St. Thomas, Tortola, St. Maarten & San Juan: Norwegian's 2027 Eastern Caribbean Ports of Call

Table of Contents

• Quick Facts
• Introduction
• Season Highlights
• Why Choose an Eastern Caribbean Itinerary in 2027?
• Port Breakdown
• Month-by-Month Eastern Caribbean Cruise Calendar for 2027
• Ship Deployment
• Planning Tips
• How to Find the Best Deals on Eastern Caribbean Cruises
• Related Guides
• Frequently Asked Questions

Quick Facts

How we source these figures: CabinSaver tracks published Norwegian Cruise Line fares daily and has recorded 364 pricing snapshots for these sailings between 2025-08-16 and 2026-08-14. The ranges below reflect 136 unique 2027 departures calling at St. Thomas, Tortola, St. Maarten or San Juan, priced for solo travelers at single occupancy (which includes the single supplement), and are subject to change. Verify current fares directly with Norwegian Cruise Line before booking.

Introduction

The Eastern Caribbean is the part of the region most people picture first, and in 2027 Norwegian Cruise Line reaches it through four anchor ports: St. Thomas in the US Virgin Islands, Tortola in the British Virgin Islands, Philipsburg on the Dutch side of St. Maarten, and San Juan in Puerto Rico. Those four ports appear on 136 distinct 2027 sailings, but they are not evenly distributed: St. Thomas and Tortola are the workhorse pair, turning up on 116 itineraries together, while St. Maarten appears on just 32 and San Juan on 55. Knowing which ports travel together is the single most useful thing to understand before you book, because a seven-night round trip from Miami and a seven-night round trip from San Juan visit almost entirely different islands.

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Season Highlights

Eastern Caribbean coverage in 2027 splits cleanly into two very different halves. From November through April, 101 of the 136 tracked sailings operate, with as many as 23 departures in December alone and a fleet that includes Norwegian Prima, Viva, Bliss, Epic, Pearl, Luna and Dawn. This is when all four ports are genuinely available: every one of the 32 St. Maarten calls falls between November and March, and San Juan's mid-itinerary calls follow the same pattern.

From May through October, coverage narrows to 35 sailings and the port list narrows with it. Every summer sailing in the tracked data calls at St. Thomas and Tortola, and none call at St. Maarten. Norwegian Aura carries the bulk of the summer season with 19 sailings between June 19 and October 23, all seven-night round trips from Miami, while Norwegian Aqua runs the parallel seven-night rotation from Orlando (Port Canaveral). May is the thinnest month of the year with three departures, all on Aqua.

Why Choose an Eastern Caribbean Itinerary in 2027?

The Eastern Caribbean's appeal is short sea distances. Because the islands sit close together, a seven-night itinerary can deliver three or four island days rather than the two-plus-a-sea-day pattern common further west. Norwegian's 2027 core routing shows this directly: the most-repeated itinerary in the data, sailed 19 times by Norwegian Aura, runs Miami to Puerto Plata to St. Thomas to Tortola to Great Stirrup Cay and back, packing four port days into seven nights.

The second reason is the variety of starting points. Unlike some regions that funnel through a single homeport, these ports of call are reachable from nine different embarkation points in 2027, from drive-to options on the East Coast such as Philadelphia and New York to fly-in Caribbean starts in San Juan. San Juan sailings are the most port-dense of all: the seven-night Prima round trips from there fit six island calls into a single week, because the ship never spends a day steaming out from Florida.

Third, the season is long. St. Thomas and Tortola appear in all twelve months of 2027, so this is not a winter-only region if you are flexible about which islands you see. Travelers specifically chasing St. Maarten or a San Juan port day, however, should plan on a winter sailing.

Solo travelers have unusually good options here as well. Studio cabins, Norwegian's dedicated single-occupancy category, are priced on 121 of the 136 tracked sailings, spanning nine ships including Aqua, Prima, Aura, Luna, Escape, Epic, Viva, Bliss and Breakaway. Based on CabinSaver's own fare tracking as of August 2026, studio fares on these 2027 Eastern Caribbean sailings typically run approximately $202-264 per night at single occupancy (subject to change), against approximately $221-330 per night for an inside cabin booked solo over the same set of sailings.

Port Breakdown

St. Thomas, US Virgin Islands (STT)

St. Thomas is on 116 of the 136 tracked Norwegian 2027 sailings, making it the most-visited of the four in practical terms and the port most likely to appear whatever month you sail. It is served from five embarkation points: Miami (45 sailings), Orlando/Port Canaveral (36), San Juan (20), New York (8) and Philadelphia (7). Ships calling here in 2027 include Aqua (28), Prima (21), Aura (19), Escape (14), Luna (11), Epic (9), Bliss (7) and Pearl (7).

