POS - SXM

$310 Find Cheap Flights from Port of Spain to Simpson Bay - Compare and Save

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Everything you should know

Cheapest round-trip
$551
Typical prices: $489-$611
Caribbean Airlines
Tue 11/27Fri 11/30
POS - SXM • Non-stop
Cheapest one-way
$310
Typical prices: $277-$403
Winair
Sun 12/30
POS - SXM • Non-stop
Nonstop flights
You can fly direct with Caribbean Airlines and Winair. Average duration is 2h 21m
Direct flights
+1
Direct flights
+1
When to book
in advance
Our data shows that travelers who book at least 21 weeks in advance save around 48% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 12% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $441 (round-trip)
Shortest trip • 3h 12m (one-way)
Insights
Insights
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We hope you love your trip to Simpson Bay!
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Booking Insights
Flight Deals

Cheap Flights from Port of Spain to Simpson Bay (POS-SXM)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Port of Spain to Simpson Bay

Fri, Nov 27 - Mon, Nov 30
Caribbean Airlines Logo
3:10 pm - 5:45 pmPOS  Port of Spain Piarco Intl-SXM Simpson Bay Princess Juliana
2h 35mnonstop
Caribbean Airlines Logo
5:50 pm - 8:20 pmSXM  Simpson Bay Princess Juliana-POS Port of Spain Piarco Intl
2h 30mnonstop
$551Caribbean Airlines
Mon, Jan 25 - Mon, Feb 1
Caribbean Airlines Logo
2:30 pm - 5:05 pmPOS  Port of Spain Piarco Intl-SXM Simpson Bay Princess Juliana
2h 35mnonstop
Caribbean Airlines Logo
5:50 pm - 8:20 pmSXM  Simpson Bay Princess Juliana-POS Port of Spain Piarco Intl
2h 30mnonstop
$579Caribbean Airlines
Sat, Dec 12 - Fri, Mar 5
Caribbean Airlines Logo
7:45 am - 9:25 amPOS  Port of Spain Piarco Intl-SXM Simpson Bay Princess Juliana
1h 40mnonstop
Caribbean Airlines Logo
6:30 pm - 9:00 pmSXM  Simpson Bay Princess Juliana-POS Port of Spain Piarco Intl
2h 30mnonstop
$595Caribbean Airlines
Wed, Dec 23 - Mon, Dec 28
Multiple Airlines Logo
1:20 pm - 3:45 pmPOS  Port of Spain Piarco Intl-SXM Simpson Bay Princess Juliana
2h 25mnonstop
Multiple Airlines Logo
12:24 pm - 2:01 amSXM  Simpson Bay Princess Juliana-POS Port of Spain Piarco Intl
13h 37m1 stop Panama City Tocumen Intl
$595Multiple Airlines
Wed, Dec 23 - Sun, Dec 27
Multiple Airlines Logo
1:20 pm - 3:45 pmPOS  Port of Spain Piarco Intl-SXM Simpson Bay Princess Juliana
2h 25mnonstop
Multiple Airlines Logo
10:30 am - 10:30 amSXM  Simpson Bay Princess Juliana-POS Port of Spain Piarco Intl
24h 00m1 stop St. John's V.C. Bird Intl
$596Multiple Airlines
Thu, Apr 15 - Mon, May 3
Multiple Airlines Logo
5:00 pm - 10:00 amPOS  Port of Spain Piarco Intl-SXM Simpson Bay Princess Juliana
17h 00m2 stops St. John's V.C. Bird Intl Basseterre Robert Bradshaw Intl
Multiple Airlines Logo
5:50 pm - 8:20 pmSXM  Simpson Bay Princess Juliana-POS Port of Spain Piarco Intl
2h 30mnonstop
$600Multiple Airlines
Wed, Dec 23 - Sun, Dec 27
Winair Logo
1:20 pm - 3:45 pmPOS  Port of Spain Piarco Intl-SXM Simpson Bay Princess Juliana
2h 25mnonstop
Winair Logo
10:10 am - 12:35 pmSXM  Simpson Bay Princess Juliana-POS Port of Spain Piarco Intl
2h 25mnonstop
$618Winair
Sat, Dec 12 - Fri, Mar 5
Caribbean Airlines Logo
7:45 am - 9:25 amPOS  Port of Spain Piarco Intl-SXM Simpson Bay Princess Juliana
1h 40mnonstop
Caribbean Airlines Logo
6:30 pm - 9:00 pmSXM  Simpson Bay Princess Juliana-POS Port of Spain Piarco Intl
2h 30mnonstop
$618Caribbean Airlines
Wed, Nov 25 - Sun, Dec 6
Winair Logo
1:20 pm - 3:45 pmPOS  Port of Spain Piarco Intl-SXM Simpson Bay Princess Juliana
2h 25mnonstop
Winair Logo
10:10 am - 12:35 pmSXM  Simpson Bay Princess Juliana-POS Port of Spain Piarco Intl
2h 25mnonstop
$667Winair
Wed, Nov 25 - Wed, Dec 2
Winair Logo
1:20 pm - 3:45 pmPOS  Port of Spain Piarco Intl-SXM Simpson Bay Princess Juliana
2h 25mnonstop
Winair Logo
10:10 am - 12:35 pmSXM  Simpson Bay Princess Juliana-POS Port of Spain Piarco Intl
2h 25mnonstop
$667Winair
Booking Insights

