Bermuda for City Dwellers Turned Island Hoppers

Embark on an unforgettable twin destination trip with JetBlue from either London or Edinburgh to the vibrant city of New York and the tranquil island of Bermuda. From the bustling streets of NYC to the serene beaches of Bermuda, this itinerary promises to offer a perfect blend of urban excitement and tropical relaxation.

  • Itineraries,
  • Travel Tips
Aerial view of Bermuda railway trails

With a quick 90-minute flight separating these two distinct destinations, get lost in the hustle and bustle of the Big Apple, only to find yourself in the tranquil beauty of the island paradise that is Bermuda.

Jet into NYC with JetBlue

Get a taste of the city that never sleeps. New York City’s iconic landmarks, diverse culture, and endless possibilities await at every corner. This 2-day pit-stop tour touches on some of the most show-stopping attractions the city has to offer.


The Hilton Garden Inn Financial Center is a modern hotel located in the ever-expanding lower Manhattan district. Offering convenient access to unmissableattractions such as the Statue of Liberty, One World Trade Center, 9/11 museum and Wall Street.

Day 1


Kick start your first morning with breakfast at the exciting new district of Seaport and the beautiful Tin Building. An old fish market turned trendy market hall with plenty of acclaimed cafes and restaurants to choose from. From here, take a 5 minute stroll to catch the ferry to DUMBO. Once in the neighbouring borough of Brooklyn, don't miss the Brooklyn Flea Market under the railway arches, where you can expect to find anything from vintage clothing and eclectic jewellery to old music records. Time for a coffee? Head over to Time Out Food Market and enjoy the buzz as well as the views back over to Manhattan. If you fancy the walk, take the pedestrian route across Brooklyn Bridge and enjoy the stunning skyline as you head back towards Manhattan.

Eye level view of the Brooklyn Bridge

For lunch, you can choose between Chinatowna and Little Italy, both conveniently located right next to each other. Each with their own abundance of restaurants to explore. One suggestion is Lombardi’s Pizzeria, thought to be the first ever pizzeria in America - opened in 1905. Make sure you save enough room for dessert at Ferrara Bakery which sells some of the best gelato, cappuccino and cannoli you’ll findoutside Italy!

From there, head over to the Financial District, and to the One World Observatory for the highest panoramic view of the city. Then spend some time at the 9/11 Museum and Memorial - a touching and beautiful tribute to the events of 2001.

As the evening sets in and the lights come up, it's the perfect time to head to Times Square. Enjoy the street artists, walk a few blocks and work up an appetite before heading to Ellen's Stardust Diner - take in the world famous singing waters whilst you enjoy American classics on the menu. If you have any energy left in the tank, take in a magical Broadway show such as; The Lion King, Chicago or Hamilton to name but a few.

Day 2


Refreshed from a good night's sleep, grab a coffee and head into Midtown. Fancy some retail therapy? Head to Fifth Avenue, Madison Avenue or Macy’s flagship store in Herald Square, the largest department store in the US - with no less than 10 stories of a shoppers paradise.

If you’d prefer to get above ground, you have the choice of some incredible observation decks including Top of The Rock, SUMMIT One Vanderbilt and Empire State Building all within close proximity. Don't miss Grand Central Station, so much more than a commuter railway station. The beautiful architecture of this building houses plentiful shopping and eating opportunities, not to mention the oldest restaurant in the building - the Oyster Bar.

Interior view of Grand Central Station

Don't forget to check out what’s on at Madison Square Garden, home to the New York Knicks basketball team and countless concerts throughout the year.

From there, walk a couple of blocks to 230 Fifth Rooftop Bar where you can grab a pre-dinner cocktail at the largest year-round indoor/outdoor space in NYC. Time it right with sunset and take in the beautiful backdrop of the iconic skyline. Head south into the trendy Nomad and Flat Iron neighbourhoods to soak up the atmosphere whilst enjoying some alfresco dining along the pedestrianised avenues.

Find Yourself in Bermuda: 3-Day Itinerary

Leave behind the skyscrapers of the big city and, instead, look up to see bright blue skies and towering palm trees swinging in Bermuda’s sweet sea breeze. Embark on a 3-day journey that transcends the hustle and bustle of city life, inviting you to immerse yourself in Bermuda's exquisite blend of natural beauty, cultural richness, and unparalleled adventure.


Indulge in the ultimate relaxation at Azura Bermuda, a haven perched atop cliffs with panoramic views of the Atlantic Ocean. Azura offers a luxurious retreat from the city and offers an infinity pool, private beach, restaurant and fitness centre. Located centrally, you will have easy access to Bermuda’s famous pink sand beaches and the City of Hamilton easily.

View of Seascape pool at Azura Bermuda

Day 1


Start your Bermuda adventure by heading East to St George’s, a UNESCO World Heritage Site brimming with history and charm. Before you arrive at the town centre you will find Temptations Café, a warm and welcoming spot with a charming balcony to sit out and enjoy both traditional and Bermudian inspired breakfast and lunch menu, fresh baked goods and organic coffee. For something local, try a Bermuda fishcake or some fresh baked honey cornbread.

For the remainder of your stay, you are going to have a Rugged Rental electric microcar, a fun and sustainable way to move around the island (remember we drive on the left!). Just a short walk from Temptations, you will pick up your microcar ready to explore in style. Take a slow drive around St Georges, travel up the lanes, get lost in the beauty of the Unfinished Church, Tobacco Bay and all the forts dotted around the most Eastern tip of the island.

A person is driving an electric microcar by a scenic building.