Notably, every single St. Thomas sailing in the 2027 data also calls at Tortola. The two are effectively a package: the standard seven-night Florida routing puts Puerto Plata first, then St. Thomas, then Tortola, then Great Stirrup Cay. Inside-cabin fares on St. Thomas sailings typically run approximately $226-333 per night for solo travelers at single occupancy across the 116 departures (subject to change, as of August 2026).

Tortola, British Virgin Islands (TOV)

Tortola edges out St. Thomas on raw count with 121 sailings, because five 2027 itineraries call at Tortola without stopping in St. Thomas. It draws from the widest set of embarkation ports of the four, including two transatlantic crossings from Lisbon on Norwegian Viva in November and a fourteen-night Norwegian Breakaway sailing from New Orleans departing April 4, 2027.

Tortola's practical role on most itineraries is as the second Virgin Islands day, usually immediately after St. Thomas, which makes it the port where a lot of travelers slow down after a busier shopping and excursion day. Inside-cabin fares on Tortola sailings typically run approximately $221-330 per night for solo travelers at single occupancy across the 121 departures (subject to change, as of August 2026).

Philipsburg, St. Maarten (PHI)

St. Maarten is the thinnest of the four in 2027 with 32 tracked sailings, and it is strictly a winter port: every call falls between November 2027 and March 2027, with none at all between April and October. Norwegian Prima dominates with 17 of those calls, followed by Bliss (7), Viva (4), Pearl (2), Epic (1) and Escape (1).

Access is narrower too. Nineteen of the 32 St. Maarten sailings depart from San Juan, eight from New York, and the remainder from Philadelphia, Port Canaveral and Lisbon. The signature routing is the Prima seven-night round trip from San Juan, which runs San Juan to Philipsburg to St. Thomas to Basseterre to Castries to Bridgetown to Tortola and home, sailed eight times in 2027 on that exact sequence. Inside-cabin fares on St. Maarten sailings typically run approximately $221-333 per night for solo travelers at single occupancy across the 32 departures (subject to change, as of August 2026).

San Juan, Puerto Rico (SJU)

San Juan is a dual-role port, which matters when reading the numbers. Of the 55 tracked 2027 sailings that include San Juan, 28 begin there and 27 visit it as a mid-itinerary call. As a port of call it is served mainly by longer East Coast itineraries: ten sailings from Philadelphia on Norwegian Pearl, eight from New York, three from Miami, and two each from Port Canaveral and Jacksonville. Ships calling at San Juan mid-itinerary include Pearl (10), Bliss (7) and Dawn (3).

Every one of the 32 St. Maarten sailings also touches San Juan, so if a Puerto Rico port day matters to you, the St. Maarten itineraries are the reliable way to get one. Like St. Maarten, San Juan calls concentrate in winter, with 27 of the 55 falling in November and December. Inside-cabin fares on San Juan sailings typically run approximately $189-333 per night for solo travelers at single occupancy across the 55 departures (subject to change, as of August 2026), the widest spread of the four ports because it mixes seven-night Caribbean weeks with longer repositioning voyages.

Month-by-Month Eastern Caribbean Cruise Calendar for 2027

January 2027

January opens the year strongly with 18 tracked departures, all 18 of which call at both St. Thomas and Tortola. Norwegian Aqua and Norwegian Prima each run five weekly sailings, Escape adds four from Port Canaveral, and Norwegian Pearl operates three ten-night round trips from Philadelphia departing January 3, 13 and 23. Six January sailings include St. Maarten and ten include San Juan, making it one of the better months for a full four-port sweep. Post-holiday demand generally eases after the first week, and the January 4 Norwegian Bliss twelve-night from New York is the longest departure of the month.

Ships: Aqua, Prima, Escape, Pearl, Bliss Destinations: Caribbean Duration: 7 to 12 nights

February 2027

February holds 15 departures with a steady weekly rhythm: Aqua sails every Sunday from Miami on February 7, 14, 21 and 28, while Prima matches that cadence from San Juan on the same dates. Escape runs four Fridays from Port Canaveral, and Pearl adds ten-night Philadelphia round trips on February 2 and 20. Five February sailings call at St. Maarten and seven at San Juan. Every February departure in the data calls at both St. Thomas and Tortola, and twelve of the fifteen are seven nights.

