BOS - EIS

$320 Find Cheap Flights from Boston to Road Town - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$643
Typical prices: $827-$1,407
American Airlines
Thu 11/1Sun 11/4
BOS - EIS • 1 stop
Cheapest one-way
$320
Typical prices: $486-$710
Multiple Airlines
Sun 10/28
BOS - EIS • 2 stops
Nonstop flights
Not available
There are currently no direct flights between Boston and Road Town. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
February
Cheapest • 29% price drop
March
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Simpson Bay Princess Juliana (SXM)
Cheapest • Avg $1,025 (round-trip)
San Juan Luis Munoz Marin Intl (SJU)
Shortest trip • 7h 23m (one-way)
Insights
Insights
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Flight Deals

Cheap Flights from Boston to Road Town (BOS-EIS)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Boston to Road Town

Sun, Nov 1 - Wed, Nov 4
American Airlines Logo
4:56 pm - 6:20 pmBOS  Boston Logan Intl-EIS Road Town Beef Island
24h 24m1 stop Miami
American Airlines Logo
7:00 pm - 10:20 amEIS  Road Town Beef Island-BOS Boston Logan Intl
16h 20m1 stop Miami
$643American Airlines
Sun, Nov 1 - Wed, Nov 4
American Airlines Logo
4:56 pm - 6:20 pmBOS  Boston Logan Intl-EIS Road Town Beef Island
24h 24m1 stop Miami
American Airlines Logo
5:38 pm - 7:46 amEIS  Road Town Beef Island-BOS Boston Logan Intl
15h 08m2 stops Miami Washington, D.C. Reagan-National
$647American Airlines
Sun, Nov 1 - Wed, Nov 4
American Airlines Logo
4:56 pm - 6:20 pmBOS  Boston Logan Intl-EIS Road Town Beef Island
24h 24m1 stop Miami
American Airlines Logo
7:00 pm - 10:20 amEIS  Road Town Beef Island-BOS Boston Logan Intl
16h 20m1 stop Miami
$663American Airlines
Sun, Nov 1 - Wed, Nov 4
American Airlines Logo
4:56 pm - 6:20 pmBOS  Boston Logan Intl-EIS Road Town Beef Island
24h 24m1 stop Miami
American Airlines Logo
5:38 pm - 7:46 amEIS  Road Town Beef Island-BOS Boston Logan Intl
15h 08m2 stops Miami Washington, D.C. Reagan-National
$668American Airlines
Thu, Jan 28 - Thu, Feb 4
American Airlines Logo
5:00 am - 6:21 pmBOS  Boston Logan Intl-EIS Road Town Beef Island
12h 21m1 stop Miami
American Airlines Logo
4:55 pm - 12:59 amEIS  Road Town Beef Island-BOS Boston Logan Intl
9h 04m1 stop Miami
$708American Airlines
Thu, Jan 28 - Thu, Feb 4
American Airlines Logo
6:00 am - 6:21 pmBOS  Boston Logan Intl-EIS Road Town Beef Island
11h 21m2 stops New York LaGuardia Miami
American Airlines Logo
1:21 pm - 12:59 amEIS  Road Town Beef Island-BOS Boston Logan Intl
12h 38m1 stop Miami
$713American Airlines
Wed, Jan 27 - Wed, Feb 3
American Airlines Logo
6:00 am - 5:16 pmBOS  Boston Logan Intl-EIS Road Town Beef Island
10h 16m1 stop Miami
American Airlines Logo
1:21 pm - 8:33 pmEIS  Road Town Beef Island-BOS Boston Logan Intl
8h 12m1 stop Miami
$713American Airlines
Thu, Jan 28 - Thu, Feb 4
American Airlines Logo
6:00 am - 6:21 pmBOS  Boston Logan Intl-EIS Road Town Beef Island
11h 21m2 stops New York LaGuardia Miami
American Airlines Logo
1:21 pm - 10:49 pmEIS  Road Town Beef Island-BOS Boston Logan Intl
10h 28m2 stops Miami New York LaGuardia
$713American Airlines
Fri, Dec 11 - Sun, Dec 20
Multiple Airlines Logo
11:57 am - 10:55 amBOS  Boston Logan Intl-EIS Road Town Beef Island
21h 58m2 stops Orlando San Juan Luis Munoz Marin Intl
Multiple Airlines Logo
4:00 pm - 11:39 amEIS  Road Town Beef Island-BOS Boston Logan Intl
20h 39m1 stop San Juan Luis Munoz Marin Intl
$733Multiple Airlines
Mon, Dec 14 - Sat, Dec 19
Multiple Airlines Logo
11:57 am - 2:05 pmBOS  Boston Logan Intl-EIS Road Town Beef Island
25h 08m2 stops Orlando San Juan Luis Munoz Marin Intl
Multiple Airlines Logo
4:00 pm - 11:39 amEIS  Road Town Beef Island-BOS Boston Logan Intl
20h 39m1 stop San Juan Luis Munoz Marin Intl
$742Multiple Airlines
Booking Insights

