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Best Caribbean Islands: How to Choose the Right One for Your Trip
- Heather Vergara
- Jan 8, 2023
- 18 min read
Updated: May 14
Imagine clear blue water, soft white sand, and a slower rhythm to your days—where your only decisions are when to swim, when to nap, and what to wear to dinner that evening.
The Caribbean is often imagined this way, but the reality is far more nuanced. Not all Caribbean islands offer the same experience, and choosing the right destination is what ultimately shapes your trip.
If you’re trying to decide which Caribbean island is right for you, the differences—from atmosphere and beaches to resorts, dining, activities, and overall pace—matter more than most travelers expect.
So which Caribbean island is best for your vacation?” With more than 20 destinations to choose from, and each one offering something unique, it can be overwhelming to determine the best options for your vacation. It all comes down to what's most important to you.
Do you want to stay in U.S. territory so you don't have to deal with passports and the hassle of going through immigration? Best Caribbean Destinations in the U.S.
Do you want the convenience of an all-inclusive resort so everything is taken care of and you can leave your wallet in the room? Best Destinations for All-Inclusive Resorts
Are you looking for clear turquoise water and white sand beaches but still want a lively vibe and don't want to spend the whole day getting there? Best Beach and Clear Water Destinations in the Caribbean that are "easy"
Do you want lush landscapes, natural adventures, and culture to keep everyone entertained once they're bored with the beach? Best Dramatic Landscapes in the Caribbean
Or do you want something off-the-beaten path and don't mind more difficult travel days and fewer options for accommodations? Off-the-beaten-path Caribbean Destinations
The Caribbean offers incredible diversity; the key question is:
What is the right Caribbean island ... for you?
I’m here to help you determine the best destination to suit your interests, wish-fors, and budget. I’ve done all the research, visited almost half of the 23 islands reviewed here, and have created an overview to make it easy for you! I've evaluated each destination on the following:
Claim to fame - what the destination has to offer
How easy is it to get there. For you local Indianapolis folks, I've also included details on how long it takes to get there from IND. Destinations that are difficult to get to are highlighted in red or yellow depending on level of difficulty.
How easy is it to explore once you're there
What kind of accommodations are prevalent
Best beach and why it's a favorite
The islands of the Caribbean
Note: All the destinations included here are considered part of the Caribbean from a tourist point of view, although not all of them technically are. And not all of them are islands either. So pardon my simplification for the sake of making it easy for you to digest!
Best Caribbean Destinations in the U.S.
No passport is required and no waiting in immigration lines when you visit these U.S. territories: Puerto Rico and the U.S. Virgin Islands.
Puerto Rico is the easiest destination by far.
The three islands that make up the U.S. Virgin Islands (USVI) are all quite different, so I will summarize each individually.
Puerto Rico
PUERTO RICO | |
Claim to fame | Culture, nightlife, history, unique natural adventures - rainforest, caves, bioluminescent bays |
Ease getting there | Non-stops from many major U.S. hubs |
Trip from IND | 2 legs (1 stop) to SJU, about 6 hours total |
Ease once in destination | Rental cars are a must if staying outside San Juan. Island is easy to explore on your own. |
Accommodations | No All-Inclusive resorts. Several large beachfront resorts near the rainforest plus many hotels near Old San Juan. |
Best beach | Playa Flamenco on Culebra Island, a 50-minute ferry ride from the mainland. White/pink sand and clear water surrounded by the Culebra National Wildlife Refuge. |
Puerto Rico: Culture, history, unique natural attractions (caves, bioluminescent bays, rainforest), and beautiful beaches!