Price, demand and travel trends for Port of Spain to Simpson Bay flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Port of Spain to Simpson Bay?

Round-trip flights from Port of Spain to Simpson Bay typically range from $489 to $611. The lowest price found in the past 5 days was $551, on Caribbean Airlines.

What's the cheapest day of the week to fly from Port of Spain to Simpson Bay?

Based on deals KAYAK users found in the last 12 months, Sunday is the cheapest day of the week to fly from Port of Spain to Simpson Bay. It’s 26% cheaper than the average day, while Thursday is the most expensive, with prices 56% higher.

What’s the cheapest month to fly from Port of Spain to Simpson Bay?

•June is the cheapest month to fly from Port of Spain to Simpson Bay at $491 round-trip.
•January ($1,064) and May ($599) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 116% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Port of Spain to Simpson Bay the cheapest?

Flights from Port of Spain to Simpson Bay are cheapest 21 weeks before departure. Booking in this window typically costs about 48% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Key details for Port of Spain to Simpson Bay flights

Low season

January

Cheapest flight

$310
Beat the crowds with an average 68% drop in travelers.
The most popular month to fly with an average 52% increase in travelers.
One-way flight from Port of Spain to Simpson Bay

When to book flights from Port of Spain to Simpson Bay

Are your dates flexible? Find out the best times to travel from Port of Spain to Simpson Bay based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Port of Spain to Simpson Bay flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Port of Spain to Simpson Bay?

    These are the earliest and latest flight times currently scheduled from Port of Spain to Simpson Bay:

    • Earliest: departs at 7:45 am and lands at 10:06 am
    • Latest: departs at 3:10 pm and lands at 5:31 pm.

    The flight takes about 2h 21m.

  • What cabin classes can I book on flights from Port of Spain to Simpson Bay?

    Two cabin classes are available on flights from Port of Spain to Simpson Bay:

    • Economy Class
    • Business Class

  • How long is a flight from Port of Spain to Simpson Bay?

    A nonstop flight from Port of Spain to Simpson Bay takes about 2h 21m, covering 528 miles.

  • Do I need a passport to fly from Port of Spain to Simpson Bay?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • How much should I expect to pay for a Port of Spain to Simpson Bay flight?

    Round-trip flights from Port of Spain to Simpson Bay range from $489 to $611, with an average of $557 over the past 12 months. Anything below $489 counts as a good deal.

  • How expensive are last-minute Port of Spain to Simpson Bay flights?

    Last-minute fares on this route (booked within two weeks of departure) run 37% above the $557 route average. Book 21 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Port of Spain to Simpson Bay?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $441 round-trip via Willemstad Hato Int. (CUR), compared to $533 for nonstop.

  • What is the standard checked-bag allowance on flights from Port of Spain to Simpson Bay?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $49–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Port of Spain to Simpson Bay?

    The ATR 72-201 / 202 family is used most often on this route, operated mainly by Caribbean Airlines. Other aircraft seen on the route include ATR 42-300 / 320 variants.

  • How are flight departures from Port of Spain to Simpson Bay spread across the day?

    Flights between Port of Spain and Simpson Bay typically depart in the afternoon.

  • Have flight prices from Port of Spain to Simpson Bay changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $551 to $1,298. That means the highest observed fare was about 2x higher than the lowest one.

  • How are flight prices from Port of Spain to Simpson Bay looking right now?

