Lost Yet Found: A Unique 3 Day Itinerary

WHERE TO STAY

Accommodation in Bermuda ranges from intimate guest houses in traditional Bermuda homes to luxury resorts and everything in between! Select the accommodation that suits your style of vacation. 
 
If you would like a hotel resort, Grotto Bay is a great option with a pool, private beach, tennis courts, its own underground swimming cave, a spa (which is also in a cave), an inflatable waterpark and a watersports and dive shop. It is located on the eastern end of the island and is Bermuda’s only all-inclusive resort.
 
Pompano Beach Club is located on the Western side of the island and has, arguably, the best ocean views that look out over a turquoise sandbar. The hotel has a pool, private beach, spa, tennis/pickleball courts, watersports centre and is located right next to the PGA Grand Slam golf course Port Royal. 

Day 1

DRIFT

Start your vacation with a splash by choosing between a stand-up paddleboard or kayak tour with BDA Watersports. You will explore the exquisite Elys Harbour, dotted with small islands, mangroves, beautiful rock formations and little bays. In this sheltered area of flat calm water, you will spot turtle heads popping up for a breath of air. Your tour will also take you under Somerset Bridge, the world’s smallest drawbridge. 
 
Stop by The Bridge Trading Post after your tour for a coffee and fresh Bermuda Banana Bread. This cake shop is owned by Alaina Trott who was born and raised in Somerset, and who bakes all the sweet treats daily. The building located right next to the bridge was once the Somerset post office and the old mailboxes can still be seen on the patio. Interestingly, Alaina’s dad worked at this post office for over 20 years before it closed. 

From here you will find the opening to the Railway Trail, a walking and cycling path that, until 1948, was a functioning train track. This section of the trail is far from the road and provides a nice tranquil walk with shade from the overhanging trees. Start walking west along the trail for about 15-20 minutes until you get to Scaur Hill Fort and Park. 

Once you reach Fort Scaur climb the stairs to the Fort on the Hill. Here you will have a beautiful vista of Hamilton Harbour on one side and the western side of Elys Harbour on the other side. The Fort sits on 22 acres of land, with paths and picnic areas. 
 
To finish of your first day in Bermuda, continue west to Cambridge Beaches, a resort with pastel pink cottages and a beach restaurant called Breezes. Enjoy sunset cocktails and dinner with your toes in the sand.

Day 2

MEANDER

The south shore beaches between Warwick Long Bay and Horseshoe Bay are connected by walking trails. Walk at your own pace walking through the trails taking a peak at some inviting small coves as you go. 
 
Horseshoe Bay has been voted one of the top 10 beaches in the world by many top magazines, but due to its popularity, it can become crowded with visitors, so we are going to skip this one in order to truly get Lost Yet Found. For a more local beach feel, head to John Smith’s Bay in Smith’s parish.

If you are interested in learning to surf in Bermuda’s crystal-clear waters, book a private surf lesson in advance. The waves in Bermuda break a little differently to many other popular surf destinations, but for beginners, it is a good place to get acquainted to the mechanics of surfing. 
 
After a morning swim, it's time to freshen up and visit the Masterworks Museum of Bermuda Art. Located in the Botanical Gardens this gallery is a vibrant energy centre that celebrates Bermuda’s culture and intrinsic beauty. The art exhibitions are rotated regularly throughout the year, but it is always enjoyable to look at Bermuda through the lens of the artist.

Following the gardens, make your way to The Tasting Room for a pre-dinner wine tasting. You can either arrive unannounced to try some of the premium wines available on tap, or you can book a private tasting session, which can include wines, rum, whiskey and more!
 
After your wine-tasting experience, you will walk about 30 steps across the parking lot to 10 South, a bistro focusing on local, in-season ingredients. Sit on the outside patio with the ambiance of the fire pit burning close to you.

Day 3

GLIDE

Today you will start with a boat charter with Castaway Charters. As you set sail across Castle Harbour, sticking close to the shoreline you will come across Tuckers Town, where some of Bermuda’s most rich and famous residents live. After admiring the multimillion-dollar homes continue to Castle Roads, a shallow area of water between a string of private islands where you can anchor up and go for a snorkel and a swim. 

After a wonderful morning on the boat, continue to head east and make a stop at the Crystal Caves, Bermuda’s most spectacular natural wonder. Formed over millions of years these caves feature icicle-like stalactites that hang down over the stunning crystal-clear waters. A tour guide will take you through and explain exactly how the caves were found, and even more interestingly, how they were discovered. 
 

Finally, you will make your way to the historic town of St George, the UNESCO World Heritage site. This is the place where the settlers made their home in 1612. The history of St George’s is fascinating and can be felt in the ambiance and seen in the architecture around the town. Wander the narrow alleyways and find points of interest like the Unfinished Church, The State House, the House of George Tucker, and the oldest Anglican church in the Western Hemisphere, St Peter’s Church. It is a tradition by both locals and visitors to get a picture of these steps. 
 
After exploring St George’s either by foot or by electric bicycle, you can head to Tobacco Bay to finish up the day. Here you will find a beach bar that has a real island vibe. Grab a drink (may we suggest a rum swizzle) and let the sun set on your short but sweet Bermuda adventure.