The first part of your Caribbean island hopping adventure kicks off with an afternoon landing in San Juan. As you disembark, you’ll be met by your guide for a quick twelve-minute private transfer to the Condado Vanderbilt. Upon arrival, indulge in a glass of champagne at check-in. Afterwards, spend a few minutes taking in the views of the Atlantic Ocean before being escorted to your suite. Don’t miss the grand staircase that leads to where the original lobby once welcomed guests who arrived by ship.
It’s our belief that everyone could benefit from syncing up with island time once in a while. With so many Caribbean islands to choose from, it can be overwhelming to pick just one; we’ve put together an itinerary with some of the best Caribbean island hopping.
Our team at SmartFlyer knows that a Caribbean island retreat is always in season. Whether you’re escaping colder weather or longing for the ocean breeze, nothing quite beats sipping handcrafted rum cocktails on a white-sand beach. Island hopping between the Caribbean islands of San Juan, Puerto Rico and sunny St. Kitts are guaranteed to provide you with a mix of culture, adventure, and – most importantly – well-deserved R&R. Of course, each trip is highly customizable for each of our clients’ unique needs. But this outline gives you a solid springboard into the crystal Caribbean waters.
In Puerto Rico, wake up just walking distance from some of the best dining venues in the capital. Then, take a private tour through the picturesque streets of Old San Juan. Afterwards, indulge in a day trip to the only tropical rainforest in the U.S. National Forest Service. While you’re there, pick up some new dance moves with a Bomba class. Finally, retire to a champagne deck floating in the middle of a lagoon. While in St. Kitts, you can’t go wrong with Park Hyatt’s pristine property and culinary experiences as your sanctuary to retire after a guided hike up a dormant volcano. Finally, cap off your island getaway with a quick day trip to the neighboring island of Nevis.
Eight nights, nine days
Families with kids 21 and up will love this itinerary, as well as couples craving solo exploration and professionals looking for the ideal Work From Hotel home base
A blend of buzzing cosmopolitan highlights and classic island serenity
Ron del Barrilito and Brinley Gold Shipwreck Rum are excellent options for a taste of the Caribbean when you’re back home
SmartFlyer Puerto Rico + St Kitts Picks
With 210 hotel guest rooms and 107 suites of varying size, Condado Vanderbilt provides guests with sweeping views of the Atlantic Ocean. This refined 20th-century hotel retains its original lobby and grand, formal double level staircase and dark marble floors belie a very modern property. Sightlines through the lobby draw the eye to the vast Caribbean Sea beyond the floor-to-ceiling windows which surround the bar and lounge area.
The resort’s spacious and chic 126 guest rooms and suites combine contemporary architecture with a feel that taps into the rich historic roots of St. Kitts. Many of the suites offer individual pools with private sundecks and unobstructed views of the Caribbean Sea and the neighboring island of Nevis. All the rooms and suites face the turquoise water of the Caribbean Sea and feature spa-inspired baths. For those looking for an enhanced stay, their three-bedroom Presidential Villa includes a private sundeck and rooftop infinity pool with panoramic Caribbean views.
After settling into either your accommodation – we love the Presidential Suite – spend the rest of your afternoon in one of the property’s three pools overlooking the ocean. Top off your plunge with a sampling of authentic Pina Coladas. Fancy dipping your toes in the sand instead? Then walk one minute to the hotel’s reserved area at Condado Beach. Your personal attendant will help you pick the best spot and set up your chairs and umbrellas so you can head straight to the ocean.
Cap off your first day with dinner at José Enrique. This renowned restaurant is known around the island for its authentic Puerto Rican cuisine and located just five minutes within walking distance from Condado Vanderbilt. Chef José is an award-winning chef native to Puerto Rico who helped to spearhead the island’s focus on farm-to-table dining. The Puerto Rican culinary scene encompasses everything from traditional dishes like mofongo and empanadillas to multi-course tasting menus and seafood. The menu at José Enrique changes daily, but the pinchos and alcapurrias are always safe bets. Make sure you ask for the house-made hot sauce if you want an extra kick with your meal.
