Everybody knows about the Caribbean’s white-sand beaches and turquoise-blue waters. But look beyond the island’s coastlines, and you’ll find a diverse region of vibrant cultures, fresh food, and lush flora and fauna. This trip will take you to four islands, each of which has its own flavor, unique scenery, and a novel set of experiences. Start your honeymoon in romantic Saint Lucia, which is arguably the most beautiful island in the Caribbean.
The island’s lush rainforests, frothy waterfalls, blossoming orchids, bright markets, and colorful fishing villages create a palette of visual delights, and I’ll show you how to best take in these gorgeous views. Continue on to Anguilla, where relaxation is the name of the game. Though it has some of the best beaches in the Caribbean, Anguilla is still a well-kept secret. Embrace the island’s low-key, luxe style with long days on the beach followed by splurge-worthy spa treatments and gourmet meals. Even Anguilla’s nightlife is relaxing; join an inviting reggae circle where you can enjoy the local culture. Next you’ll visit Jamaica; nowhere in the Caribbean is African culture more alive and well than on this island. You’ll sense the island’s roots in its musical beats, spicy food, and cultural offerings. Enjoy unique experiences like climbing waterfalls, swimming in cenotes, and sipping beers at a bar built in the middle of the ocean. For your final stop, I can help with outlining your options for getting in to Cuba. If you decide against them, Puerto Rico could be a nice alternative. Though the cultural opportunities may not be as unique as those in Cuba, there is beautiful Spanish colonial architecture in Old San Juan and a unique bioluminescent bay that offers a spectacular after-dark kayaking experience.
Rustic, Historic Charm
Upon your arrival in St. Lucia, you’ll want to pick up a rental car; taking taxis around the island is relatively expensive, and buses are unreliable. Make the short drive to your cottage near Laborie where you’ll be staying at the Balenbouche Estate, a guest house set on a 70-acre historic plantation, complete with tropical gardens, an old sugar mill, nature trails, and access to several beaches.
Spend your first day exploring these grounds, testing out its beaches, or trying out one of their onsite yoga classes. Eat at the guest house restaurant or choose one of the more affordable options nearby. Go to the colorful fishing town of Laborie where you’ll get a dose of the local culture and a multiple dining options to choose from. A local favorite here is the Big Bamboo Cafe.
By now you’ve likely spotted the island’s most iconic site: the lush, twin peaks of its Piton Mountains. Start your day with an easy hike that gets you up close and personal with this gorgeous landscape. The Tet Paul Nature Trail runs along the rise between Gros Piton and Petit Piton, providing incredible views of the mountains, Jalousie Bay, and even Martinique and St. Vincent on a clear day. Morning is the best time to beat the heat and the tour groups that crowd the trail later in the day. The hike is moderately easy and takes about 45 minutes to complete. Guides are mandatory.
For more picture-perfect scenery, spend your afternoon on one of the island’s most idyllic beaches, Anse Mamin. This secluded, palm-tree-lined stretch of soft sand is located on the grounds of the Anse Chastanet Resort but is open to all visitors. Spend a few hours in this tropical and tranquil paradise, taking in the waves, the surf, and a few cocktails from the Beach Bar. This is also one of the best places to snorkel or scuba dive on the island.
Now that you’ve seen the Pitons up close, you may want to take in a panoramic view of these beauties from afar. Splurge tonight on dinner at the Ladera Resort, located about 1,000 feet above the shoreline. Enjoy island-to-table dishes like sweet potato and coconut soup or Caribbean lamb salad on the terrace at the Dasheene Restaurant, or just pop in for a drink at the restaurant bar; you’re mainly here for the scenery afterall.
A Tale of Two Islands
Like many Caribbean islands, St. Lucia is one of contrasts. Luxury resorts are found down the road from quaint fishing villages. During certain times of year, equal numbers of visitors and islanders co-mingle in the lush environs, all with the intent of enjoying the beautiful surroundings. Today, experience both the island’s residential and resort worlds, all within the span of a few hours.
