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Expat Exchange - Best Places to See While on a Look-See Trip to Bermuda (Plus, Itineraries) 2024
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Horseshoe Bay in Bermuda

Best Places to See While on a Look-See Trip to Bermuda (Plus, Itineraries)

By Joshua Wood, LPC

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Summary: Considering a move to Bermuda but uncertain about where to settle? Venturing on an exploratory trip to visit multiple popular expat destinations can be incredibly enlightening. Here's a list of recommended places to consider during your exploration of Bermuda.

Taking a Look-See trip to Bermuda is an essential step for anyone considering relocating to this idyllic island. Such a trip allows potential expats, retirees, and digital nomads to get a firsthand experience of the Bermudian lifestyle, culture, and communities. It's an opportunity to explore residential areas, understand the cost of living, and assess the amenities and services available. This reconnaissance can help in making an informed decision about which part of Bermuda aligns best with personal preferences and needs.

Recommended Itineraries

For a comprehensive Look-See trip to Bermuda, it's important to visit a variety of cities, towns, and regions to get a well-rounded view of what the island has to offer. For a 10-day trip, consider starting in the capital city of Hamilton, then moving on to St. George's, Warwick Parish, and Southampton. If you have 20 days, you can extend your visit to include Paget Parish, Pembroke Parish, and the Dockyard area in Sandys Parish. This extended itinerary allows for a deeper exploration of each area and a better understanding of the different lifestyles across the island.


Hamilton, the capital city of Bermuda, is a bustling hub of activity and the commercial heart of the island. With a population of just over 1,000, it's a small city by international standards but offers a cosmopolitan lifestyle with numerous dining, shopping, and entertainment options. Expats and digital nomads are drawn to Hamilton for its vibrant atmosphere, employment opportunities, and the convenience of city living. The cost of living here is relatively high, but the amenities and proximity to various businesses make it a popular choice for those looking to integrate quickly into Bermudian society.

Travel Tip: While in Hamilton, be sure to visit the iconic Front Street, which overlooks the harbor. A favorite spot for dining and relaxation is the Barracuda Grill, known for its fresh seafood and inventive cocktails.

St. George's

St. George's, a UNESCO World Heritage site, is steeped in history and charm. This northeastern town offers a quieter pace of life compared to Hamilton, with well-preserved colonial architecture and quaint cobblestone streets. It's a favorite among expats who appreciate culture and history. The cost of living is slightly lower here, and the community is tight-knit, offering a sense of belonging. St. George's also provides beautiful beaches and scenic views, making it an attractive location for those seeking a balance between work and leisure.

Travel Tip: Don't miss the chance to dine at Wahoo's Bistro and Patio, where you can enjoy local specialties like the Bermuda fish chowder with an oceanfront view.

Warwick Parish

Warwick Parish is known for its stunning beaches, such as Warwick Long Bay and Jobson's Cove. It's a residential area that offers a more laid-back lifestyle, suitable for families and individuals looking for a peaceful environment. The cost of living here is moderate, and the community is welcoming to newcomers. Expats and digital nomads often choose Warwick for its natural beauty and outdoor activities, including golfing, water sports, and horseback riding.

Travel Tip: For a unique dining experience, visit The Swizzle Inn, famous for its rum swizzle cocktail and lively atmosphere.


Southampton is known for its luxurious resorts, golf courses, and some of the island's most beautiful beaches, including Horseshoe Bay Beach. It's an ideal location for those who enjoy a resort-like atmosphere and outdoor activities. The cost of living can be high due to the upscale nature of the area, but the quality of life is exceptional. Expats and retirees favor Southampton for its stunning ocean views and relaxed pace of life.

Travel Tip: The Waterlot Inn offers a fine dining experience with a rich history dating back to the 17th century. It's a perfect place to enjoy a sophisticated meal in a classic Bermudian setting.

Paget Parish

Paget Parish is centrally located and offers a blend of residential comfort and convenience. With attractions like the Bermuda Botanical Gardens and Elbow Beach, Paget is popular among those who want to be close to nature while still having easy access to Hamilton. The cost of living is on par with much of Bermuda, offering a range of housing options. The parish is particularly appealing to expats and digital nomads who seek a balance between work and relaxation.

Travel Tip: Coco Reef Resort is not only a great place to stay but also offers one of the best beachfront dining experiences at Café Coco, where you can savor local flavors with a stunning view.

Pembroke Parish

Pembroke Parish, adjacent to Hamilton, is a convenient location for those who want to be near the capital but prefer a more residential setting. It's home to the Spanish Point Park and Admiralty House Park, offering beautiful landscapes and outdoor activities. The cost of living is slightly lower than in Hamilton, and the area is well-suited for expats and digital nomads looking for a blend of urban and suburban life.

Travel Tip: Ascots Restaurant is a hidden gem offering an exquisite menu in a charming and intimate setting, perfect for a relaxing evening after exploring the parish.

Sandys Parish (Dockyard Area)

The Dockyard area in Sandys Parish is a cultural and historical center, once a British Royal Navy stronghold. Today, it's a bustling tourist spot with shops, museums, and art galleries. The region offers a more relaxed lifestyle with a strong sense of community. It's a bit more remote compared to other parts of Bermuda, which can be appealing for those looking for a quieter place to live. The cost of living here is moderate, and the area is well-liked by expats who enjoy maritime history and culture.

Travel Tip: The Frog and Onion Pub, located in the heart of the Royal Naval Dockyard, is a favorite among locals and visitors for its traditional pub fare and locally brewed beers.

About the Author

Joshua Wood Joshua Wood, LPC joined Expat Exchange in 2000 and serves as one of its Co-Presidents. He is also one of the Founders of Digital Nomad Exchange. Prior to Expat Exchange, Joshua worked for NBC Cable (MSNBC and CNBC Primetime). Joshua has a BA from Syracuse and a Master's in Clinical and Counseling Psychology from Fairleigh Dickinson University. Mr. Wood is also a licensed counselor and psychotherapist.

Some of Joshua's articles include Pros and Cons of Living in Portugal, 10 Best Places to Live in Ireland and Pros and Cons of Living in Uruguay. Connect with Joshua on LinkedIn.

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Horseshoe Bay in Bermuda

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SJB Global is a top-rated financial advisory firm specializing in expat financial advice worldwide, offering retirement planning & tax-efficient solutions with a regressive fee model.
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SJB Global is a top-rated financial advisory firm specializing in expat financial advice worldwide, offering retirement planning & tax-efficient solutions with a regressive fee model.
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