Ships: Aqua, Prima, Escape, Pearl, Bliss Destinations: Caribbean Duration: 7 to 12 nights

March 2027

March carries 16 departures, the last full month of peak winter coverage. The weekly Aqua and Prima pairings continue on March 7, 14, 21 and 28, joined by four Escape Fridays from Port Canaveral. Two unusual sailings stand out: a fifteen-night Norwegian Star departure from Miami on March 1 and an eleven-night Norwegian Pearl from Philadelphia on March 28. Only two March sailings include St. Maarten, so spring-break travelers hoping for Philipsburg should book early and confirm the itinerary.

Ships: Aqua, Prima, Escape, Pearl, Bliss, Star Destinations: Caribbean, Extraordinary Journeys Duration: 7 to 15 nights

April 2027

April is the transition month, dropping to seven departures as the winter fleet repositions. Escape closes out its Port Canaveral season with sailings on April 2 and 9, and Aqua runs three more from Miami including a six-night on April 18, the shortest itinerary of the year in this set. Two long voyages depart April 4: a fourteen-night Norwegian Breakaway from New Orleans and a seventeen-night Norwegian Prima from San Juan, the longest tracked 2027 sailing calling at these ports. No April sailing calls at St. Maarten.

Ships: Escape, Aqua, Breakaway, Prima Destinations: Caribbean, Extraordinary Journeys Duration: 6 to 17 nights

May 2027

May is the quietest month of 2027 with just three departures, all on Norwegian Aqua from Port Canaveral, sailing May 2, 16 and 30. Each is a seven-night round trip calling at St. Thomas and Tortola. Travelers looking for St. Maarten or a San Juan port day will not find one in May in the tracked data. The trade-off is a much less crowded shoulder period before hurricane season attention builds.

Ships: Aqua Destinations: Caribbean Duration: 7 nights

June 2027

June brings Norwegian Aura into the rotation, with its first Eastern Caribbean departures from Miami on June 19 and 26, alongside Aqua sailings from Port Canaveral on June 13 and 27. All four June departures are seven-night round trips calling at St. Thomas and Tortola. This is the start of the summer pattern that holds through October: two ships, two Florida homeports, one repeated island sequence.

Ships: Aura, Aqua Destinations: Caribbean Duration: 7 nights

July 2027

July has seven departures, the busiest summer month. Norwegian Aura runs five consecutive Saturdays from Miami on July 3, 10, 17, 24 and 31, while Aqua adds July 11 and 25 from Port Canaveral. Every July sailing is seven nights and calls at both St. Thomas and Tortola, typically with Puerto Plata and Great Stirrup Cay filling out the week. School-holiday demand makes this one of the busier stretches of the summer.

Ships: Aura, Aqua Destinations: Caribbean Duration: 7 nights

August 2027

August holds six departures split between Aura from Miami on August 7, 14, 21 and 28, and Aqua from Port Canaveral on August 8 and 22. All are seven-night round trips calling at St. Thomas and Tortola. August sits in the heart of Atlantic hurricane season, so itinerary substitutions are more likely than in winter months; confirm the current routing with Norwegian Cruise Line closer to sailing.

Ships: Aura, Aqua Destinations: Caribbean Duration: 7 nights

September 2027

September mirrors August with six departures: Aura from Miami on September 4, 11, 18 and 25, and Aqua from Port Canaveral on September 5 and 19. All are seven-night sailings visiting St. Thomas and Tortola. September is historically the lowest-demand month for Caribbean cruising, which shows in the thin schedule, and it carries the same seasonal weather caveat as August.

Ships: Aura, Aqua Destinations: Caribbean Duration: 7 nights

October 2027

October steps up to nine departures as Norwegian Luna joins the Miami rotation with sailings on October 17, 24 and 31. Aura continues its Saturday pattern on October 2, 9, 16 and 23, and Aqua runs October 3 and 17 from Port Canaveral before its season ends. All nine are seven-night round trips calling at St. Thomas and Tortola, and none include St. Maarten or San Juan.

Ships: Aura, Aqua, Luna Destinations: Caribbean Duration: 7 nights

November 2027

November is the year's inflection point, jumping to 22 departures as the winter fleet arrives. Norwegian Viva opens the month with two transatlantic crossings from Lisbon on November 1, and Norwegian Dawn sails a fourteen-night from Barcelona on November 5. Prima returns to weekly San Juan round trips from November 13, Viva joins it from November 14, Epic starts Port Canaveral sailings on November 12, and Luna runs four Sundays from Miami. Nine November sailings call at St. Maarten and 14 at San Juan, making it the month the full four-port map reopens.

