5-Day Barbados Group Trip Itinerary

Intro

Make no mistake about it…Barbados is a party island. Not the type of party island that you might fantasize about like in Ibiza, Mykonos, or St. Barths. Bajans don’t have to rely on tourists to fuel their party atmosphere, they create it themselves. And with all of the rum they produce, they don’t need to go far to have a good time.

My first introduction to this lively island culture actually came in the U.S. Washington D.C. hosts “Embassy Day” every May, which features historical and cultural parties and exhibits hosted at embassies all over the city. Everyone came to know soon that Barbados throws the biggest party. Think free shots of rum inside which preps you for the festival out back complete with local dancers, rum punch, ox tail stew, and all sorts of other local treats. It was when the ambassador stood on stage passing rum shots out to the crowd when I immediately knew it was time to book a trip.

Figuring we were in for a good time; I gathered 7 of my closest friends for a winter trip down to the birthplace of rum. We locked in an AirBnB with a private pool, booked flights, and started dreaming of unlimited punch on the beach. Below is a recap of the itinerary we built; complete with the best food, dancing, and, of course, rum that we could find on the island.

Day 1 – Arrival; Bridgetown & Booze

4pm Thursday arrival in Bridgetown. We grabbed the rental car from the airport and headed straight into town to fill up our stomachs. With no clear direction except for our noses, we wandered through streets in search of local fare. It didn’t take much time to find a food stall near Marhill Street Public Market serving up mac pie and cou cou, which is an okra and cornmeal-based dish. Wash that down with a few local Deputy beers and let the good times begin.

Continuing our walk-through of Bridgetown, we toured through the UNESCO Site Synagogue Historic District and found a few local markets to shop at.

Overall, there are a few historical sites to see in Bridgetown, but we didn’t find it necessary to spend more than 2-3 hours here. The island has much more to see.

Back in the car and off to the AirBnB. We chose a location in the parish of St. Philip on the southeastern side of the island. About a 30-minute drive from Bridgetown, this parish is quieter with more of a local feel compared to the busier, resort heavy beaches on the island’s western shore. We found it made for an authentic experience.

After check-in and a bit of freshening up, we made our way to Le Shack, a local watering hole and restaurant specializing in seafood and local flavors. Come here for the food, stay for the vibes and their rum punch. Le Shack is Bajan hospitality at its finest. More on this later as we’ll be back to this spot before the trip is over.

Day 2 – Rum Distillery & Fish Fry

Night 1 was a success. How can we top that? Sample some of the island’s best rum of course! But first, breakfast. Nearby sits a locally run, healthy smoothie shack called Sun Life Juice and Smoothie Spot. An easy walk from our spot near Crane Beach made it a no brainer to fuel up with nutrients to both recover and prepare for what lies ahead.

A morning laying by the pool was well deserved. I went and picked up a few “Cutters” from the island famous food stand of the same name for the crew. A cutter is a sandwich of fish, usually flying fish, on special bread. A must try. They even bottle their rum punch, which was an obvious choice to keep at the house for the weekend. Make it a point to stop here for a meal if you’re on this side of the island.

Finally, it was time to head to Foursquare, one of Barbados’ most well-known and sought after rum producers. We handed ourselves a self-guided tour of the facilities before making our way to the tasting room where we either over-ordered or were over-served. Maybe both, I really don’t remember. I do remember nabbing a few bottles as souvenirs before, in true Bajan fashion, they kindly offered us a ride home. This was a highlight of the trip.

Time to freshen up and head out to one of Barbados’ most time-honored traditions, the Oistins Friday night Fish Fry. We hired a driver for the night to lug us 45 minutes or so to Oistins where the party was just getting started around 6:30 when we arrived. Just in time for us to get in line for Pat’s Place. Widely known as the best fish at the fish fry, Pat’s Place gets busy quick. Serving up fresh catch like mahi, flying fish, kingfish, snapper, and lobster, you can’t go wrong here. Fill up early so you can get your dance on with the locals all night.

Day 3 – Booze Cruise

As if Oistins wasn’t enough of a party, we had to keep it going the next day on our chartered yacht with Cat & the Fiddle. A 9:30am arrival may have pushed our bodies limits, but damn it was worth it to feel like Rihanna for a day. The staff at Cat & the Fiddle were incredibly friendly and welcoming. We were quickly awoken by their energetic crew who made quick duties of the rules before setting sail for our 5-hour adventure at sea. Needless to say, our drinks were always full, the music was always a vibe, and the locally inspired food was perfect. Couldn’t recommend this experience enough.

Back at the house, the vibes were high, and the crew was ready for another night at Le Shack. This time, the staff was ready for us with a table right in the middle of the dining room. They knew we wanted to be a part of the action. We got started with drinks and apps like smoked flying fish mousse, fresh fish ceviche of the day, and grilled octopus before diving into the main attractions of local fish and Bajan chicken. I won’t go into too many details, but we may have had too good of a time. Before we knew it, our crew had become the life of the party. I told you…the Bajans know how to get down.

Day 4 – Beach Club & Private Chef

I can’t speak for the others in our group, but this is where my age starts to catch up with me. I can’t hang as much as I used to. At this point in the trip, my body needs a virgin coconut water under a shady tree on the beach with no one to talk to. But it is the last day of the trip, and I can’t quit now, so off to Deia Beach club we go.

Deia Beach is definitely a vibe. Modern amenities, solid food and a lively atmosphere make it a perfect day on the beach for a group. I did get my virgin coconut water after all before being pressured to switch to a real drink by my degenerate friends. A couple hours here and I’m feeling both energized and refreshed. It was then back to the house to prep for our last night, a family style dinner cooked by a private chef.

We booked our private chef experience through a local purveyor. Our chef prepared a menu of incredible Bajan dishes including all of the staples like mac pie, flying fish and cou cou, crab ceviche, and jerk chicken. It was the perfect experience to end the trip with a group I consider like family. Needless to say, this was the ideal sendoff.

Day 5 – Departure

A 2pm flight back home gave us enough time to sleep in and prep for our journey back home. Looking back on the time we had in Barbados, it was one of the best friends trips I’ve ever taken. Not just because of the amazing company of my pals, but also because of the amazing hospitality of the Bajan people. Their kindness, generosity, authenticity, and love for a good time allowed us to feel like we belong from the moment we landed. Even though this was a group trip clearly planned with a party theme in mind, Barbados is a place where anybody can have a blast. From the food to the beautiful beaches and landscapes that we didn’t even get to explore, this Caribbean Island has everything to offer. If you can’t get along and have fun with the Bajans, maybe it’s a “you” problem.