Start your day in Canaries, arguably the most beautiful town on the island. Here, candy-colored houses dot the hills and spill down into the ocean below. The road into town has only existed for the past few decades; the village’s isolation has likely contributed to its authentic feel and the intensity of its character. Spend an hour or two wandering the streets of this charming town to getting a taste of real island life. If you’re especially enjoying your time taking in the local culture, also consider checking out the town of Soufriere on the way to your next stop. The lunch stop of choice in this former capital city is Martha’s Table.
Spend the rest of your day at the ultra-upscale Sugar Beach Resort. You don’t have to be staying at the hotel to enjoy its accommodations – just park in the guest lot, and a shuttle will take you down to the scenic beach, where you can enjoy luxe lounge chairs and dramatic views of the Pitons. You can use their snorkeling gear if you feel like exploring the water’s coral reefs. Or, if you’re looking for some true R&R, check out their spa, which is spread throughout seven separate thatched-roof bungalows.
Consider staying at the resort for a bite to eat. Choose between four different bars and three different restaurants, which cater to a variety of tastes and budgets.
Getting Interactive With Nature
A unique morning activity can be found at the Hotel Chocolat, a boutique hotel built on a working cocoa estate. On weekday mornings you can join the Tree-to-Bar Experience, a tour that takes you on a walk through the property’s cocoa groves, where you can cut ripe cocoa pods from the trees. You’ll use them to make your own sweet creations during the candy-making demonstration. Enjoy frequent tastings, but don’t spoil your appetite! You may decide that you want to stay at the hotel for lunch.
In the afternoon, take a closer look at St. Lucia’s diverse flora and fauna with visits to some of its most beautiful natural attractions. Start at the Diamond Falls Botanical Gardens, a six-acre nature area displaying the island’s vibrant, tropical flowers amidst a peaceful historic estate.
Continue on to nearby Sulphur Springs where you can take a soak in the healing, mineral-rich mud baths. The naturally heated pools are found in the collapsed caldera of a dormant volcano which makes for a unique spa experience. The tour groups usually clear out by 4:00 p.m., which is when the locals arrive. Though the posted closing time is 5:00, they usually keep their doors open longer.
Spend your last day on the island relaxing close to home at one of the attractions on or near the Balenbouche Estate so you can just soak in the St. Lucia experience one last time before tomorrow’s departure.
Visit Choiseul, a small town just up the road with a beautiful church and vendors selling traditional arts and crafts. Relax on one of the hotel’s beaches, or go down the road to Anse de Sable, one of the longest stretches of sand on the island.
Dine nearby at Debbie’s, or take advantage of the hotel’s onsite restaurant, which serves Creole-Asian fusion fare.
If you were hoping for a little more adventure on your last day in St. Lucia, you can always go at a more relaxed paced earlier in the week and spread out some of the suggested activities from days two through four.
LIAT Airlines flights from St. Lucia to Puerto Rico have a stopover on the lush island paradise of Dominica, so why not spend a couple of days exploring this Caribbean wonder? Leave St. Lucia early on Flight 308, and you’ll be in Dominica by 8:00 in the morning! Enjoy free transportation from the airport, courtesy of your hosts, to the Liberty Jungle guest house in the jungle near Belles Village. They can also arrange a car rental for you during your stay… if you ever feel inclined to leave this gorgeous property!
Belles is located in the island’s Central Region. Covered in lush forests, this sparsely populated area is considered by many to be the most beautiful part of Dominica. Spend your first day relaxing in or near your cottage. Roam the grounds, make friends with the hummingbirds, relax in your hammock, and enjoy the onsite food and drink services. Some travelers have called this “the best place” they’ve ever stayed – you’ll want to spend at least a day just enjoying your surroundings.
Off the Beaten Path
While the entire island of Dominica could be considered “off the beaten path,” the forested area that you are staying in is virtually tourist-free. Explore outside of the hotel grounds today with a hike through this lush paradise. One of the best treks on the island goes to and from the Jaco Flats, a secluded area once occupied by the island’s Maroons, or escaped African slaves.
The hike starts in Belles at the Paradise Bar, where you can hire a guide. You’ll traverse the stairs that the Maroons manually built into the cliff and explore the surrounding wildlife areas. At times, the path cuts through a mountain river, which you can cool off in along our journey. Don’t forget to wear a bathing suit!
Finish off the day with some relaxation time at the bar in town, or enjoy the heavenly views from the porch of your cottage!
