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The BEST and WORST of the Caribbean

Based on my personal experience, I will outline for you the BEST and the WORST of the Caribbean. You could ask other people, who have had completely different experiences, who may give different responses. Below are my opinions, as unbiased as I can be, objectively evaluating each Caribbean destination on the following factors: Value for the Money, Walkability, Accommodations, Safety, and Other out of a total of 5 stars.

I did not evaluate these Caribbean destinations based on natural beauty or beaches. Every Caribbean island will afford you warm turquoise waters, sandy beaches, palm trees, and warm sun.

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As a whole, the Caribbean is a fantastic vacation destination. If you are looking for a tropical paradise, the Caribbean will deliver. Especially if you live in the U.S. Buying a flight for under $500 and hopping on a plane for just a few short hours to get to the Caribbean really can’t be beat.

Read on for my thoughts on each Caribbean destination, listed in order of Best to Worst; St. Lucia, Dominican Republic, Puerto Rico, Riviera Maya, Playa del Carmen, Cancun, The Bahamas, and Jamaica.

St. Lucia

best and worst caribbean leah little travel & fashion St Lucia

I traveled to St. Lucia in July 2013 for my honeymoon. St. Lucia is my favorite Caribbean destination by far. Our honeymoon was so magical, that my husband and I have not been back for fear of tainting our perfect memory of this incredible island.

Value for the Money

St. Lucia’s greatest flaw is value for the money. It is a comparatively expensive Caribbean destination. Flights are expensive since it is quite far south, and because the airport is small, they only take in a few flights each day. Once on the island, food and drinks were reasonably priced. Like any place, the more touristy a restaurant, the more expensive. St. Lucia also has fairly expensive accommodations.


St. Lucia gets a good grade for walkability. By walkability, I mean the ability to leave one’s resort and explore independently. We spent every night leaving our resort property and walking around, exploring the island. We found many hidden gems of bars and restaurants where we made friends with other travelers and with locals. We even spent one night at a pop-up outdoor karaoke bar!


Like mentioned above, the accommodations in St. Lucia are more expensive than other destinations. The good news is that there is a wide price range available. You can choose a smaller boutique hotel and save money that way. We stayed at a small boutique hotel and purchased an all-inclusive package through Groupon. The drinks were superb! All these years later I am still dreaming of the fresh fruit smoothies and rum punch. Or, you can go all out and stay in ultra luxury, like the famous Jade Mountain.


St. Lucia again gets excellent marks for safety. We never felt unsafe, even while walking down dark alleys at night (although I still would never recommend that anywhere). Every person we encountered was friendly and welcoming, in a genuine manner. One night we attended a street party full of locals and tourists, dancing to music played on speakers by DJs, with folding tables full of crazy cheap drinks. It was crowded, noisy, and so much fun. We never felt unsafe the entire time.


The moment you leave the open air airport, taxis vie for your business. We were greeted by a driver named Patrick, who took our bags and gave us St. Lucian rum punch for the ride to our hotel. During the 45 minute drive, Patrick told us interesting history about the island, stopped at lookout points and took our picture, stopped at a roadside stand selling cheese and bread, and bought us St. Lucian beer at a local bar. He refused to allow us to pay for anything beyond the cab fare. He was just one example of how incredible the local people are in St. Lucia. They really made this vacation stand out above all others.

Dominican Republic

best and worst caribbean leah little travel & fashion dominican republic

Value for Money

The Dominican Republic is the number one value for your money in the Caribbean. It continues to blow my mind how much you can get at a resort in the D.R. for just a few hundred dollars per night. There are all-inclusive resorts (meaning all food and drinks are covered), round trip transfers from the airport, with multiple pools and private beaches for around $200 per night. I mean, I can barely get a night at the Red Roof Inn in the suburbs of Michigan for under $100. As always, there is a huge price range. If you want extra bells and whistles at a budget price, the Dominican Republic is your Caribbean go-to.


The Dominican Republic is not good for walkability. The vast majority of your time there will be at your resort. There are no large metropolitan areas for tourists to shop, dine, or explore. If you feel cooped up staying on your resort property, you can always go on an excursion with a reputable tour guide. Always check tripadvisor first!


