Running the World on Points

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Travel-Hack Your Way to a Run in Bermuda

Julie Couch

Julie Couch

Travel-hacker and runner living a plant-based, NA lifestyle with her husband Darren.

Runners posing on the bridge at Bailey's Bay Bermuda as part of the Railway Trail

One of the most beautiful places to run in the world has to be Bermuda. I had the fortune of living in Bermuda for a few years pre-pandemic. It’s where I started to become a runner and where my runner-husband and I got married in 2021. Bermuda keeps us coming back with it’s sparkling turquoise water and pink(ish) beaches. And while it is beautiful, it is also one of the most expensive places in the world to live, so keeping travel costs down is a priority for us when we visit.

Bermuda Location and Climate

Most people think they know where Bermuda is, but most are surprised to find out that it is not in the Caribbean. It is about 1,000 miles due east of the North Carolina Coast in the Atlantic Ocean. Because of this, it does not have the super-hot tropical weather that you associate with the Caribbean. It has a sub-tropical climate that allows for some excellent running weather in the winter with highs in the low to mid 60’s. January is my favorite time of the year to run in Bermuda, February can be very rainy and cool – I always felt sorry for the tourists who arrived wearing sundresses and sun hats at that time of year! June is considered the best time of year to visit Bermuda with pleasant temperatures and seas warm-enough to go swimming. August can get very hot and that’s when the locals leave the island for cooler locations.

Where to Run in Bermuda

Bermuda is only 20 miles long and two miles wide, so you won’t be running any marathons there! The roads in Bermuda are paved-over old horse-trails which are narrow, curvy, and generally not safe for running. The speed limit is about 20 mph, but many motor bikes drive much faster and it is sometimes difficult to see around heavily foliaged corners.

Trail through palms
The Railway Trail

The Railway Trail

Fortunately for runners, Bermuda has an island-long trail system called The Railway Trail. This is where I did most of my runs. In the 1930’s and ’40s there was a train that went from one end of the island to the other. It no longer exists, but now it is a mostly pedestrian/cyclist trail that passes through beaches, cliffs, and villages. There are many places to enter and exit the trail, but finding them can be a challenge, so study this explanation of the different sections! The trail isn’t contiguous, so there are places you’ll have to merge onto a street for a bit until the next section starts. Some sections of the trail are paved, while others are sandy, grassy, or muddy. There are moderate elevation gains depending on which section you run and you’ll experience a mix of shade and sun.

My favorite section of the trail is from Bailey’s Bay. There is a small parking area near the Bailey’s Bay footbridge. From there, head over the bridge and keep following the trail. It will lead you through gorgeous beaches, cliffs, palms, and to the new pedestrian bridge that crosses over Flatt’s Inlet.

Couple standing in front of a sign that says "beautiful dead end"
When you are at Tobacco Bay Beach, be sure to run to the “Beautiful Dead End”!

St.George’s

St. George’s is a township on the East end of the island that is dotted with quaint colorful period homes and an historical town square. Running in the town is a bit tricky, but if you go early-enough to miss crowds, it can be lovely (if short!) To extend a run from St. George, I recommend getting some good hill-work in by running from the main street up to the Unfinished Church and onto Tobacco Bay Beach. This run will treat you to gorgeous vistas over Tobacco Bay. From there, head towards the St. Regis resort for a stop at St. Catherine’s Beach – arguably the prettiest beach on the island (and less touristy!)

Hamilton

Hamilton is the only city in Bermuda (and I use the term “city” lightly as the entire island only has about 60,000 people without tourists). It is where you will find most of the island’s dining, shopping, and businesses. If you want some hill-work, you’ll find it here! Just zig-zag from Front Street by the harbor up any street to Church street and back down. I love running in Hamilton because it has sidewalks and there is always something going on. This was my everyday easy-run location when I lived there.

Runners in a race in Bermuda.

Races in Bermuda

The Chubb Bermuda Triangle Challenge: This race series occurring over a long weekend in January has something for everyone: a mile, 10k, half-marathon, an d full marathon (two half-marathon loops). Sign up for one or go for the full triangle challenge with either the half or full marathon plus the mile and 10k.

