While some people daydream about spending weeks island hopping in the Caribbean, it was definitely not at the top of my list of places to go. I’m not a huge fan of beaches or hot weather. As a full-time budget traveler, I’m also not a huge fan of spending a ton of money on hotel rooms or transport. However, I’m happy to say that I was pleasantly surprised by how many budget-friendly activities and accommodations there were there.
Four Weeks Island Hopping in the Caribbean
Below is a breakdown of how I spent four weeks traveling through the Caribbean on a budget. I did a combination of flights, ferries, and a five-day cruise to get between the islands. I had already been to Antigua, Jamaica, and Cuba before this trip so I didn’t revisit them. Instead, I focused on getting to the remaining islands of St. Vincent, Grenada, Martinique, Guadalupe, St. Lucia, Dominica, St. Kitts, St. Martin, and Puerto Rico. Many people start their island hopping from Puerto Rico but I did it in the opposite direction since I was starting from Guyana.
I have included the accommodation I stayed in, all of which was under $50 per night except San Juan which cost $55 per night for a week-long stay. All of them provided great value for money and I had good experiences with each one. I have included the Airbnb and Booking.com links to help make your own trip planning a little bit easier!
Day 1 & 2 – St. Lucia
Highlights: Sugar Beach and the Pitons, Sulphur Springs
Accommodation: Amazing Beach View Apartments
I started off my Caribbean adventure by flying from Georgetown, Guyana to Castries, St. Lucia via a one-night layover in Barbados. I had originally planned on exploring the island later on in my trip by taking a 7-hour ferry there from Dominica. However, after reading traveler reviews
I arrived in St Lucia early in the morning and immediately hit the ground running. I knew that there was a lot of stuff that I wanted to see and do within the next two days and that I needed to be very careful with planning and timing. So naturally, the first thing I did was stop at the beach bar that is located directly across the street from the airport. Yes, you read that right. You cross the two-lane street from the tiny airport and you have a handful of beach bars nestled along a nice beach. I knew that this was going to be a good place!
Over the next two days, I did a land and sea tour that drove through the capital city of Castries down to Soufriere, arguably the heart of St. Lucia’s tourism hotspots. Just outside of this small town that was once the capital of St. Lucia, you’ll find Sugar Beach and the striking pitons that bookend it, Sulphur Springs with its geothermal activity and mineral baths, and St. Lucia’s botanical gardens.
It was a great tour and at $115, I think it was definitely worth the money. I had thought about renting a car and exploring the island myself but a few things stopped me from doing it. The first was that the rental cars cost close to $60 per day and I would have needed it for two days. The second was that there was limited budget accommodation located near Soufriere. Everything reasonable (less than $50) seemed to up around Castries which would have meant either driving a lot of extra miles to be able to stay in an inexpensive place or spending more money on gas (which is $7 a gallon there) or paying way too much money for a hotel. Plus, I would have had to drive on some windy, hilly roads which wasn’t very appealing!
I also went up to Pigeon Island which is located in the northern part of the island, less than an hour by public bus from Castries. Now a lovely park, Pigeon Island was once the location of a British fort. Not much remains of the fort but it was still interesting to see the ruins. The walk up to the fort was also relatively short but you get some amazing views up there. Although it was almost closing time when I was there, I also decided to rush up to Signal Hill where I get even better views. The park cost $10 to enter which was a little steep considering I was only there for an hour but it was still worth the money.
After around 48 hours on the island, I boarded an early morning, 40-minute flight back to Barbados where I would be boarding a cruise at noon.
Travel tip: For some reason, I had it in my mind that most of the Caribbean islands were relatively flat. I was pleasantly surprised to find that St Lucia is really freaking hilly. And this could end up having a bigger impact on your stay here than you would originally think, especially if you are planning on taking public transport and then walking afterward. Although the buses are frequent along the main roads, walking from the bus stop to your intended tourist attraction could end up being very long and exhausting.
Endearing cultural anecdote: St. Lucians use the street that runs between the airport and the beach as a morning walking track. As I made my way to the airport at 5:45 a.m., I was being passed by older ladies in exercise clothes.
Day 3 – Barbados & Embarking on a Caribbean Cruise
Highlight: Snorkeling above shipwrecks
Accommodation: Cozy Corner
I got an early morning flight from St Lucia to Barbados which gave me just enough time to do a very quick paddle board and snorkel at Pebbles Beach. This beach is famous for its shipwrecks located just off the shoreline that you can snorkel or dive to. I was debating on trying to jump on one of the short snorkel tours but then realized that I could rent a paddle board and a snorkel for the same price. I love both these activities so that was an easy winner.