Ships: Viva, Prima, Dawn, Luna, Bliss, Epic, Joy, Pearl Destinations: Caribbean, Extraordinary Journeys, Transatlantic Duration: 7 to 14 nights

December 2027

December is the busiest month of 2027 with 23 departures. Epic runs six from Port Canaveral including a December 31 New Year's sailing, Prima and Viva each run four weekly San Juan round trips, and Luna runs four from Miami. Bliss operates twelve-night New York round trips on December 10 and 22, and Pearl sails ten and eleven-night Philadelphia itineraries on December 13 and 23. Ten December sailings include St. Maarten and 14 include San Juan. Holiday-week departures around December 22 to 31 are the most in-demand of the year, so book well ahead.

Ships: Epic, Prima, Luna, Viva, Dawn, Bliss, Pearl Destinations: Caribbean, Extraordinary Journeys Duration: 7 to 12 nights

Ship Deployment

• Norwegian Aqua - January 3 to October 17, 2027, 29 sailings, the longest continuous presence of any ship in this set; alternates seven-night round trips from Miami and Port Canaveral calling at Puerto Plata, St. Thomas, Tortola and Great Stirrup Cay
• Norwegian Prima - January 3 to December 25, 2027, 22 sailings, almost entirely seven-night round trips from San Juan; the most port-dense itineraries in the group, adding Basseterre, Castries and Bridgetown alongside St. Maarten and Tortola
• Norwegian Aura - June 19 to October 23, 2027, 19 sailings, the dedicated summer ship; weekly seven-night round trips from Miami on the Puerto Plata, St. Thomas, Tortola, Great Stirrup Cay rotation
• Norwegian Escape - January 6 to April 9, 2027, 14 sailings, a winter-only Port Canaveral deployment on the same seven-night Eastern Caribbean pattern
• Norwegian Luna - October 17 to December 26, 2027, 11 sailings, arriving in the fall for weekly seven-night Miami round trips
• Norwegian Pearl - January 3 to December 23, 2027, 10 sailings, the Philadelphia specialist; ten and eleven-night itineraries pairing San Juan with St. Thomas and Tortola
• Norwegian Epic - November 12 to December 31, 2027, 9 sailings from Port Canaveral, including a ten-night December 10 departure that adds St. Maarten and San Juan
• Norwegian Viva - November 1 to December 26, 2027, 9 sailings, opening with two Lisbon transatlantic crossings then settling into seven-night San Juan round trips
• Norwegian Bliss - January 4 to December 22, 2027, 7 sailings, all twelve-night round trips from New York calling at St. Maarten, St. Thomas, San Juan and Tortola
• Norwegian Dawn - November 5 to December 9, 2027, 3 sailings, including a fourteen-night Barcelona crossing and a Jacksonville departure
• Norwegian Breakaway - April 4, 2027, a single fourteen-night sailing from New Orleans
• Norwegian Joy - November 18, 2027, a single nine-night sailing from Miami
• Norwegian Star - March 1, 2027, a single fifteen-night sailing from Miami

Planning Tips

• Match the port to the season, not the other way around. St. Thomas and Tortola appear in all twelve months of 2027, but St. Maarten calls only between November and March. If Philipsburg is non-negotiable, you are shopping a 32-sailing winter list, not a 136-sailing year.
• Pick your embarkation port for the island mix. Florida departures follow the Puerto Plata, St. Thomas, Tortola, Great Stirrup Cay pattern; San Juan departures skip Florida sea days entirely and add Basseterre, Bridgetown and Castries. Both are seven nights, and they see very different islands.
• In St. Thomas, decide early between town and beach. Charlotte Amalie's shopping district and the beaches on the island's north side are in different directions from the pier, and ship time in port is limited. Confirm your ship's actual arrival and all-aboard times with Norwegian Cruise Line, as they vary by itinerary.
• Treat Tortola as the slower day. It typically follows St. Thomas on the same itinerary, and its draw is generally beaches and boat trips rather than shopping. Ferry-based excursions to nearby islands run on their own schedules; verify timings against your ship's all-aboard before booking independently.
• Check documentation early. These itineraries cross between US, British and Dutch territories in a single week. A valid passport book is typically required (passport cards are generally not sufficient for cruise travel), requirements vary by itinerary and citizenship, and you should always verify current documentation requirements with Norwegian Cruise Line and official government travel advisories before your trip.
• Longer is not always more islands. The seventeen-night Prima sailing on April 4, 2027 and the fifteen-night Star sailing on March 1 include substantial sea time. The seven-night San Juan round trips actually deliver more island days per night than most of the long voyages in this set.

