Best Caribbean Islands | A Well Traveled Pair

The Best Islands to Visit in the Caribbean

by Katie McCabe | @awelltraveledpair | October 1st, 2021

Before John and I met, I traveled a lot around the Caribbean and Central America. I’d like to think that my sense of wanderlust formed while I was adventuring from one beautiful tropical destination to the next. There are so many incredible places in this area of the world to explore, each one offering its own definition of paradise.

John and I have yet to travel to the Caribbean together, but I look forward to the day when we will swim in the turquoise waters, drink coconuts under massive palm trees, and watch some of the best sunsets in the world while hand in hand. Until then, these places will continue to hold a special, and personal, place in my heart.

If you have yet to visit the Caribbean, and you aren’t sure where to start, I’ve listed my favorite destinations below.

Jamaica

Jamaica gave me my love of mango, waterfalls, and Bob Marley. This was the very first island I visited in the Caribbean, and it definitely made a great first impression. Bouncing from the main areas of Ocho Rios, Negril, and Montego Bay, I was in awe of Jamaica in every single way. I ate fresh fruit and jerk chicken daily, cliff-jumped from Rick's Cafe, hiked up Dunn's River Falls, and listened to as much reggae music as possible. If you're thinking about planning a trip to Jamaica, do it! There's no place like it, and it's definitely worth a visit. I have a feeling you'll fall in love with this incredible island just as much as I did.

Must-Sees: Seven Mile Beach, the Blue Hole, YS Falls, Rick's Cafe, Dunn's River Falls, and the Blue John Crow Mountains National Park

Where to Stay: GoldenEye (Luxury Resort in Oracabessa), The Royalton (All-Inclusive in Negril), The Caves (Adults-Only All-Inclusive in Negril), Sunset at the Palms (Adults-Only All-Inclusive in Negril), Beaches Negril (All-Inclusive in Negril), Jamaica Inn (Ochos Rios), Sandals Ochi (All-Inclusive in Ochos Rios), Half Moon (Luxury Resort in Montego Bay), Sandals Royal Caribbean (All-Inclusive in Montego Bay)

When to Go: December through April

Seven Mile Beach

The Blue Hole

Dunn's River Falls

Rick's Cafe

Bahamas

Probably my favorite place in the whole Caribbean, the Bahamas offers a plethora of unbelievable sights. From the pink-sand beaches of Harbour Island to the electric blue waters of Exuma Cay, there are over 700 amazing islands to explore. Probably the most famous sight in all of the Bahamas is Atlantis Resort. Found on the beautiful Paradise Island, this incredible hotel has exquisite rooms, breathtaking grounds, and one adrenaline-pumping water slide. I highly recommend staying here, but if you're looking for a more remote and quiet vacation, then head to the Exumas, Bimini, or Harbour Island. You really can't go wrong in the Bahamas.

Must-Sees: Atlantis Resort, the Exumas, Blue Lagoon Island, Cable Beach, Pink Sands Beach, Bimini, Nassau

Where to Stay: The Ocean Club (Paradise Island), Atlantis Resort (Paradise Island), Fowl Cay Resort (Exumas), Grand Isle Resort (Exumas), The Cove (Eleuthera), Pink Sands Resort (Harbour Island), Graycliff (Nassau)

When to Go: December through April

Atlantis Resort

Atlantis' Water Slide

Nassau

One and Only Ocean Club Resort

Pink Sands Beach on Harbour Island

Pig Beach in Exuma Cays

British Virgin Islands

Some say the British Virgin Islands are pure heaven on earth, and it's hard to argue with that statement once you lay eyes on this magnificent archipelago. Consisting of four main islands - Tortola, Virgin Gorda, Anegada, and my personal favorite, Jost Van Dyke - the British Virgin Islands have so much beauty to explore. Some must-see sights are definitely the Baths in Virgin Gorda, the rainforest-filled Sage Mountain National Park in Tortola, and the Soggy Dollar Bar on Jost Van Dyke. One of my favorite days in the BVI was when I took a catamaran to Jost Van Dyke, drank Painkillers at the Soggy Dollar Bar (a must-do), and swam in the azure waters of White Bay. The British Virgin Islands are what dreams are made of.