Snorkeling and paddle boarding together was a little bit harder than I thought as I couldn’t figure out how to keep the board from bothering other people while I snorkeled. In the end, I ended up holding it next to me while I swam with one arm. This kind of worked and I got to see huge schools of fish, about five or six enormous sting rays, and what I swear was a reef shark. After about an hour and a half, I paddled back to the rental place to hand everything in and realized that I had lost the goggles somewhere along the way. I ended up paying $45 for the rental and to replace the goggles that I lost. Considering how expensive paddle board rentals are in the US, I still think I got a good deal!
After stopping for my morning exercise, I headed over to the cruise ship where I was able to check in around noon and then spent the rest of the day working. I emerged a few times to explore the ship and to eat but was a bit overwhelmed by the sheer amount of people on board so I decided hiding out in my cabin was a better way to spend the evening!
The cruise finally left Bridgetown port and we were on our way!
Day 4 – Sail Day
Accommodation: Cruise
I spent the entire next day on board the cruise ship as it made its way to St. Vincents. I didn’t really want to pay the $140 to access the Internet on the ship so I decided to take the day off work and just relax instead. I slept in until 10:30, had a relaxing breakfast, went hard out at the gym, took a dip in one of the many swimming pools, and “data mined” the cruise excursion options to find the best things to do on each island. I booked the cruise at a heavily discounted rate of $260 including the port fees so I assumed that the cruise line was desperately trying to sell empty rooms. Boy was I wrong. The amount of people that had overwhelmed me the day before was even worse since everyone was on the ship at the same time. Everywhere you went there were tons of people. And all of them seemed to be having a great time except for me.
Day 5 – St. Vincent & the Grenadines
Highlight: Kayaking in Buccament Bay
Accommodation: Cruise
We arrived at Kingstown, St. Vincent early the next morning. I got off the boat, did a quick stroll through Kingstown and headed up to the botanical gardens located on the edge of town. These gardens are considered to be some of the oldest botanical gardens in the Western Hemisphere. Since I love botanical gardens AND I love old things, I knew that I had to go. The gardens, although pretty, were a bit underwhelming and I had walked through them within about 20 minutes.
From the gardens, I caught a minivan up the coastline to Willilabou Bay. This tiny bay was one of the filming locations for The Pirates of the Caribbean and there are still a handful of buildings left over from the film set plus a few prop cannons located on the waterfront. I had a celebratory beer with an almost-life-size Jack Sparrow, took a few photos, and got on the next bus to Buccament Bay.
I had never heard of Buccament Bay until I was reading the cruise excursion brochure. It seemed like every other tour went there so I decided to go check it out. While I was there, I rented a kayak and a guide and went for a paddle across the bay to a nearby bat cave. I was expecting a large cavernous space but instead, it was basically a slot canyon that was just wide enough for a kayak to slip through. Although I am normally terrified of things like that, this was so cool that I didn’t even think to be scared! I soon popped out the other side of the cave. We paddled a bit further to check out another beach and then made my way back to the starting point.
I made my way back to Kingstown, stopping at Fort Charlotte on the way. The fort was closed but you could get incredible views from the surrounding gardens so it was definitely worth the trek up to the top. I made my way back to the cruise terminal, greatly in need of some relaxation!
Day 6 – Grenada
Highlights: Fort Frederick
Accommodation: Cruise
The cruise docked early in the morning in St. George’s, Grenada and I headed off for another day of exploring. I made my way to the bus terminal where I was able to catch the #6 bus up to Grand Etang National Park. I checked out the tiny crater lake and did a 30-minute hike through the surrounding forest before grabbing another bus down to Annandale Waterfall. This tiny waterfall is a huge tourist trap and I paid $4 to look at it for 30 seconds and turn around and walk right back out again.
I was able to snag a spot in a tourist taxi that took me back down to the edge of town. From there, I walked up to Fort Matthew and Fort Frederick, two 18th century fort standing proudly above the city. The view from Fort Frederick was spectacular while Fort Matthew was just creepy enough that it was interesting yet not so creepy that I was terrified.
I headed back to the ship for another afternoon and evening of work, travel planning, and trying to avoid the 5,000 other people on my ship.
Day 7 – Martinique
Highlight: Wandering around Fort-de-France
Accommodation: Cruise
I will admit. I didn’t really have high hopes for Martinique. I had already been to a few different French islands before arriving there and I always found them to be overpriced and underwhelming. I am happy to admit that I was pleasantly surprised by Martinique in general and Fort-de-France in particular. I took a bus to visit the botanical gardens and walked around for a while, I was a little disappointed as a large part of the garden seemed to be under renovation. It was also full of other tourists from cruise ships which made me want to get out of there as fast as possible.
