4-Day Incentive Itinerary: A Bermuda Getaway

Island beauty, luxury experiences, and a range of curated activities for groups make Bermuda an ideal destination for incentive trips. From oceanfront golf to island galas, here’s a sample itinerary for four unforgettable, well-deserved days.

  • Itineraries
A group of people are sitting at an outdoor picnic.

Bermuda’s island allure makes it feel a world away, but it’s just a short nonstop flight from east coast hubs such as New York and Boston. The pristine pink-sand beaches, azure waters, natural attractions, deep culture, and impressive luxury offerings create the perfect blend of relaxation and adventure, making Bermuda an exceptional and enriching place for reward travel. 

This four-day itinerary immerses your group in classic Bermuda experiences, from serene mornings on stunning beaches to festive sunset sails; from sumptuous island cuisine and vibrant local entertainment to deep dives into the island's rich cultural heritage. A Bermuda getaway isn’t your average incentive trip – it's an opportunity for authentically rewarding experiences in a truly alluring destination.


When considering your group’s home-away-from-home, one option is the elegant Rosedon Hotel in the City of Hamilton. You can book the entire hotel, which features lush gardens and delicious onsite dining just a short walk from the city center. Another option is a private retreat at Leamington Caves, an 8-bedroom luxury rental property on the East End. At this island hideaway, guests are surrounded by natural wonders and can enjoy two separate outdoor dining areas.

Aerial View of Leamington Caves.

Day 1


As guests arrive, treat them to some poolside relaxation Bermuda-style. Host a welcome reception by the Rosedon Hotel’s freshwater pool, tucked away in the beautiful back garden. At the Leamington Caves, host a poolside reception with magnificent views of Harrington Sound. Leamington Caves is also home to Bermuda's largest private natural caves, giving guests a fascinating glimpse into natural history and the chance for a refreshing swim in a deep natural pool. 

Exterior view of Rosedon's pool

For dinner, both the Rosedon Hotel and Leamington Caves offer convenient dining options. In the Rosedon Hotel, Huckleberry Restaurant – named as a tribute to Mark Twain, who visited Bermuda – offers a menu blending Southern influences with Bermudian roots using fresh produce from their gardens. Near Leamington Caves, the Swizzle Inn serves up favourite local dishes in a rustic island atmosphere. Guests can indulge in a fruity, refreshing Rum Swizzle – Bermuda’s national drink – and toast to a great getaway.

Day 2


The second day kicks off with a private guided tour of the island. A memorable stop is the Masterworks Museum of Bermuda Art, whose impressive fine art collection celebrates the island's culture and natural beauty. On display are renowned local artists along with famous artists from around the world, including Georgia O’Keeffe, Winslow Homer, and Henry Moore.

After lunch, the group can get on the water with a catamaran and snorkel adventure. With Restless Native Catamaran, you'll set sail on a bright and spacious vessel offering a full bar, a state-of-the-art stereo system and a variety of water sports equipment. Relax on bean bag chairs on deck, go snorkelling amidst vibrant marine life, or go kayaking or paddleboarding.

Rising Son Catamaran Cruise

Another option for an aquatic adventure is the Rising Son II catamaran, where guests can swim, kayak, go standup paddleboarding, or snorkel the nearby reef. Complimentary Rum Swizzles are served as you cruise back to the pier.

Wrap the day with a celebration at Hawkins Island, a private island that’s ideal for a VIP Appreciation Gala. With lush woodlands, an oceanside pavilion, and sweeping ocean views, it's one of the island's most sought-after venues. The experienced team and in-house catering crew ensure your event is tailored to perfection, whether it's an intimate gathering or a grand soiree for up to 200 guests.

Day 3


The third and final full day begins with a round of golf at one of Bermuda's legendary courses. With more golf courses per square mile than anywhere else in the world, the island offers many incredible courses to choose from to meet your group’s abilities.

A group of people are playing golf on the course.

After a morning on the green, head to the spa for a rejuvenating experience. A sublime option is the warm bamboo massage at the oceanfront La Serena Spa at The Reefs Resort & Club. At Natura Spa at Grotto Bay Beach Resort, guests can get a soothing hot stone massage in an ancient cave surrounded by shimmering pools and candlelight. 
For the final dinner, guests can relish a decadent meal at BLT Steak NY at The St. Regis Bermuda. Treat your group to the finest cuts of steak and fresh seafood paired with an upscale cocktail menu and breathtaking ocean views.
End the day at Tobacco Bay Beach, famous for its dramatic rock formations. Guests can take in the gorgeous scenery while relaxing by a bonfire, enjoying live music, and sipping cocktails. 

Day 4


Professional transportation services make getting back to the airport a breeze, and clearing customs in Bermuda makes for an easy transition home. The island’s L.F. Wade International Airport boasts a modern new terminal and a range of convenient nonstop flights.
As guests bid farewell to Bermuda, the island’s warm hospitality, captivating landscapes, and memorable island experiences will no doubt leave them happy and refreshed. 



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