The Bermuda Day Half-Marathon Derby: This is a really fun one because it takes place on Bermuda Day, a national holiday on the last Friday in May. You can run the half on your own or bring a team to run it as a relay. Because it is a holiday, the route is lined with spectators cheering you on the entire way! Expect signs, balloons, and all kinds of revelry! It is also an excellent time to visit the island. The weather is great, the seas are warm enough to swim, and you’ll get to experience all kinds of special Bermuda Day events and parties. Since it typically lines up nicely with the USA’s Memorial Day weekend, it can also mean you don’t have to miss much work!

The Hacks and Money-Saving Tips for Bermuda

Bermuda is expensive. There is no way around that. Even if you get there for free and get the cheapest accommodations, other expenses like dining out and groceries are likely to shock your budget. EVERYTHING has to be imported to the island, so you can expect to spend three times what you would spend in the U.S. That makes travel-hacking your way there even more important.

Wing of a plane flying over the island of BermudaFlights

The general rule for finding the cheapest or points-booked flights is to book either far in advance or look for last minute deals. I’m a planner and we usually have to work around fairly specific schedules, so we start looking for flights 11 months out (although some airlines don’t let you book that far ahead). Hacks for flights start with earning credit card points. If you are just getting started in travel-hacking, I recommend the Chase Sapphire Preferred. Airlines that fly into Bermuda include: American Airlines, British Airways, United, Jet Blue, Air Canada, and Delta. Chase Ultimate Rewards transfer to all of these airlines except American and Delta. For Delta, you can use Amex Membership Rewards points, and you can book AA through BA. With the 80,000 point bonus from the Chase Sapphire Preferred card, you could book an economy United Airlines flight from Chicago to Bermuda for as low as 19.3K miles one way. American has the best deals, though, with one-way flights regularly posted for 10K on the same route.

Accommodations

There is no good travel hack for accommodations in Bermuda. There is only one chain hotel – the Marriot St. Regis – and it starts at about 88,000 points per night. This is an absolutely gorgeous property right on St. Catherine’s Beach, so if you have the points, it might be worth a splurge! For the rest of us Bonvoy points-poor people, the best option is probably an Airbnb. When I book Airbnb’s, I usually try to stack points to get more value. If you have a Chase Ink Cash card that earns 5x points at office supply stores, you can purchase gift cards when they are on sale. Load those into your Airbnb account. Then when you book your Airbnb, go through a shopping portal (like Delta’s Skymiles Shopping). These portals will give you airline points for booking through their Airbnb link even if you are paying with a gift card. By doing it this way, you are at earning points on Delta for whatever you spend at Airbnbs. In Bermuda, Airbnbs start at about $80/night for the most basic accommodation.

Getting Around

Couple riding motor bikes in Bermuda

We found Lovers Lane while putting around on our bikes during our honeymoon!

There are no Ubers, Lyfts, or traditional rental cars in Bermuda and the taxi’s are very expensive. You can rent tiny electric vehicles, but the easiest way to get around in Bermuda is by motor bike. It gives you the freedom to really explore the island for about $120/day (yes, you could really spend more than this on a taxi per day!) For the most economical option, get a bus pass. The buses in Bermuda are clean, safe, easy to use, and mostly run on schedule. You’ll need to check the schedule for the bus stops that are closest to where you are staying, though. If you are a night owl, it may not work for you as buses stop serving some stops by 7 pm and have reduced weekend schedules. To get the most out of your spend on transportation, use a card that has good everyday points for spend and zero foreign transaction fees. I like our IHG Premier card which gets us 3X points on everyday purchases.

Food

Picnic dinner in a garden in Bermuda
Our grocery store bounty on the patio of our Airbnb

Food is three times the cost of what it costs in the U.S. If you’ve rented an Airbnb, skip the dining out and use your kitchen. To save money on groceries, skip the higher-end touristy grocery stores (like Miles Market) and go where the locals shop – The Market Place. They deliver so you can order your groceries before you even arrive on the island which will save you time and stress as well as help you budget. To get the most points out of what you spend on groceries, use a credit card with a 3x grocery category and no foreign transaction fees like the Chase Sapphire Preferred.

Bermuda is definitely worth a destination run, and with a little planning, you can visit this expensive paradise on a budget!

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