I caught the bus back to town and walked around a bit more before hopping on another bus to a town called Saint Pierre. Located at the northern end of the island, Saint Pierre is full of historic buildings and is very charming. I wandered along the waterfront and some of the smaller side streets. I eventually got nervous about missing the last bus back to Fort-de-France so I jumped back on the bus and made my way back to town. The hour-long drive is beautiful with sweeping views of the coastline and I almost felt like I was getting a special tour of the island.
I made it back to Fort-de-France with just enough time to mooch some free internet and drink an IPA at the historic Hotel L’Imperatrice, a historic hotel located right on the edge of the Parc La Savane. I headed back to the ship before it got too dark and spent the rest of the evening working out, eating, sleeping, and generally trying to avoid interacting with other people.
Day 8 & 9 – Disembarking from the cruise in Guadeloupe
Highlight: getting off the cruise ship, the Pointe des Chateaux, Porte d’Enfer
Accommodation: Happy Hippies House (do not recommend), Chambre Rouge in Pointe-a-Pitre
After a horrendously stressful breakfast where I watched what felt like 5,000 hyenas fighting over the breakfast buffet, I happily got off the boat, ready to explore Guadeloupe. I was eager to spend the night on dry land and hopefully get rid of the incessant heartburn that I had had for the previous 5 days. I headed straight to the airport and picked up a rental car. From there, I drove around the eastern wing of this butterfly-shaped island, stopping at the beautiful Pointe des Chateaux, a gorgeous spit at the far southeastern corner of the island.
From there, I made my way up the east coast of the island, checking out the viewpoints as I went. There is a lovely swimming spot and restaurant at the northeastern tip of the island. This is also the trailhead of a hiking trail that takes you south along the coastline. I originally wanted to do this hike and planned my day around it but couldn’t figure out how to work the transport as it is a one-way trail with no bus service. I was a bit bummed at first about this as I thought I would miss out on some of the sweeping views that I had seen pictures of when planning what I would do on the island. I didn’t need to worry though as the northern coastline is full of viewpoints that you can access via mini hiking trails as well as plenty of places where you could pull off onto the side of the road and quickly take photos.
I drove completely around the eastern side of the island and onwards toward the western half. I spent the night at the Happy Hippies Hostel which was owned by a pompous French guy who gave me bad vibes so after I got my work done the next morning, I hit the road as fast as I could. I drove around the northwestern edge of the island and then cut through the center to make my way back to Pointe-a-Pitre. I still had a little bit of time before I needed to drop the rental car off so I drove down to Sainte-Anne to have a late lunch and a quick swim in the crystal clear waters.
I dropped the car off at the airport and then took a bus back to Pointe-a-Pitre. I had booked a room in a lovely little Airbnb right by the bus stop and within walking distance to the ferry that would take me to Dominica the following morning.
Day 10 – Ferry to Dominica
I arrived at the ferry terminal in Pointe-a-Pitre at 7 a.m. for the 8 a.m. Express des Iles ferry and the line to check in was already hundreds of people long. I finally managed to get through check in and immigration by 8 and the ferry left at 8:30. After roughly two hours, we arrived in Rousseau and I headed straight to the Starline Ital Kitchen for some much-needed vegetarian food. The food choices on the ferry were dismal with a choice of cheese and ham or salami and cheese sandwiches.
After getting fortified with some tasty food, I caught the bus to Soufriere. The ride took about 30 minutes on a very windy road and I arrived feeling a little disoriented and nauseous. Luckily, a fellow tourist saw me and directed me towards my guest house. I was able to drop my bags off and relax for a little bit before heading out to explore.
Day 10 – 17 – Dominica
Highlights: Titou Gorge, Trafalgar Falls, Champagne Reef
Accommodation: Soufriere Guesthouse
I had heard a ton of great things about the country and most people I know who had traveled extensively through the Caribbean say that it’s their favorite island in the entire region. Needless to say, I was super excited to get there. And I am happy to say that it exceeded my expectations! I spent the next week having one wonderful experience after another and can confidently say that this is the best Caribbean island to spend a month in thanks to the relatively low cost of living and the ton of things to do there.
To start, Dominica is rightfully called the Nature Island. I have never seen a place so lush yet so easily accessible before. I spent all six nights that I was there at the Soufriere Guesthouse on the southwestern end of the island. My original plan was to move every couple of days but Soufriere Guesthouse was so great that I decided to stay (and there was no public transportation for three out of six of the days I was there!).
