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The Caribbean's Most Overrated Cities and Towns

Undoubtedly, the Caribbean is one of the most beautiful places on Earth, but some spots are overhyped and overrun by tourists and families. You'll pay more than you need to for excursions, wait in lines for bland food, and be at risk of a mediocre experience. There are countless Caribbean towns with pristine beaches and the same tropical vibes, so don't settle. A vacation should be an escape without frustrations, clichés, and screaming children. We know you want a unique experience in the Caribbean, so skip these famous resort destinations and major cities that are guilty of being overrated.


01 Reassess Nassau's Bahamian allure

Tourists from cruise walking the streets of Nassau Juan Silva / Getty Images

Nassau is the Bahamas' largest city and the capital, so it's no surprise it's an overrated hotspot. Margaritaville is one of the many resorts there, with a bowling alley, movie theater, and American-inspired eateries, all things you can find in the United States. Millions of tourists come through Nassau on cruise ships, eager to be in the Bahamas but not to get a real taste of the culture. Less frequented islands, like Eleuthera, showcase the natural beauty of the Bahamas without Nassau's crowds.


02 Debunk the hype of Dominican Republic's Punta Cana

crowd on a beach at Punta cana lena_serditova / Getty Images

If you know anyone who's visited the Dominican Republic, they were probably in Punta Cana. Across the island's stunning landscape are commercial resorts blocked off from Dominican communities, meaning travelers miss out on truly exploring the country they're visiting and eating Dominican food. Although the resorts are beautiful, they'll surely be overcrowded since everyone's sequestered into one area of the island.


03 Question Montego Bay, Jamaica's charm

crowd at Montego Bay Holger Leue / Getty Images

Montego Bay is on Jamaica's northwest coast and is one of the island's most popular tourist destinations. Jamaica is rich in culture, but an all-inclusive resort can dilute that. If you're excited to see incredible marine life, you may have to rethink visiting Montego Bay. Ocean creatures have migrated farther away from the coast due to the number of people crowding the beaches and snorkels in the area.


04 Downplay Cancun's reputation

crowd at Xcaret g01xm / Getty Images

If you want to go to Cancun, make sure you have plenty of money to spare. Cancun is a city in Mexico with packed resorts and nightlife activities. Due to its popularity, the prices are inflated. Excursions like scuba diving and ziplining will be more expensive in Cancun than in other parts of Mexico. Although you'll still have a great experience, why pay more than you need to?


05 Challenge Maho, Sint Maarten's appeal

sint maarten air view majaiva / Getty Images

Maho, on the Dutch side of Sint Maarten, may seem like an ideal Caribbean getaway, but you should consider a few things before planning a vacation there. The city, and the island, are incredibly commercialized, so it's overcrowded and expensive. A lot of traffic also makes it difficult to get around efficiently. Some find that the casino and topless bars detract from the island's beauty, but everyone has a different perspective.


06 Rethink Bridgetown's draw

Promenade at marina of Bridgetown, Barbados. NAPA74 / Getty Images

Bridgetown, Barbados, is a popular port for major cruise lines, meaning there will always be a lot of tourists in the area. It's easy to understand why everyone would want to visit since it has incredible beaches and fascinating history; however, you might find the costs overpriced for your ideal Caribbean vacation. Bridgetown has a high cost of living, so it isn't budget-friendly.


07 Doubt San Juan Puerto Rico's vibrance

people standing in downtown San Juan sanniely / Getty Images

San Juan is the capital of Puerto Rico, and although it's a hub for culture and history, you may want to avoid it. San Juan is a kid-friendly and commercialized city with resorts and activities catering to young families, which may be a perk for some, but if you're looking for a Caribbean getaway that's more secluded and will guarantee some peaceful relaxation, you may want to skip San Juan.


08 Disagree with the fame of Cayman Islands' George Town

George Town waterfront at sunset, Grand Cayman, Cayman Islands Philippe TURPIN / Getty Images

George Town is another port city that brings in many cruises and tourists seeking out the vibrancy of the Cayman Islands. Unfortunately, George Town has a smaller coastline than some islands, so these tourists overcrowd the beaches. The influx of people also allows shops, restaurants, and resorts to inflate prices. If you'd prefer a Caribbean vacation where you don't have to fight for a spot on the sand and wait in lines, maybe find somewhere other than George Town.


09 Reevaluate Havana's nostalgia

old vintage car in the streets of old havanna golero / Getty Images

Havana, Cuba, has become increasingly popular due to the lifted travel ban in 2016. For some, visiting Havana is like going back in time, but this nostalgia has some clear cons. Cuba is a cash-only economy, so you'll need a lot of green to convert and cover expenses, and the government controls many hotels, so they're overpriced.


10 Scrutinize Kingstown's allure

City center of caribbean town Kingstown, Saint Vincent and the Grenadines Vadim_Nefedov / Getty Images

Kingstown is the main port in Saint Vincent and the Grenadines, so once again, we have a place where cruise ships are constantly coming through, which brings a lot of people and a lot of costs. One of the main attractions is the Market Square. It can be very difficult to enjoy when you're trying to squeeze through a crowd and fight your way to the front to see what the vendors have to offer.


