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Road Town Cruise Specials

We've gathered all of the Road Town 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 Road Town cruises) to receive multiple custom cruise options to compare, please visit our Cruise Search page.

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Explora Journeys, EXPLORA III
Family
EXPLORA III14 Nights An Extended Journey Of Maritime Soul & Island Zest from $10010 pp
14 Night - An Extended Journey of Maritime Soul & Island Zest - Starting in Miami, St John VI (Cruz Bay), US Virgin Islands, St Johns AG, Antigua, Terre-De-Haut, St Maarten / Philipsburg, San Juan, Tortola / Road Town, Basseterre, Gustavia, Road Bay, Miami
2026 Sails: Oct 25 Get a Quote
Azamara Cruises, Azamara Journey
Family
Azamara Journey9 Nights Bermuda & Caribbean Cruise from $1,459 pp plus OBC
9 Night - Bermuda, Sint Maarten & British Virgin Islands Cruise : Hamilton, Philipsburg & Road Town - Starting in New York City, New York, Hamilton, Philipsburg, Road Town, Tortola, San Juan
2026 Sails: Oct 29 Get a Quote
Explora Journeys, EXPLORA III
Family
EXPLORA III7 Nights A Journey Into Caribbean Exploration&Island Delightsfrom $5120 pp
7 Night - A Journey Into Caribbean Exploration & Island Delights - Starting in San Juan, Tortola / Road Town, Basseterre, Gustavia, Road Bay, Miami
2026 Sails: Nov 1 Get a Quote
Explora Journeys, EXPLORA III
Family
EXPLORA III14 NT An Extended Journey Into Island Delights, Hidden Coves from $9450 pp
14 Night - An Extended Journey Into Island Delights, Hidden Coves & Chic Coastlines - Starting in San Juan, Tortola / Road Town, Basseterre, Gustavia, Road Bay, Miami, Providenciales, Puerto Plata, Dominican Republic, La Romana, Jost Van Dyke, Gustavia, San Juan
2026 Sails: Nov 1 Get a Quote
Azamara Cruises, Azamara Journey
Family
Azamara Journey7 Nights Eastern Caribbean Cruise from $1,569 pp plus OBC
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
Explora Journeys, EXPLORA III
Family
EXPLORA III14 Nights A Journey Of Sunlit Horizons & Sapphire Bays from $8400 pp
14 Night - An Extended Journey of Sunlit Horizons & Sapphire Bays - Starting in Miami, St John VI (Cruz Bay), US Virgin Islands, St Johns AG, Antigua, Terre-De-Haut, St Maarten / Philipsburg, San Juan, Tortola / Road Town, Basseterre, Gustavia, Grand Turk, Miami
2026 Sails: Nov 22 Get a Quote
Explora Journeys, EXPLORA III
Family
EXPLORA III7 Nights A Journey Through A Caribbean Tapestry Of Serenity from $4725 pp
7 Night - A Journey Through a Caribbean Tapestry of Serenity & Splendour - Starting in San Juan, Tortola / Road Town, Basseterre, Gustavia, Grand Turk, Miami
2026 Sails: Nov 29 Get a Quote
Explora Journeys, EXPLORA III
Family
EXPLORA III14 NT An Extended Journey Through Golden Shores &Island Grace from $8400 pp
14 Night - An Extended Journey Through Golden Shores & Island Grace - Starting in San Juan, Tortola / Road Town, Basseterre, Gustavia, Grand Turk, Miami, St John VI (Cruz Bay), US Virgin Islands, St Johns AG, Antigua, Terre-De-Haut, Gustavia, San Juan
2026 Sails: Nov 29 Get a Quote
Explora Journeys, EXPLORA III
Family
EXPLORA III16 NT A Journey Of Sparkling Skies & Dramatic Natural Beautyfrom $12000 pp
16 Night - An Extended Journey of Sparkling Skies & Dramatic Natural Beauty - Starting in Miami, Ocho Rios, Jamaica, Isla Catalina, Jost Van Dyke, St Maarten / Philipsburg, Charlotte Amalie (Saint Thomas), San Juan, St Johns AG, Antigua, Pointe-a-Pitre, Tortola / Road Town, New Year Fireworks Sju, Samana, Puerto Plata, Dominican Republic, Miami
2026 Sails: Dec 20 Get a Quote
Azamara Cruises, Azamara Journey
Family
Azamara Journey17 Nights Western Caribbean Cruise from $5,719 pp plus OBC
17 Night - Caribbean Combination Cruise : Barbados, Aruba & St. Barts - Starting in Bridgetown, Oranjestad, Willemstad AN, Castries, Charlestown, Nevis, Frederiksted, Saint Croix, San Juan, Virgin Gorda, Gustavia, Philipsburg, St Johns AG, Basseterre, St Kitts, Road Town, Tortola, Miami, Florida
2026 Sails: Dec 28 Get a Quote

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Road Town Cruise Specials