U.S. Virgin Islands - St. Thomas, St. John, St. Croix
U.S. VIRGIN ISLANDS | ST. THOMAS, ST. JOHN, ST. CROIX |
Claim to fame | St. Thomas: shopping, nightlife, sailing, fishing, cruise port St. John: beaches, national parks, snorkeling St. Croix: shopping, history, sleepy island |
Ease getting there | St. Thomas: Non-stops from many major U.S. hubs St. John: quick ferry from St. Thomas St. Croix: limited non-stops |
Trip from IND | St. Thomas: 2 legs (1 stop) to STT, about 6 hours total St. Croix: 2 legs (1 stop) to STX, about 7 hours total but limited options |
Ease once in destination | You'll want to explore by taxi or rental car. Drive on the left and roads are tricky given steep, winding roads. |
Accommodations | No All-Inclusives. Only a couple traditional resorts. Condos/villas are main offering. St. Thomas: Ritz, Marriott, Westin, and Secret Harbour St. John: Westin timeshare is only resort. Villas plentiful but most not beachfront St. Croix: The Buccaneer is only resort. Condos/villas |
Best beach | St. Thomas: Magens Bay - heart-shaped stretch of white sand and calm water St. John: Trunk Bay - underwater trail for snorkeling |
USVI: Beautiful water and beaches abound, plus hiking, snorkeling, diving, and shopping. The only thing missing from the USVI is traditional resorts.
Best Destinations for All-Inclusive Resorts
The big 3 destinations for All-Inclusive resorts are:
Jamaica
Dominican Republic
Riviera Maya, Mexico - almost always the best value of the big 3
Given the sheer number of resorts, these destinations offer the best value due to competition. Plus, you get the convenience of having all your food, drinks, and activities included - all you have to do is show up.
Jamaica
JAMAICA | |
Claim to fame | Birthplace of All-Inclusive, plus music, food, culture |
Ease getting there | Non-stops from many major U.S. hubs |
Trip from IND | 2 legs (1 stop) to MBJ, around 6 hours |
Ease once in destination | Use tour operators/transfer companies to explore outside the resort because of crime. Island is 4,000 square miles, so drive time between airport in Montego Bay and resort areas of Negril and Ocho Rios can be long. For South Coast and east side, fly into Kingston. |
Accommodations | Many large all-inclusives serving both adult-only and all-family guests. Sandals has 7 resorts (adult-only) and Beaches has 2 with another being built (all-family) plus many other resort brands. |
Best beach | Negril's seven-mile beach on the western tip of the island - white sand, amazing sunsets |
Jamaica: The birthplace of All-Inclusives, plus beautiful beaches, waterfalls, culture, and music
Dominican Republic
DOMINICAN REPUBLIC | |
Claim to fame | 1000 miles of beaches, vibrant culture, diverse landscape (mountains, rainforests, rivers), whale watching in winter |
Ease getting there | Non-stops from many major U.S. hubs to PUJ, the airport closest to top resort areas. 2 other international airports depending on destination. |
Trip from IND | 2 legs (1 stop) to PUJ, about 6 hours |
Ease once in destination | Use tour operators/transfer companies to explore outside resort. |
Accommodations | Many large all-inclusive resorts serving both adult-only and all-family guests. Punta Cana/Cap Cana (east) and La Romana (southeast) are most popular resort areas. |
Best beach | Playa Grande on north shore - mile of golden sand, cliffs and jungle |
Dominican Republic: Lush landscapes, whale watching, beautiful beaches, vibrant culture, and all-inclusive resorts
Cancun & Riviera Maya, Mexico
CANCUN & RIVIERA MAYA | |
Claim to fame | Culinary, culture, Cancun and Playa del Carmen nightlife, adventure parks, cenotes, turtles, Isla Mujeres |
Ease getting there | Non-stops from most major U.S. hubs |
Trip from IND | Non-stop on Southwest during peak travel, 3.5 hours 2 legs (1 stop) on other airlines, about 5.5 hours |
Ease once in destination | Use tour operators/transfer companies to explore outside resort. |
Accommodations | Countless resorts line the coast from Costa Mujeres north of Cancun's Hotel Zone down south to Playa del Carmen and on to Tulum |
Best beach | Isla Mujeres Playa Norte - a short ferry ride away from Cancun and Costa Mujeres |
Note: Riviera Maya, Mexico encompasses an 80-mile stretch of beachfront resorts and requires a separate story all on its own. The destination is reviewed at a very high level here for comparison purposes.
Cancun/Riviera Maya, Mexico: Culture, history, nightlife, food, natural adventures, amazing resorts, best value, and more!
Best Beach and Clear Water Destinations in the Caribbean That are "Easy"
This category is difficult because every island delivers on beautiful beaches and water, to some degree. I've prioritized destinations that are known for:
Long stretches of amazing white sand beaches
Clear turquoise water everywhere
Relatively easy travel (non-stop flights, no extra travel)
Plenty of lodging options
The obvious islands that belong in this category are:
Turks & Caicos
The Bahamas
Antigua
Cayman Islands
Barbados
Aruba
Other islands may have pretty water and beaches, but are difficult to get to or have limited lodging options, or both, so those are included in the "off-the-beaten-path" section.
