Cruise itinerary
14-Night Caribbean Cruise from Miami, Florida
14 nights · Caribbean · 10 ports of call
14-night Caribbean cruise aboard Azamara Onward, departing Miami, Florida and calling at Saint Thomas, Philipsburg, Saint-Anthony, Newfoundland and Labrador, Castries, Bridgetown and Roseau and 3 more.
- Free advisor
- No booking fees
- 10,000+ sailings
At a glance
- Ship
- Azamara Onward
- Cruise line
- Azamara
- Duration
- 14 nights
- Region
- Caribbean
- 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 Azamara Onward sailing, typically within 24 hours.
Where this voyage takes you
Day-by-day itinerary
- Day1
Miami, Florida
Depart 17:00
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
Saint Thomas
Arrive 10:30 · Depart 18:00
An island in the U.S. Virgin Islands known for its deep harbour at Charlotte Amalie and its red-roofed hillsides. It offers duty-free shopping along the waterfront, the beach at Magens Bay, and a short ferry hop to quieter St. John.
- Magens Bay
- Charlotte Amalie
- Ferry to St. John
- Day5
Philipsburg
Arrive 08:00 · Depart 18:00
The Dutch-side capital of St. Maarten, set behind the long curve of Great Bay. Front Street is wall-to-wall duty-free; a short water taxi or drive reaches the French side's Marigot market and the famous low-flying jets over Maho Beach.
- Great Bay Beach
- Front Street duty-free
- Maho Beach plane-spotting
- Day6
Saint-Anthony, Newfoundland and Labrador
Arrive 10:00 · Depart 22:00
- Day7
Castries
Arrive 08:00 · Depart 20:00
The capital of St. Lucia, tucked into a sheltered harbour on the island's northwest coast. Beyond the market town rise the rainforested interior and the iconic twin Piton peaks further south along the volcanic coastline.
- The Pitons
- Central market
- Pigeon Island
- Day8
Bridgetown
Arrive 06:00 · Depart 06:00
The capital of Barbados on the island's southwest coast, a long-standing Caribbean cruise port. Its colonial centre and Garrison Savannah are UNESCO-listed, with the white sand of Carlisle Bay and turtle-filled waters close to the harbour.
- Carlisle Bay
- Garrison Savannah
- Rum distilleries
- Day9
Roseau
Arrive 08:00 · Depart 18:00
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
- Day10
Basseterre, Saint Kitts
Arrive 08:00 · Depart 18:00
The capital of St. Kitts, set below the green slopes of a volcanic Caribbean island. Its colonial centre circles The Circus and Independence Square, while the hilltop fortress of Brimstone Hill and a scenic railway lie out along the coast.
- Brimstone Hill Fortress
- The Circus
- Scenic railway
- Day11
San Juan
Arrive 08:00 · Depart 20:00
The capital of Puerto Rico and a major Caribbean cruise homeport. The walled colonial quarter of Old San Juan keeps blue-cobbled streets, pastel facades and two Spanish fortresses, El Morro and San Cristóbal, guarding the harbour mouth.
- Old San Juan
- El Morro
- Castillo San Cristóbal
- Day12At sea
- Day13At sea
- Day14
Key West, Florida
Arrive 08:00 · Depart 17:00
The southernmost city in the continental United States, an island town at the end of the Florida Keys. Pastel conch houses line Duval Street, Ernest Hemingway's home is a landmark, and crowds gather at Mallory Square for the nightly sunset.
- Duval Street
- Hemingway House
- Mallory Square sunset
- Day15
Miami, Florida
Arrive 06:00
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
- 30 Nov 2027
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, Saint Thomas, Philipsburg, Saint-Anthony, Newfoundland and Labrador, Castries, Bridgetown, Roseau, Basseterre, Saint Kitts, San Juan and Key West, Florida.
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 Azamara Onward.
When does this itinerary sail?
Upcoming departures include 30 Nov 2027. A NestCruise advisor can confirm current availability.