If you were interested in snorkeling during your trip, Dominica is the place to do it. Located along the island’s southwest shore, Champagne Reef is one of the best snorkeling spots in the Caribbean. The reef lies in close proximity to a submerged volcanic crater with underwater fumaroles that vent gases, forming thousands of water bubbles. Navigating the waters around the reef is like swimming through a glass of champagne! Take a tour through this fascinating place with guides from Champagne Reef Dive & Snorkel.
Champagne Reef is well-known and can get a lot of attention from tourists on cruise ship days. For a more secluded experience, check out the Scott’s Head Marine Reserve at the southern tip of the island. Here, you can rent some snorkeling gear from the vendors along the beach, and just dive right in!
Dry off and refuel with a beer and some freshly caught fish at one of the local restaurants in either Scott’s Head or Soufriere. Then, head to Soufriere Bay where you can take a soak in its natural hot springs, located in front of the town church at the Bubble Beach Spa. While relaxing in the warm water, you can watch the bubbles rise below the water, drink in hand.
Spend your last day in Dominica at Morne Trois Pitons National Park, a UNESCO World Heritage Site centered on a large volcano and home to several hot springs, beautiful lakes, and dramatic valleys.
The park contains the world’s second largest Boiling Lake, a flooded fumarole – or opening in the Earth’s crust releasing steam and gas – filled with bubbling grey-blue water surrounded by a cloud of vapor. While this is arguably the most impressive attraction in Dominica, seeing it requires a fairly strenuous, 12-mile roundtrip hike. Guides are strongly encouraged, as the parts of the trail that run through the Valley of Desolation can be indistinct and other sections are steep and muddy. If you decide you want to do this hike, you can hire guide in the town of Laudat.
There are plenty of other intriguing sites in the park for those who are looking for a more relaxed day. The hike to Ti Tou Gorge can be done without a guide. Once there you’ll enjoy a natural water ride through cavern-like passageways – you’ll instantly be able to tell why this was used as one of the filming locations for the Pirates of the Caribbean! This site can be enjoyed after a hike to Boiling Lake, or on its own.
Also in the park are several gorgeous waterfalls. The mammoth Trafalgar Falls is made up of two cascades flowing down a lush mountainside, one of which flows into a refreshing natural swimming hole. Another spectacular waterfall can be found at the end of a leisurely hike down the Emerald Pool Nature Trail. The swimming pool at the bottom of Emerald Falls is chilly, but its stunning, electric-blue color can easily be admired from dry land.
You’ll arrive in Puerto Rico in the midafternoon, making the capital of San Juan your base. You won’t need a car for your time on the island; you can access the best city sites on foot or by way of short taxi rides, and your hotel will arrange your tour to the bioluminescent bay.
From the airport, take a taxi to your hotel in the heart of the historical district, an area celebrated for its old-world charm. Old San Juan has some of the best-preserved colonial architecture in the entire world. The city’s characteristic pastel-painted buildings with their open-air courtyards and inviting balconies will transport you back in time.
After checking into Hotel La Terraza, spend some time familiarizing yourselves with your urban surroundings. Wander the streets and alleyways, relax by a fountain or in park, and pop into some inviting shops. While you’ll find that certain strips are filled with souvenir stores catering to the cruise-ship crowd, the longer you explore, the more tucked-away surprises you’ll find. Local favorites include Franky’s, an old thrift store that’s packed to the rafters with vintage treasures, and Ole, a shop that specializes in hand-fitted and customizable Panama hats.
Once you’ve worked up an appetite, a great dinner spot is the Patio Del Nispero located within the open-air patio of Hotel El Convento. Shaded by the nispero fruit tree and overlooked by the hotel’s interior, colonial-style balconies, Patio Del Nisperio provides an intimate and atmospheric al fresco dining experience. You’ll love the decor’s authentic, Spanish details so much, you’ll probably want to stay put for after-dinner drinks!
History With A View
Charming residences aren’t the only buildings that are well preserved in Old San Juan. Dive a little deeper into the city today with visits forts, its most famous church, and a fascinating cemetery.
Start your walking tour at the Castillo San Felipe Del Morro, a majestic, mid-16th Century seaside fortress that is among the largest military structures built by the Spanish in the Caribbean. Troops stationed here resisted several maritime attacks; you can almost imagine these altercations as you look through the fort’s cannon windows.