Anytime I'm in water like this, I have to be forced back on the boat. So heavenly.
Turks & Caicos
TURKS & CAICOS | PROVIDENCIALES |
Claim to fame | Clear turquoise water and white sand beaches as far as the eye can see, snorkeling/diving, slower pace, pricey |
Ease getting there | Non-stops to Providenciales from many U.S. hubs |
Trip from IND | 2 legs (1 stop) to PLS, about 5.5 hours |
Ease once in destination | Easy to get around by taxi, although pricey, or can rent a car. Although most travelers hardly leave their resort, except by boat! |
Accommodations | Only 3 All-Inclusive resorts: Beaches, Alexandra, Blue Haven. Many other luxury resorts, but the whole island is pricey. |
Best beach | Grace Bay Beach (where most resorts are), Half Moon Bay (by boat) |
Turks & Caicos is made up of 40 islands with just eight of them inhabited. Grand Turks where the cruise ships dock is the capital, but Providenciales (summarized here) is the tourism hub. The most famous Turks resorts are on Grace Bay Beach in Providenciales - the most gorgeous stretch of white sand beach and stunningly blue water I’ve ever seen. Middle Caicos, North Caicos, and South Caicos each have unique natural adventures, but resorts are few – for now! You'll take a puddle jumper if you're visiting the smaller Caicos islands. I've had the pleasure of visiting Turks three times and have toured most of the Grace Bay resorts.
The Bahamas
THE BAHAMAS | |
Claim to fame | Beautiful water, diving/snorkeling, many islands, mega resorts and waterparks, swimming with pigs, bonefishing |
Ease getting there | Closest Caribbean island to the U.S. Non-stops from many U.S. hubs to Nassau (NAS) Some non-stops from U.S. hubs to Exuma (GGT) |
Trip from IND | 2 legs (1 stop) to NAS, under 5 hours short travel time 2 legs (1 stop) to GGT, about 5.5 hours |
Ease once in destination | Taxis and transfers are easy |
Accommodations | Nassau/Paradise Island: Atlantis and Baha Mar mega resorts and waterparks (NOT All-Inclusive). Sandals Royal Bahamian ADULT-only All-Inclusive. Plus many smaller lodging options. Exuma: Very few resorts - Beaches Exuma family All-Inclusive (under construction), Grand Isle Resort and February Point (family properties). |
Best beach | Harbour Island's Pink Sand Beach - 2.5 hour boat ride from Nassau. Harbour Island is considered the Nantucket of the Bahamas. |
The Bahamas is made up of 700 islands, of which only 16 are inhabited, and only 3 have major international airports: Nassau on New Providence, Exuma, and Grand Bahama Island (Freeport). Our overview here focuses on Nassau (including Paradise Island) and the island of Exuma, the two most popular areas. The other islands would fit into our "off-the-beaten-path" section, as they're more difficult to reach and offer limited accommodations.
The Bahamas: Mega resorts and waterparks, swimming with pigs, snorkeling, tranquility on the out-islands
Antigua
ANTIGUA | |
Claim to fame | 365 beaches - 1 for every day of the year, sailing |
Ease getting there | Non-stops from a few major U.S. hubs |
Trip from IND | 2 legs (1 stop) to ANU, about 7 hours |
Ease once in destination | Island is small (100 square miles) and road conditions are good. Easy to rent a car to explore but driving is on the left! |
Accommodations | Most resorts are all-inclusive but expect high prices. Many adult-only offerings. A few for families. |
Best beach | Pink Beach on Barbuda - 17 miles of soft sand from crushed pink shells. Barbuda is 1-hour ferry ride from Antigua, but Pink Beach is difficult to get to. |
Antigua: 365 beaches, sailing, watersports, shopping, "boutique" all-inclusive resorts but pricier than what you're used to.
