The Best Caribbean Cruise for Country Counters

EAST CARIBBEAN

Updated as of October 2023:

There are eight countries in the eastern Caribbean that aren’t the easiest, logistics-wise. You can fly, but a single flight might cost $400+ with a strange layover, whereas a direct flight (if there even is one) would be fifteen minutes. Then you have to purchase hotels, plan enough time to do all your activities, etc. There is a ferry but they only go between certain islands. So, what’s the most cost-effective way to visit all of the Caribbean islands? A cruise!

What’s the best cruise line?

Before the pandemic, there was an MSC cruise that went to all eight, but currently there’s only one line that goes to six countries. But still, that’s a great deal — and it’s $400 per person! Transport between all the countries, accommodation, and food? It’s too good to pass up.

I went with Royal Caribbean, but unfortunately it doesn’t look like they’re offering the cruise anymore. I’ll go over the cruise I went on before giving suggestions for current cruises with similar itineraries, but if you’d rather jump to that section click here.

The Itinerary

• DAY 1: Barbados

• DAY 2: Tobago

• DAY 3: Trinidad

• DAY 4: Grenada

• DAY 5: St. Vincent & the Grenadines

• DAY 6: Dominica

• DAY 7: St. Lucia

• DAY 8: Barbados

Barbados

My family actually joined on this trip since it was my 30th birthday, so we got in a couple days before to explore Bridgetown before hopping on the cruise. My favorite activity was watching all the racehorses bathing in front of the hotel. Other points of interest were the George Washington House and St. Nicholas Abbey.

TOBAGO

A lot of people would argue that you don’t get to truly “experience the culture” hopping to each island for one day. But what I think is great about the cruise is just getting a little taste of each place and going back to the places you want to explore deeper. Tobago was one of those places where I felt that there just wasn’t a whole lot to do so I was glad I only spent a day here. The beach at Pigeon Point was beautiful, and I enjoyed getting to go on the glass bottom kayak.

Trinidad

Don’t get fooled into feeling like you need to book a tour or excursion for every stop. We got off the ship and found a driver to take us to all the points of the city — check out the Magnificent Seven, then head over the hills to Maracas Beach to try their famous bake ‘n’ shark. Doubles is also another popular food dish in Trinidad.

GRENADA

Welcome to the Spice Island! This was probably one of my favorite stops of the trip — check out the Underwater Sculpture Park (visibility isn’t great most days, so something to be wary of), Annandale Falls, and Fort Frederick for views of the entire island.

St. Vincent & the Grenadines

We did a catamaran day tour, which was a great option since there isn’t a whole lot to do in the port of Kingstown. Most people suggest going to the actual Grenadines than St. Vincent so I loved this little trip! We visited Dark Falls and a Pirates of the Caribbean set before doing a catamaran ride to a black sand beach.

Dominica

Dominica was also another favorite stop of the trip and I wish I had another day to explore! It’s known as “the nature island,” so naturally we did a day hike to Boiling Lake. On All Trails it says about 6 miles but we clocked it at 8 miles. It took a good chunk of the day so we didn’t have much time to do anything else afterwards.

st. lucia

This was another island I wish I had an extra day in! We did another catamaran trip to the famous Pitons, which included a swim stop at Marigot Bay. I would’ve also loved doing the mud baths, but will save that for another time.

Alternative Cruises Currently Offered

As of October 2023, they are no longer offering the Royal Caribbean cruise to the six countries I mentioned, BUT there is an alternative that’s also a great option! Unfortunately they’re a bit pricier, but if you take transport, food, and accommodation into account they’re actually great alternatives.

MSC Cruises: Currently MSC offers two cruises that covers a few of the countries mentioned, but also territories. The countries it goes to are St. Kitts & Nevis, Antigua & Barbuda, Barbados, and St. Lucia. This starts from $550 so it’s not a bad deal, but unfortunately it doesn’t go to all the eastern Caribbean countries.

