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Transatlantic cruises

Transatlantic Crossing via San Juan, Philipsburg & Funchal, Madeira

San Juan · Philipsburg · Funchal, Madeira · Cadiz · Málaga

Balanced itinerary with more sea time than port-packed variants. Covers Puerto Rico, Sint Maarten (Dutch part), Portugal, and Spain.

16 nights Miami Transatlantic 5 ports 10 sea days
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What this trip feels like

Easygoing, familiar and ship-focused

10 sea days give you plenty of uninterrupted time onboard, while San Juan, Philipsburg, and Funchal, Madeira provide the trip's main day ashore. You're choosing this route for an easy break with minimal logistics, not destination variety.

Relaxed pace

5 ports in 16 nights

Plenty of uninterrupted ship time.

Broad destination variety

San Juan · Philipsburg · Funchal, Madeira + more

Frequent changes of scenery across the itinerary.

Route logistics

Sails from Miami

Check the exact departure and arrival ports before arranging flights.

Port experience

San Juan · Pick your date carefully

Cruise traffic varies substantially by date, so your specific port day can feel very different depending on when you visit.

Best for · First-time cruisers · Ship-focused trips · Easy short getaways

Think twice if · You want a port-intensive Transatlantic itinerary

Best departures

Best upcoming sailings

Start here. These departures surface first because they combine stronger pricing, useful timing, or a notable warning signal for this itinerary.

Best overall value
Explora Journeys

Explora I

Miami → San Juan → Málaga → Barcelona

Mar 8 · 16 nights

About average

$8,315 suite · $520/night

All departures

All upcoming departures

Compare all sailings for this itinerary.

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Itinerary pricing

What this itinerary usually costs

Typical pricing runs around $559/night, with most departures landing in the $544-$620/night band across 1 tracked sailing.

Typical price

$559/night

$8,944 total

Normal range

$544-$620/night

$8,710-$9,920 total

Lowest recent fare

Building history

$7,425 total

Comparison set

1 sailings

Used for itinerary baseline

When should I go?

Not enough departures yet to identify a reliable cheaper season.

Route overview

How this route is built

Compare sailings →

16 nights · 5 port calls · 10 sea days · 4 countries

5 port calls across Puerto Rico, Sint Maarten (Dutch part), Portugal, Spain · Leans more toward sea time than a port-packed 16-night route.

  1. 1

    Embark in Miami

    Embarkation ports can vary by sailing

  2. 2

    San Juan

    Puerto Rico · Eastern Caribbean

  3. 3

    Philipsburg

    Sint Maarten (Dutch part) · Eastern Caribbean

  4. 4

    Funchal, Madeira

    Portugal · Madeira

  5. 5

    Cadiz

    Spain · Portugal & Spain Atlantic Coast

  6. 6

    Málaga

    Spain · Western Mediterranean

  7. 7

    Disembark in Barcelona

    Disembarkation ports can vary by sailing

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Embark port
Disembark port
Port of call

Other routes to consider

Not quite the right itinerary? Compare routes that trade a little simplicity for more ports, different destinations, or a longer trip.

FAQ

What’s the best month to sail this itinerary?
It depends on weather and crowd levels. Use the sailing list to compare dates and prioritize port days with comfortable conditions.
Are these sailings all the same route?
They can be close but not identical. Look for differences in port order, arrival times, and sea day placement.
How should I choose between two similar sailings?
Compare: (1) ship, (2) port day timing, (3) number of sea days, (4) price vs cabin value, and (5) flight convenience.