11 Discredit Charlotte Amalie's charm

street in Charlotte Amalie Walter Bibikow / Getty Images

Charlotte Amalie is one of the most popular cities to visit in the U.S. Virgin Islands because it's the capital and a major port on St. Thomas. Even though it may seem quaint due to its size, plenty of other tourists have the same notion. This leads to high congestion in the streets and shops, making it harder to enjoy your experience. There are fewer crowds on the neighboring St. Croix island which is also a part of the U.S. Virgin Islands.


12 Question the appeal of Castries in Saint Lucia

Wide shot of couple relaxing in lounge chairs by pool at luxury hotel Thomas Barwick / Getty Images

Castries in Saint Lucia is a huge honeymoon destination. That should tell you all you need to know. It's a beautiful hotspot, but it's filled with cliché spas, restaurants, and amenities that you can find anywhere in the U.S. It also lacks adventure-seeking excursions because you're expected to remain within the all-inclusive resort. Traveling to other areas is both expensive and challenging.


13 Reconsider the reputation of Bermuda's Hamilton

Front Street, Hamilton, Bermuda, with traffic and pedestrians. wwing / Getty Images

Bermuda's capital city, Hamilton, was once an underrated vacation spot, but it's lost some of its charm in recent years. Countless tourists discovered that Hamilton was a unique place to visit in the Caribbean, and this has influenced local businesses to cater to those tourists. It's now a very commercial city, so if you want to get off the beaten path, this is not the place.


14 Challenge Oranjestad's vibrance

Colorful Souvenir Stands in Downtown Oranjestad in Aruba Aaron Hawkins / Getty Images

Oranjestad is a resort-centric city in Aruba. Although resorts can be a great part of your vacation package, the ones here are highly Americanized. Aruba has a wonderful culture to offer, but you won't find it in Oranjestad. If you leave the downtown area, you'll find a more enriching cultural experience where you can mingle with the locals and try the cuisine.


15 Downplay Gustavia, St. Barts' prestige

Harbor view of Gustavia, St. Barts (Saint Barthelemy) NAPA74 / Getty Images

Gustavia is the affluent capital city of Saint Barthélemy, a.k.a. St. Barts. Most people consider St. Barts very exclusive, and that's not a myth. It is extremely expensive and filled with yachts and villas that aren't meant for the general public. If you're looking for an exciting and adventure-filled vacation, Gustavia may not be the place for you. There are more affordable cities that are less exclusive but still have the same beautiful beaches.


16 The deceptive allure of Freeport, Bahamas

Aerial view of Freeport Port Lucaya on Grand Bahama Island

Freeport, on the island of Grand Bahama, often lures tourists with its promise of idyllic beaches and bustling markets. However, visitors quickly discover that the city's charm is overshadowed by its commercialization. The once quaint town is now filled with generic resorts and shopping centers that could be found anywhere in the world, leaving little room for authentic Bahamian culture.


17 Overpriced luxury in Philipsburg, St. Maarten

Philipsburg, Sint Maarten - November 16 2018: Philipsburg, Sint Maarten. Blue Bitch Restaurant, other shops & buildings Caribbean island coast. Tourist couple holding hands walk on paved street. Debbie Ann Powell /

Philipsburg, the capital of Dutch St. Maarten, is famed for its duty-free shopping and luxury boutiques. But this shopping paradise comes with a hefty price tag. The city's main streets are lined with high-end stores that cater to cruise ship crowds, offering little in terms of unique local products. The inflated prices and tourist-centric atmosphere detract from the genuine Caribbean experience.


18 The crowded shores of Playa del Carmen, Mexico

Playa Del Carmen Quintana Roo Mexico 07. May 2023 Tourist

While technically not in the Caribbean, Playa del Carmen's proximity to it often includes it in Caribbean travel plans. Known for its vibrant nightlife and stunning beaches, this destination is now a victim of its own popularity. The beaches are overcrowded, the once charming town is now overrun with tourists, and the local culture is often overshadowed by commercial tourist traps.


19 The lost charm of Willemstad, Curaçao

Sunny day in Willemstad, Curacao

Willemstad, with its colorful Dutch architecture, is a UNESCO World Heritage site. However, the influx of tourists and cruise ships has transformed this historic city into a crowded and overpriced destination. The authentic Curaçaoan lifestyle is hard to find among the throngs of souvenir shops and chain restaurants that cater to short-term visitors.


20 The overhyped beaches of Varadero, Cuba

VARADERO,CUBA - JUNE 3,2023 : Tourists enjoy the beautiful beach of Varadero in Cuba on a sunny summer day Kamira /

Varadero is often celebrated for its long stretches of sandy beaches and all-inclusive resorts. But this Cuban tourist hotspot is far from the paradise it's made out to be. The beaches, while beautiful, are packed with tourists and lined with resorts that offer little in terms of Cuban culture. The area is heavily commercialized, and visitors often miss out on the rich history and vibrant life found in other parts of Cuba.


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