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, Basseterre, Saint Kitts, Gustavia, Road Bay, At Sea and Miami, Florida and 4 more.
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- 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 18:00
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
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
- Day4
Gustavia
Arrive 09:00
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
- Day5
Gustavia
Depart 01:00
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
Road Bay
Arrive 09:00 · Depart 17:00
- Day6
At Sea
- Day7
At Sea
- 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
Providenciales
Arrive 09:00 · Depart 18:00
- Day11
Puerto Plata
Arrive 09:00 · Depart 16:00
A port on the north coast of the Dominican Republic, backed by the flat-topped Mount Isabel de Torres. A cable car climbs to its summit, the old town keeps a district of gingerbread Victorian houses, and amber and rum are local specialities.
- Mount Isabel cable car
- Amber Museum
- Victorian houses
- Day12
La Romana
Arrive 09:00 · Depart 17:00
A resort town on the southeast coast of the Dominican Republic, set where the Chavón river meets the Caribbean. Nearby lie the cobbled artisans' village of Altos de Chavón, the white sands of Bayahibe and boat trips to Saona island.
- Altos de Chavón
- Saona Island
- Bayahibe beach
- Day13
Great Harbour, Jost Van Dyke
Arrive 10:00 · Depart 18:00
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
- Day14
Gustavia
Arrive 08:00 · Depart 19:00
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
- 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
- 1 Nov 2026
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, Basseterre, Saint Kitts, Gustavia, Road Bay, At Sea, Miami, Florida, Providenciales, Puerto Plata, La Romana and Great Harbour, Jost Van Dyke.
How many days are spent at sea?
3 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 1 Nov 2026. A NestCruise advisor can confirm current availability.