EIS - SXM

$174 Find Cheap Flights from Road Town to Simpson Bay - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Road Town to Simpson Bay departing on 9/26. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$383
Typical prices: $357-$369
Winair
Fri 9/4Fri 9/11
EIS - SXM • Non-stop
Cheapest one-way
$174
Typical prices: $158-$267
interCaribbean Airways
Sat 9/26
EIS - SXM • Non-stop
Nonstop flights
You can fly direct with Winair, interCaribbean Airways and Fly Salone. Average duration is 0h 44m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top layover airports
Cheapest • Avg $379 (round-trip)
Shortest trip • 1h 50m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 30% price drop
Most popular
Good to know
Good to know
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Good to know
Good to know
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Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Road Town to Simpson Bay (EIS-SXM)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Road Town to Simpson Bay that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Road Town to Simpson Bay

Fri, Sep 4 - Fri, Sep 11
Winair Logo
9:55 am - 10:35 amEIS  Road Town Beef Island-SXM Simpson Bay Princess Juliana
0h 40mnonstop
Winair Logo
10:20 am - 11:10 amSXM  Simpson Bay Princess Juliana-EIS Road Town Beef Island
0h 50mnonstop
$383Winair
Sun, Aug 23 - Sun, Aug 30
Multiple Airlines Logo
7:15 am - 9:10 amEIS  Road Town Beef Island-SXM Simpson Bay Princess Juliana
1h 55m1 stop Basseterre Robert Bradshaw Intl
Multiple Airlines Logo
1:25 pm - 2:05 pmSXM  Simpson Bay Princess Juliana-EIS Road Town Beef Island
0h 40mnonstop
$413Multiple Airlines
Fri, Sep 4 - Fri, Sep 11
Winair Logo
9:55 am - 10:35 amEIS  Road Town Beef Island-SXM Simpson Bay Princess Juliana
0h 40mnonstop
Winair Logo
4:30 pm - 6:55 pmSXM  Simpson Bay Princess Juliana-EIS Road Town Beef Island
2h 25m1 stop St. John's V.C. Bird Intl
$426Winair
Sun, Aug 23 - Sun, Aug 30
Multiple Airlines Logo
10:50 am - 11:30 amEIS  Road Town Beef Island-SXM Simpson Bay Princess Juliana
0h 40mnonstop
Multiple Airlines Logo
1:25 pm - 2:05 pmSXM  Simpson Bay Princess Juliana-EIS Road Town Beef Island
0h 40mnonstop
$438Multiple Airlines
Sat, Sep 19 - Sat, Sep 26
Winair Logo
7:15 am - 9:10 amEIS  Road Town Beef Island-SXM Simpson Bay Princess Juliana
1h 55m1 stop Basseterre Robert Bradshaw Intl
Winair Logo
5:15 pm - 7:15 pmSXM  Simpson Bay Princess Juliana-EIS Road Town Beef Island
2h 00m1 stop Basseterre Robert Bradshaw Intl
$439Winair
Sat, Sep 12 - Tue, Sep 15
Winair Logo
7:45 pm - 8:35 pmEIS  Road Town Beef Island-SXM Simpson Bay Princess Juliana
0h 50mnonstop
Winair Logo
10:20 am - 11:10 amSXM  Simpson Bay Princess Juliana-EIS Road Town Beef Island
0h 50mnonstop
$439Winair
Sat, Sep 19 - Sat, Sep 26
Winair Logo
7:15 am - 9:10 amEIS  Road Town Beef Island-SXM Simpson Bay Princess Juliana
1h 55m1 stop Basseterre Robert Bradshaw Intl
Winair Logo
10:20 am - 11:10 amSXM  Simpson Bay Princess Juliana-EIS Road Town Beef Island
0h 50mnonstop
$439Winair
Sat, Sep 12 - Tue, Sep 15
Multiple Airlines Logo
8:50 am - 10:05 amEIS  Road Town Beef Island-SXM Simpson Bay Princess Juliana
25h 15m2 stops St. John's V.C. Bird Intl Basseterre Robert Bradshaw Intl
Multiple Airlines Logo
10:20 am - 11:10 amSXM  Simpson Bay Princess Juliana-EIS Road Town Beef Island
0h 50mnonstop
$519Multiple Airlines
Sat, Sep 12 - Tue, Sep 15
Multiple Airlines Logo
1:45 pm - 2:25 pmEIS  Road Town Beef Island-SXM Simpson Bay Princess Juliana
0h 40mnonstop
Multiple Airlines Logo
4:25 pm - 6:45 pmSXM  Simpson Bay Princess Juliana-EIS Road Town Beef Island
26h 20m2 stops Basseterre Robert Bradshaw Intl St. John's V.C. Bird Intl
$534Multiple Airlines
Sat, Sep 19 - Sat, Sep 26
interCaribbean Airways Logo
8:50 am - 12:40 pmEIS  Road Town Beef Island-SXM Simpson Bay Princess Juliana
27h 50m2 stops St. John's V.C. Bird Intl Bridgetown Grantley Adams Intl
interCaribbean Airways Logo
3:10 pm - 11:10 amSXM  Simpson Bay Princess Juliana-EIS Road Town Beef Island
44h 00m2 stops Bridgetown Grantley Adams Intl St. John's V.C. Bird Intl
$1,065interCaribbean Airways
Booking Insights