If you walk east along the water following the old city walls, you’ll soon get to the Cementerio Santa Maria Magdalena de Pazzis, a colonial-era cemetery that serves as the final resting place for many of Puerto Rico’s most famous citizens.
Eventually you’ll also come upon the Castillo San Cristobal, San Juan’s other fort, which is also worth exploring. It stands at the eastern gate of the old city and was once its land entrance.
On the way to your next stop, you’ll pass by the Plaza de Armas, which is a great place to stop for a rest and a snack. Most days you can find street vendors selling piraguero. This classic treat is the Peruvian take on a snow cone. Locals love the sesame seed- and anise-flavored syrup; be adventurous and try one or both of them out!
Continue on to the Catedral de San Juan Bautista, a beautiful, 16th-Century church where you’ll find the grave of the famous Spanish explorer, Ponce de Leon. Peek in and appreciate this little piece of history, along with the building’s beautiful stained glass and intricate domed ceiling.
From here, if you go east along the water, you can find some of the best mofongo in San Juan. This typical Puerto Rican dish is made using a base of mashed, fried plantains and covered with a vegetable, chicken, beef, or seafood stew. Punto De Vista Restaurant cooks up a great version of this yummy dish and also has a great buy-one-get-one special on mojitos. Don’t let the cruise ship dock deter you – the food really is that good.
Spend your afternoon relaxing on your hotel’s incredible rooftop pool; you’ll want to save up some energy for tonight’s nighttime kayaking trip through the island’s famous bioluminescent bay.
A Little Bit of Glitz and Glam
Puerto Rico is one of the few stops on your tour through the Caribbean that offers travelers a little bit of flare. For a taste of upscale island life, spend some time appreciating San Juan’s glam side.
If you’re a rum fan, take the tour of Casa Bacardi. Here, you’ll learn about the history of the largest spirits company in the world. The tour is short, but interesting and informative. The best part of the experience is sampling free drinks at the outdoor bar, where you can ask bartenders to get creative with rare Bacardi flavors like Dragon Berry and Arctic Grape. Warning: this attraction is a little touristy, but still a fun stop for spirits fans.
El Condado is the Miami-esque section of San Juan, characterized by its high rise hotels and exciting nightlife. Cruise Avenida Ashford, the area’s main strip, popping into the boutiques, bars, and casinos that strike your fancy. If you’ve been missing the beach, bring your bathing suit along; there is also a long stretch of sand where you can take in the sun.
Spend one last morning in Old San Juan enjoying a leisurely breakfast at Caficultura. They serve breakfast all day at this coffee house, popular with both locals and tourists. Grab a table with a view over the streetscape, and enjoy standard morning fare with a local twist. Here, French toast is sprinkled with coconut and dipped in pineapple marmalade and pancakes are flavored with bananas and rum.
Take the mid-afternoon LIAT flight from San Juan to Anguilla, and take a taxi to your boutique hotel in the West End Village. You shouldn’t need a car on this small island.
Hotels on this luxury island are relatively pricey, but the main activity here – lying on the beach – is always free. Settle into this ultra-relaxing island in Anacaona Boutique Hotel and have a stroll along the sand and dinner at Blanchards Beach Shack. This restaurant serves some of the tastiest food on the island, has relatively reasonable prices, and is only a 15-minute walk from your hotel.
Ever wanted to try T’ai Chi? Your hotel holds free classes on the beach every Friday from 8:30 to 9:30. It’s a great way to clear your mind in preparation for a day of doing and thinking about nothing.
Spend the afternoon lounging on Meads Bay, a gorgeous one-and-a-half mile stretch of white sand that can be accessed from your hotel via a garden footpath. Once on the beach, you can take advantage of complimentary chairs and umbrellas. There is also food and drink service available from the hotel’s beach bar, D’Sand Pit.
For a break from the sun and the sand, head back to your hotel and consider one of their enticing spa treatments. The Sri Balinese Petite Spa offers a wide range of traditional and exotic services, including four different types of massages.
