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Cruise Dates

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October 2026

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Rhapsody of the Seas

Royal Caribbean

Jan 16, 2027 - Jan 23, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico

Average Starting Price

$532pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Azamara Quest

Azamara

Aug 25, 2027 - Sep 10, 2027 (16 Nights)

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

49% OFF

Jan 1, 2028 - Jan 8, 2028 (7 Nights)

Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Roseau, Dominica • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • Fort-De-France, Martinique

Average Starting Price

29% OFF

Feb 23, 2027 - Mar 9, 2027 (14 Nights)

Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • St John's, Antigua • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Bridgetown, Barbados

Average Starting Price

Dec 17, 2026 - Dec 27, 2026 (10 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Fort Lauderdale

Average Starting Price

$1,179pp

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, 2028 - Feb 20, 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 • 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

Dec 27, 2026 - Jan 3, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

$1,011pp

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 29, 2028 - Mar 11, 2028 (11 Nights)

Bridgetown, Barbados • Bequia Island, Saint Vincent • Grenada • Willemstad, Curacao • Oranjestad, Aruba • Gustavia, St. Barts • St John's, Antigua • Fort-De-France, Martinique • Castries, St. Lucia • Bridgetown, Barbados

Average Starting Price

$4,100pp

Jim's Onboard Credit

29% OFF

Seven Seas Grandeur

Regent Seven Seas Cruises

Feb 14, 2028 - Feb 24, 2028 (10 Nights)

Bridgetown, Barbados • Grenada • Kingstown, Saint Vincent Island, Saint Vincent • Castries, St. Lucia • Fort-De-France, Martinique • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • St John's, Antigua • Roseau, Dominica • Bridgetown, Barbados

Average Starting Price

46% OFF

Sep 20, 2027 - Sep 27, 2027 (7 Nights)

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

Average Starting Price

$612pp

Jim's Onboard Credit

25% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Aug 27, 2028 - Sep 10, 2028 (14 Nights)

Southampton, England • Fowey, Cornwall • Cork (Cobh), Ireland • Dublin, Ireland • Belfast, Northern Ireland • St John's, Newfoundland • Quebec City, Quebec • Montreal, Quebec • Quebec City, Quebec • Montreal, Quebec

Average Starting Price

Aug 10, 2027 - Sep 7, 2027 (28 Nights)

Copenhagen, Denmark • Visby (Gotland), Sweden • Stockholm, Sweden • Helsinki, Finland • Tallinn, Estonia • Riga, Latvia • Klaipeda, Lithuania • Gdynia, Poland • Oslo, Norway • Oslo, Norway • Skagen, Denmark • Copenhagen, Denmark • Gothenburg, Sweden • Runavik (Faroe Islands), Denmark • Seydisfjordur, Iceland • Akureyri, Iceland • Isafjoerdur, Iceland • Reykjavik, Iceland • St John's, Newfoundland • Halifax, Nova Scotia • Boston

Average Starting Price

$6,919pp

Jim's Onboard Credit

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