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Adventuring With Friends

4 Day Bermuda Itinerary

Bermuda, a British territory in the middle of the Atlantic Ocean, has been a haven for wealthy travelers for centuries. As the world becomes more globalized and available to the general public, its popularity has only grown. Known for its colorful homes and crystal clear waters, Bermuda is so much more than what meets the eye. An archipelago made of seven main islands, about 24 miles long, and 650 miles from the closest mainland, this nation has been resourceful, innovative, and independent in many ways. Known as the shipwreck capital of the world, its mystery and lore is another key draw for tourists. Whatever it was that brought you to Bermuda, you’ll be glad you came!

Logistics: Transportation and Where to Stay

Travel to, from, and in between can be one of the more daunting tasks for a visit to Bermuda. At the time of this post, they require travelers to complete a travel authorization application up to a month in advance. You can find that form HERE. While many come by cruise ship, those arriving by plane will have to fly on just one of the four American, two Canadian, or singular British carriers that service the island. Once you land, you’ll need to get around the island via taxi or bus, as there is no Uber or Lyft. Taxis are readily available at the airport. 

Grotto Bay

Your home base

Stay at Grotto Bay Beach Club and Resort. Grotto Bay is a mere 5 minutes from the airport and puts you in a great location to get to the different parts of the island. Though you can expect to pay over $500 per room per night during peak season, and an additional $120 per day for each adult all inclusive plan, it is less than many other resorts on the island, provides exceptional service, and it’s inclusive plan more than covers itself (given the high price of food and drinks on the island).

Getting Around

A bonus to staying at Grotto Bay is their complimentary bus passes. Buses in Bermuda cost between $3.50 – $5.00 per ride depending on the zone, which can add up (though day passes are available). While Bermuda has its own currency, they accept United States Dollars at a 1:1 exchange. Buses do require exact change. You can find the schedule HERE, but be warned that while visiting Bermuda, you will have to live on their island time. It’s not uncommon to see cars or buses stop in the street to just say hello to a friend passing by. Take the schedule with a grain of salt, and be patient if you have to wait a bit longer than expected, that’s part of the island experience. If you are looking for something a little more on your own schedule, check out Whip, Bermuda’s e-scooter ride share that costs just $3 to unlock and $0.50 a minute. Make sure to wear the provided helmet, stay off sidewalks, and park in the designated Whip zones.

Day 1: St. George’s and Tobacco Bay

Experience Downtown

Start your trip off with a bang by visiting the surreal town of St. George’s, this author’s favorite part of the island. Colorful cottages and crystal clear currents make up this charming town. A UNESCO World Heritage site, it blends nature with human history harmoniously and makes for the perfect first taste of this island nation.

Of course, every good day or trip starts with coffee. Walk through the Candyland colored lane of Water St until you come to an alley with a tent sign for Temptations. Temptations’ Baby Bean truck is stationed right on the water. They offer a variety of espresso and tea based beverages as well homemade pastries. Try their coconut latte to commence the island vibes while getting your daily jolt. 

Continuing down Water Street will lead you right to King’s Square. You won’t need long to explore here, but the highlights are an old school telephone booth and the Town Hall from 1782. The Town Hall is open to the public and is home to placards that describe the early comings and goings of the island. One of the most interesting displays dictates how the island was settled in 1609, by accident, when the ship Sea Venture, headed for Jamestown, was steered off course due to a storm.

Religious History

St. Peter's
St. Peter's

Just around the corner from King’s Square is St. Peter’s Cathedral. What started as a thatch church in 1612 is now a beautiful cedar masterpiece with impressive stone steps leading to its door. If you explore the interior, a $2 donation is recommended. Take a moment to pay respects as you walk through the churchyard. You’ll notice a stone wall and plaque that explains that beyond the wall are graves of both enslaved and free black Bermudians. While they were members of the parish, this separate graveyard exemplifies the segregation and haunting history of slavery that has scarred and shaped the island. 

Next, walking up Government Hill Rd, you can’t miss the Unfinished Church, a continuation of the parish. In the second half of the 1800’s, the town decided they wanted a new church that would replace St. Peter’s Cathedral. This was when the construction of the Unfinished Church began. Simultaneously, the church in Hamilton (the island’s capital city) was burned down, and money that was headed to St. George’s was redirected to Hamilton. This led the progress on the Unfinished Church to slow and eventually stop altogether. Today, it stands as a picturesque ruin that is great for photos, weddings, and events. Stop and take a look on your way to…

Stepping into Nature and the Past

Tobacco Bay, one of the best known bays on the island, is just a 10 minute walk continuing on Government Hill Rd before veering right onto Barry Rd. Like many other parts of the island, you will be greeted by the crystal clear, turquoise waters. These, of course, make for perfect snorkel and paddle boarding conditions that enable you to see the plethora of fish below the surface in relatively safe and shallow waters. Keep your eyes peeled for the large and colorful parrot fish as well as schools of smaller varieties. While you are welcome to bring your own gear, there is a facility on site to rent from as well as buy food and drinks. Experienced swimmers can also climb the limestone rock formations that encircle the bay and jump into the waters below. This national park is more than just beautiful, it’s historical too. Though it’s about 600 miles off of the United States mainland, it had a key role in the American Revolution, being the location where U.S. sympathizing Bermudians helped steal British gunpowder in what is now known as the Gunpowder Plot of 1775. 