KAYAK's insights & trends for Road Town to Simpson Bay flights

Get data-powered insights and trends into flights from Road Town to Simpson Bay to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Road Town to Simpson Bay?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Road Town to Simpson Bay departing in September.

Flight prices are typical for this route right now.

Flights to Simpson Bay from Road Town usually cost between $360 and $412 in September.
The lowest price found in the past 5 days was $383 on Winair (Sep 4-Sep 11).

What’s the cheapest day of the week to fly from Road Town to Simpson Bay?

The average price of all round-trip flights from Road Town to Simpson Bay clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Simpson Bay on a Tuesday and more expensive on a Wednesday. On your return trip to Road Town, you should consider flying back on a Tuesday, and avoid Fridays for better deals.

What is the cheapest month to fly from Road Town to Simpson Bay?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Road Town to Simpson Bay, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Road Town to Simpson Bay is June, where tickets cost $267 (return) on average. On the other hand, the most expensive months are April and January, where the average cost of round-trip tickets is $452 and $442 respectively.

Can I save money by flying with a layover from Road Town to Simpson Bay?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $183, prices are generally cheapest when you fly direct.

Good to know

Low season

June

Cheapest flight

$174
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from Road Town to Simpson Bay

When to book flights from Road Town to Simpson Bay

Are your dates flexible? Find out the best times to travel from Road Town 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
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Road Town to Simpson Bay

  • How many flights are there between Road Town and Simpson Bay per day?

    Each day, there are between 1 and 5 nonstop flights that take off from Road Town and land in Simpson Bay, with an average flight time of 0h 44m. The most common departure time is 7:00 pm and most flights take off in the morning. Each week, there are 13 flights. The most frequent day of departure is Saturday, when 38% of all weekly flights depart. The fewest flights depart on a Monday.

  • What is the cheapest flight from Road Town to Simpson Bay?

    In the last 5 days, the lowest price for a flight from Road Town to Simpson Bay was $174 for a one-way ticket and $383 for a round-trip.

  • Do I need a passport to fly between Road Town and Simpson Bay?

    Yes

  • Which airports will I be using when flying from Road Town to Simpson Bay?

    On your way to Simpson Bay, you’ll fly out from Road Town Beef Island. You’ll be landing at Simpson Bay Princess Juliana.

  • Which aircraft models fly most regularly from Road Town to Simpson Bay?

    The ATR 42 / ATR 72 is the aircraft model that flies most regularly on the Road Town to Simpson Bay flight route.

  • On which days can I fly direct from Road Town to Simpson Bay?

    There are nonstop flights from Road Town to Simpson Bay on a daily basis.