Seabourn Cruise Line: On the other hand, Seabourn cruises to Barbados, St. Lucia, Antigua & Barbuda, St. Kitts & Nevis, St. Vincent & the Grenadines, and Grenada. This covers six of the eight (only missing Trinidad & Tobago and Dominica), but is a little pricier and can probably compare to the cost of taking flights everywhere. The only upside is, everything is taken care of and is included in the cost.

Best Itinerary for St. Kitts & Nevis

ST. KITTS & NEVIS

A twenty minute short flight from Antigua & Barbuda, I headed to my 120th country, St. Kitts & Nevis! I only visited two countries on this short trip because I was planning on doing a cruise to the other six islands in the eastern Caribbean in January 2023. Whether you’re doing a different cruise or looking for things to do, here is the best itinerary for St. Kitts & Nevis!

ROMNEY MANOR

Romney Manor dates back to the early 17th century when it was established as a sugar plantation. Once owned by the Earl of Romney, this sprawling estate played a significant role in the region's sugar industry, where it thrived for centuries. Today, it stands as a historical landmark, offering visitors a glimpse into the past and showcasing the island's colonial legacy.

Timothy Hill overlook

This photo was actually taken with a drone of the area! But Timothy Hill overlook is probably the best area for views of the whole island.

BRIMSTONE HILL FORTRESS NATIONAL PARK

Brimstone Hill Fortress holds a wealth of historical significance, showcasing the architectural prowess of the British Empire in the 17th and 18th centuries. Its strategic location made it a formidable stronghold during colonial times, protecting against invasions and guarding the valuable sugar plantations of St. Kitts.

Most Instagrammable Places in Antigua & Barbuda

ANTIGUA & BARBUDA

My last countries in North America were all in the eastern Caribbean, which aren’t the most easy countries to visit and are logistically pretty expensive. There are eight countries in the eastern Caribbean, and I happened to find a cruise that goes to six within a week’s time for $400. Sure, you might spend a day in each country, but you get a taste and can decide later which ones you want to go back to and spend more time in. Also, $400, which covers food, accommodation, and the transport is an amazing deal versus a single flight that would potentially cost the same amount. The only two countries that this cruise doesn’t cover is Antigua & Barbuda and St. Kitts & Nevis; so I decided to hop on a flight to visit these countries. Anyways, let’s get into the “most instagrammable spots” of Antigua & Barbuda!

Shirley Heights

This overlook in English Harbour is incredible for sunset. I actually stayed in this area the whole time I visited Antigua because of how beautiful the area is!

Pineapple beach club

These colorful huts can be found right along the beach of the Pineapple Beach Club! You can pay for a day pass to hang out for the day, and the beach is stunning.

Tyrell’s Catholic Church

This bright pink church is iconic on the island; I recommend going later in the day for the best lighting!

Telephone booth

Located on the beach in front of Siboney hotel, this is also a stunning beach to hang out at!

Best Dominican Republic Road Trip Itinerary

DOMINICAN REPUBLIC

After being in the remote jungles of Panama, the Dominican Republic was a great place to relax and soak up the beaches before heading to the next destination! Here are some of my favorite places to visit on a road trip around Dominican Republic!

Punta Cana

Most people fly into the airport at Punta Cana, which is known for its all-inclusive resorts. You can always find some good deals if you’re looking to just relax and have food and drinks included. One thing to note that I didn’t know, was that most restaurants need a reservation the day before to eat there. There usually is one cafeteria-type area where you don’t need a reservation but it’s not the best food.

Isla Saona

This is a great day trip from Punta Cana if you have extra time to spare! The beaches are incredibly stunning, but although the photos make it look like a deserted island, it gets pretty packed with tourists and there are long lines for lunch.

Playa Macao

This beach was probably my personal favorite! It’s big enough so tourists can spread out, the water is clear, and there’s cute huts and surf spots!

Montana Redonda

The view at Montana Redonda is insane! If you don’t have a 4x4 vehicle, you can leave your car parked at the bottom of the hill and take a truck up to the top. I highly recommend going close to sunset for the best colors for photography. Relax and enjoy the swings and view!