Tobacco Bay isn’t the only place of military significance on St. George’s island. While there are many forts throughout Bermuda and specifically on St. George’s, Fort St. Catherine has arguably the best view. Once used to protect the island’s eastern shores, it now acts as a museum. You can visit between 10 am – 4 pm daily for only $7 per adult and $3 per child.

Day 2: Crystal Caves and Swizzle Inn

Cascade into the Caves

As you may be a little tired from the exertion of snorkeling the day prior, spend your second day staying close to the resort. Less than 10 minutes walk from Grotto Bay is The Crystal Caves of Bermuda. This popular attraction is actually the site of two caves; Crystal Cave, and Fantasy Cave. While millions of years old, Crystal Cave wasn’t discovered until 1907 when two boys chasing their cricket ball lowered themselves into the hole and discovered this wonder. The family who owned the property began giving tours, and now millions have marveled at the 55 feet deep clear and tranquil water as well as the plethora of different limestone formations. As the caves only connect via dangerous underwater tunnels, there are two separate tours. It is $24 ($10 for kids) to see an individual cave or $35 ($12 for kids) for both. Both show impressive formations and are enjoyable, but if pressed for time or money, choose to tour Crystal Cave, as you get to walk along paths right over the water.

Grab a Rum Swizzle from Swizzle Inn

Directly across the street from the path that first led you to the caves is The Swizzle Inn. The Swizzle Inn is a comfortable and unique pub that resembles a typical English sports bar, that is, with a few distinct features. The main one being the graffitied walls tacked with business cards and dollar bills, covered with the names of past guests. Even without a game on the television, The Swizzle Inn provides plenty of entertainment as you peruse the names and comments of those who visited before you. Of course, the atmosphere isn’t the only reason why you are here. Not only is The Swizzle Inn the oldest pub on the island, it is considered to be “the home of the rum swizzle,” Bermuda’s national drink. While the regular version is already great, the frozen version is simply devine. If traveling with kids, you can get them their own treat across the street at Bailey’s Bay Ice Cream Parlour.

Enjoy Grotto Bay’s Amenities

In addition to its prime location, the biggest draw to staying at Grotto Bay Beach Resort is its on site amenities. Their all inclusive package includes breakfast, lunch, an afternoon tea with pastries, and dinner as well as unlimited drinks from two separate bars, one in the main lodge and one down by the pool. Just steps away from the pool bar is the beach where chairs both in and out of the water make for the perfect spot to savor a piñacolada. If you are feeling up for the task, there are paddle boards, kayaks, and pool noodles to allow you to further enjoy the tranquil waters. Seasonally, they have a larger, floating raft with a climbing wall and swing which is enjoyed by all ages. The ocean and the pool aren’t the only spots to swim on the property. From 9am to 5pm daily, guests can take a dive in Cathedral Cave, a refreshing and remarkable feature just between the rooms and the pool facilities. If you are looking for something a little more relaxing, for an additional charge guests can book spa treatments in the adjacent Nature Spa inside Prospero’s Cave. You’ll be rejuvenated enough for a game of corn hole or shuffleboard, right outside the door.

Day 3: Royal Navy Dockyard and Hamilton

Discover Dockyards

Located at the northernmost tip of Bermuda’s Ireland Island is the Royal Navy Dockyard and ferry terminal. You’ll need about one hour to get here by public bus, switching buses in Hamilton or opting for the ferry. Being that the Dockyard is right where the cruise ships let off, this can seem like the most touristy part of the island, but there are many reasons to include this on your itinerary. First and foremost, the stonework of the buildings makes this area feel distinctly different from other parts of the island. A walk through the Victualling Yard, where the British Royal Navy used to store its food and drink, is particularly calming.

Sometimes, things are popular for good reason. Bermuda Fudge Co. is one of those things. With unique flavors, fair prices, and friendly customer service, this needs to be on your list. Try one of their bestsellers; Buccaneer, a chocolate and rum delite, or Pirate, a vanilla and rum fantasy. Don’t worry, if you are having a tough time deciding, they provide samples. At $10 a box, this makes the perfect treat to bring back home. If you are looking for additional momentos, look no further than Clocktower Mall. You’ll find plenty of authentic Bermuda souvenir shops in this once Royal Navy warehouse.

