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Charlestown Cruise Specials

We've gathered all of the Charlestown cruise specials ordered by sail date. Click on a special and select a sail date to get a single cruise quote from the cruise agency that posted that particular special. To search through all cruise itineraries (not just Charlestown cruises) to receive multiple custom cruise options to compare, please visit our Cruise Search page.

All Cruise Specials


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Azamara Cruises, Azamara Journey
Discount
Azamara Journey14 Nights Caribbean Cruise: San Juan, St. Lucia & St. Kitts from$3249 pp
14 Night - Caribbean Combination Cruise : San Juan, St. Lucia & St. Kitts - Starting in San Juan, Virgin Gorda, St Johns AG, Saint-Pierre, Port Elizabeth VC, Bequia, Saint Georges, Grenada, Scarborough, Tobago, Bridgetown, Castries, Roseau, Basseterre, St Kitts, Charlestown, Nevis, Philipsburg, Road Town, Tortola, San Juan
2026 Sails: Nov 7 Get a Quote
Azamara Cruises, Azamara Journey
Discount
Azamara Journey14 Nights Caribbean Cruise: Barbados, St. Lucia & St. Kitts from$3309 pp
14 Night - Caribbean Combination Cruise : Barbados, St. Lucia & St. Kitts - Starting in Bridgetown, Castries, Roseau, Basseterre, St Kitts, Charlestown, Nevis, Philipsburg, Road Town, Tortola, San Juan, Virgin Gorda, St Johns AG, Saint-Pierre, Port Elizabeth VC, Bequia, Saint Georges, Grenada, Scarborough, Tobago, Bridgetown
2026 Sails: Nov 14 Get a Quote
Azamara Cruises, Azamara Journey
Discount
Azamara Journey7 Nights Eastern Caribbean Cruise:St.Lucia, Dominica &St.Kitts from$1329 pp
7 Night - Eastern Caribbean Cruise : Barbados, Saint Lucia & British Virgin Islands - Starting in Bridgetown, Castries, Roseau, Basseterre, St Kitts, Charlestown, Nevis, Philipsburg, Road Town, Tortola, San Juan
2026 Sails: Nov 14 Get a Quote
Azamara Cruises, Azamara Journey
Discount
Azamara Journey14 Nights Caribbean Cruise: San Juan, Antigua & Barbados from$3089 pp
14 Night - Caribbean Combination Cruise : San Juan, Antigua & Barbados - Starting in San Juan, Virgin Gorda, St Johns AG, Saint-Pierre, Port Elizabeth VC, Bequia, Saint Georges, Grenada, Scarborough, Tobago, Bridgetown, Castries, Roseau, Basseterre, St Kitts, Charlestown, Nevis, Philipsburg, Gustavia, San Juan
2026 Sails: Nov 21 Get a Quote
Azamara Cruises, Azamara Journey
Discount
Azamara Journey7 Nights Eastern Caribbean Cruise:St.Lucia,Dominica & St.Kitts from$1369 pp
7 Night - Eastern Caribbean Cruise : Saint Kitts, Nevis & Saint Barthelemy - Starting in Bridgetown, Castries, Roseau, Basseterre, St Kitts, Charlestown, Nevis, Philipsburg, Gustavia, San Juan
2026 Sails: Nov 28 Get a Quote
Azamara Cruises, Azamara Journey
Discount
Azamara Journey1 Nights Caribbean Cruise: Barbados, St. Lucia & St. Maarten from$3099 pp
14 Night - Caribbean Combination Cruise : Barbados, St. Lucia & St. Maarten - Starting in Bridgetown, Castries, Roseau, Basseterre, St Kitts, Charlestown, Nevis, Philipsburg, Gustavia, San Juan, Virgin Gorda, St Johns AG, Saint-Pierre, Port Elizabeth VC, Bequia, Saint Georges, Grenada, Scarborough, Tobago, Bridgetown
2026 Sails: Nov 28 Get a Quote
Azamara Cruises, Azamara Journey
Discount
Azamara Journey13 Nights Caribbean Cruise: San Juan, Antigua & St. Lucia from$3059 pp
13 Night - Caribbean Combination Cruise : San Juan, Antigua & St. Lucia - Starting in San Juan, Virgin Gorda, St Johns AG, Saint-Pierre, Port Elizabeth VC, Bequia, Saint Georges, Grenada, Scarborough, Tobago, Bridgetown, Castries, Roseau, Basseterre, St Kitts, Charlestown, Nevis, Philipsburg, San Juan
2026 Sails: Dec 5 Get a Quote
Azamara Cruises, Azamara Journey
Discount
Azamara Journey8-Nights New Year's Cruise on Azamara Journey $2389pp plus OBC
8 Night - Caribbean New Year's Cruise : Aruba, Saint Lucia & Saint Croix - Starting in Bridgetown, Oranjestad, Willemstad AN, Castries, Charlestown, Nevis, Frederiksted, Saint Croix, San Juan
2026 Sails: Dec 28 Get a Quote
Azamara Cruises, Azamara Journey
Family
Azamara Journey11 Nights Eastern Caribbean Cruise from $3,699 pp plus OBC
11 Night - Eastern Caribbean : St.Kitts, Antigua & Martinique - Starting in Miami, Florida, St John VI, US Virgin Islands, Charlotte Amalie, St Thomas, Philipsburg, Charlestown, Nevis, St Johns AG, Saint-Pierre, Port Elizabeth VC, Bequia, Saint Georges, Grenada, Bridgetown
2027 Sails: Jan 14 Get a Quote

Charlestown Cruise Specials