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Cheap flights from Road Town to Simpson Bay from $156

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Road Town to Simpson Bay departing on 11/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Road Town to Simpson Bay (EIS-SXM)

Cheap round-trip flights

Logo
7:35 pm - 8:25 pmEIS-SXM
0h 50mnonstop
Logo
10:15 am - 10:55 amSXM-EIS
0h 40mnonstop
$343
Find Deal
Mon, Aug 18 - Thu, Aug 21
Logo
12:20 pm - 2:45 pmEIS-SXM
2h 25m1 stop
Logo
10:15 am - 10:55 amSXM-EIS
0h 40mnonstop
$357
Find Deal
Mon, Aug 18 - Thu, Aug 21
Winair Logo
7:05 pm - 7:50 pmEIS-SXM
0h 45mnonstop
Winair Logo
10:20 am - 11:05 amSXM-EIS
0h 45mnonstop
$360Winair
Find Deal
Thu, Oct 9 - Sun, Oct 12
Winair Logo
11:55 am - 2:20 pmEIS-SXM
2h 25m1 stop
Winair Logo
10:40 am - 11:25 amSXM-EIS
0h 45mnonstop
$370Winair
Find Deal
Mon, Sep 1 - Mon, Sep 8
Winair Logo
12:20 pm - 2:45 pmEIS-SXM
2h 25m1 stop
Winair Logo
4:15 pm - 6:35 pmSXM-EIS
2h 20m1 stop
$373Winair
Find Deal
Mon, Aug 18 - Thu, Aug 21
Logo
1:15 pm - 1:55 pmEIS-SXM
0h 40mnonstop
Logo
10:20 am - 11:05 amSXM-EIS
0h 45mnonstop
$387
Find Deal
Fri, Sep 26 - Sun, Sep 28
Logo
7:05 pm - 7:50 pmEIS-SXM
0h 45mnonstop
Logo
10:45 am - 12:35 pmSXM-EIS
25h 50m2 stops
$407
Find Deal
Thu, Oct 9 - Sun, Oct 12
Sunrise Airways Logo
1:15 pm - 1:55 pmEIS-SXM
0h 40mnonstop
Sunrise Airways Logo
10:45 am - 12:35 pmSXM-EIS
25h 50m2 stops
$424Sunrise Airways
Find Deal
Fri, Sep 26 - Sun, Sep 28
Winair Logo
11:55 am - 8:35 pmEIS-SXM
8h 40m2 stops
Winair Logo
5:00 pm - 6:35 pmSXM-EIS
25h 35m1 stop
$501Winair
Find Deal
Mon, Sep 1 - Mon, Sep 8
Sunrise Airways Logo
1:05 pm - 3:15 pmEIS-SXM
26h 10m2 stops
Sunrise Airways Logo
3:30 pm - 1:25 pmSXM-EIS
21h 55m3 stops
$502Sunrise Airways
Find Deal
Mon, Aug 18 - Thu, Aug 21

Winair flights from Road Town to Simpson Bay

Our best Winair deals on Road Town to Simpson Bay flight tickets
Winair
Oct 9
EIS7:05 pmRoad Town Beef Island
0h 45m
SXM7:50 pmSimpson Bay Princess Juliana
Oct 12
SXM10:20 amSimpson Bay Princess Juliana
0h 45m
EIS11:05 amRoad Town Beef Island
$360
Find similar
Winair
Sep 1
EIS11:55 amRoad Town Beef Island
2h 25m
1 stop
SXM2:20 pmSimpson Bay Princess Juliana
Sep 8
SXM10:40 amSimpson Bay Princess Juliana
0h 45m
EIS11:25 amRoad Town Beef Island
$370
Find similar
Winair
Aug 18
EIS12:20 pmRoad Town Beef Island
2h 25m
1 stop
SXM2:45 pmSimpson Bay Princess Juliana
Aug 21
SXM4:15 pmSimpson Bay Princess Juliana
2h 20m
1 stop
EIS6:35 pmRoad Town Beef Island
$373
Find similar

Sunrise Airways flights from Road Town to Simpson Bay

Our best Sunrise Airways deals on Road Town to Simpson Bay flight tickets
Sunrise Airways
Sep 26
EIS1:15 pmRoad Town Beef Island
0h 40m
SXM1:55 pmSimpson Bay Princess Juliana
Sep 28
SXM10:45 amSimpson Bay Princess Juliana
25h 50m
2 stops
EIS12:35 pmRoad Town Beef Island
$424
Find similar
Sunrise Airways
Aug 18
EIS1:05 pmRoad Town Beef Island
26h 10m
2 stops
SXM3:15 pmSimpson Bay Princess Juliana
Aug 21
SXM3:30 pmSimpson Bay Princess Juliana
21h 55m
3 stops
EIS1:25 pmRoad Town Beef Island
$502
Find similar

momondo 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, momondo users made 832,500 searches. Data last updated August 5, 2025.
Use the filters below to find and compare flights from Road Town to Simpson Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Mon 8/18

