The Ultimate Five-Day Friends Trip: From A-Town to the Rock

If you’re scouting for a destination for your next island getaway with your best pals that blends the perfect combination of luxury, culture, good eats, and an overall good time, look no further. From luxury catamaran charters and indulgent brunches to historic sights and natural wonders, Bermuda is the ideal vacation location for your group’s next vacation. 

  • Beyond the Beach,
  • Friend Getaways,
  • On the Beach

Atlanta-based influencers Kara Chin, Coya Houston, Ariel Hakim, and Kourtney Ashley embarked on a fun-filled trip to Bermuda in the fall to take in everything the island has to offer. They’ve shared their itinerary so you and your friends can live your best life, too.

Day 1

Take Off to Bermuda

The group met at the Hartsfield-Jackson Atlanta International Airport in the morning to embark on their island getaway. They booked a direct flight from Atlanta to Bermuda with Delta Air Lines. In just under three hours, they arrived to the island for their getaway.

Once they landed, it was time for the group to head to their oceanside oasis at the St. Regis Bermuda for their five-day retreat. If you’re looking for an airport transfer, you can reserve your spots with Bermuda Transit Services or ball out from arrival with Adventure Transport’s limousine or on a private bus with Island Express Mini Bus. 

Get a Taste of the Island

After a 13-minute drive, they checked into their home-away-from-home in Bermuda’s East End at the St. Regis. Located in the historic town of St. George’s, the luxury resort sits on the historical ground of Gates’ Bay (also known as Fort St. Catherine’s Beach). It provides guests blissful amenities such as two swimming pools equipped with luxuriant loungers and private cabanas, fresh local dining, an 18-hole golf course, and a full-service spa. 

The group got acquainted with the St. Regis and then freshened up for their first dinner at the resort’s BLT Steak NY Restaurant. This elegant venue serves fresh and local ingredients with a Latin twist, paired with stunning views of the surrounding azure waters. 

After an intimate dinner and a Dark 'n Stormy® (the official cocktail of Bermuda) or two, it was time to bid farewell to their first day on the island. 

A group of women are sitting on a bed reading and drinking cocktails.

Day 2

Bask in Your Balcony Views

After a good night's sleep and to kick off their first full day on the island, the group had a little solo time and enjoyed a tasty breakfast on their private balconies before embarking on their day of adventure in Bermuda. Each accommodation at the St. Regis features a private balcony, allowing guests to take in the expansive ocean views and salty air directly from their guestroom. 

Take a Walk Through History in The Old Towne of St. George’s 

After their gourmet breakfast, the group hopped in a taxi for their first excursion to the Town of St. George, a UNESCO World Heritage Site, for a Long Story Short historical tour hosted by local Bermudian Kristin White. 

During this history tour, Kristin focuses on the stories of people of African descent and their impact on Bermuda. She is passionate about telling the whole story of Bermuda’s illustrious past — the one you won’t traditionally find in textbooks. Notable sights through the tour include the Bermuda Old State House from 1620, the Old Rectory from 1699 and St. Peter’s Church, Their Majesties Chappell, one of the oldest churches in the Western Hemisphere.

A group of friends are walking down stairs outside of an old church.

Delight in a Cliffside Lunch at The Loren

Following their insightful walk through the historic St. George’s, the group was ready for lunch at The Loren’s Pink Beach Club. The scenic restaurant is perched on a cliff’s edge above Bermuda’s southern shore. It boasts panoramic views of the Atlantic Ocean, setting the scene for the perfect photo op for you and your friends. 

Relax at the Beach & Enjoy a Sunset Dinner at Blû Bar and Grill

Kara, Coya, Ariel, and Kourtney ventured back to the St. Regis to spend the afternoon on Fort St. Catherine’s Beach and in the resort’s two pools with a swizzle in hand. Before they knew it, it was time to get ready for their dinner at Blû Bar and Grill

Once they were ready for dinner, they celebrated a flawless day in paradise at Bermuda’s premier bar and grill restaurant. Located in the scenic beauty of the Belmont Hills Golf Course, Blû Bar and Grill offers spectacular views overlooking the Great Sound and Hamilton Harbour.

Day 3

Explore Bermuda’s Crystal Caves 

The following day, the group grabbed breakfast on their own at the resort. Then, they wandered around the scenic property to take in the views and capture content around the beautiful St. Regis. Soon after, they ventured to one of Bermuda’s most famous natural wonders — the Crystal Caves

Formed in the Ice Age, the Crystal Caves is the island’s largest and most dramatic cave system. It is home to an underground grotto, an electric-blue subterranean lake, and intricate rock formations. The group wandered through the soaring stalagmites and icicles of white limestone dripping from the ceiling as they took in the scenery and revelled in one of Bermuda’s most extraordinary natural wonders. 

Embark on a Catamaran Tour

It’s not a trip to Bermuda without a boat cruise on the island’s vibrant waters. The group hopped aboard the 77-foot Zara private catamaran charter, one of Bermuda’s largest sailing yachts, to take in the views of Bermuda’s picturesque coastline while they sipped on champagne and raised their glasses from the top deck of the luxury sailing yacht. 

An aerial view of the great sound with a large catamaran in the middle.

Dine at Bermuda’s Longest Dinner Table 

After their unforgettable catamaran cruise, the group returned to the hotel to get dressed up for the Formal Party on Front Street in the City of Hamilton. This is a unique culinary event included in this year’s three-day Taste of Bermuda food festival — the biggest food-centric event on the island. For the first-ever Formal Party — where white attire is required — the iconic Front Street shut down in style to assemble Bermuda’s longest dinner table for a three-course plated meal with local entertainment, including live art displays, glass blowing showcases, ballet performances, and much more. 

Kara, Coya, Ariel, and Kourtney feasted on the perfectly-curated menu, sipped on cocktails from specialty bars lining Front Street, and closed the evening out dancing to music provided by DJ Rusty G.

Day 4

Devour a Champagne Brunch at 1609 Bar & Restaurant 

Is it really a fun-filled friends’ getaway without an indulgent, boozy brunch? They started their fourth day in Bermuda at 1609 Bar & Restaurant overlooking Hamilton Harbour at the Hamilton Princess & Beach Club. They enjoyed a Bermudian brunch that offered unlimited food and drinks while the latest tunes were spun by a live DJ.

Feast on a Festival of Flavours on Front Street

Next stop: Bermuda’s Tasting Village! The ladies wandered down Front Street to sample tasty bites from some of the island’s most beloved institutions as the festival of flavours continued during the finale event of the Taste of Bermuda. This lively street festival featured a range of entertainment and culinary delights served by the island’s most talented chefs and bartenders. There’s no doubt about it, everyone’s taste buds were satisfied.

Cheers to the Ultimate Trip 

After a day full of delicious eats, they returned to the St. Regis and enjoyed a nightcap at the St. Regis Bar, the social centre of the luxury resort. The group reminisced about their incredible getaway while they sipped on hand-crafted cocktails and watched the sun go down over the Atlantic. 

Day 5

Find Your Zen on the Beach

Before heading off to the airport and back to Atlanta, the group took some time to reflect on their Bermudaful experience with a morning yoga session on Fort St. Catherine’s Beach in front of the St. Regis. Book this private experience by reaching out to Akilah Beckles directly at [email protected] to bask in the morning sunshine and fresh ocean air to have a moment of mindfulness.

A group of women are doing yoga on the beach.

Book Your Getaway with Your Pals 

Does this jam-packed, fun-filled itinerary sound good to you and your friends? Start planning your getaway to Bermuda and live it up just like Kara, Coya, Ariel, and Kourtney did. 



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