Next on the agenda, we have something special. Experience Bermuda from a totally unique perspective as you soar above the island on a Blue Sky Flights aerial tour. Marvel at the breathtaking views from the comfort of a small Cessna aircraft, gaining a newfound appreciation for Bermuda's enchanting topography showing the entire 21-mile archipelago shape ironically resembling a fishhook.

Ground yourself after the tour by taking a short 5-minute drive to Cooper’s Island Nature Reserve. Walk through the reserve and along the beaches and find total tranquility and peace.

An aerial view of Cooper's Island with various beaches.

On your way back to your hotel, stop at the famous Swizzle Inn for a bite to eat and a must-try pitcher of Rum Swizzle, one of Bermuda’s signature cocktails. The Swizzle Inn is the oldest pub in Bermuda and has a famous slogan, ‘Swizzle Inn Swagger Out’ due to the delicious but slightly punchy rum drink that will sneak up on you quickly.

Take a slow ride back to your hotel, travelling around Harrington Sound and stopping at any viewpoints along the way. Once you are back at your home base you can start to get ready for your dinner plans at Blû Bar and Grill, located in Warwick. Overlooking the Great Sound, Blû offers fine steak, fresh Bermuda fish, Asian influences, and a delightful sushi menu.

Day 2


Your second day takes you out on the beautiful azure waters that have been inviting you to dive in since you arrived. On your way to the island’s Western end, stop in for breakfast at The Bridge Trading Post, a small café and coffee shop that sits right on the side of Somerset Bridge (the world’s smallest drawbridge). Try the fresh daily rotation of baked goodies and pair them with a specialty coffee to get your day started right.

When you arrive in Dockyard, there is no shortage of boat options to get you out on the water. Try a snorkel and sail on catamaran boats like Island Time Bermuda or Sail Bermuda or any boats that Island Tour Centre offers. You will take a slow cruise to different snorkelling spots, where you can expect to swim with colourful tropical fish and vibrant sea corals. For a one-off experience, try Hartley’s Helmet Diving – an activity that feels like something between walking on the moon and scuba diving (no experience necessary).

Sail Bermuda – Sail Bermuda Main Image

For lunch, you are going to experience a traditional Bermuda fish sandwich at Woody’s Sports Bar and Grill. This side-of-the-road hot spot is loved by the locals to ‘greeze’ on their favourite local catch. Just trust us and order the fish sandwich (your choice of fresh catch) with the works complete with raisin bread, tartar sauce, coleslaw, cheese and hot sauce and a side of fries. Yes, we know it sounds weird, but the explosion of sweet and savory in your mouth is an experience you don’t want to miss.

You are going to want to sit down somewhere nice and comfortable after a meal like that. Head to Somerset Long Bay and enjoy the ocean views and afternoon on the beach. If you fancy a cocktail or other light refreshment, you can head to Breezes at Cambridge Beaches Resort and Spa, an oceanside restaurant and bar that is open to the public.

For dinner, you will head into Hamilton to Harbourfront Restaurant. This restaurant is on the water, so on a nice evening you will want to book a table outside to enjoy the sunset and maybe feed the fish. The menu offers an elegant dining experience of fresh seafood, dried-aged meats, handcrafted salads and irresistible desserts.

Day 3


It’s your last day in Bermuda, but the itinerary today will make the most of every minute. Grab your breakfast at Paraquet Restaurant, a diner-style establishment where you will find an extensive breakfast menu, and one of the best milkshakes on the island.

Walk on over to Elbow Beach Cycles to rent a bicycle, either electric or standard geared mountain bike. The staff will show you on a map the best route to see Bermuda’s famous pink sand beaches along the South Shore. Make sure you have aGo-Pro or your camera/phone handy, you will be making plenty of pit stops to take photographs along the way.

Slowly make your way to Gibbs Hill Lighthouse, one of the most iconic structures on the island. Enjoy the views of the Great Sound and South Shore from the bottom of the lighthouse or climb 186 steps to the top for even better views. Gibb’s Hill Lighthouse has been shining its light to seafarers every night since 1846, making it the oldest of its kind and one of only two cast-iron lighthouses still in existence.

Aerial view of Gibbs Hill Lighthouse and Riddle's Bay

You will have worked up a hearty appetite after all that cycling and climbing, so head around the corner to Boundary Sport Bar and Grille to replenish your energy. This sports bar has plenty of TVs and games for you to play while you dive into the menu filled with bold and artisanal flavours of smokey BBQ and pub favourites. For a good sharing plate try the Macho Nachos with smoked brisket.

Ask your server for directions to the Railway Trail, an old railbed turned into a national park trail that spans the length of the island. Use the trail to get you back to Elbow Beach Cycles to return your rental before squeezing in your final activity of the trip – an art gallery.

Interior of Masterwork's Rick Faries Gallery

Masterworks Museum of Bermuda Art, located in Botanical Gardens is one of Bermuda’s museums of art, and boasts an astonishing permanent collection from international artists like Georgia O’Keefe and Winslow Homer, as well as Bermudian art that celebrate the island’s culture and intrinsic beauty.

For your last meal in Bermuda, we suggest heading to Hamilton Princess’ 1609 restaurant to watch the sunset across the water and enjoy a spirited cocktail menu and a fusion of island and Latin flavours for dinner. Try the catch of the day ceviche, the charred corn salad and a range of tacos that use fresh, local ingredients.

As the sun sets on your Bermuda trip, reflect on your island life experience with your travel partner(s) and start planning for your return – we’d love to have you return.



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