How to Find the Best Deals on Eastern Caribbean Cruises

Norwegian Cruise Line pricing fluctuates based on demand, booking time, and availability. Here's how to time your booking:

• Book early - Promotional fares are often available 12-18 months in advance, which for a 2027 Eastern Caribbean sailing means shopping now
• Monitor price drops - Fares change weekly; set up deal alerts to track your preferred sailings. Across the 364 daily snapshots recorded since August 2025, the median 2027 sailing in this set has moved through a roughly 24 percent spread between its highest and lowest observed inside fare, and 108 of the 136 sailings are currently priced below the midpoint of their own observed range (as of August 2026, subject to change)
• Consider shoulder season - May, June, August and September each carry six or fewer departures and sit outside peak demand windows, though the summer months trade St. Maarten and San Juan access for that
• Compare the two seven-night patterns - A Florida round trip and a San Juan round trip are the same length but different products; check both before assuming one is priced better for your dates
• Look at the longer East Coast itineraries - The ten and twelve-night Philadelphia and New York sailings cover the same islands without a flight, which changes the total trip cost calculation

Our deal finder shows real-time pricing across all 136 tracked 2027 departures, helping you compare fares for your preferred dates and ports.

With 13 ships, nine embarkation ports and itineraries running from six to seventeen nights, Norwegian's 2027 Eastern Caribbean schedule offers a wide enough spread that the harder question is which islands you want rather than whether a sailing exists.

Ready to book? Check live pricing and availability for any of these sailings.

Data current as of August 2026, derived from CabinSaver's own cruise fare tracking. Always verify availability and details directly with the cruise line.

Related Guides

• The ABC Islands and Barbados: Norwegian's 2026 Southern Caribbean Ports of Call - Covers Aruba, Curacao and Barbados, which appear on several of the San Juan round trips in this guide.
• Western Caribbean: Cruising Cozumel, Roatan, Belize & Costa Maya on NCL in 2026 - The alternative Caribbean loop, with longer sea distances and a different island mix.
• 2026 Bahamas Cruises on Norwegian Cruise Line - Great Stirrup Cay appears on 85 of the sailings in this guide; this covers the Bahamas side of those itineraries.
• Norwegian Aura: Sneak Peek at NCL's Newest Announced Ship - Background on the ship carrying the entire summer 2027 Eastern Caribbean season from Miami.
• Introducing the Norwegian Luna: Initial Itineraries - Details on the ship that joins the Miami rotation in October 2027.

Frequently Asked Questions

Which Norwegian ships visit St. Thomas and Tortola in 2027?

Thirteen ships call at these four Eastern Caribbean ports across 2027, led by Norwegian Aqua with 29 sailings, Norwegian Prima with 22, Norwegian Aura with 19 and Norwegian Escape with 14. Norwegian Luna, Pearl, Epic, Viva, Bliss, Dawn, Breakaway, Joy and Star each appear on a smaller number of itineraries. Verify ship assignments with Norwegian Cruise Line, as deployments can change.

Which departure ports reach these Eastern Caribbean ports of call?

Miami accounts for 48 of the 136 tracked Norwegian 2027 sailings, Orlando (Port Canaveral) 36, San Juan 28, Philadelphia 10 and New York 8, with a handful more from Jacksonville, New Orleans, Lisbon and Barcelona. Most are seven-night round trips, so the departure port you choose largely determines which of the four ports appear on the itinerary.

When is the best time to cruise to St. Thomas and St. Maarten in 2027?

Coverage is heaviest between November and April, which holds 101 of the 136 tracked Norwegian 2027 sailings, and December is the single busiest month with 23 departures. St. Maarten and San Juan are almost entirely winter ports in 2027, so a summer sailing will typically reach St. Thomas and Tortola but not the other two.

How long are cruises that call at these Eastern Caribbean ports?

Seven nights is the dominant length, covering 106 of the 136 tracked Norwegian 2027 sailings. Ten-night and twelve-night itineraries from Philadelphia and New York make up most of the rest, and a small number of longer repositioning and transatlantic voyages run up to 17 nights.

Do all these itineraries visit all four ports?

No. Only 26 of the 136 tracked Norwegian 2027 sailings call at all four. St. Thomas and Tortola are almost always paired, appearing together on 116 sailings, while St. Maarten shows up on 32 sailings and San Juan on 55, of which 27 are mid-itinerary calls rather than embarkation.