I used the guesthouse as a pseudo-base to explore the rest of the island including the top tourist sites of Titou Gorge, Trafalgar Falls, and Champagne Reef. While all of these things were impressive, the thing that I liked the most about the island was chatting with people and simply hanging out. After six days on a cruise, this was the perfect way to spend a week!
Day 17 – 20 – St. Martin
Highlight: Mero Beach, Shrimpy’s Hostel
Accommodation: Shrimpy’s Hostel
After having a 25-hour flight delay, I flew from Dominica to St. Martin. I landed around 8 p.m., picked up the rental car, and drove straight to Shrimpy’s Hostel which was going to be my home for the next three nights. I was greeted by the charismatic Austrian/South African owner and one of his Czech guests who immediately offered me a beer. I spent the rest of the evening petting his adorable pit bulls and looking out over the water. I can’t recommend this place enough for anyone who is a budget traveler. You get your own room, access to a well-equipped kitchen and clean bathrooms, and you physically can’t get any closer to the water since you are right on the edge of a canal that connects the marina to the open water.
Over the next two days, I drove completely around the island, did a three-island snorkeling trip (which I don’t really recommend), checked out the surprisingly pleasant city of Phillipsburg, and swam at the famous Maho Beach (otherwise known as the airport beach). I crossed from the French side to the Dutch side more times than I could count and ate as much ice cream and rotis as I could.
Overall, I was surprised at how much I actually liked St. Martin. It was very different than what I expected, which was that it would be a bit hoity-toity. Instead, I found it to be very welcoming. Most of the expats seemed to be either living there long-term or staying in St. Martin as part of a longer sailing trip. It made the whole environment feel much more “shorts, flip flops, and tank tops” than flowing sun dresses if you know what I mean.
Day 21 – 23 – St Kitts & Nevis
Highlight: Brimstone Fort
Accommodation: Mountain and Sea View Stay
I arrived in St. Kitts and immediately rushed to the northern end of the island to drop off my stuff so I could freely explore the islands. I took the ferry from Basseterre to Charleston, Nevis. The ferry ride was beautiful and we made our way up the coastline of St. Kitts towards Nevis, crossing a two-mile channel along the way. The views were beautiful and I was able to grab a seat outside at the front of the ferry and watched Nevis come closer and closer.
The small island of Nevis was the birthplace of Alexander Hamilton. Being a huge history nerd, I immediately walked over to the Museum of Nevis History but almost decided against going inside. Although it is situated on the location of Hamilton’s childhood home, it’s actually a replica of his house (the real one was destroyed). I almost decided to skip the museum because a) I felt really tired and b) I refused to pay $10 for the non-local price while locals paid $.30. I don’t mind paying more than locals but that price difference is absurd. It’s also a bit crazy because the museum itself is tiny. I eventually decided to go in, thinking that I would regret it later if I didn’t. Turns out, I actually ended up regretting going in and wish I would have saved that $10!
I walked up to the Bath Hotel, expecting to find a run-down historic hotel. Instead, I found a property that was still under renovation and was basically inaccessible. Next door to it, there was a tiny thermal bath that was open to the public. I put my legs in the water for a bit in the hopes that it would make my knees stop hurting. After a quick rest, I knew that I had to get a move on in order to get all the way back to my guest house before it got dark.
The next morning, I got up nice and early to hike up Mount Liamuiga, a 1,000+ meter tall volcano in the middle of the northern section of the island. It’s the highest point on the island and was a surprisingly difficult climb. It took me around two and a half hours to get to the top and a painful four hours to get back down. I was expecting some beautiful views but was hiking through the jungle for the entire time until I got to the very top where the trees opened up and I was able to get a view of the crater down below. The pathway itself was well-maintained and very easy to follow. Unfortunately, it’s also covered in tree roots and stones which made part of it feel like playing a game of hopscotch.
I started making my way back down and right before the end of the trail, I ran into an American guy who was about to leave. I managed to get a ride with him to Frigate Bay at the southern end of the island. I went for a swim and had a few beers on the beach before getting a ride back up to Bassetterre and then a bus to Sandy Point where my guest house was.
The next morning, I headed to Brimstone Fort, UNESCO’s World Heritage Site. Known for being one of the best-preserved fortresses in the Americas, this British fortress was built by African slave labor starting in the late 17th century. It was fascinating to wander around the sprawling site and the sweeping views alone made it well worth the $15 entry fee. I spent about an hour and a half wandering around the site before having to make my way back to the guest house and onwards to the airport.
