Cruise itinerary
14-Night Caribbean Cruise from San Juan (Puerto Rico)
14 nights · Caribbean · 11 ports of call
14-night Caribbean cruise aboard EXPLORA III, departing San Juan (Puerto Rico) and calling at Tortola, Saint John's, At Sea, Providenciales, Key West, Florida and Miami, Florida and 4 more.
- Free advisor
- No booking fees
- 10,000+ sailings
At a glance
- Ship
- EXPLORA III
- Cruise line
- Explora Journeys
- Duration
- 14 nights
- Region
- Caribbean · Americas · South America
- Departs
- San Juan (Puerto Rico)
- Returns
- San Juan (Puerto Rico)
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 EXPLORA III sailing, typically within 24 hours.
Where this voyage takes you
Day-by-day itinerary
- Day1
San Juan (Puerto Rico)
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
- Day2
Tortola
Arrive 09:00 · Depart 19:00
The main island of the British Virgin Islands, where steep green hills drop to a yacht-filled harbour at Road Town. It is a noted sailing base in the Caribbean, with quiet bays such as Cane Garden and ferries out to neighbouring Virgin Gorda.
- Road Town
- Cane Garden Bay
- Sailing charters
- Day3
Saint John's
Arrive 08:00 · Depart 17:00
The capital of Antigua, set around a deep natural harbour in the eastern Caribbean. The island is known for its many sandy beaches and for Nelson's Dockyard, a restored Georgian naval base on the south coast that is now a World Heritage site.
- Nelson's Dockyard
- Dickenson Bay
- Shirley Heights
- Day4
At Sea
- Day5
Providenciales
Arrive 09:00 · Depart 18:00
- Day6
At Sea
- Day7
Key West, Florida
Arrive 08:30 · Depart 17:30
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
- Day8
Miami, Florida
Arrive 08:00 · 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
- Day9
At Sea
- Day10
At Sea
- Day11
Philipsburg
Arrive 09:00 · Depart 21:00
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
- Day12
Gustavia
Arrive 09:00 · Depart 23:00
The harbour capital of St. Barthélemy, a chic French island in the Caribbean. Yachts crowd the small port below red-roofed hills, with designer boutiques along the quay and quiet coves and beaches scattered around the rugged coast.
- Shell Beach
- Designer boutiques
- Gustavia harbour
- Day13
Basseterre, Saint Kitts
Arrive 09:00 · Depart 19:00
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
- Day14
Cruz Bay, Saint John
Arrive 08:00 · Depart 17:00
- Day15
San Juan (Puerto Rico)
Arrive 08:00
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
Upcoming departures
- 29 Jan 2027
Upcoming sailings of this itinerary — a NestCruise advisor confirms current availability and your fare.
14-Night Caribbean Cruise from San Juan (Puerto Rico) FAQ
Which ports does this cruise visit?
This 14-night Caribbean cruise calls at San Juan (Puerto Rico), Tortola, Saint John's, At Sea, Providenciales, Key West, Florida, Miami, Florida, Philipsburg, Gustavia, Basseterre, Saint Kitts and Cruz Bay, Saint John.
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 San Juan (Puerto Rico).
How long is this cruise?
14 nights aboard EXPLORA III.
When does this itinerary sail?
Upcoming departures include 29 Jan 2027. A NestCruise advisor can confirm current availability.