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Cheap flights from Portland, Maine to Road Town from $376

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Portland, Maine to Road Town departing on 9/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Portland, Maine to Road Town

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
6:09 pm - 2:06 pmPWM  Portland-EIS Road Town Beef Island
19h 57m2 stops Chicago O'Hare Intl Miami
American Airlines Logo
2:32 pm - 1:05 pmEIS  Road Town Beef Island-PWM Portland
22h 33m2 stops Miami Chicago O'Hare Intl
$783American Airlines
Tue, Sep 1 - Thu, Sep 10
American Airlines Logo
5:30 am - 4:25 pmPWM  Portland-EIS Road Town Beef Island
10h 55m2 stops Philadelphia Miami
American Airlines Logo
2:46 pm - 1:05 pmEIS  Road Town Beef Island-PWM Portland
22h 19m2 stops Miami Chicago O'Hare Intl
$788American Airlines
Wed, Sep 2 - Tue, Sep 8
American Airlines Logo
6:02 am - 4:25 pmPWM  Portland-EIS Road Town Beef Island
10h 23m2 stops Washington, D.C. Reagan-National Miami
American Airlines Logo
2:46 pm - 9:21 amEIS  Road Town Beef Island-PWM Portland
18h 35m2 stops Miami New York LaGuardia
$858American Airlines
Mon, Aug 24 - Tue, Sep 1
United Airlines Logo
6:00 am - 3:38 pmPWM  Portland-EIS Road Town Beef Island
9h 38m2 stops Newark San Juan Luis Munoz Marin Intl
United Airlines Logo
9:20 am - 6:29 pmEIS  Road Town Beef Island-PWM Portland
33h 09m2 stops San Juan Luis Munoz Marin Intl Newark
$921United Airlines
Tue, Sep 1 - Sat, Sep 5
Multiple Airlines Logo
6:00 am - 7:15 pmPWM  Portland-EIS Road Town Beef Island
13h 15m3 stops New York John F Kennedy Intl Simpson Bay Princess Juliana Basseterre Robert Bradshaw Intl
Multiple Airlines Logo
4:06 pm - 1:45 pmEIS  Road Town Beef Island-PWM Portland
21h 39m2 stops San Juan Luis Munoz Marin Intl New York John F Kennedy Intl
$1,130Multiple Airlines
Mon, Aug 24 - Tue, Sep 1
American Airlines Logo
6:40 pm - 4:36 pmPWM  Portland-EIS Road Town Beef Island
20h 56m2 stops Philadelphia Miami
American Airlines Logo
5:58 pm - 12:11 pmEIS  Road Town Beef Island-PWM Portland
19h 13m2 stops Miami Philadelphia
$1,485American Airlines
Sat, Dec 19 - Sun, Dec 27

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American Airlines flights from Portland, Maine to Road Town

Our best American Airlines deals on Portland, Maine to Road Town flight tickets
American Airlines
Sep 1
PWM6:09 pmPortland
19h 57m
2 stops
EIS2:06 pmRoad Town Beef Island
Sep 10
EIS2:32 pmRoad Town Beef Island
22h 33m
2 stops
PWM1:05 pmPortland
$783
American Airlines
Sep 2
PWM5:30 amPortland
10h 55m
2 stops
EIS4:25 pmRoad Town Beef Island
Sep 8
EIS2:46 pmRoad Town Beef Island
22h 19m
2 stops
PWM1:05 pmPortland
$788
American Airlines
Aug 24
PWM6:02 amPortland
10h 23m
2 stops
EIS4:25 pmRoad Town Beef Island
Sep 1
EIS2:46 pmRoad Town Beef Island
18h 35m
2 stops
PWM9:21 amPortland
$858

momondo Fare Finder

 
Customize your flight search to find flights from Portland, Maine to Road Town 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 6, 2026.
Use the filters below to find and compare flights from Portland, Maine to Road Town that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandRoad Town