For dinner, take a short walk up the shore to the Straw Hat Restaurant, a beachside spot serving up freshly caught fare. On Fridays, the restaurant hosts a local musician who serenades diners with smooth, Caribbean beats. Try to book your dinner here ahead of time – the earlier you reserve a table, the more likely you are to be seated on the beach.
By Land or By Sea
Sailing is one of the premier activities on the island of Anguilla. Today, consider exploring the blue waters surrounding the island by boat. Tradition Sailing Charters offers day trips to Prickly Pear Island. From the moment you step on board the Tradition, you’ll be treated like royalty. Enjoy a lovely boat breakfast of mimosas, muffins, and fruit. Once on the island, you’ll have plenty of time for lunching, relaxing, and snorkeling.
Alternatively, you could spend the day exploring the island by bike. Have a taxi take you to the Anguilla Ferry Dock where you can rent from Premier Mountain Bikes, located right on the port. Bicycling here is safe, as roads are developed, and drivers go slowly. Take advantage of Anguilla’s size, and make a day of it by exploring the entire island! On bike, it’s easy to eat like a true islander, and stop at one of the local roadside grill shacks.
Beaches, Beaches, and More Beaches
Consider trading in one beautiful stretch of shore for another today. Anguilla has several gorgeous beaches, each of which has a unique combination of traits. The pros and cons of each are outlined below.
Celebrated for its scenery and calm waters, Maundays Bay is arguably the most pleasant beach in Anguilla. The walk here takes about 25 minutes, or you can have your hotel call you a taxi. Note that the food options in Maundays Bay are not as plentiful as those on some of Anguilla’s other beaches.
Shoal Bay is considered one of the most beautiful beaches in the entire world. Here, the shore seems to go on for miles, giving this place an “end of the earth” feel. On the downside, this beach’s stellar reputation means more tourists and more hawkers trying to sell you souvenirs and trinkets.
Little Bay is one of the most unique beaches on the island. This small stretch of shore situated in a rocky cove is difficult to reach and is thus very serene and private. You can reach Little Bay one of two ways. To travel there by boat, go to Crocus Bay, and ask for Calvin, who will be happy to shuttle you to the cove. Or, you can scale the rocks above the shoreline using a rope left there for adventurous travelers.
It will take multiple airport and airline transfer to get from Anguilla to Havana, which means you’ll be in transit most of today. I recommend traveling to Cuba through Grand Cayman for the combination most convenient/cheapest/fastest option. Your Cape Air flight to San Juan leaves Anguilla at 2:10 p.m., giving you time for one last leisurely breakfast on the beach.
Once in San Juan, you’ll switch to American Airlines, which will take you to Grand Cayman through Miami. You’ll need to spend the night in Grand Cayman, as you’ll be arriving at 10:55 p.m. The Riviera, Grand Cayman is the cheapest hotel that’s close to the airport.
Your flight on Cayman Airways leaves at 1:35 this afternoon; you’ll be arriving in Havana just after 2:30 p.m. Arrive at your Hotel Raquel in La Habana Vieja, or the old city, via taxi, making sure to hail one of the official government vehicles.
Spend the afternoon and evening getting acquainted with the area around your hotel, an atmospheric neighborhood that is feels stuck in time. Wander the beautiful plazas making sure to peek in the Cathedral at the Plaza de la Catedral, peruse the book stands at the Plaza de Armas, take in the sheer magic of the Plaza Vieja, and check out the church in the Plaza de San Francisco.
Enjoy dinner at Paladar Los Mercaderes. Housed in a 19th-century colonial home, this restaurant serves traditional food with a heaping side of charm. Ask for a seat on the balcony so you can take in the scene on the cobblestone below while being serenaded by the melodious music from the musicians within the restaurant.
Yesterday you scratched the surface of old Havana’s alluring, faded glamour. Today, do some more exploring and immerse yourselves even further in the old-world charms of La Habana Vieja.
Spend some time exploring the sites around the beautiful Parque Central. Take a gander at the Capitol building, and then head to your next stop by way of the Paseo del Prado. This tree-lined pedestrian boulevard is a gathering spot for locals and a scenic avenue on which to stroll.
Next, learn about the Cuban government at the Museo de la Revolucion. Or, if art is more your thing, check out the highly praised Museo Nacional de Bellas Artes, which features beautiful works from Cuban masters.
