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Caribbean | A Few Nights Away in Bermuda

Sample Itinerary


Bermuda, Caribbean

Trip Duration

4 nights / 5 days

With 21 miles of tropical paradise along its turquoise shores, Bermuda, the Jewel of the Atlantic, exudes beauty and tranquility for those seeking a quick escape with their loved ones.

Below is just a sample of the immersive itineraries our Destination Specialists can create. Our Destination Specialists are happy to book our hotels highlighted in the itinerary below, or let them know if you would like something customized. And, feel free to offer our non-hyperlinked suggestions to your clients to further explore the destination.


Day 1: Your Home Town, USA / Bermuda, Caribbean

Less than a two hours flight from the United States' eastern seaboard, arrive in Bermuda and begin your getaway to paradise. Enjoy your private transfer to Rosewood Bermuda, where you will be greeted with a refreshing welcome drink before settling into your Oceanview guestroom with Castle Harbour vistas for four nights of rest and relaxation.

Take a refreshing afternoon dip in the infinity Horizon pool at the Bermuda Beach Club, offering beachfront views and relaxation. Then, soak in your oversized bathtub before getting ready for your night's dining experience.

This evening, indulge in exquisite cuisine at the resort's signature restaurant, Island Brassierie. This delectable steakhouse fuses modern cuisine with local ingredients. Adore the restaurant's hand-painted murals and cathedral ceilings before enjoying a cocktail on the terrace, with sweeping views of Harrington Sound.

Day 2: Spa Rejuvenation

Indulge in renewal and rejuvenation at Sense, A Rosewood Spa. Laze by the reflection pool before being pampered with the Rosewood Retreat spa day. Begin with a full-body honey and cane sugar exfoliation, followed by a Bermuda Pawpaw Massage. Enjoy a leisurely lunch by the reflection pool, then sip your signature Swizzle drink while receiving a calming manicure and pedicure.

Conclude your day with the Sunset to Stargazing dinner experience, with the entire stretch of the beach and evening sky as your backdrop. Your beach lounge area with mini fireplace awaits as the sun sets peacefully while you watch cocktail in hand. Delight in a five-course dinner with wine pairing and stargazing.

Day 3   Island Exploration

Explore the beauty of Bermuda as you venture across this breathtaking island. Grab your locally roasted morning coffee at Rock Island Coffee in the City of Hamilton. Then, stroll the city, stopping in the local shops and boutiques, including Atelerie, offering local finds as well as designer brand collections.

For lunch, picnic at Admiralty House Park with your delectable meal from Art Mel's Spicy Dicy, known for its fried fish on toasted raisin bread and topped with its famous tartar sauce and coleslaw. After your scenic picnic, explore the park's trails, ruins and tunnels.

Next, climb to the top of Gibbs Hill Lighthouse for stunning views and visit Horseshoe Bay Beach, with its pink sands and crystal clear turquoise waters. Or, consider exploring Crystal Caves, an awe-inspiring natural underground attraction. Thought to be millions of years old, these dramatic formations and clear ocean-fed lake have inspired everyone from Mark Twain to the creators of Fraggle Rock.

Your day concludes at the East End of the island and Tobacco Bay Beach, with its limestone bluffs. Snorkel in its shallow waters, or play pool at its beachside pool table. Then, join the restaurant's iconic summer beach bonfire for a unique island experience.

Day 4: Day at Leisure

Spend your day relaxing at the resort's two pools. First, laze at the Palm Court Pool, overlooking Harrington Sound and the Coffee Chine Grotto. Follow your relaxing morning with lunch at the Beach Club Restaurant, featuring local and imported seafood, rose wines, Champagne, tequila and classic frozen cocktails amidst views of the ocean and Bermuda's iconic pink sands.

After your casual beachfront lunch, the Castle Harbour Pool awaits with harbor and St George Parish views.

For dinner, embark on the Bermuda Gourmet Safari, conducted in the resort's coffee chine and Chef's garden. Take a guided sunset walk into the coffee chine, enjoying a rum tasting highlighted with local botanicals and spices. Afterwards, indulge in a five-course degustation dinner in the herb garden. Local seafood and produce are the stars of this outdoor dinner, and are paired with the sommelier's choice wine.

Day 5: Bermuda, Caribbean / Your Home Town, USA

Discover tranquility as you stroll to the beach for sunrise beach yoga before embarking on your comfortable return flight and dreaming of your next quick escape to paradise.

Distinguished Recognitions, Pleasant Holidays Family of Brands