The Dominican Republic scores high for its incredible accommodations. The sheer number of resort options in the Dominican Republic can even be overwhelming. There are three main areas for resorts; Punta Cana, Puerto Plata, and La Romana. We always stay in Punta Cana because it is closest to the airport. I suggest deciding on a nightly price range and which of the three locations you want to help narrow down your options.


I score the Dominican Republic’s safety to be in the middle range. As long as you remain in labeled taxis, on your resort, or with verified tour guides, you should have no safety concerns. However, safety is significantly more of an issue (mostly theft/robbery) if you venture out of these bounds on your own.

Puerto Rico

best and worst caribbean leah little travel & fashion puerto rico infinity pool
The infinity pool at the Condado Vanderbilt Hotel

Value for the Money

Puerto Rico is in the mid range for value. San Juan, the capital, will be the most expensive for accommodations, food, and activities. If you can find more local bars and restaurants, you will likely save money and get better quality!


I cannot speak for all of Puerto Rico, but San Juan has excellent walkability. The city is bustling and vibrant, with anything you could want. You can easily spend all day walking around town exploring. Be sure to visit Old San Juan for some cool, vintage vibes!

best and worst caribbean leah little travel & fashion old san juan


The accommodations in Puerto Rico are good, but much fewer options than you’d find in some other Caribbean destinations. Some structures in Puerto Rico were damaged in the hurricane in 2016, however most of this has been repaired. The benefit of the rebuilding is that you will find newer structures than before. If you are staying in San Juan and would enjoy a spectacular view of the ocean, I recommend the Condado Vanderbilt Hotel.


Puerto Rico overall is a safe destination for tourists. However, one night my husband and I went out dancing in an area known for bars and nightclubs where both tourists and locals go. The scene was fun until about midnight. After that time, my husband felt the bouncer check his back pocket for his wallet, so he moved it to his front pocket. 10 or so minutes later, he felt someone try and lift it from his back pocket.

The club was starting to get extremely rowdy and crowded, so we decided to leave. We could not find a marked taxi cab and kept asking around, while people directed us down dark alleys and shady highway overpasses. In all my travels, this is the only time I felt truly afraid and worked not to panic.

Eventually, we found a labeled taxi that returned us to our hotel and nothing bad happened. This is of course only one specific incident that should be taken as such, but it is worth noting.


Puerto Rico is an easy travel destination for U.S. Citizens. Spanish is the official language of Puerto Rico, however many people, especially in San Juan speak English. Additionally, since Puerto Rico is a U.S. Territory, you can easily use U.S. currency and you do not need a passport!


best and worst caribbean leah little travel & fashion mexico

I am going to rate Mexico a little differently, since I have experience at 3 separate areas in Mexico that border the Caribbean; Riviera Maya, Cancun, and Playa del Carmen. Read each section for specifics related to each of these cities.

Value for the Money

Mexico rates highly for cost effectiveness. Airfare from the U.S. is extremely affordable, as are the various options for accommodations, dining, and entertainment. Costs have continued to drop considerably since recent safety concerns have arisen (see Safety section below).


Mexico’s walkability varies greatly depending on the specific location. The best place I have experienced for walkability is Playa del Carmen. There is an entire shopping/dining/entertainment district along 5th Avenue. Second for walkability would be downtown Cancun. There are bars, clubs, and restaurants that remind me of a mini Vegas. I was last in Cancun in 2016, and although I enjoyed it, I felt very uncomfortable with dozens of people offering me drugs and dozens of police officers carrying machine guns. This was before the upswing in violence in this area, so I imagine it has only worsened. Finally, Riviera Maya rates low for walkability. This area is similar to the Dominic Republic in that you are restricted to resort properties only.


I rate Mexico 5 stars for accommodations for the sheer volume of options available. There is something available at any price point. From shared room hostels, to AirBnB condos, to family-friendly hotels, to ultra luxury resorts. I stayed at a Generations resort in Riviera Maya, and absolutely loved this resort!