Make sure to take a break from all the sightseeing to refuel at La Bodeguita del Medio. This electric spot, which was once a favorite of Hemingway, plays lively music throughout the day and serves tasty Cuban food and drink. Though inarguably touristy, it’s a great place for a fun lunch and is not to be missed on a trip to Havana.
Evening is the best time for a stroll along El Malecon, the waterfront promenade that runs alongside the old town. This is pleasant walkway is a prime people-watching spot; locals and tourists alike can be found relaxing and mingling. The scene is especially inviting under the setting sun.
End your walk at Atelier, a paladar, or family-run restaurant, providing an authentic Cuban dining experience. Atelier has delicious food, a lovely ambiance and a pleasant terrace with outdoor seating. Finish your evening with a mojito night cap at the Hotel Nacional, the city’s grandest and most famous hotel.
Wander further afield, and spend most of the day exploring Vedado, a pleasant and relatively modern neighborhood with a number of interesting sites. Start at the Plaza de la Revolucion, an immense square presided over by a statue of Jose Marti and the iconic image of Che Guevara displayed on the wall of the Ministry of the Interior.
Next, head to the Cementerio de Colon, a gorgeous cemetery with ornate and intricate mausoleums. Spend some time wandering this peaceful place, appreciating the work in its sculptures.
If you’re up for a walk, go to your next stop on foot. It will take you about an hour to get to the Callejon de Hamel, the “shortest street” in Havana. What this avenue lacks in size, it makes up for in character. Nearly every square inch is covered in colorful art murals and sculptures, representing the Santeria faith. This open-air art gallery provides an interesting glimpse into a vibrant Cuban subculture.
By now you’ve likely worked up an appetite, so make your way to the nearby waterfront for lunch at Sociedad Asturiana Castropol. Ask for a table on the second floor balcony, where you enjoy views of the El Malecon and the bay. The international food is decent, but you’re mainly here for the scenery.
After lunch, make your way El Morro, that waterfront fort you’ve been eyeing across the bay. This imposing piece of architecture juts out over the sea and offers great views of Old Havana. If you can, try to time your visit to coincide with sunset when the views over the water are the most remarkable.
End your day with a riveting cabaret performance at the Tropicana. Like so many other experiences, this show evokes the spirit of 1950’s Havana, but perhaps no other places does it with as much glitz and flare. The dinner here is mediocre, but the entertainment is stellar. After the show, keep the party going with some serious salsa dancing at the adjacent nightclub.
If you’re itching to get out of the city after a few days of urban exploration, take a day trip to Vinales located in one of Cuba’s most beautiful national parks. In this lush, electric green valley, hills rise up like haystacks to create a unique, lumpy landscape.
Travel here by way of a Transtur or the Viazul bus. To secure reservations, you’ll need to ask your hotel to contact these companies immediately upon your arrival in Cuba, as bookings cannot be completed online.
Once in the valley, explore it by horse. This is the best way to immerse yourselves in the unspoiled agricultural landscape, tobacco farms, and fascinating history of this scenic region.
Depending on the time of your flight tomorrow, you may want to stay here overnight to avoid a long day of commuting to and from the valley. Or, consider making this trip early on during your stay in Cuba to avoid any transportation mishaps.
If you’re looking… for a more challenging trek in St. Lucia, try the hike up Gros Piton, which takes between three and four hours, round trip.
If you decide… to swim the Ti Tou Gorge, rent the life vests at the entrance, and bring water shoes if you have them.
Make sure to… make bioluminescent bay tour reservations long before you arrive on the island; this unique site is one of the most popular attractions in Puerto Rico, and spots fill up fast.
You’ll need to… take a taxi to the Bacardi tour and the Condado casinos.
Cuba Money Tips… Due to the embargo on Cuba from USA, bank cards and credit cards with affiliations to US institutions do not work in Cuba. Double check with your banking institution to confirm that your cards will work in Cuba. Triple check with a quick google search on your bank institution and Cuba travel.
Carrying cash in Cuba… Even if you’ve confirmed that you card will work in Cuba, it’s smart to carry additional cash along to convert at the Havana airport. Converting US dollars to Cuban Convertibles has a 10% surcharge and Australian dollars may or may not be accepted based on the moods of the cashiers so Euros are the choice to carry.