Day 23 – 30 – Puerto Rico
Highlights: Old San Juan, Mosquito Bay
Accommodation: Cozy Studio Apartment
From St. Kitts, I caught an afternoon flight to Puerto Rico. My flight touched down just as the sun was setting so I didn’t get a chance to see anything on the first day. However, I did decide to treat myself to an American guilty pleasure – Olive Garden! There was one just a short walk from my Airbnb so I decided to have a little taste of home to finish off the day.
The next morning, I got up early for a client meeting in Old San Juan. After the meeting, I took some time to wander around the city and was surprised at how much it resembled Panama and Cartagena, Colombia in both the architecture and in the touristy-ness of it. It was lovely to walk around with most of the colonial buildings being freshly painted, the sidewalks being completely intact, and the store signs being almost entirely in English. It was lovely to wander around but I knew that I needed to save some of the best sights for later on in the week when I had a special friend meeting me there.
The next few days were pretty low-key as I took advantage of the nice comfortable bed in my Airbnb and the cloudy weather to take some time to rest, go for runs without sweating to death, and catch up on work. My favorite travel buddy arrived later on in the week so we spent some more time hanging around Old San Juan and visiting all the historic sites including the Castillo San Cristobal and the Castillo San Felipe del Morro which were amazing. We also walked along the Paseo del Morro, a lovely pathway that runs between the walls of Castillo San Felipe and the Atlantic Ocean. The views of the castle walls were spectacular and it was a pleasant walk with lots of shade and the ocean breeze cooling the entire area.
After seeing everything that the city center of San Juan had to offer, we went on an overnight trip to the island of Vieques, stopping at El Yunque National Park on the way. El Yunque National Park was significantly smaller than I imagined. In some ways, this was a good thing as it was pretty rainy while we were there which meant that we weren’t able to take advantage of any of the hiking trails there. We did get to climb to the top of an observation tower, a waterfall, and an old swimming hole that was dug out of stone as part of the New Deal of the 1930s. It was an interesting place to spend a few hours but probably not worth allocating a lot of time for unless you are really into hiking.
Vieques is about a 40-minute ferry ride from the Puerto Rican town of Ceiba which is about an hour and a half drive from San Juan. The island is known for being home to Mosquito Bay, one of the best places to see bioluminescence in the world. When we arrived on the ferry, it was raining pretty hard so we grabbed an early dinner at a waterfront restaurant in Esperanza and waited impatiently at our Airbnb for our kayaking tour of Mosquito Bay to start.
We were picked up in the center of town for the tour and drove about 20 minutes to Mosquito Bay. We, along with six other people, boarded kayaks and began kayaking into the bay. Within minutes, the magic began! With each paddle, the water lit up with a bright white light as the glow-in-the-dark plankton began to do their little dance. Although I have gone to places renowned for their bioluminescence before, nothing quite compared with this. We were out on the water for about an hour and our guide showed us all kinds of fun tricks that we could do to make the experience even better (by the way, did you know that you can make “smoke rings” by spinning your kayak paddle through the water really quickly? Or that you can turn your hand into a fire bomb simply by sticking your hand in the water and flicking one finger?). The kayaking tour cost around $80 and was worth every penny!
The next morning, our Airbnb host took us on a tour of the island. We stopped by the ruins of an old sugar cane plantation, saw one of Vieques’ most impressive trees, and visited some of the US military relics that were left behind from when it served as a base. It was a very interesting experience and much better than spending a few hours sitting on the beach. The tour cost only $35 per person and was the perfect way to spend the morning.
We took the ferry back to the island of Puerto Rico and did a mini road trip around the eastern part of the island before cutting back up to San Juan. We finished off the day with another dinner at Olive Garden before passing out for the night. We got up early the next morning to squeeze in another walk through Old San Juan and brunch (complete with pina coladas!) before heading to the airport for an afternoon flight.
The Caribbean in a Coconut Shell
The Caribbean ended up being much more budget-friendly than I thought it would. I ended up averaging around $45 per night for accommodation while each flight I took was around $150 – 200 which means that I traveled through the Caribbean islands for less than what I would pay for a studio apartment in New York. I visited five new countries including St. Vincent, Grenada, St. Lucia, Dominica, and St. Kitts, as well as the four new territories of St. Martin, Guadeloupe, Martinique, and Puerto Rico. I met tons of great people and had many wonderful experiences and actually really enjoyed this leg of the journey to 195.
My favorite islands were Dominica and St. Lucia simply because the people were lovely and there was a ton of stuff to do. However, I was blown away by how beautiful Guadeloupe was and was surprised by how much I liked St. Martin. Although I spent a week in both Dominica and Puerto Rico, I really wish I had more time to spend on both of those islands.
