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caribbean

Airmail Notecard

The Caribbean is a region of the Americas that comprises the Caribbean Sea, its surrounding coasts, and its islands. The region lies southeast of the Gulf of Mexico and of the North American mainland, east of Central America, and north of South America.

What We Love About The Caribbean

Known for their hospitality, gorgeous beaches, and natural beauty, the islands have long attracted visitors from around the world. The Caribbean is also one of the most versatile regions, perfect for honeymoons, baby moons, and solo travelers.

Our Favorite Hotels
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  • Kimpton Seafire Resort & Spa, Cayman Islands

  • Eden Rock Cap Cana, Dominican Republic

  • Amanyara, Turks & Caicos

  • Rosewood Baha Mar, Bahamas

Traveller's Compass
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Our Favorite Islands

  • St. Lucia 

  • Aruba

  • Anguilla

  • Turks & Caicos

  • Aruba

Bucket List Experiences

Swim with pigs in the Bahamas

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Hike Gros Piton in St. Lucia

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Swim in Dunn's River Falls in Jamaica

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Visit The Baths in Virgin Gorda

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Ideas for Your Trip to The Caribbean

  • DAY 1

    CARLISLE BAY You’ve Arrived

    • Airport with Meet & Greet - Vehicle/Driver-Guide

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  • DAY 2

    CARLISLE BAY TO ST. MARY Explore with an Expert

    • Begin the day with a private drive from the pier to                                                                      through the village of Piggots, passing the Sir Vivian                                                                Richards Cricket Stadium, which was built for the 2004 Cricket World Cup.

    • Visit the small village of Pares with a stop at Betty's Hope Sugar Plantation. 

    • Your tour continues through the quaint villages of All Saints, Liberta and Horsford Hill, for stunning views of Falmouth Harbour. Stopping in Shirley Heights, you will see a rambling array of gun emplacements, military buildings and a cemetery in which stands an obelisk erected in honor of the soldiers of the 54th regiment. 

    • The tour continues to Nelson's Dockyard in Antigua's historical district.  It is the only continuously working Georgian Dockyard in the world.

    • Lunch at Pillars Restaurant in Nelson's Dockyard, overlooking the harbor.

    • Continue through the Antigua Rainforest and the sleepy village of Old Road.

    • Enjoy time at leisure at your resort

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  • DAY 3

    ST. MARY TO CARLISLE BAY Nurtured by Nature 

    • Indulge in some well-deserved pampering at the Cara Organic Beauty Spa. Cara Organic Beauty Spa offers an extensive list of treatments to choose from, including hot stone massage and foot reflexology.

    • Set out from your hotel this evening to enjoy an evening hike to Shirley Hights and the iconic Pillars of Hercules. These breathtaking sights are best enjoyed in the evening at sunset. With your private guide, you will marvel at the tropical views over the Atlantic Ocean.  The first stop is the UNESCO World Heritage Site of Nelson’s Dockyard. Make sure to pack your camera as there is guaranteed to be some once in a lifetime photo opportunities. End your day on arrival back at your hotel.

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  • DAY 4

    ST. MARY Sun and Sand

    • Experience true relaxation at Carlisle Bay's beautiful private beach and on-site pool. 

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  • DAY 5

    CARLISLE BAY TO ST. MARY Live Like a Local

    • Fasten your seat belts in a fully-loaded 4x4 SUV, touring the island’s historical sites and must-see attractions. Experience the picturesque beauty of the bay's lush rainforest while indulging in Antigua’s favorite seasonal treat - black pineapple. Marvel at the unique and varied work of local artists at the Art Gallery by Gunpowder Suites before enjoying lunch at Boom Restaurant, overlooking the English Harbor and Fryes Beach.

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  • DAY 6

    CARLISLE BAY TO ST. MARY Creative Cuisine 

    • Set out today to the home of a renowned local chef for a half-day culinary experience over lunch. This private class takes place in a beautiful home in the mountains with incredible views. Learn how to create gastronomic masterpieces with the locally farmed produce and herbs.  You will then be invited to sit and eat your lunch with your own, personally made rum punch! 

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  • DAY 7

    ST. MARY TO CARLISLE BAY An Evening Out 

    • Today, enjoy one of the many complimentary watersports on offer at Carlisle Bay. Kayaking, sailing and paddle boarding are among guest favorites and are all suitable for beginners, with expert tuition and equipment provided by the resort staff.

    • Nestled just below the peak of the hill, with spectacular views of two of the island’s most beautiful beaches – Ffryes and Jolly Beach – you will find Dennis Beach Bar and Restaurant, popular with both tourists and locals alike. This is the perfect place to sip a cocktail while watching the sunset. Every Friday night Dennis hosts a BBQ and Fish Fry with a bonfire on the Beach, featuring his now famous "Pig Roast" drawing people from across the island, but if you arrive a little late, don’t worry, there is always lobster, fish and chicken to enjoy! 

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  • DAY 8

    CARLISLE BAY TO ST. JOHNS  Depart 

    • Meet your driver for your transfer to the airport.

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WHITE GLOVE DESTINATIONS

Want to built an itinerary from scratch?

All of our itineraries are starting points, created to inspire and are always customized for our clients.

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The Best of Antigua

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