Cruise itinerary
25-Night Caribbean Cruise from Miami, Florida
25 nights · Caribbean · 14 ports of call
25-night Caribbean cruise aboard Oceania Insignia, departing Miami, Florida and calling at Tortola, Antigua, Castries, Scarborough, Santarém and Boca da Valeria and 7 more.
- Free advisor
- No booking fees
- 10,000+ sailings
At a glance
- Ship
- Oceania Insignia
- Cruise line
- Oceania Cruises
- Duration
- 25 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 Oceania Insignia 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
Tortola
Arrive 10:00 · 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
- Day5
Antigua
Arrive 07:00 · Depart 17:00
- Day6
Castries
Arrive 08:00 · Depart 17:00
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
- Day7
Scarborough
Arrive 07:00 · Depart 16:00
- Day8At sea
- Day9At sea
- Day10At sea
- Day11
Santarém
Arrive 09:00 · Depart 18:00
- Day12
Boca da Valeria
Arrive 07:00 · Depart 15:00
- Day13
Manaus
Arrive 10:00 · Depart 16:00
The largest city of the Brazilian Amazon, rising deep in the rainforest where the dark Rio Negro meets the sandy Solimões. Grown rich on the rubber boom, it is known for its opulent opera house and as the gateway to jungle lodges and the Meeting of the Waters.
- Amazonas Opera House
- Meeting of the Waters
- Adolpho Lisboa Market
- Day14At sea
- Day15
Parintins
Arrive 11:00 · Depart 19:00
- Day16
Santarém
Arrive 07:00 · Depart 15:00
- Day17At sea
- Day18At sea
- Day19At sea
- Day20
Bridgetown
Arrive 11:00 · Depart 18:00
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
- Day21
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
- Day22
Philipsburg
Arrive 08:00 · Depart 17:00
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
- Day23
San Juan
Arrive 07:00 · Depart 13:00
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
- Day24At sea
- Day25
Nassau
Arrive 11:00 · Depart 17:00
The capital of the Bahamas on New Providence Island, one of the most-visited cruise ports anywhere. Pastel colonial buildings and the Queen's Staircase sit near the harbour, with the sands of Cable Beach and the Atlantis resort just across the water.
- Cable Beach
- Atlantis resort
- Queen's Staircase
- Day26
Miami, Florida
Arrive 08:00
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
- 24 Nov 2026
Upcoming sailings of this itinerary — a NestCruise advisor confirms current availability and your fare.
25-Night Caribbean Cruise from Miami, Florida FAQ
Which ports does this cruise visit?
This 25-night Caribbean cruise calls at Miami, Florida, Tortola, Antigua, Castries, Scarborough, Santarém, Boca da Valeria, Manaus, Parintins, Bridgetown, Roseau, Philipsburg, San Juan and Nassau.
How many days are spent at sea?
10 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?
25 nights aboard Oceania Insignia.
When does this itinerary sail?
Upcoming departures include 24 Nov 2026. A NestCruise advisor can confirm current availability.