7:35 pm-8:25 pm

Nonstop0h 50m

Simpson Bay Princess Juliana

Thu 8/21

10:15 am-10:55 am

Nonstop0h 40m

$343

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Mon 8/18

12:20 pm-2:45 pm

1 stop2h 25m

Simpson Bay Princess Juliana

Thu 8/21

10:15 am-10:55 am

Nonstop0h 40m

$357

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Thu 10/9

7:05 pm-7:50 pm

Nonstop0h 45m

Simpson Bay Princess Juliana

Sun 10/12

10:20 am-11:05 am

Nonstop0h 45m

$360

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Mon 9/1

11:55 am-2:20 pm

1 stop2h 25m

Simpson Bay Princess Juliana

Mon 9/8

10:40 am-11:25 am

Nonstop0h 45m

$370

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Mon 8/18

12:20 pm-2:45 pm

1 stop2h 25m

Simpson Bay Princess Juliana

Thu 8/21

4:15 pm-6:35 pm

1 stop2h 20m

$373

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Fri 9/26

1:15 pm-1:55 pm

Nonstop0h 40m

Simpson Bay Princess Juliana

Sun 9/28

10:20 am-11:05 am

Nonstop0h 45m

$387

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Thu 10/9

7:05 pm-7:50 pm

Nonstop0h 45m

Simpson Bay Princess Juliana

Sun 10/12

10:45 am-12:35 pm

2 stops25h 50m

$407

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Fri 9/26

1:15 pm-1:55 pm

Nonstop0h 40m

Simpson Bay Princess Juliana

Sun 9/28

10:45 am-12:35 pm

2 stops25h 50m

$424

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Mon 9/1

11:55 am-8:35 pm

2 stops8h 40m

Simpson Bay Princess Juliana

Mon 9/8

5:00 pm-6:35 pm

1 stop25h 35m

$501

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Mon 8/18

1:05 pm-3:15 pm

2 stops26h 10m

Simpson Bay Princess Juliana

Thu 8/21

3:30 pm-1:25 pm

3 stops21h 55m

$502

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 resultsSorted by cheapest first
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See travel insights to Simpson Bay from

How to get the cheapest flight ticket from Road Town to Simpson Bay

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Simpson Bay?

In general, September is the cheapest month to fly from Road Town to Simpson Bay. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $362. If you aren’t able to travel to Simpson Bay during the month of September, then flying in July is also cheap. Prices for this month can be found on momondo for an average of $366.

What is the cheapest day to depart on your flight to Simpson Bay?

Our data shows that Thursday is the least expensive day to fly to Simpson Bay. Tickets to fly out on this day can be as low as $374. Flights from Road Town to Simpson Bay on a Monday will generally be more expensive and average around $399. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Simpson Bay?

According to our data, the cheapest time of day to fly to Simpson Bay is in the afternoon. momondo users have found flights departing from Road Town to Simpson Bay in the afternoon for as low as $373. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Simpson Bay is at noon when prices are around $440.

What is the cheapest Road Town Beef Island to Simpson Bay Princess Juliana flight route?

Fly from Road Town Beef Island to Simpson Bay Princess Juliana for the best Road Town Beef Island - Simpson Bay Princess Juliana flight prices

What cabin class options are available on Road Town Beef Island to Simpson Bay Princess Juliana flights?

There are 1 cabin classes available to choose from on Road Town Beef Island to Simpson Bay Princess Juliana flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Road Town to Simpson Bay flight prices changed over time?

When to book flights from Road Town to Simpson Bay

Are you open to changing your travel dates? Check out the ideal times to fly from Road Town to Simpson Bay according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Road Town to Simpson Bay (EIS to SXM) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Road Town to Simpson Bay

Best Price Found

$156

Fastest flight time

0h 40m

Direct flights

Tue, Fri, Sat and Sun

Airports in Simpson Bay

1 airport
The best one-way flight to Simpson Bay from Road Town in the past 72 hours is $156. The best round-trip flight deal from Road Town to Simpson Bay found on momondo in the last 72 hours is $343.
The fastest flight from Road Town to Simpson Bay takes 0h 40m
Direct flights go from Road Town to Simpson Bay on Tuesday, Friday, Saturday and Sunday. The only airline offering direct flights is Winair.
There is 1 airport near Simpson Bay: Simpson Bay Princess Juliana (SXM)
Search flight deals

  • How far is Road Town Beef Island to Simpson Bay Princess Juliana by plane?

    There are 102.2 mi between Road Town Beef Island and Simpson Bay Princess Juliana. A reasonable flight in good conditions will take 0h 40m.

  • When did momondo last update prices for flights from Road Town Beef Island Airport to Simpson Bay Princess Juliana Airport?

    Prices for flights from Road Town Beef Island Airport to Simpson Bay Princess Juliana Airport refresh daily.

  • How many operators does momondo search for flights from Road Town Beef Island Airport to Simpson Bay Princess Juliana Airport?

  • How old do you have to be to fly from Road Town Beef Island Airport to Simpson Bay Princess Juliana Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Road Town Beef Island Airport to Simpson Bay Princess Juliana Airport.

  • What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?

    The travel and health documents you'll need for your trip to Simpson Bay Princess Juliana Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Simpson Bay Princess Juliana Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Road Town to Simpson Bay?

  • What is the most popular airline from Road Town to Simpson Bay?

Best airlines flying from Road Town to Simpson Bay

Compare and see reviews for airlines that fly from Road Town to Simpson Bay with momondo
Airline
Rating
Free Cancellation
Price
WinairPriceFrom $333Free CancellationRating
10.0
2 reviews
Search Winair flights

  • Winair Flights From Road Town to Simpson Bay

    Winair flies from Road Town to Simpson Bay around 10 times per week, with 2 momondo users rating the airline 10.0/10. The cheapest Winair deal from Road Town to Simpson Bay in the last 72 hours was $333 (round-trip), much lower than the average airfare cost of $374 for Winair flights on this route.

Traveling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Philipsburg

Why use momondo?

Why should I use momondo to find a flight deal from Road Town to Simpson Bay?

Finding the right flight to Simpson Bay from Road Town is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Simpson Bay quick and easy, saving you time and money.

Can I find flights from Road Town to Simpson Bay with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Simpson Bay from Road Town with this policy.

How can momondo help me find flights from Road Town to Simpson Bay?

Once you have performed a search for Road Town to Simpson Bay flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Road Town to Simpson Bay right now. Can momondo alert me if prices change?

Price alerts on flights to Simpson Bay from Road Town are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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