Cayman Islands
CAYMAN ISLANDS | |
Claim to fame | 7-Mile Beach, diving/snorkeling, busy cruise port (#3 in Caribbean), safe but pricey, banks |
Ease getting there | Plenty of non-stops from U.S. to GCM |
Trip from IND | 2 legs (1 stop), about 5-6 hours |
Ease once in destination | Can rent a car but beware of traffic and expensive gas |
Accommodations | Most accommodations are timeshare or condo rentals. A few large resorts on 7-Mile Beach - Kimpton, Ritz, Westin, Hotel Indigo. |
Best beach | 7-Mile Beach, the best in the Caribbean |
Cayman Islands: 7-mile beach (considered best in the Caribbean), cruise port, and Stingray City.
Barbados
BARBADOS | |
Claim to fame | Golf, nightlife, British culture, pink sands and beautiful beaches, varied landscape |
Ease getting there | Limited non-stops from U.S. to BGI |
Trip from IND | 2 legs (1 stop) but limited flights, 8-9 hours |
Ease once in destination | Should get out and explore the island, good roads but drive on the left and watch for heavy traffic in areas |
Accommodations | Sandals is the only traditional All-Inclusive resort. Sandy Lane most luxurious. Many other boutique offerings. |
Best beach | Bottom Bay Beach - soft white sand surrounded by cliffs |
Barbados: Golf, pink sand beaches, nightlife, British culture, boutique accommodations
Aruba
ARUBA | |
|---|---|
Claim to fame | Nightlife, casinos, culinary scene, welcoming culture Outside the hurricane belt - dry, windy, desert-like island Most repeat visitors of any island in the Caribbean |
Ease getting there | Non-stops from most major U.S. hubs |
Trip from IND | 2 legs (1 stop) to AUA, about 6.5 hours total |
Ease once in destination | Small island (77 square miles). Easy to rent a car for a day or two to explore. 4WD needed for the Outback. |
Accommodations | NOT an All-Inclusive destination (although it's offered) because the culinary scene is amazing and you don't want to tie yourself to one resort's selections. Hotels are divided into Hi Rise and Lo Rise. |
Best beach | Eagle Beach - widest beach, white sand, clear water, gentle surf, divi-divi trees |
Aruba: No hurricanes, sunny and dry year-round, casinos and nightlife, culinary hot spot, most repeat visitors
Best Dramatic Landscape Destinations in the Caribbean
Many travelers come to me thinking they want white sandy beaches and clear turquoise water, but when I ask them what kind of activities they're looking for, they talk about hiking and adventure, and say their kids tire of the beach quickly. A destination with diverse landscapes with mountains, caves, waterfalls, and jungle is better suited to these travelers as they will never run out of natural adventures - ziplining, waterfall rappelling, mountain tubing, hiking, ATV, wildlife spotting, whitewater rafting, and more! While you can find beautiful beaches and water here, they're typically not as blindingly beautiful nor as widespread as they are on flat islands. The top picks for landscape and adventure are:
Costa Rica
St. Lucia
Belize
St. Kitts/Nevis
Costa Rica
COSTA RICA | |
Claim to fame | Most biodiversity on the planet - rainforests, volcanos, cloud forests, dry forests, beaches, wildlife. Natural adventure. |
Ease getting there | Many non-stops from U.S. hubs to both San Jose (SJO) and Liberia (LIR) |
Trip from IND | 2 legs (1 stop), around 6-7 hours |
Ease once in destination | Best to stay in 2-3 destinations to see the country. Roads are difficult, so a driver is recommended. |
Accommodations | Unique accommodations: eco-lodges built into treetops, beachfront jungle resorts, hotels with hot springs and volcano views. Handful of All-Inclusive options, but they aren't recommended as you'll miss out on an authentic experience. |
Best beach | No clear winner so will list favorites in popular tourist areas: Manuel Antonio Beach - National Park and wildlife Guanacaste: Conchal, Tamarindo, Flamingo Beaches Papagayo Peninsula: Nacascolo Beach Nicoya Peninsula: all of them |
Costa Rica: rainforests, volcanoes, cloudforests, wildlife, natural adventures, unique eco lodges
St. Lucia
ST. LUCIA | |
