Cruise itinerary
14-Night Caribbean Cruise from Miami, Florida
14 nights · Caribbean · 10 ports of call
14-night Caribbean cruise aboard Seabourn Quest, departing Miami, Florida and calling at San Juan (Puerto Rico), Road Bay, South Friars Bay, Roseau, Fort-de-France and Terre-de-Haut and 3 more.
- Free advisor
- No booking fees
- 10,000+ sailings
At a glance
- Ship
- Seabourn Quest
- Cruise line
- Seabourn
- Duration
- 14 nights
- Region
- Caribbean · Americas · South America
- Departs
- Miami, Florida
- Returns
- Miami, Florida
How NestCruise works:we're advisor-led, not a booking engine. No fares are listed and there are no booking fees — tell an advisor your dates and party and they price your exact Seabourn Quest sailing, typically within 24 hours.
Where this voyage takes you
Day-by-day itinerary
- Day1
Miami, Florida
Depart 16:00
The cruise capital of the world — Miami sends more ships to sea than any port on earth. Most sailings board mid-afternoon, leaving the morning for South Beach, Little Havana or the Wynwood murals before you cast off.
- South Beach
- Little Havana
- Wynwood murals
- Day2At sea
- Day3At sea
- Day4
San Juan (Puerto Rico)
Arrive 10:00 · Depart 18:00
The capital of Puerto Rico and a major Caribbean homeport. Old San Juan's pastel colonial streets sit behind the massive El Morro and San Cristóbal forts, with rum distilleries and the beaches of Condado close to the cruise piers.
- Old San Juan
- El Morro fort
- Condado beaches
- Day5
Road Bay
Arrive 08:00 · Depart 17:00
- Day6
South Friars Bay
Arrive 08:00 · Depart 17:00
A calm sand beach on the narrow southeast peninsula of St. Kitts, looking across The Narrows toward Nevis. A handful of casual beach bars line the shore, and the rugged volcanic hills rise close behind.
- Beach bars
- Nevis views
- Calm swimming
- Day7
Roseau
Arrive 08:00 · Depart 17:00
The capital of Dominica, a green volcanic island in the eastern Caribbean known as the Nature Isle. The town sits below forested peaks, with the botanic gardens, sulphur springs and the trail to Trafalgar Falls a short drive inland.
- Trafalgar Falls
- Botanic Gardens
- Boiling Lake
- Day8
Fort-de-France
Arrive 08:00 · Depart 18:00
The capital of Martinique in the French Caribbean, set on a wide bay beneath green volcanic hills. Fort-de-France is known for the ornate Schoelcher Library, the Savane gardens by the waterfront, and views toward the Mont Pelée volcano.
- Schoelcher Library
- La Savane park
- Fort Saint-Louis
- Day9
Terre-de-Haut
Arrive 08:00 · Depart 17:00
- Day10
Montserrat
Arrive 08:00 · Depart 18:00
- Day11
Virgin Gorda
Arrive 08:00 · Depart 17:00
One of the British Virgin Islands, a hilly cay in the eastern Caribbean known for The Baths — a beach where giant granite boulders form tidal pools and grottoes. Quiet bays, yacht anchorages and a relaxed, low-key pace define the island.
- The Baths
- Granite boulders
- Spring Bay
- Day12
Great Harbour, Jost Van Dyke
Arrive 07:00 · Depart 14:00
The main anchorage of Jost Van Dyke, smallest of the British Virgin Islands' main islands, in the Caribbean. A laid-back yachting stop, its sheltered bay is fringed by sand and beach bars, with the natural rock pools of the Bubbly Pool a short walk away.
- Bubbly Pool
- White Bay
- beach bars
- Day13At sea
- Day14At sea
- Day15
Miami, Florida
Arrive 07:00
The cruise capital of the world — Miami sends more ships to sea than any port on earth. Most sailings board mid-afternoon, leaving the morning for South Beach, Little Havana or the Wynwood murals before you cast off.
- South Beach
- Little Havana
- Wynwood murals
Upcoming departures
- 22 Nov 2026
- 6 Dec 2026
Upcoming sailings of this itinerary — a NestCruise advisor confirms current availability and your fare.
14-Night Caribbean Cruise from Miami, Florida FAQ
Which ports does this cruise visit?
This 14-night Caribbean cruise calls at Miami, Florida, San Juan (Puerto Rico), Road Bay, South Friars Bay, Roseau, Fort-de-France, Terre-de-Haut, Montserrat, Virgin Gorda and Great Harbour, Jost Van Dyke.
How many days are spent at sea?
4 days are spent at sea; the rest are in port.
Where does this cruise depart from?
It is a round-trip sailing from Miami, Florida.
How long is this cruise?
14 nights aboard Seabourn Quest.
When does this itinerary sail?
Upcoming departures include 22 Nov 2026 and 6 Dec 2026. A NestCruise advisor can confirm current availability.