Must-Sees: The Baths, Necker Island, Jost Van Dyke, The Soggy Dollar, Smuggler's Cove, Tortola Pier Park, Treasure Point

Where to Stay: Sugar Mill Hotel (Tortola), White Bay Villas (Jost Van Dyke), Rosewood Little Dix Bay (Virgin Gorda)

When to Go: December through May

The Baths on Virgin Gorda

White Bay on Jost Van Dyke

The Soggy Dollar on Jost Van Dyke

US Virgin Islands

Just west of the British Virgin Islands, are the US Virgin Islands. The three main islands - St. Thomas, St. John, and St. Croix - are the main attractions, while the other fifty smaller islands are rarely visited. St. Thomas is the most popular cruise port in all of the Caribbean, and it's here that you'll find loads of shops, restaurants, hotels, and the capital city Charlotte Amalie. St. John is more remote, and resembles a large national park. It's filled with white sand beaches, emerald cays, and woodland trails. St. Croix is the largest island, and some say the most unique. What was once the sugar producing king of the Caribbean, today tourists visit St. Croix to go on plantations tours and partake in excellent diving opportunities. No matter which island you choose, you’ll surely enjoy your stay in the US Virgin Islands.

Must-Sees: Magens Bay Beach (St. Thomas), Paradise Point (St. Thomas), Coki Point Beach (St. Thomas), Cruzan Rum Distillery (St. Croix), Estate Whim Sugar Mill (St. Croix), Virgin Islands National Park (St. John), Great Cruz Bay (St. John)

Where to Stay: The Ritz-Carlton (St. Thomas), The Westin St. John (St. John), The Buccaneer Beach & Golf Resort (St. Croix)

When to Go: December through May

St. Croix

St. John

Paradise Point on St. Thomas

Turks and Caicos

Just southeast of the Bahamas lie the breathtaking Turks and Caicos. This exquisite archipelago is made up of forty low-lying coral islands, with Providenciales serving as the main island, and the one you will want to stay on. It's here that you will find beautiful resorts, heavenly beaches, and some of the tastiest food in all of the Caribbean. I'm sad that I have only visited this island paradise once, but the memory of walking along the powder sand beaches of Grace Bay, swimming with stingrays in Gibbs Cay, and eating my weight in conch will forever live on in my mind. There is so much to see and do here, from whale watching in Salt Cay and exploring the historic Cockburn Town to gasping at the natural beauty of Chalk Sound and living it up with locals at Thursday night's weekly Fish Fry. I miss this island immensely, and I look forward to visiting it again in the future.

Must-Sees: Grace Bay Beach, Bight Reef, Parrot Cay, Governor's Beach, Cockburn Town, Turks & Caicos National Museum, Da Conch Shack, Island Fish Fry at Bight Park (every Thursday night)

Where to Stay: Seven Stars Resort & Spa, COMO Parrot Cay, Grace Bay Club, Club Med Turkoise (All-Inclusive)

When to Go: February through May

Grace Bay

Gibbs Cay

da Conch Shack

da Conch Shack

Aruba

One of the best things about Aruba is that it lies far outside the hurricane belt. This makes it a fantastic destination to visit year-round. From June through November, when other islands are experiencing frequent rain showers and strong winds, Aruba is usually calm, sunny, and dry. Some other reasons to visit are the gorgeous Eagle Beach, flamingo feeding at the Renaissance Hotel's private island, and submarine rides past shipwrecks and colorful coral reefs. Aruba is the island you come to for the perfect mix of relaxation and fun.

Must-Sees: Eagle Beach, Palm Beach, Charlie's Bar, Flamingo Beach, Baby Beach, The Natural Pool, Arikok National Park, Oranjestad

Where to Stay: Renaissance Wind Creek Aruba Resort, Renaissance Ocean Suites, Hotel Riu Palace Aruba (All-Inclusive), The Ritz-Carlton Aruba

When to Go: Year-round

A Divi Divi Tree on Eagle Beach

Oranjestad

Flamingo Beach at The Renaissance Hotel

Unique Architecture in Oranjestad

Cayman Islands

Just 150 miles south of Cuba are the luxurious Cayman Islands. Grand Cayman is the largest island, and known for its beach resorts, shopping, and diving sites. Cayman Brac is a popular launch spot for first-class fishing expeditions, and Little Cayman is home to diverse wildlife and endangered species. While Grand Cayman and Cayman Brac are the bigger and busier islands, Little Cayman is where people come to find solitude and relaxation. With more iguanas than people, it's quite easy to achieve isolation on Little Cayman. Whether you are looking for a quiet spot to read a book, an epic diving experience, or a hoppin' beach bar to drink rum punch at, the Cayman Islands have it all.