Price, demand and travel trends for Boston to Road Town flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Boston to Road Town with more confidence.

How much is a round-trip flight from Boston to Road Town?

Round-trip flights from Boston to Road Town start at $643. Prices are below average for this route right now, with typical round-trip fares ranging from $827 to $1,407. The lowest price found in the past 5 days was $643 on American Airlines.

What's the cheapest day of the week to fly from Boston to Road Town?

Wednesday is the cheapest day of the week to fly from Boston to Road Town, it is 15% cheaper than the average day. Thursday is the most expensive day with flight prices 16% higher than average. Based on deals found by KAYAK users in the last 12 months.

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Key details for Boston to Road Town flights

Low season

September

Cheapest flight

$320
Most popular time to fly with an average 11% increase in price.
Flight from Boston to Road Town

When to book flights from Boston to Road Town

Are your dates flexible? Find out the best times to travel from Boston to Road Town based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Boston to Road Town flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Which airports can I use when flying from Boston to Road Town?

    Flights from Boston to Road Town usually depart from Boston Logan Intl (BOS) and arrive at Road Town Beef Island (EIS).

  • What cabin classes can I book on flights from Boston to Road Town?

    Two cabin classes are available on flights from Boston to Road Town:

    • Economy Class
    • First Class

  • Which airports do connecting flights from Boston to Road Town pass through?

    One-stop flights from Boston to Road Town most commonly connect through:

    • Miami (MIA) - 50% of one-stop connections
    • San Juan Luis Munoz Marin Intl (SJU) - 49% of one-stop connections
    • Simpson Bay Princess Juliana (SXM) - 1% of one-stop connections

    Miami (MIA) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Boston to Road Town?

    Yes. Being flexible with your travel dates can save you up to 27% on the Boston to Road Town route. Wednesday is the cheapest departure day at $898 round-trip on average, while Thursday is the most expensive at $1,220, a difference of $322. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How long is a flight from Boston to Road Town?

    A nonstop flight from Boston to Road Town takes 0h 00m, covering 1,695 miles.

  • Do I need a passport to fly from Boston to Road Town?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • Have flight prices from Boston to Road Town changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $643 to $4,037. That means the highest observed fare was about 6x higher than the lowest one.

  • How are flight prices from Boston to Road Town looking right now?

    One-way fares from Boston to Road Town are currently lower than usual. Average one-way flight prices are about $404, which is 34% below the typical average for this route.

  • How much time can I save by choosing a different layover airport from Boston to Road Town?

    Flying via San Juan Luis Munoz Marin Intl (SJU) gives the shortest average 1-stop total travel time at 7h 23m, compared with 8h 40m via Miami (MIA) and 18h 36m via Simpson Bay Princess Juliana (SXM).

  • What car rental options are available at Road Town Beef Island Airport (EIS)?

    Road Town Beef Island Airport (EIS) hosts 5 major car rental companies, with daily rates starting from around $24 for economy cars. Top options include:
    • Alamo
    • Hertz
    • Avis
    • Enterprise Rent-A-Car
    • National

  • How much should I expect to pay for a Boston to Road Town flight?

    Round-trip flights from Boston to Road Town range from $827 to $1,407, with an average of $1,046 over the past 12 months. Anything below $827 counts as a good deal.

Your guide to booking Boston to Road Town flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Wednesday departure instead of Thursday. On this route, Wednesday flights average $898 - about $322 less than Thursday (26% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Boston to Road Town trip for February. Fares historically average $741 round-trip in that month - typically $595 less than the most expensive month, which is April (based on the last 12 months).

More options for your flight from Boston to Road Town

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