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Simpson Bay

$159+ Cheap flights from Road Town (EIS) to Simpson Bay (SXM)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/20. Fares are subject to change and may not be available on all flights or dates of travel.
EIS — SXM
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheap flight deals from Road Town to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Road Town (EIS) to Simpson Bay (SXM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 12, 2025.

Round-trip from

$368
(Trip.com)

One-way from

$159
(Mytrip)

Popular in

October

Cheapest in

September

Average price

$380
From Road Town Beef Island to Simpson Bay Princess Juliana
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One-way flight from Road Town Beef Island to Simpson Bay Princess Juliana
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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Find flight deals from Road Town to Simpson Bay

Cheapest flights from Road Town to Simpson Bay
Explore the most affordable flight options available from Road Town to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.

This Trip.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/411:55 amEIS - SXM
1 stop2h 25mWinair
Mon 7/75:00 pmSXM - EIS
1 stop25h 35mWinair
Deal found 6/10$368
This CheapOair deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/187:05 pmEIS - SXM
Nonstop0h 45mHahn Air
Sun 7/209:55 amSXM - EIS
Nonstop0h 45mHahn Air
Deal found 6/10$391
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/59:50 amEIS - SXM
Nonstop0h 40mMultiple Airlines
Wed 7/910:20 amSXM - EIS
Nonstop0h 45mMultiple Airlines
Deal found 6/10$445
This Caribbean Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Caribbean Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/74:50 pmEIS - SXM
3 stops17h 55mCaribbean Airlines
Tue 7/86:45 pmSXM - EIS
3 stops16h 55mCaribbean Airlines
Deal found 6/10$629

Cheapflights Fare Finder

Customize your flight search to find flights from Road Town to Simpson Bay that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 12, 2025.
Use the filters below to find and compare flights from Road Town to Simpson Bay that are best for you.

Fly from

Road Town

Fly to

Simpson Bay

Route

Depart

Return

Price

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Fri 7/4

11:55 am-2:20 pm

1 stop2h 25m

Simpson Bay Princess Juliana

Mon 7/7

5:00 pm-6:35 pm

1 stop25h 35m

$368

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Fri 7/18

7:05 pm-7:50 pm

Nonstop0h 45m

Simpson Bay Princess Juliana

Sun 7/20

9:55 am-10:40 am

Nonstop0h 45m

$391

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Sat 7/5

9:50 am-10:30 am

Nonstop0h 40m

Simpson Bay Princess Juliana

Wed 7/9

10:20 am-11:05 am

Nonstop0h 45m

$445

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Mon 7/7

4:50 pm-10:45 am

3 stops17h 55m

Simpson Bay Princess Juliana

Tue 7/8

6:45 pm-11:40 am

3 stops16h 55m

$629

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Sun 7/20

7:15 am-9:05 am

1 stop1h 50m

$159

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Sun 7/20

11:35 am-1:30 pm

3 stops25h 55m

$302

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Best time to book a flight from Road Town to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Road Town with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest month to book a flight from Road Town to Simpson Bay?

Currently, September is the cheapest month in which you can book a flight from Road Town to Simpson Bay (average of $459). Flying from Road Town to Simpson Bay in March is currently the most expensive (average of $657). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from EIS to SXM?

Find hourly flight availability from Road Town to Simpson Bay. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 12, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 16% on flights from Road Town to Simpson Bay by exploring options for tickets in the afternoon.

Reviews of airlines servicing Simpson Bay

Get insights into the airlines that provide service to Simpson Bay. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Simpson Bay. Reviews last updated June 12, 2025.
Caribbean Airlines
8.2
Very good
157 reviews

Boarding

8.2

Comfort

7.9

Food

6.8

Overall

8.2

Entertainment

6.8

Crew

8.5

Reviews

1 / 9
6.0
Good

Anonymous,Mar 2025

JFK - GEO

Air hostesses were friendly. There should be more options for tea.
Caribbean Airlines
8.2
Very good
157 reviews
Caribbean Airlines
8.2
Very good
157 reviews

Boarding

8.2

Comfort

7.9

Food

6.8

Overall

8.2

Entertainment

6.8

Crew

8.5

Reviews

1 / 9
6.0
Good

Anonymous,Mar 2025

JFK - GEO

Air hostesses were friendly. There should be more options for tea.

Related info for your journey

Find useful and relevant information for your journey from Road Town to Simpson Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airports do I use to fly from Road Town to Simpson Bay?

    Simpson Bay Princess Juliana is the airport most travelers will use when flying to Simpson Bay from Road Town Beef Island. Booking flights from Beef Island (EIS) to Princess Juliana (SXM) should be relatively easy as there is 1 daily flight to Simpson Bay from 1 airline. 23h 55m is how long a flight from Road Town to Simpson Bay Princess Juliana will take if you book a nonstop flight.

  • How popular is this Road Town to Simpson Bay flight route?

    Within the past month, 1 users have taken a look at flights from Road Town Beef Island to Simpson Bay Princess Juliana.

  • What are the cheapest airlines flying from Road Town to Simpson Bay round-trip?

    Flying on Winair is currently your cheapest option to Simpson Bay, with prices starting at $368. Additional round-trip tickets that might be worth considering are offered by Hahn Air and Caribbean Airlines, with the lowest prices starting at $391 and $629, respectively. Winair is priced at 2% lower than the current average price of a flight leaving 3 months from now.

  • What are the most reliable airlines from Road Town to Simpson Bay?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Road Town to Simpson Bay on time: KLM (100%), Air France (100%), Winair (88%).

  • What are the cheapest flights from Road Town to Simpson Bay?

    Looking at all options, your cheapest flight can be booked for $162. While the most popular route (Road Town Beef Island - Simpson Bay Princess Juliana) can be booked for $8,265 on average our data indicates $164 when flying from Road Town to Simpson Bay.

  • Can I find deals for flights from Road Town to Simpson Bay that include hotel bookings?

    Yes. In addition to deals on Road Town to Simpson Bay flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Road Town to Simpson Bay?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Road Town to Simpson Bay.

  • Can I find deals for business class flights from Road Town to Simpson Bay?

    Yes. Cheapflights offers flight deals from Road Town to Simpson Bay by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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

    Currently, September is the cheapest month in which you can book a flight from Road Town to Simpson Bay (average of $459). Flying from Road Town to Simpson Bay in March is currently the most expensive (average of $657). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Complete your trip

Complete your trip to Simpson Bay by adding a car rental and/or hotel reservation to your travel itinerary.
Simpson Bay Princess Juliana Airport car rentals

Top airline flying from Road Town to Simpson Bay

Discover the top airline that operate flights from Road Town to Simpson Bay. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
WinairCheapest$332Average$377FlexibilityNo cancel feeOn-timeN/A

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