Claim to fame | Lush dramatic landscape, pitons, honeymooners, welcoming culture |
Ease getting there | Non-stops from many U.S. hubs to UVF |
Trip from IND | 2 legs (1 stop), around 7.5 hours |
Ease once in destination | Curvy mountain roads not recommended for rental cars. Long drive from airport to resorts up north - helicopter or boat best for speed and beautiful views! |
Accommodations | Boutique luxury resorts - Sugar Beach, Jade Mountain, Cap Maison my favorites 3 Sandals adult-only all-inclusive resorts Smaller hotels in Rodney Bay and Marigot Bay |
Best beach | Sugar Beach between the pitons where they imported white sand. Rest of island's beaches are more golden brown. |
St. Lucia: dramatic landscapes, the pitons, honeymoons/adult destination, boutique luxury resorts
Belize
BELIZE | |
Claim to fame | Diving (world's 2nd largest barrier reef, Great Blue Hole), snorkel Hol Chan, diverse culture, Mayan ruins, dense jungles, cave tubing, uncrowded |
Ease getting there | Several non-stops from U.S. hubs to BZE |
Trip from IND | 2 legs (1 stop), around 6-7 hours |
Ease once in destination | Most travelers split their stay between the jungle and the coast. Coastal stays typically on an island and require a puddle jumper |
Accommodations | Smaller boutique offerings vs. large resorts Mainland: Placencia Peninsula beachfront, Cayo District eco lodges Ambergris Caye: luxury and boutique hotels Caye Caulker: budget-friendly island, golf carts no cars, cabins and condos |
Best beach | Placencia Peninsula - miles long with calm, protected waters. Much of Belize's coastline is lined with mangroves or is rocky rather than sandy. Belize is more about the water than the beaches. |
Belize: For serious divers, Great Blue Hole, more about the water than the beaches, jungle inland for caves and adventures
St. Kitts/Nevis
ST. KITTS/NEVIS | |
Claim to fame | Great for history buffs and Hamilton fans, hiking, diving, windsurfing, unspoiled/uncrowded |
Ease getting there | A few non-stops from U.S. to St. Kitts (SKB) Ferry or catamaran to Nevis from St. Kitts |
Trip from IND | 2 legs (1 stop) but limited options, about 7 hours |
Ease once in destination | Rent a car on St. Kitts to explore. Taxi on Nevis. |
Accommodations | 5-star luxury (Four Seasons Nevis, Park Hyatt St. Kitts) or boutique hotels and inns |
Best beach | Pinney's Beach on Nevis - long stretch of golden sand shaded by palm trees |
We spent Spring Break 2024 on St. Kitts/Nevis, and we LOVED it! So peaceful, so picturesque, so chill. If you want to get away from it all, this is the place!
St. Kitts/Nevis: Watersports, hiking, history, Hamilton, unspoiled/uncrowded
Best Off-The-Beaten-Path Destinations in the Caribbean
These islands are beautiful but out-of-the-way, which means your travel days will be longer and more difficult. In addition, the islands are typically less developed, which means fewer options for accommodations, dining, and entertainment. Some, but not all, offer peaceful seclusion as reward for your longer travel days.
Anguilla
British Virgin Islands
Curacao
Bonaire
Martinique
St. Barts
St. Maarten/St. Martin
Anguilla
ANGUILLA | |
Claim to fame | 33 beautiful beaches (many among the world's best), luxury resorts, culinary and music scene |
Ease getting there | No non-stops from the U.S. Easiest to fly to St. Maarten (SXM) - but limited options -and then ferry to Anguilla |
Trip from IND | 2 legs (1 stop) to SXM, transfer to ferry port, ferry to Anguilla. Estimate 9-10 hour travel day. |
Ease once in destination | Small island but roads can be rough, drive on the left |
Accommodations | Need big budget if you want luxury. Four Seasons, Cap Juluca, Malliouhana, Zemi Beach House, and Aurora Anguilla are top resorts. Villa properties available. |
Best beach | Shoal Bay - 2 miles of white sand, crystal clear water, and family-friendly surf |
We spent Spring Break 2026 on Anguilla and split our stay between Aurora and Zemi Beach House. I also toured Four Seasons and Cap Juluca. We will be back! The water, beaches, food, and chill vibe are not to be missed! The experience was worth a longer travel day.
