What is the cheapest day to fly from Portland, Maine to Road Town?

Travelers seeking maximum savings on their Portland, Maine to Road Town flight should consider departing on Tuesday mornings when fares are most often at their lowest. Tuesday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

In terms of precipitation, rainfall in Road Town ranges from 1.9 - 5.8 inches per month. October is typically the wettest month, when rainfall can reach 5.8 in. February is typically the driest time to visit Road Town when rainfall is around 1.9 in.

If weather is an important factor for your trip to Road Town, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of February, when temperatures are typically at their lowest (around 75.2 F).

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

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Portland, Maine to Road Town as you normally would.

Can I find deals for flights from Portland to Road Town that include hotel bookings?

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

How can I find direct flights from Portland to Road Town?

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

Can I find deals for business class flights from Portland to Road Town?

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

$916+ Flights from Portland, ME to Road Town

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Cheap flight deals from Portland to Road Town

Round-trip from	$916 (United Airlines)

From Portland to Road Town Beef Island

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Find flight deals from Portland to Road Town

Cheapest flights from Portland to Road Town
Explore the most affordable flight options available from Portland to Road Town. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 30, 2025.

Tue 8/196:00 amPWM - EIS

2 stops12h 55mUnited Airlines

Wed 8/207:55 amEIS - PWM

2 stops15h 08mUnited Airlines

Deal found 7/28

$916

Best flights from Portland to Road Town
Discover carefully curated flight deals from Portland to Road Town that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 30, 2025.

Tue 8/196:00 amPWM - EIS

2 stops12h 55mUnited Airlines

Wed 8/207:55 amEIS - PWM

2 stops15h 08mUnited Airlines

Deal found 7/28

$916

Last-minute flights from Portland to Road Town
Discover last-minute flight deals from Portland to Road Town. Data last updated July 30, 2025 and is based on user searches.

Tue 8/196:00 amPWM - EIS

2 stops12h 55mUnited Airlines

Wed 8/207:55 amEIS - PWM

2 stops15h 08mUnited Airlines

Deal found 7/28

$916

Fly from

Fly to

Route

Depart

Return

Price

PortlandRoad Town

PWM - EIS

PWMEIS

Portland

Tue 8/19

6:00 am-6:55 pm

2 stops12h 55m

Road Town Beef Island

Wed 8/20

7:55 am-11:03 pm

2 stops15h 08m

$916

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Best time to book a flight from Portland to Road Town

Have a flexible travel schedule? Discover the best time to fly to Road Town from Portland 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 Portland to Road Town

What is the cheapest month to book a flight from Portland, Maine to Road Town?

Currently, August is the cheapest month in which you can book a flight from Portland, Maine to Road Town (average of $702). Flying from Portland, Maine to Road Town in April is currently the most expensive (average of $958). 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.

Reviews of airlines servicing Road Town

Read through reviews of airlines operating flights from Portland to Road Town, such as United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

United Airlines

7.4

Good

8,896 reviews

Reviews

1 / 20

4.0

Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

United Airlines

7.4

Good

8,896 reviews

United Airlines

7.4

Good

8,896 reviews

Reviews

1 / 20

4.0

Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

Related info for your journey

Can I find deals for flights from Portland to Road Town that include hotel bookings?
Yes. In addition to deals on Portland to Road Town flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Portland to Road Town?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Road Town.
Can I find deals for business class flights from Portland to Road Town?
Yes. Cheapflights offers flight deals from Portland to Road Town 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 Portland, Maine to Road Town?
Currently, August is the cheapest month in which you can book a flight from Portland, Maine to Road Town (average of $702). Flying from Portland, Maine to Road Town in April is currently the most expensive (average of $958). 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.

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$916+ Cheap flights from Portland, ME (PWM) to Road Town (EIS)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/19. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Portland to Road Town with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Portland to Road Town

Round-trip from

Find flight deals from Portland to Road Town

Cheapest flights from Portland to Road TownExplore the most affordable flight options available from Portland to Road Town. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 30, 2025.

Explore the most affordable flight options available from Portland to Road Town. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 30, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Portland to Road Town that are best for you.

Best time to book a flight from Portland to Road Town

Have a flexible travel schedule? Discover the best time to fly to Road Town from Portland with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Portland to Road Town

What is the cheapest month to book a flight from Portland, Maine to Road Town?

Reviews of airlines servicing Road Town

Read through reviews of airlines operating flights from Portland to Road Town, such as United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

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

Can I find deals for flights from Portland to Road Town that include hotel bookings?

How can I find direct flights from Portland to Road Town?

Can I find deals for business class flights from Portland to Road Town?

What is the cheapest month to book a flight from Portland, Maine to Road Town?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Portland to Road Town

See prices for flight routes from nearby airports that may be better suited for you.

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Book with Flexibility

Travel Smart

Cheapest flights from Portland to Road Town
Explore the most affordable flight options available from Portland to Road Town. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 30, 2025.