Delve into History and Mystery

On the small slope overlooking the dockyards, you’ll find the National Museum of Bermuda, along with a spectacular view. Whilst it can be easy to get distracted by the endless rum swizzles and turquoise waters, it is imperative that you take some time to engage with the rich history of the island, gaining perspective on the cultures and peoples that have called this island home for the past four hundred years. Within the island’s largest fort, the National Museum of Bermuda houses the largest collection of historical artifacts and actively works to restore and maintain areas of historical significance. Educate yourself on the 200 years slavery on the island, learn about Portugese immigrants, or admire the artisty of Bermudian bank notes over the years. 

If you would rather spend your day perusing a museum a little outside of the ordinary, jump on a bus and head to Hamilton’s Bermuda Triangle Museum. Located at Bermuda Underwater Exploration Institute’s Ocean Discovery Centre, the Bermuda Triangle Museum takes visitors through thirteen theories as to why so many ships and planes have disappeared in the famed and feared Bermuda Triangle. The theories range from the practical, methane gas and rogue waves, to the otherworldly, the lost city of Atlantis and aliens. The combination of devoted research and fun, interactive exhibits makes it worth spending a couple hours here. You’ll also get to appreciate an early scuba suit, videos on history of diving as well as shipwrecks, a collection of enchanting shells, and a captivating treasure room that will excite anyone’s inner pirate.

Hang out in Hamilton

Hamilton, the capital city of Bermuda, is an energetic hub for culture. Though Hamilton has a population of less than 1,000 people, it does not skimp on providing plenty to do. While there are galleries to view, high end shops to fantasize over, and even an aquarium to explore, one of the best things to do in this city is to simply walk around the streets and admire all the colorful buildings with stark white roofs you’ll soon miss after you return home. Not only do these make for great photos, but they are practical too, as the island uses the roofs to clean and collect rain water that they need to simply exist surrounded by so much ocean.

While on your walk, make sure to swing into a grocery store. With limited land available to farm, Bermuda has to predominately import its provisions and goods (80% of all food is imported). In turn, this results in extraordinarily high prices that make you appreciate the all inclusive dining at Grotto Bay Resort. 

As you are exploring, make sure to pass the Cathedral of the Most Holy Trinity. Yes, this is the church that brought you the Unfinished Church, as it used the funds that had been allotted for St. George. If you find yourself there between 8am and 5pm, you are able to enter free of charge and view the ornate stained glass and majestic organ. For just $3, you can climb the cathedral tower for panoramic views of the island.

Day 4: Horseshoe Bay and Gibb’s Hill Lighthouse

Bays and Beaches

Butts Beach
Horseshoe Bay
Horseshoe Bay
Jobson's Cove
Jobson's Cove

Enjoying the beauty of Horseshoe Bay requires your ability to share. As this is the most well-known beach on the island, it is a hot spot for those venturing on shore from the cruise ships. While you have probably heard of Bermuda’s famous pink sand beaches, you may be a bit disappointed to learn that the majority of photos you have seen are over-saturated. Looking closely at the sand, you’ll see pink pieces that give it a slight, rosy hue, but what it lacks in pigment, it makes up for in texture. These may be the softest sands you ever step onto. Chairs and umbrellas are available for rent and there are changing/shower facilities as well as a bar. To avoid crowds, set up camp on the far end of the beach. Just past the rocks, you will find Butts Beach and Middle Beach which will likely be far less congested. For another island highlight that doesn’t get quite so much tourist attention, head a bit further up the road to Jobson’s Cove. If you have snorkel gear, this is a great place to bust it out.

Enjoy the Island’s Best View

Just a few bus stops past Horseshoe Bay is Gibb’s Hill Lighthouse. With all destinations, you can inform the bus driver when boarding which stop you are looking to get off at, and they will help get you there. A short walk up Lighthouse Rd, and you’re there. For just $2.50 per person, you can climb the 185 steps to the top of this 117 foot tall, cast iron lighthouse. While those with a fear of heights may squirm, you’ll be rewarded with the best view on the island from the 360 degree outdoor balcony. On the way up or down, stop to read the interesting exhibits of the lighthouse’s history.

Additional Recreation

If you need to soak up just a bit more of the outdoors, golf fans can book a tee time at Port Royal Golf Course. Likely the most beautiful course you could ever ask for right on the ocean, this 18-hole, PGA course runs about $150. Due to the heat, tee times after 2pm drop significantly. If you’re looking for some free recreation instead, spend your time walking along the Railtrail. Split up into nine sections, this 18 mile trail, now a designated national park, was once the path of the Bermuda Railway, which while popular, only ran from 1931 – 1948 because of its costly upkeep. Now (though you will at times have to cross motorways), it allows you to meander through the flora and fauna of the island, a perfect way to end a trip before heading back for final all-inclusive daiquiris at Grotto Bay. 

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