    One-way fares from Port of Spain to Simpson Bay are currently higher than usual. Average one-way flight prices are about $345, which is 7% above the typical average for this route.

  • What car rental options are available at Simpson Bay Princess Juliana Airport (SXM)?

    Simpson Bay Princess Juliana Airport (SXM) hosts 5 major car rental companies, with daily rates averaging $40 for economy cars. Top options include:

    • Right Cars
    • Ace
    • Budget
    • Avis
    • Final Rentals

  • Which airports can I use when flying from Port of Spain to Simpson Bay?

    Flights from Port of Spain to Simpson Bay usually depart from Port of Spain Piarco Intl (POS) and arrive at Simpson Bay Princess Juliana (SXM).

  • Which airports do connecting flights from Port of Spain to Simpson Bay pass through?

    One-stop flights from Port of Spain to Simpson Bay most commonly connect through:

    • Bridgetown Grantley Adams Intl (BGI) - 37% of one-stop connections
    • Willemstad Hato Int. (CUR) - 37% of one-stop connections
    • Panama City Tocumen Intl (PTY) - 26% of one-stop connections

  • Can I save money by using flexible dates for flights from Port of Spain to Simpson Bay?

    Yes. Flexible dates can save you up to 53% on flights from Port of Spain to Simpson Bay. Sunday is the cheapest departure day at $415 round-trip on average, while Thursday is the most expensive at $871, a difference of $456.

    Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • What airlines fly from Port of Spain to Simpson Bay?

    Only Caribbean Airlines and Winair currently operate flights between Port of Spain and Simpson Bay on a regular basis.

  • How much time can I save by choosing a different layover airport from Port of Spain to Simpson Bay?

    Flying via Bridgetown Grantley Adams Intl (BGI) gives the shortest average 1-stop total travel time at 3h 12m, compared with 10h 37m via Panama City Tocumen Intl (PTY) and 18h 06m via Willemstad Hato Int. (CUR).

  • Which airlines offer free seat selection on Port of Spain to Simpson Bay flights?

    None of the airlines on this route currently offer free seat selection. Seat selection is typically fee-based on this route, with availability depending on fare class.

  • Which airlines offer extra legroom on Port of Spain to Simpson Bay flights?

    None of the airlines on this route currently offer extra legroom.

  • Which airlines include bags at no extra cost on Port of Spain to Simpson Bay flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Caribbean Airlines: a cabin bag and a checked bag in Business Class
    • Winair: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Port of Spain to Simpson Bay flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Sunday departure and avoid flying on Thursday. On this route, Sunday flights average $415, about $456 less than Thursday fares (52% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 21 weeks before you fly. On this route, that window historically saves about 48% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Port of Spain to Simpson Bay trip for June. Fares historically average $491 round-trip in that month - typically $573 less than the most expensive month, which is January (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Willemstad Hato Int. Airport (CUR) can be cheaper than flying direct. The cheapest layover option averages $441 round-trip on this route - about $92 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Simpson Bay Princess Juliana Airport.

    • Simpson Bay Resort Marina & Spa
    • Hilton Vacation Club Flamingo Beach St. Maarten
    • The Atrium Beach Resort and Spa Sint Maarten, an Ascend Collection Hotel

Prefer to fly direct from Port of Spain to Simpson Bay?

 
Find which airlines fly direct from Port of Spain Piarco Intl Airport to Simpson Bay Princess Juliana Airport, which days they fly and book direct flights.

Direct departures

Port of Spain Piarco Intl to Simpson Bay Princess Juliana

Monday

Caribbean Airlines

Caribbean Airlines

Wednesday

Winair

Winair

Friday

Caribbean Airlines

Caribbean Airlines

Saturday

Caribbean Airlines

Caribbean Airlines

Sunday

Winair

Winair

See more direct flights

Direct returns

Simpson Bay Princess Juliana to Port of Spain Piarco Intl

Monday

Caribbean Airlines,KLM

Caribbean Airlines,KLM

Wednesday

KLM,Winair

KLM,Winair

Friday

Caribbean Airlines,KLM

Caribbean Airlines,KLM

Saturday

Caribbean Airlines,KLM

Caribbean Airlines,KLM

Sunday

KLM,Winair

KLM,Winair

See more direct flights

More options for your flight from Port of Spain to Simpson Bay

Complete your trip to Simpson Bay with a hotel stay or car rental