10 Insider Tips for the Best Luxury Vacation in Bermuda

If you’re planning to visit the island of Bermuda for the first time, perhaps for a destination wedding, a babymoon or a romantic getaway over a long weekend, you’ve got questions. When is the best time to visit? Where’s the best place to stay? What are the must-do activities and the best secret places for a wonderful meal? We’ve done the work, and we’ve got answers. Here’s our report from an insider with tips on the best first luxury vacation trip to Bermuda, including when to go, where to stay, top restaurants and essential activities (plus the real story on which ones to skip).

our insider itinerary series

Insider Itinerary is an occasional series here at Dandelion Chandelier that shines a light on the best places to see, stay, and dine in some of the hottest travel destinations worldwide. Our far-flung correspondents are sharing their inside tips on how to best experience their chosen cities, especially if you’re visiting for the first time. Consider it your local luxury GPS. You’re welcome!

We began this series with Cape Town. Since then, we’ve shared insider itineraries for Ljubljana, Reykjavik, Copenhagen, Oslo, Porto, Nantucket and East Hampton, among others. Next up? Our friend and colleague Kevin Dallas shares the inside scoop on Bermuda, his childhood and current home. Full disclosure: our Founder & CEO is on the board of NT Butterfield & Son, a consumer bank and trust company headquartered in Bermuda.

insider itinerary for the best first luxury vacation trip to Bermuda

1. Why Bermuda? Why should we go?

Most people don’t realise that Bermuda is less than two hours from NYC (and only two to three hours from most other East Coast gateways).  That makes Bermuda one of the closest and easiest places to get far away from your daily grind.  Our mid-Atlantic location means Bermuda is counter-seasonal to the Caribbean. Summer is the high season, but the weather is temperate year-round. And late Spring is an ideal time to visit before the crowds and humidity arrive.  

2. How long is the ideal first visit?

Bermuda is an ideal long-weekend trip, and the average visitor stays four or five days. The islands’ proximity, small size (only twenty one square miles) and instant familiarity make it possible to cover a lot of ground in just a few days without much friction or lost transit time. Visitors who stay longer don’t need to worry about running out of things to do, though – there’s plenty to keep them entertained.    

3. What hotel(s) do you recommend? Or should we rent an apartment/house/villa?

Bermuda doesn’t really have big resort hotels – I like to say that Bermuda is the resort.  The major properties are all very different, and the same visitor might make very different choices depending on the purpose of their trip.

For a long weekend with friends, I always recommend the Fairmont-managed Hamilton Princess Hotel. One of Bermuda’s bigger hotels, the Princess has an urban location on the outskirts of the City of Hamilton (population 854!), making it a convenient walk to local shops and restaurants. It has fantastic views of the harbor, and their restaurant is excellent.  

For a romantic getaway, I’d suggest either the trendy and cool boutique hotel the Loren at Pink Beach (which would not be out of place in the Hamptons).

Or the recently revitalized Cambridge Beaches, which offers a more shabby-chic “barefoot luxury” vibe. Cambridge is a traditional “cottage colony” hotel. Meaning the rooms and suites are distributed across the thirty-acre property in freestanding low-rise buildings. Several of the cottages also feature private plunge pools, which is a worthwhile upgrade.  

4. What are the 5 most important “must see” sights – natural wonders, museums and the like?

Top Must-See Areas in Bermuda: St. George’s.

The historic Town of St. George’s, on Bermuda’s east end, is a UNESCO World Heritage Site. Permanently settled in 1612, St. George’s is the oldest surviving British settlement in the Americas and a treasure trove of history.  As a living town, it’s easy for visitors to miss the richness hidden just below the surface. Which is why I’d recommend booking a tour with town resident, shop owner, and story-teller Kristin White of Long Story Short.  

An important series of stops on any tour of St. George’s would be some of the notable elements of the African Diaspora Heritage Trail (ADHT). It was created in 2001 as part of the UNESCO Slave Route Project. Many of the sites along the ADHT are not always open to the public , so it’s best to take an organised tour or hire a guide. Kristin White of Long Story Short covers many of the east end sites in her St George’s tours, including:

Barber’s Alley.

This is the site where Joseph Hayne Rainey operated a barbershop from the kitchen of Tucker House during the US Civil War. After returning to Charleston, he became the first African-American elected to the US House of Representatives in 1870.

Pilot Darrell’s house.

Darrell was the first black landowner in Bermuda. After steering the HMS Resolution expertly through Bermuda’s reefs in 1795, he was granted his freedom. Editor’s note: when we visited, an adorable black cat seemed to be proudly showing us the way to the historic home.

The Segregated Graveyard. 

St. Peter’s is the oldest Anglican church in the new world. In a poignant walk through the adjacent cemeteries, you can see where the church continued to bury Black people in the “Burial Ground for Slaves and Free Blacks” until 1854. Twenty years after Emancipation.

The contrast in the size of the headstones and the space between them in the Black section of the cemetery versus the White one tells its own story.

Top Must-See Areas in Bermuda: Tom Moore’s Jungle.

Blue Hole Park & Walsingham Nature Preserve are two adjacent green spaces that are more colloquially known to locals as “Tom Moore’s Jungle.” Moore was an Irish poet who was posted to Bermuda by the British Admiralty in 1804, but who spent most of his time writing poetry under a large Calabash tree. 

The area showcases Bermuda’s rich bio and geo diversity, including a number of caves to explore and a spectacular swimming hole surrounded by mangroves.

Top Must-See Areas in Bermuda: Masterworks Museum of Bermuda Art.

