Bermuda – 5 Days Exploring Paradise


I was once standing in the dark depths of Downtown Crossing train station waiting for the Orange line, when I saw an ad to the effect of: “Get to Bermuda in less time than the Cape”. It indicated a flight from Boston to Bermuda was around 2 hours. My mind was blown at realizing how close it was. So when, it came time to plan a trip for my 30th birthday (June 2019), I thought I must go.

We had a spectacular time in Bermuda exploring the scenes, beaches and taking in the natural beauty.

The Basics

  • Getting to Bermuda from Boston: It was a super easy direct flight, under 2.5 hours.  Getting out of the Hamilton airport was a total breeze, it is small and wasn’t very crowded. You can kind of forget its another country, but you do need to bring a passport, go through Passport control etc. That whole process was quick.
  • Go For: Relaxation, Beautiful Beaches, Warm Weather
  • Length of Trip: 5 Days/Nights
  • Time of Visit: June 12 – 17. June was a good time to go because it wasn’t super crowded, it was hot but not insufferable. People warned us that it gets more crowded in the summer months when school is out.
  • Weather: 80s and sunny almost everyday, some rain towards the end

Activities/Things to Do in Bermuda:

There is so much to do and explore in Bermuda! Bermuda’s different sections are called “Parishes” . The first day we went to St. George Parish and did The Crystal Caves, Tobacco Bay, The Unfinished Church and Blue Hole Park. Other days we hung around the AirBnB pool/beach, went into Hamilton at night, or ventured around walking to explore different nearby beaches.

Crystal Caves

Tobacco Bay
Tobacco Bay, St. George Bermuda: We went to Tobacco Bay in St. George’s after visiting the Crystal Caves. There is a bar to get drinks at and a beach to swim at and explore. Cool place to hang out for awhile.

The Unfinished Church

Hamilton – Hamilton is the capital city of Bermuda, with a whopping population of about 1,000 people. There’s a good amount of restaurants and people traffic. There are some shops and what not, but we went after 6:00 PM a couple of times and none were open. If looking to bar hop, this is the spot.

Explore & Beach Hop

Bermuda has many spectacular beaches, and is known to have Pink Sand beaches. The pink sand was kind of an instagram vs. reality situation where in pictures/ads it looks fluorescent pink, when really it’s more of a hint pink. That didn’t take away from how beautiful and natural the beaches were. We had a great time exploring the island going to see different spots. Here are some areas we checked out.

Blue Hole Park

Other Spots: Elbow Beach, Jobson’s Cove

Food & Drinks:

Mad Hatters – Hamilton, Bermuda: This was our one big meal out. They have a bunch of silly hats to wear during dinner

Scallops and Shrimp at Mad Hatters in Hamilton

Pickled Onion – Hamilton, Bermuda. Went heavy apps here, quite delicious.

Apps at Pickled Onion

Happy Hour at Hamilton Princess – Big outdoor area with bars set up and a DJ and a lot of people.

The Swizzle Pub and Restaurant – Place near the airbnb we stayed at, good for drinks and apps. Ate here a few times.

Wahoo’s Bistro and Patio – St. George – Nice place to sit on the patio by the harbor, went here while in St. George after the Crystal Caves excursion.
Wahoo’s Bistro and Patio Menu St. George

Things to Try in Bermuda:

  • Wahoo – Local Fish – had some of this at Wahoo’s Bistro.
  • Rum Swizzle – Rum Drinks. Had a few of these at the nearby Swizzle Pub.


Where to stay in Bermuda: There were many different options in terms of areas to stay in Bermuda and the type of lodging. We ended up in an AirBnB in Warwick, named Marley Beach Cottages, which worked out great. There were many beautiful looking hotels, but the AirBnB was substantially cheaper.

The AirBnB location in Warwick where we Stayed

Link to the Place we Stayed

Pros: It had a pool and access to a private beach which was clutch. The hammock was completely electric – Josh spent hours there. The private beach access was clutch because some airbnbs did not seem within walking distance to a beach, and some of the beaches were owned by resorts.

Cons: Wasn’t near much in terms of places to eat. There was one restaurant within walking distance “The Twizzle Inn” and a grocery store semi-nearby.

Scenes from around the AirBnB

Things to Know about visiting Bermuda from the US :

  • Exchange Rate: American Dollars accepted everywhere
  • Expensive: Its a remote island, so food is expensive, and gas was super expensive. It was around $9 a gallon when we were there (June 2019).
  • Grocery Shopping: We typically are too lazy to grocery shop or are somewhere in a short period of time where it doesn’t make sense, but on this trip it made a lot of sense because 1. Food was very expensive and 2. we weren’t super close to anything, aside from one Pub.
  • It can be easy to forget that Bermuda is another country, but Bermuda is actually a British Territory. Population is 65,000 and is only about 20 square miles, so compare that to a single large suburb or small city in the US.
  • Safety: One thing that was great about Bermuda is you aren’t limited to a resort like in some island destinations. We could roam all over. We didn’t feel unsafe anywhere. Bermuda has kind of a regal vibe. It was very clean and there was not outward poverty, or people on the beaches selling things etc. Also didn’t see any homeless people anywhere.
  • Another cool thing about Bermuda is its not commercial at all. It feels very remote and authentic, and filled with natural beauty. There aren’t skyscrapers and MacDonalds littering the blocks.

Transportation and Getting Around Bermuda

In Bermuda they drive on the opposite side of the road from the US, and the steering wheel is on the opposite side as well. The roads were narrow and winding. Many people rent mo-peds, however it seemed dangerous to my cautious self. I’m sure it would have been fun. Many people told me before I went to be ware of the Mo-Peds, I heard many stories of people hurting themselves on them.

There are no ubers/lyfts there. Cabs were not reliable. They had an app called Hitch, but only sometimes would the cab drivers pick us up. When we called the dispatch line, two times they said people were on the way in 10 minutes and no one ever showed up. Cabs were also pretty expensive, it was around $50 one way to get from Warwick to St. George (13 miles).

Another option is the bus, which I heard was a decent way to get around. There was a bus stop nearby the house, but I couldn’t quite figure out the bus schedule so we never really tested it out.

If I had to do it again I’d consider renting a “Twizy”, which is a little mini car that kind of looks like a golf cart. I don’t like driving to begin with so nevermind with the added obstacles of the roads and the opposite driving, I was all set. Cabs weren’t the most efficient way to go so twizzles could be a fun option instead.

Next Time/Things We Didn’t Get To:

Would I return to Bermuda? Absolutely. I felt like we covered a lot of ground, but some things we didn’t get to:

  • Ride in a Twizy
  • Naval Yard
  • Bike Path
  • Fairmount SouthHampton


5 Days in Bermuda Cost Summary: Bermuda is not exactly a cheap place to go. Had we stayed in a hotel it would have been a good amount more expensive. Cabs were also not cheap getting around, but it would have been a wash if we rented a car or mo-ped. It was definitely worth it though, and we would definitely return to Bermuda!

Length of Stay: 5 Days & Nights

  • Food & Drink:
    • Grocery Store: ~$200
    • Dining Out Food & Drink: $800
  • Cab: ~$200
  • Activities: ~$48 for Caves, everything else free
  • AirBnB: $1569.11 (Around $250 a Night + Fees) 
  • Flights: $829.38 (Boston to Hamilton Direct, about $415 a piece)
  • Total: ~$3500 for 2 People for 5 Days/Nights,
    • $1750 per person
    • $700 a Night Per Couple

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