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Cheap flights from Road Town to Simpson Bay from $162

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 11/6. 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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Find the cheapest flights from Road Town to Simpson Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
Winair Logo
11:35 am - 9:20 amEIS-SXM
21h 45m1 stop
Winair Logo
4:15 pm - 6:40 pmSXM-EIS
2h 25m1 stop
$358Winair
Find Deal
Tue, Mar 3 - Sun, Mar 8
Winair Logo
7:10 pm - 7:55 pmEIS-SXM
0h 45mnonstop
Winair Logo
10:40 am - 11:25 amSXM-EIS
0h 45mnonstop
$359Winair
Find Deal
Thu, Mar 26 - Mon, Mar 30
Winair Logo
7:15 am - 9:05 amEIS-SXM
1h 50m1 stop
Winair Logo
10:20 am - 11:05 amSXM-EIS
0h 45mnonstop
$366Winair
Find Deal
Sun, Dec 14 - Wed, Dec 17
Winair Logo
8:10 am - 9:00 amEIS-SXM
0h 50mnonstop
Winair Logo
10:20 am - 11:05 amSXM-EIS
0h 45mnonstop
$386Winair
Find Deal
Fri, Dec 12 - Tue, Dec 16
Multiple Airlines Logo
4:50 pm - 9:25 amEIS-SXM
16h 35m2 stops
Multiple Airlines Logo
5:15 pm - 7:05 pmSXM-EIS
1h 50m1 stop
$464Multiple Airlines
Find Deal
Fri, Mar 27 - Mon, Mar 30
Multiple Airlines Logo
4:50 pm - 10:50 amEIS-SXM
18h 00m2 stops
Multiple Airlines Logo
5:00 pm - 6:40 pmSXM-EIS
25h 40m1 stop
$469Multiple Airlines
Find Deal
Thu, Mar 26 - Mon, Mar 30
Sunrise Airways Logo
1:05 pm - 3:25 pmEIS-SXM
2h 20m1 stop
Sunrise Airways Logo
10:45 am - 12:35 pmSXM-EIS
25h 50m2 stops
$571Sunrise Airways
Find Deal
Sat, Dec 20 - Sun, Jan 4
Sunrise Airways Logo
1:15 pm - 1:55 pmEIS-SXM
0h 40mnonstop
Sunrise Airways Logo
4:15 pm - 12:45 pmSXM-EIS
20h 30m3 stops
$601Sunrise Airways
Find Deal
Fri, Dec 19 - Sat, Jan 3
Caribbean Airlines Logo
4:50 pm - 9:25 amEIS-SXM
16h 35m2 stops
Caribbean Airlines Logo
11:35 am - 11:40 amSXM-EIS
24h 05m2 stops
$604Caribbean Airlines
Find Deal
Fri, Dec 19 - Fri, Jan 2
Hahn Air Logo
9:50 am - 10:30 amEIS-SXM
0h 40mnonstop
Hahn Air Logo
10:10 am - 10:50 amSXM-EIS
0h 40mnonstop
$613Hahn Air
Find Deal
Sat, Dec 20 - Fri, Jan 2

Winair flights from Road Town to Simpson Bay

Our best Winair deals on Road Town to Simpson Bay flight tickets
Winair
Mar 3
EIS11:35 amRoad Town Beef Island
21h 45m
1 stop
SXM9:20 amSimpson Bay Princess Juliana
Mar 8
SXM4:15 pmSimpson Bay Princess Juliana
2h 25m
1 stop
EIS6:40 pmRoad Town Beef Island
$358
Find similar
Winair
Mar 26
EIS7:10 pmRoad Town Beef Island
0h 45m
SXM7:55 pmSimpson Bay Princess Juliana
Mar 30
SXM10:40 amSimpson Bay Princess Juliana
0h 45m
EIS11:25 amRoad Town Beef Island
$359
Find similar
Winair
Dec 14
EIS7:15 amRoad Town Beef Island
1h 50m
1 stop
SXM9:05 amSimpson Bay Princess Juliana
Dec 17
SXM10:20 amSimpson Bay Princess Juliana
0h 45m
EIS11:05 amRoad Town Beef Island
$366
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
Dec 20
EIS1:05 pmRoad Town Beef Island
2h 20m
1 stop
SXM3:25 pmSimpson Bay Princess Juliana
Jan 4
SXM10:45 amSimpson Bay Princess Juliana
25h 50m
2 stops
EIS12:35 pmRoad Town Beef Island
$571
Find similar
Sunrise Airways
Dec 19
EIS1:15 pmRoad Town Beef Island
0h 40m
SXM1:55 pmSimpson Bay Princess Juliana
Jan 3
SXM4:15 pmSimpson Bay Princess Juliana
20h 30m
3 stops
EIS12:45 pmRoad Town Beef Island
$601
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 October 12, 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

Tue 3/3

11:35 am-9:20 am

1 stop21h 45m

Simpson Bay Princess Juliana

Sun 3/8

4:15 pm-6:40 pm

1 stop2h 25m

$358

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Thu 3/26

7:10 pm-7:55 pm

Nonstop0h 45m

Simpson Bay Princess Juliana

Mon 3/30

10:40 am-11:25 am

Nonstop0h 45m

$359

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Sun 12/14

7:15 am-9:05 am

1 stop1h 50m

Simpson Bay Princess Juliana

Wed 12/17

10:20 am-11:05 am

Nonstop0h 45m

$366

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Fri 12/12

8:10 am-9:00 am

Nonstop0h 50m

Simpson Bay Princess Juliana

Tue 12/16

10:20 am-11:05 am

Nonstop0h 45m

$386

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Fri 3/27

4:50 pm-9:25 am

2 stops16h 35m

Simpson Bay Princess Juliana

Mon 3/30

5:15 pm-7:05 pm

1 stop1h 50m

$464

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Thu 3/26

4:50 pm-10:50 am

2 stops18h 00m

Simpson Bay Princess Juliana

Mon 3/30

5:00 pm-6:40 pm

1 stop25h 40m

$469

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Sat 12/20

1:05 pm-3:25 pm

1 stop2h 20m

Simpson Bay Princess Juliana

Sun 1/4

10:45 am-12:35 pm

2 stops25h 50m

$571

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Fri 12/19

1:15 pm-1:55 pm

Nonstop0h 40m

Simpson Bay Princess Juliana

Sat 1/3

4:15 pm-12:45 pm

3 stops20h 30m

$601

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Fri 12/19

4:50 pm-9:25 am

2 stops16h 35m

Simpson Bay Princess Juliana

Fri 1/2

11:35 am-11:40 am

2 stops24h 05m

$604

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Sat 12/20

9:50 am-10:30 am

Nonstop0h 40m

Simpson Bay Princess Juliana

Fri 1/2

10:10 am-10:50 am

Nonstop0h 40m

$613

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 $360. 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 $361.

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 $369. 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 is only 1 cabin class 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.

Can stopping save me money on Road Town to Simpson Bay flights?

You could potentially save up to 1% on your flight if you consider stops on a Road Town to Simpson Bay flight.

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

Fastest flight time

0h 40m

Direct flights

Mon, Thu, Fri, Sat and Sun

Airports in Simpson Bay

1 airport
The fastest flight from Road Town to Simpson Bay takes 0h 40m
Direct flights go from Road Town to Simpson Bay on Monday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
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 $336Free 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 3 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 $336 (round-trip), much lower than the average airfare cost of $373 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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