Anguilla: Picture-perfect beaches and water, but expect high prices and longer travel days
British Virgin Islands
BRITISH VIRGIN ISLANDS | |
Claim to fame | Sailing, diving/snorkeling, The Baths, island hopping, laid back luxury |
Ease getting there | No non-stops from U.S. to Tortola (EIS) or Virgin Gorda (VIJ). Tortola more options than Virgin Gorda. Best to fly to St Thomas or San Juan and ferry or small plane to destination |
Trip from IND | 3 legs (2 stops) or 2 legs (1 stop) to St. Thomas plus ferry |
Ease once in destination | Can rent a car to explore but drive on left. Ferry between Virgin Gorda and Tortola. |
Accommodations | Limited options - mostly small luxury resorts or condos Tortola: more choices for dining, shopping, resorts Virgin Gorda: Better resorts |
Best beach | The Baths - small beach with excellent snorkeling in and around the huge boulders. But gets crowded with daytrippers. |
British Virgin Islands: Sailing, island-hopping, diving, The Baths, can day-trip from USVI.
Curacao
CURACAO | |
Claim to fame | Diving - coral walls full of marine life, colorful architecture, City of Willemsted (UNESCO World Heritage Site), 38 beaches, sunny and dry year-round (outside hurricane belt) |
Ease getting there | Limited non-stops from U.S. to CUR |
Trip from IND | 2 legs (1 stop), around 7-8 hours |
Ease once in destination | Free shuttles into Willemsted or cheap taxi. 4WD needed to explore whole island. |
Accommodations | Limited All-Inclusive resorts (Sandals, Dreams). Beyond that, mostly villas. |
Best beach | Playa Portomari - white sand, double reef for snorkeling/diving |
Curacao: No hurricanes, sunny and dry year-round, diving, colorful architecture, a few all-inclusive resorts plus condo/villas, longer travel time/more limited flight options
Bonaire
BONAIRE | |
Claim to fame | Shore diving and snorkeling (near perfect visibility), peaceful, flamingoes, outside hurricane belt |
Ease getting there | Very LIMITED non-stops from U.S. to BON |
Trip from IND | 2 legs (1 stop) limited options, 7-9 hours |
Ease once in destination | Taxis and rental cars cheap and easy |
Accommodations | Limited options, more rustic accommodations |
Best beach | Sorobon Beach - white sand, shallow clear water, great for kitesurfers when windy |
Bonaire: Near-perfect visibility for diving, sunny and dry year-round (no hurricanes), but difficult to get to
Martinique
MARTINIQUE | |
Claim to fame | French culture, culinary, beaches/water, pricey |
Ease getting there | Only 1 non-stop a day from Miami. Pricey. |
Trip from IND | 2 legs (1 stop) if flight is available. Around 8 hours. |
Ease once in destination | Rent a car for a day or two to explore. Roads are good but are not lit at night. Heavy traffic during rush hour. |
Accommodations | Only boutique hotels, inns, villas |
Best beach | Josephine's Baths - white sandbars |
Martinique: French culture, culinary scene, beautiful beaches, pricey and difficult travel
St. Barts
ST. BARTHELEMY | (ST. BARTH, ST. BARTS) |
Claim to fame | The "scene", style, culinary, luxury shopping, watersports |
Ease getting there | Island is only 8 square miles so no international airport Fly to St. Maarten (SXM) and ferry to St. Barts |
Trip from IND | 2 legs (1 stop) to SXM, transfer to ferry port, ferry to St. Barts. Estimate 9-10 hour travel day. |
Ease once in destination | Taxis aren't cheap or plentiful, but renting a car can be tricky due to narrow, steep, and often unmarked roads |
Accommodations | Small luxury (pricey) hotels and villas |
Best beach | Saline Beach - unspoiled beachfront on the south shore with salt pond nearby |
St. Barts: The "scene", luxury shopping, yachts, very small island that's difficult to get to
St. Martin
ST. MAARTEN/ST. MARTIN | |
Claim to fame | European dual nation: southern half is French (St. Martin), northern half is Dutch (St. Maarten) but open borders. Culinary hot spot, shopping, nightlife, 37 beaches, busy cruise port |
Ease getting there | Few non-stops from U.S. to SXM |
Trip from IND | 2 legs (1 stop) but limited flights, around 7-8 hours |
Ease once in destination | Explore with rental car but traffic can be an issue |
Accommodations | Larger resorts and timeshares in St. Maarten, more intimate resorts/inns in St. Martin. |
Best beach | Mullet Bay - mile long white sand with calm clear water. Good for surfing when it's windy. |
St. Maarten/St Martin: Half Dutch, half French with open borders so you can experience two cultures. Shopping, nightlife, busy cruise port
Caribbean: When To Go
When the weather is bad in the U.S., that's high season in the Caribbean. Prices and crowds will be highest in winter (mid-December through mid-April), with the Christmas holidays being the highest. If you want to travel during high season, you should book 12 months out for the best prices and availability.