PWM Portland - EIS Road Town Beef Island

PWMEIS

Portland

Tue 9/1

6:09 pm-2:06 pm

2 stops19h 57m

Road Town Beef Island

Thu 9/10

2:32 pm-1:05 pm

2 stops22h 33m

$783

PortlandRoad Town

PWM Portland - EIS Road Town Beef Island

PWMEIS

Portland

Wed 9/2

5:30 am-4:25 pm

2 stops10h 55m

Road Town Beef Island

Tue 9/8

2:46 pm-1:05 pm

2 stops22h 19m

$788
Quickest round-trip

PortlandRoad Town

PWM Portland - EIS Road Town Beef Island

PWMEIS

Portland

Mon 8/24

6:02 am-4:25 pm

2 stops10h 23m

Road Town Beef Island

Tue 9/1

2:46 pm-9:21 am

2 stops18h 35m

$858

PortlandRoad Town

PWM Portland - EIS Road Town Beef Island

PWMEIS

Portland

Tue 9/1

6:00 am-3:38 pm

2 stops9h 38m

Road Town Beef Island

Sat 9/5

9:20 am-6:29 pm

2 stops33h 09m

$921

PortlandRoad Town

PWM Portland - EIS Road Town Beef Island

PWMEIS

Portland

Mon 8/24

6:00 am-7:15 pm

3 stops13h 15m

Road Town Beef Island

Tue 9/1

4:06 pm-1:45 pm

2 stops21h 39m

$1,130

PortlandRoad Town

PWM Portland - EIS Road Town Beef Island

PWMEIS

Portland

Sat 12/19

6:40 pm-4:36 pm

2 stops20h 56m

Road Town Beef Island

Sun 12/27

5:58 pm-12:11 pm

2 stops19h 13m

$1,485
Cheapest one-way

PortlandRoad Town

PWM Portland - EIS Road Town Beef Island

PWMEIS

Portland

Fri 9/18

6:00 am-10:55 am

3 stops52h 55m

$376
Quickest one-way

PortlandRoad Town

PWM Portland - EIS Road Town Beef Island

PWMEIS

Portland

Thu 9/17

6:00 am-9:25 am

2 stops27h 25m

$401

PortlandRoad Town

PWM Portland - EIS Road Town Beef Island

PWMEIS

Portland

Fri 9/18

9:48 am-6:10 pm

2 stops32h 22m

$402

PortlandRoad Town

PWM Portland - EIS Road Town Beef Island

PWMEIS

Portland

Thu 9/17

10:01 am-10:55 am

3 stops48h 54m

$436

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

When to book flights from Portland, Maine to Road Town

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

Cheap Portland, Maine to Road Town (PWM to EIS) flight deals and tips

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

Fastest flight time

9h 38m

Direct flights

None
The fastest flight from Portland, Maine to Road Town takes 9h 38m
There are no direct flights from Portland, Maine to Road Town. There are no popular flight routes from Portland, Maine to Road Town.
Search flight deals

Frequently asked questions about flying from Portland, Maine to Road Town

  • How far is Portland to Road Town Beef Island by plane?

    A flight from Portland to Road Town Beef Island will travel around 1772.8 mi. In terms of flight time, this usually takes a little over 9h 38m.

  • When did momondo last update prices for flights from Portland Airport to Road Town Beef Island Airport?

    Prices for flights from Portland Airport to Road Town Beef Island Airport are updated daily.

  • How old do you have to be to fly from Portland Airport to Road Town Beef Island Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Road Town Beef Island Airport.

  • What documentation or ID do you need to fly to Road Town Beef Island Airport?

    The required travel and health documents for your Road Town Beef Island Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Road Town Beef Island Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Frequently asked questions about flying from Portland, Maine to Road Town

  • How do I get Price Alerts for flights from Portland, Maine to Road Town?

    You can take advantage of momondo’s Price Alerts by first searching for your flights to Portland, Maine from Road Town. Flight offers will be shown to you in real-time. From there you can create a Price Alert by using our on-site widget.

  • How can I save money on flights from Portland, Maine to Road Town with momondo?

    With “Price Forecast”, learn how soon you should book your flight in advance. Down to the day of week and time of day, our information can inform you on the ideal time to book to save on your travel. Our “Price Calendar” shows you at a quick glance when to book your travel for lower rates. By setting “Price Alerts” you can monitor changes in price and target the ideal time to book. Search for your trip destination by budget amount via our “Explore” feature. Whether you’re looking for ideas for your next travel adventure or cost-cutting tips, our “Discover” content is a great place to start.

  • How does momondo find its flight prices?

    We compare prices from 700+ competitors to help you find the price that works best for you. momondo operates in over 30 international markets, bringing you access to a wide range of fares and deals. Search for your travel using momondo for a diverse range of options from airlines and OTAs.

Traveling to a place near Road Town?

Book flights to Road Town if you plan to visit one of these locations
Jost Van Dyke
Scrub Island

Why use momondo?

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

It is quick and easy to find Portland to Road Town flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Road Town that suits you.

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

momondo does allow users to show only those flights to Road Town from Portland which offer a flexible booking policy as well as other useful filters and features.

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

momondo helps you find the best flight between Portland and Road Town by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Yes. momondo can track prices for Portland to Road Town flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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