Cruise itinerary
16-Night Caribbean Cruise from San Juan (Puerto Rico)
16 nights · Caribbean · 11 ports of call
16-night Caribbean cruise aboard EXPLORA III, departing San Juan (Puerto Rico) and calling at Saint John's, Pointe-à-Pitre, Cruz Bay, Saint John, At Sea, Samaná and Puerto Plata and 4 more.
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- 10,000+ sailings
At a glance
- Ship
- EXPLORA III
- Cruise line
- Explora Journeys
- Duration
- 16 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 17:00
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
Saint John's
Arrive 09:00 · Depart 18:00
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
- Day3
Pointe-à-Pitre
Arrive 08:00 · Depart 17:00
The main town of Guadeloupe, a French overseas region in the eastern Caribbean shaped like a butterfly. It sits between the two wings of the island, with a covered spice market, Creole cooking and the volcano of La Soufrière to the south.
- Spice market
- La Soufrière
- Memorial ACTe
- Day4
Cruz Bay, Saint John
Arrive 09:00 · Depart 16:00
At Sea
Arrive 23:30
- Day5
At Sea
Depart 02:00
- Day6
Samaná
Arrive 08:00 · Depart 17:00
- Day7
Puerto Plata
Arrive 08:00 · Depart 17:00
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
- Day8
At Sea
- Day9
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
- Day10
At Sea
- Day11
At Sea
- Day12
Cruz Bay, Saint John
Arrive 09:00 · Depart 18:00
- Day13
Gustavia
Arrive 08:00 · 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
- Day14
Saint John's
Arrive 08:00 · Depart 19:00
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
- Day15
Tortola
Arrive 08:00 · 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
- Day16
Basseterre, Saint Kitts
Arrive 08:00 · Depart 17:00
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
- Day17
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
- 28 Dec 2026
Upcoming sailings of this itinerary — a NestCruise advisor confirms current availability and your fare.
16-Night Caribbean Cruise from San Juan (Puerto Rico) FAQ
Which ports does this cruise visit?
This 16-night Caribbean cruise calls at San Juan (Puerto Rico), Saint John's, Pointe-à-Pitre, Cruz Bay, Saint John, At Sea, Samaná, Puerto Plata, Miami, Florida, Gustavia, Tortola and Basseterre, Saint Kitts.
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?
16 nights aboard EXPLORA III.
When does this itinerary sail?
Upcoming departures include 28 Dec 2026. A NestCruise advisor can confirm current availability.