The only true low season in the Caribbean is hurricane season - August through October - when travel is risky. Even if there's no hurricanes, the weather can be hot, muggy, and rainy. September is considered the peak of hurricane season, but on my trip to Turks & Caicos one September, the weather was beautiful.
Some Caribbean destinations are less risky than others, especially the ABC Islands (Aruba, Bonaire, Curacao), which are so far south, they're outside the hurricane belt. If you want to save money and travel during low season, talk to your Travel Advisor about the less risky destinations and purchase travel protection!
Beautiful Beaches vs. Natural Diversity?
Can you have both extraordinarily beautiful beaches and clear water plus diverse landscapes like mountains and rainforests? Unfortunately, not really. For the most part, the best white sand beaches and clearest water are on the flattest islands - Turks & Caicos, Anguilla, Antigua, Aruba, the Bahamas, the Caymans. So if you're happiest on the beach or in the water, these islands are great choices!
If you're looking for diverse landscapes (mountains, rainforests, waterfalls) and more to do than just lie on the beach, mountainous and volcanic islands may be more your speed. But know the beaches will be more golden in color (or even black sand), and the water won't be clear turquoise everywhere you look. Costa Rica, Puerto Rico, Jamaica, St. Lucia, St. Kitts/Nevis, Dominican Republic, and Belize all have natural diversity to offer you adventures and sightseeing beyond the beach.
Of course, not every destination fits into a specific box, so you'll find some islands with beautiful white sand beaches as well as varied landscapes, like Barbados and the Virgin Islands.
Are you looking for clear blue water and white sand beaches or dramatic landscapes and lots of adventure?
A Final Note About Sargassum
If you've never dealt with sargassum on your vacation, count yourself lucky. Sargassum is large brown seaweed that floats in island-like masses and never attaches to the sea floor. It's an essential fish habitat, and up until the last decade, sargassum wasn't much of an issue. However, in 2011, unprecedented quantities began inundating coastal areas, wrecking havoc on tourism as well as producing toxicities for both sea life and humans. Scientists say the inundation is likely a result of climate change and pollution from fertilizers and sewage waste. 2026 has been a record year for sargassum.
Unfortunately, the only sure thing about sargassum is its unpredictability. Some scientists say the season runs from April-August while others say it extends through December. In recent years, the season started early, which meant sargassum issues almost year-round. The resorts do their best to keep the beaches clear, including erecting barriers out in the water.
Some areas have less risk of sargassum because they're naturally protected - for example, La Romana in the Dominican Republic is shielded whereas Punta Cana is not - so it's best to work with a travel advisor who is knowledgeable about which areas pose less risk. But know there are no guarantees when it comes to Mother Nature. Conditions can change from day to day and even hour to hour. So if the conditions are bad one day, book an excursion and hope for less sargassum the next!
Sargassum on the beach and in the water. Daily sargassum report for Riviera Maya, Mexico.
Heather Vergara is a former PepsiCo marketing executive who left the corporate world to be a Mom and never found her way back. Instead, she focused on her passion for travel and adventure and created Show Them the World, a travel concierge service for busy families longing to reconnect and see the world together. She's now a Top Producer and Multi-Million Dollar Advisor with Gifted Travel Network, a boutique luxury host agency partnered with Virtuoso. Heather has helped hundreds of families experience Hawaii, Alaska, Costa Rica, the Caribbean, Italy, France, Greece, England, Ireland, Croatia, Spain, Portugal, Switzerland, Iceland, Africa, Australia, New Zealand, the Maldives, National Parks, and more to come!
Heather has an MBA in marketing from Indiana University, a Digital Marketing Executive Education certificate from Columbia University, and a BA in Journalism from the University of North Carolina at Chapel Hill. She lives with her husband, two kids, and two furry dogs in Zionsville, Indiana.