • Castries, St. Lucia • Pointe-à-Pitre, Guadeloupe • Basseterre, St. Kitts and Nevis • St John's, Antigua • Roseau, Dominica • Bridgetown, Barbados
Average Starting Price
$6,099pp
Jim's Onboard Credit
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