Must-Sees: Seven Mile Beach (Grand Cayman), Stingray City (Grand Cayman), Kittiwake Shipwreck (Grand Cayman), Mastic Trail (Grand Cayman), George Town (Grand Cayman), Bloody Bay Marine Park (Little Cayman), Captain Keith Tibbetts Wreck (Cayman Brac)

Where to Stay: The Westin Seven Mile Beach (Grand Cayman), Kimpton Seafire Resort & Spa (Grand Cayman), The Ritz-Carlton (Grand Cayman), Little Cayman Beach Resort (Little Cayman), Cayman Brac Beach Resort (Cayman Brac)

When to Go: December to June

Seven Mile Beach

George Town on Grand Cayman

An Iguana on Little Cayman

Cayman Brac

St. Lucia

St. Lucia will wow you the second you step foot on this remarkable island. Its dramatic mountains, volcanic beaches, and one of a kind diving sites, make this destination one of the most unique spots in the Caribbean. Its scenery is unlike any other island, and for that reason, it is frequently voted one of the best places to visit. St. Lucia exudes beauty at every corner, and its five star resorts will beckon you back time and time again.

Must-Sees: The Pitons, Marigot Bay, Soufrière, Sugar Beach, Pigeon Island National Park, The Tet Paul Nature Trail, Anse Chastanet National Park.

Where to Stay: Jade Mountain Resort, Sugar Beach A Viceroy Resort, Ladera Resort

When to Go: January to May

Sugar Beach

Marigot Bay

Soufrière

Sugar Beach

Belize

While Belize is not an island destination (it is attached to Central America), its eastern coast is met with the blue waters of the Caribbean. Belize is amazing in so many ways. The west coast is filled with dense jungles and ancient Mayan ruins, while the east coast offers some of the prettiest beaches around. I have to say, though, the best part of Belize lies offshore in the Belize Barrier Reef. Here, you'll find one of the most fascinating sights in all of the world - the Great Blue Hole. This incredible natural masterpiece is the world's largest marine sinkhole, and scientists believe it formed during the Ice Age more than 14,000 years ago. If you plan on visiting Belize, a trip to the Great Blue Hole is a must!

Must-Sees: The Great Blue Hole, Tobacco Caye, Caracol Mayan Ruins, Xunantunich Mayan Ruins, Lamanai Archaeological, Altun Ha, Caye Caulker, Ambergris Caye

Where to Stay: Turneffe Island Resort, Pelican Reef Villas Resort, Matachica Resort (All-Inclusive), Turtle Inn, The Lodge at Chaa Creek

When to Go: January to May

Tobacco Caye

Caracol Ruins

The Blue Hole

Bermuda

This next destination isn't necessarily located in the Caribbean, but it's close enough. Growing up on the east coast of the USA, Bermuda is where my family and I would occasionally travel to for our family vacations. Measuring in at just twenty-one miles long by one mile wide, this island may be small, but it surely packs a punch. Home to numerous museums, shops, restaurants and pristine pink sand beaches, Bermuda is one of the nicest islands in the world. It also has some of the friendliest locals. Mark Twain once said "You can go to heaven if you want. I'd rather stay in Bermuda."

Must-Sees: Horseshoe Bay Beach, Front Street in Hamilton, historic St. George's, Elbow Beach, Warwick Long Bay, Fantasy Cave and Crystal Cave, and the Royal Naval Dockyard.

Where to Stay: The Hamilton Princess & Beach Club, Cambridge Beaches Resort & Spa

When to Go: May to October

Hamilton Princess Hotel

Elbow Beach

Front Street

Royal Naval Dockyard

Cambridge Beaches Resort & Spa

Horseshoe Bay

Pretty Bermuda Houses

A WELL TRAVELED PAIR

The Best Islands to Visit in the Caribbean

Jamaica

Seven Mile Beach

The Blue Hole

Dunn's River Falls

Rick's Cafe

Bahamas

Atlantis Resort

Atlantis' Water Slide

Nassau

One and Only Ocean Club Resort

Pink Sands Beach on Harbour Island

Pig Beach in Exuma Cays

British Virgin Islands

The Baths on Virgin Gorda

White Bay on Jost Van Dyke

The Soggy Dollar on Jost Van Dyke

US Virgin Islands

St. Croix

St. John

Paradise Point on St. Thomas

Turks and Caicos

Grace Bay

Gibbs Cay

da Conch Shack

da Conch Shack

Aruba

A Divi Divi Tree on Eagle Beach

Oranjestad

Flamingo Beach at The Renaissance Hotel

Unique Architecture in Oranjestad

Cayman Islands

Seven Mile Beach

George Town on Grand Cayman

An Iguana on Little Cayman

Cayman Brac

St. Lucia

Sugar Beach

Marigot Bay

Soufrière

Sugar Beach

Belize

Tobacco Caye

Caracol Ruins

The Blue Hole

Bermuda

Hamilton Princess Hotel

Elbow Beach

Front Street

Royal Naval Dockyard

Cambridge Beaches Resort & Spa

Horseshoe Bay

Pretty Bermuda Houses

St. Peter's Church in St. George's