I hate to rate Mexico poorly on safety, but unfortunately it is the current reality. I hope this changes soon, as Mexico is a beautiful country with beautiful nature, fascinating history, and a vibrant culture. The drug wars in this country have seen huge escalations in violence across the country, now including in tourist areas. The U.S. State Department currently has a travel warning for all of Mexico set at a level 2, which means Use Increased Caution. Certain Mexican states are at levels 3 and 4, which mean Reconsider Travel and Do Not Travel, respectively.

My husband and I had a trip planned to Cancun/Playa del Carmen, however we reconsidered after alarming reports of violence on the resort beaches came out. We lost a significant amount of money cancelling this vacation, however the risk was not worth the money.

The Bahamas

best and worst caribbean leah little travel & fashion jamaica

Value for the Money

The Bahamas is one of the more expensive Caribbean destinations. Flights are fairly cheap from the U.S., however everything else once you get to the island is marked up. Since Nassau is one of the busiest cruise ship ports in the world, shopping, food, drinks, and excursions are fairly pricey.


I rate The Bahamas highly in walkability. Downtown Nassau is a bustling cruise ship port with lots of attractions. There are plenty of people walking around, dining, and shopping. This always felt safe, with minimal sales people pushing for your attention.


The Bahamas has one of the longest established tourism economies in the Caribbean, which means it started building accommodations before other Caribbean destinations. Many of the resorts are older and outdated. I have a random self-imposed rule that I will not stay anywhere that has a floral bedspread. If you want to stay in a resort in the Bahamas without floral bedspreads, and with updated d├ęcor and accommodations, then you need to spend a decent amount of money.


The Bahamas always felt safe while on the resort and while walking around downtown Nassau. Granted, we did not walk around off property at night, so I cannot attest to the vibe at that time. Unfortunately, the U.S. State Department recently issued a new security warning, moving the Bahamas to Level 2, Exercise Increased Caution for an increase in sexual assaults and theft.


Downtown Nassau has the best shopping of any Caribbean island. Particularly if you are looking for jewelry or luxury goods, it is worth a trip. Jewelry is heavily discounted and you do not pay sales tax on any items. I bought this ring with marquis shaped opal, white sapphires, and white gold plated band for $235 (haggled down from $290)!


best and worst caribbean leah little travel & fashion jamaica riu palace

Value for the Money

Jamaica is right around the middle of the pack when it comes to cost. Flights, accommodations, and excursions are all reasonably priced, but not exactly a steal.


Jamaica felt fairly unsafe everywhere we traveled, with the exception of being directly on our resort, so we were not able to walk around and explore much. There was even a clear indication where our resort property line ended, because groups of men stood at the property line aggressively selling to visitors.

We ventured to downtown Montego Bay one afternoon and experienced more aggressive salespeople there. It was not a pleasant experience, and elected to return to our resort early that afternoon.


Accommodations were plentiful to choose from, and represented a wide range of price points. There are various chain resorts too, in case you are brand loyal. We stayed at the Adults-Only Riu Palace in Montego Bay.


I was not aware of the sexual violence against tourists when I visited Jamaica several years ago, however now that I know, I would not return, nor would I recommend Jamaica as a destination for women. As a frequent tourist to Caribbean destinations, I was always told (and believed) that as long as you stay on the resort you will be safe. I always felt secure while on the resort property and while interacting with staff.

Recently, Jamaica has seen a significant increase of rapes and sexual assaults against female tourists by resort staff. The pattern is for the assault to occur on the woman’s last day of vacation. The perpetrators are betting on the fact that the survivors will not stick around to press charges, and will just go home. This has happened in many resorts, including the well known Sandals. In addition to this disturbing trend, Jamaica is inhospitable to the LGBTQ population.


In summary, each destination has been scored out of a total of 20 points. We have:

  1. St. Lucia with 15 points
  2. The Dominican Republic with 13 points
  3. Puerto Rico with 12 points
  4. Mexico with 12 points
  5. The Bahamas with 11 points
  6. Jamaica with 8 points

Leah Little has a full time job as a social worker, and has managed to travel the world while wearing beautiful clothes by knowing how to score deals in travel and fashion. Learn more about her journey here.  Join the Leah Little Travel and Fashion tribe by entering your email to subscribe to be the first to learn new ways to enjoy the best in travel and fashion for less. Say hi and send her a message! Contact

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