  • Which is the best airline for flights from Road Town to Simpson Bay, Winair or interCaribbean Airways?

    The two airlines most popular with KAYAK users for flights from Road Town to Simpson Bay are Winair and interCaribbean Airways. With an average price for the route of $403 and an overall rating of 8.5, Winair is the most popular choice. interCaribbean Airways is also a great choice for the route, with an average price of $330 and an overall rating of 5.8.

  • How does KAYAK find such low prices on flights from Road Town to Simpson Bay?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Road Town to Simpson Bay.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Road Town to Simpson Bay?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Simpson Bay from Road Town is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Road Town to Simpson Bay?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Simpson Bay with an airline and back to Road Town with another airline. Booking your flights between Road Town and SXM can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Road Town to Simpson Bay?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Simpson Bay from Road Town up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Road Town to Simpson Bay

  • Looking for a cheap flight? 25% of our users found flights on this route for $345 or less one-way and $183 or less round-trip.

Prefer to fly direct from Road Town to Simpson Bay?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Road Town Beef Island to Simpson Bay Princess Juliana.
Find which airlines fly direct from Road Town Beef Island Airport to Simpson Bay Princess Juliana Airport, which days they fly and book direct flights.

Direct departures

Road Town Beef Island to Simpson Bay Princess Juliana

Monday

Winair

Winair

Tuesday

Winair

Winair

Wednesday

Winair

Winair

Thursday

Winair,interCaribbean Airways

Winair,interCaribbean Airways

Friday

Winair

Winair

Saturday

Fly Salone,Winair,interCaribbean Airways

Fly Salone,Winair, +1 more

Sunday

Fly Salone

Fly Salone

See more direct flights

Direct returns

Simpson Bay Princess Juliana to Road Town Beef Island

Monday

Fly Salone,Winair

Fly Salone,Winair

Tuesday

Winair

Winair

Wednesday

Winair,interCaribbean Airways

Winair,interCaribbean Airways

Thursday

Fly Salone,Winair

Fly Salone,Winair

Friday

Fly Salone,Winair

Fly Salone,Winair

Saturday

Fly Salone,Winair

Fly Salone,Winair

Sunday

Winair,interCaribbean Airways

Winair,interCaribbean Airways

See more direct flights

Reviews of the top airlines flying from Road Town to Simpson Bay

 
See real verified KAYAK customer reviews for airlines flying from Road Town to Simpson Bay. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Road Town to Simpson Bay? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.5
WinairOverall score based on 4 reviews
9.5Crew
8.5Boarding
7.5Food
8.0Comfort
7.5Entertainment
Airline reviews

windsor had major problems and their flights were canceled and delayed. we got lucky and they were able to put us on another plane 1 hour late. luckily we had a long enough layover and didn’t miss our connecting flights.

6.0 GoodAnonymous, May 2026
Read more Winair reviews

windsor had major problems and their flights were canceled and delayed. we got lucky and they were able to put us on another plane 1 hour late. luckily we had a long enough layover and didn’t miss our connecting flights.

Flew St Vincent to Barbados on an ATR-40 (?), seating about 60 passengers. Pretty tight in there. Flt. attendant was very friendly. Short flight - up & down in 40 minutes.

No food, no entertainment - half-hour flight (up & down) Smallest plane I’ve ever been on - maybe 60 passenger capacity?

I've had bad flights with InterCaribbean before (cancellations, no gate agents, etc.), but this one went perfectly smoothly!

Long delay. No AC on the flight from Barbados to St. Lucia.

Did not get to travel, you canceled my flight and left me stranded for the hole day, it's another day and I can't get to my destination. I will not recommend any one to this away, bad service

Delay flight more than 8hours waiting and poor customer service!

Plane was extremely small so mind the size of your carry on

Other than lack of snacks, everything else went very well.

They don’t keep you updated on the flight status very well. It was late but nothing said

Everything you need to know for your flight from Road Town to Simpson Bay

Information on your arrival and departure airports