The Masterworks Museum of Bermuda Art, located in the Botanical Gardens (which are not especially botanical) is home to 1,500 works of Bermudian and Bermuda-inspired art, including work by Georgia O’Keeffe and Winslow Homer. 

Housed in a former arrowroot factory, the museum features a revolving series of exhibitions, including works for sale by local artists.

Top Must-See Areas in Bermuda: Warwick Long Bay.

Warwick Long Bay, part of Bermuda’s South Shore National Park, is far less famous than neighbouring Horseshoe Bay Beach. But it’s no less beautiful – and delightfully devoid of crowds.  A warren of walking / riding trails in the scrub land behind the beach connects you to a series of smaller beaches and coves to the west (in fact, you can walk all the way to Horseshoe).  On a good day, you can claim your own private beach and feel like you have Bermuda all to yourself.  

Top Must-See Areas in Bermuda: Royal Naval Dockyard.

The National Museum of Bermuda occupies several buildings at the Royal Naval Dockyard on Bermuda’s very western end.  The buildings themselves, with their distinctive architecture, ramparts and fortifications are worth a visit, but the contents of the museum are no less interesting.  The museum tells the story of five hundred years of Bermudian history through both fixed and revolving exhibits.   Since the Dockyard is also home to Bermuda’s primary cruise ship terminal, it’s worth consulting the schedule and planning your visit for a day when no ships are in port to avoid the crowds.    

5. Is there good shopping? If so, where?

In and around Hamilton you will find a number of well curated boutiques and home-grown brands with unique and distinctive offerings.   For the former, the newly opened Shops at the Princess and Atelerie on Reid Street both stock up and coming global brands chosen by expert buyers with an eye for luxury.   

There’s nothing more uniquely Bermudian than Bermuda shorts, which are actually not what you might think; these are colourful dress shorts for men, worn just above the knee, that are considered appropriate business attire out here. 

Originally worn by the British army to stay cool in Bermuda’s humid summer, they’ve been making a comeback thanks to Bermudian designer Rebecca Singleton whose refreshed line up is sold at TABS (short for, “The Authentic Bermuda Shorts”) on Reid Street.  

6. Which restaurants do you love?

Huckleberry at the Rosedon Hotel (conveniently across the street from the Hamilton Princess) does excellent fine dining for lunch and dinner, but I’d actually recommend it for what might be the best breakfast on the island.  With a southern influenced menu and a beautiful garden setting, it’s a little bit like stepping back in time.  

For fantastic steak, seafood and a raw bar with a water view, try Intrepid at the Hamilton Princess, which recently displaced Marcus Samuelsson as the hotel’s signature restaurant.  The name for the new restaurant has been taken from the codename of real-life super spy, Sir William Stephenson, who was based out of the hotel during the Second World War. He was a friend and inspiration to James Bond creator Ian Fleming – the author cited Stephenson as the ‘real thing.’  

In Hamilton, Barracuda Grill is tucked away upstairs above the Hog Penny Pub on Burnaby Street and a well kept secret with a solid wine list and some of the best prepared fish on the island.  It also has a cosy bar that’s perfect for a pre-dinner martini.    

7. Of everything one could do on a first visit, what’s the one most memorable thing to do?

Seeing Bermuda from the water for the first time is an experience everyone remembers.  Bermuda’s land mass is only twenty-one square miles, but we are surrounded by a thousand square miles of ocean, and for locals it’s our backyard and playground. 

There are several companies like KS Watersports who offer boats to rent so visitors can explore on their own, or a guided “jet ski safari” that includes passing under the world’s smallest drawbridge and a stop at a famous shipwreck.    

8. What would you advise first-timers to take a pass on? Said another way, what’s popular but a bit over-hyped?

Getting around in Bermuda can be tough.  While our taxis are clean and roomy (by law, they are all mini vans), and taxi drivers are a font of knowledge about the island, relying on them to get around can be quite constraining (not to mention expensive)! 

Many visitors rent scooters, but I wouldn’t recommend it – I’ve seen too many accidents that result from drivers unfamiliar with our winding roads, driving on the left, or being on two wheels.  

A much better idea are the relatively recently introduced two-person electric cars offered for rent by Current Vehicles or Rugged Rentals.  Current offers the Renault Twizy (an electric quadricycle whose name is a contraction of “twin” for it’s two seats and “easy”), which is an ideal vehicle for exploring Bermuda safely.  

9. What’s a good stop for return visitors, who have already done all the “first timer” recommendations?

St. John Frizell, restaurateur and founder of Brooklyn’s Sunken Harbor Club has just opened a new Bermuda ‘chapter’ of his famous cocktail bar and tavern at the Cambridge Beaches resort.  It’s getting really good reviews, and I’m excited to give it a try.    

10. Is this a good vacation for families with kids? Teenagers? Romantic partner? Solo traveler? Any or all of the above?

Bermuda is an ideal place for couples and families with young children. On the other hand, teenagers and visitors traveling solo might struggle with making their own fun – the island’s nightlife is pretty sleepy.

Solo visitors may enjoy visiting Bermuda more if they’re part of an organized group. While “tour groups” often get a bad rap in luxury travel, organisers such as Afar and Garden & Gun put together occasional bespoke themed trips to Bermuda that are a fantastic way to experience the island and meet lovely people.  

Describe Bermuda in three words. 

Familiar, but different.

tips on having the best first luxury vacation trip to Bermuda

Those are the tips our expert insider has to share regarding how to have the best first luxury vacation trip to Bermuda, including when to go, where to stay, top restaurants and activities. Having visited many times, we never get tired of going again. It’s a very special place, and not so far away.