Samana Peninsula

This is probably one of my favorite areas of the Dominican Republic! Unfortunately when I went there was a torrential downpour of rain, but it’s such a unique area with very little tourists. The beaches are the absolute best in this peninsula!

Top Things to do in Jamaica

It was a little bit of a roundabout way to get here, but crazy enough I found a bargain flight from Cairo - Frankfurt - Toronto, then a flight on Swoop Airlines to Kingston. This was my last stop on my two-month trip, so it was a nice change before heading back to the states. I’m not a huge fan of touristy places, and since Jamaica is rather known as a cruise ship destination, it was easy to spend a few days checking everything out before flying home. Here are my top things to see in Jamaica!

Getting Around

From Kingston, you can easily take a bus to anywhere around the island using Knutsford Express. Most leave by the early afternoon so if you’re looking to take the bus right away from the airport I’d recommend arriving earlier in the day.

Martha Brae River

I always love finding unique things to do in every country, and the Martha Brae River is definitely one of those attractions! If you have a taxi take you to this area, you can pay to take a bamboo raft down the iridescent emerald river waters and forest. Probably my favorite thing to do!

Pelican Bar

If you have time to check it out, the Pelican Bar is a bar in the middle of the ocean! You can take a boat out to it and hang out all afternoon having drinks or swimming in the water. It’s a bit out of the way but something else unique to Jamaica!

How to Travel from Haiti to Dominican Republic

HAITI

During my stay in Cap-Haitien, Haiti, I decided to take a bus over the border to the Dominican Republic. I see a lot of posts about traveling from the DR to Haiti, but not a lot vice-versa.

Where to stay in cap-haitien

First of all, if you’re traveling to Haiti, I recommend staying at Habitation des Lauriers. It’s clean, has great security, the owners take great care of you, and has an incredible view overlooking the city and ocean. Not to mention sunrises are spectacular! I told them I wanted to take the bus over to the DR and they arranged a driver to drop me off at the bus station the next morning at 7 AM. The bus leaves at 8 AM but it’s important to get there early to ensure you get a spot.

The journey to the Dominican Republic

I arrived at the El Caribe bus station and told them I wanted to be dropped off at Santiago since I was going to take a guagua (little bus) to Las Terrenas. Important thing to note: bring US dollars! It’s funny they don’t take Haitian gourdes or Dominican pesos… There were two European guys that had euros, gourdes, and pesos but they wouldn’t accept any of them. Another thing to note, they take your passport once you pay and they give it back to you on the bus. I got anxious because I hate not having my passport with me but I got it back!

Anyways, the border crossing takes about 1 – 2 hours. If you flew into Haiti, make sure you have your exit ticket with you so that you don’t have to pay an extra fee. After being stamped out, we went to the DR side which was a little crazier. You don’t need a PCR test to enter, but they do a bag check and you have to wait for a long time. Everything else was fairly quick but the majority of the 2 hours was spent waiting on that.

I arrived at the bus station in Santiago and needed to find the guagua station to Las Terrenas. Luckily I found a trustworthy taxi driver, Miguel (Whatsapp +18094912013), who took me over to the station and agreed to pick me up when I returned to get a PCR test and take me to the airport. When I got to Las Terrenas, I had a little mishap with a motoconcho driver. Long story short, try to avoid them if you can — I didn’t know this beforehand. They’re motorcycle taxis but are notorious for stealing. So when I pulled money out and didn’t have change, he swiped it from my hand and sped off with it. I was pretty sad.

Honestly, I didn’t have a great time in the DR. Most people go to the touristy areas and stay in an all-inclusive resort but I wanted to try something different and off-the-beaten-path. I think it was tough trying to figure out all the logistics while everything was going wrong, but I know that’s all part of the adventure. On the other hand, I loved figuring out how to cross the border from Haiti to the DR, so I hope my experience can one day help someone have a better time than I did. I also hope to return to the DR one day to gain a different perspective, but for now, I’ll always remember it as a true adventure