Kick start your day with in-room breakfast accompanied by ocean views before meeting your guide in the lobby to start your tour of Old San Juan. Crossing the Laguna del Condado and into the heart of the capital feels like stepping back in time. Historic Old San Juan’s seventy-four blocks are easily traversable and filled with beautiful Gothic, Renaissance, and Baroque architecture. Your guide will walk you through highlights like the highly-Instagrammable hanging umbrellas near Castillo San Felipe del Morro. Also known as El Morro, this 16th-century six-level fortress is considered one of Spain’s major military engineering marvels. It now serves as the governor’s house.
Pop into Barrachina for the final stop on your guided tour. This restaurant is a must-try for Caribbean island hopping trips as it’s the birthplace of piña coladas and is known for its signature cocktail and light bites. Afterwards, head back to the hotel for a quick swim before dinner or listen to live music at VCLounge. Some of our favorite spots within walking distance of the hotel are Mario Pagán, Cayo Blanco, and Ropa Vieja Grill. We also recommend stopping by Señor Paleta for gourmet popsicles on your way back to the hotel.
Today, you’ll explore some of the best beaches in San Juan located just a short drive from Condado. First, jump-start your morning with a coffee brewed from locally-sourced beans served at the hotel’s Ola Oceanfront restaurant. Then, hop into your Jeep rental and drive northwest to the beaches of Playa La Poza del Obispo. On your way out of town, stop at Panaderia Españato to stock up on sandwiches, cheeses, and sweets to enjoy on the beach. On your drive from San Juan to Manatí – also known as the Athens of Puerto Rico for its vibrant culture – you’ll see the island’s lush vegetation and cruise through the historic downtown. For the cinephiles, keep an eye out for the iconic locations that were featured in the James Bond classic GoldenEye.
There are plenty of spots to set up at the mesmerizing Mar Chiquita lagoon. The limestone outcropping boasts expansive views of the intense blue waters of the Atlantic Ocean. After soaking up some rays, cool off in Arecibo’s natural saltwater pools and dive headfirst into the cresting waves. Finally, dry off with a hike to see the 1898 neoclassical lighthouse built by the Spanish government. We recommend feasting on some locally-made camarones (shrimp) empanadillas during the journey.
Keep the top down on your Jeep for your hour ride back to Condado. After dropping off your Jeep and freshening up, dine at Cayo Caribeor La Marqueta for a delicious assortment of local favorites in a starry outdoor setting. Grab one last drink at The Lobby at La Concha Resort for a nightcap.
Take the morning to luxuriate in the sound of the ocean and wake up to some breakfast in bed. Then, make your way to the Condado Vanderbilt spa for a Hammam Ritual. The property offers a unique Turkish wellness ritual that combines purification rituals with hydro-sensorial therapy. After your treatment and lunch at the hotel, head to Santurce to visit the neighborhood’s famous street art. What started as a small artistic collective has transformed a long-forgotten neighborhood into one of the largest art districts in the Caribbean, hosting annual festivals and dozens of art galleries. These events are sure to make your Caribbean island hopping trip that much more vibrant.
This evening, join your tour guide for a rum tour through San Juan’s vibrant cocktail bars like La Factoria, Chocobar Cortés, and Carli’s Fine Bistro & Piano. We particularly love La Casita de Rones for their al fresco cocktail options. Finally, finish your rum tour off with a quick transfer to La Placita for a lively dance and tiki cocktail party and dinner featuring Junglebird’s delicious late-night grilled cheese sandwich.
Today marks this Caribbean island hopping trip’s choose your own adventure day! There are so many ways to experience all the beauty El Yunque National Forest has to offer. We recommend booking one of Condado’s full-day rainforest tours to explore four hours of pure hiking bliss. El Yunque is the only tropical rainforest in the U.S. National Forest Service where you can hike, swim in natural pools, and learn more about the 240 plant species that inhabit the island. Your private guide will also make sure you visit all the kiosks serving local delicacies that offer a unique new dish at each eatery.
This nature reserve offers two different finales to your guided tour: either an afternoon in picturesque Luquillo Beach or a Bomba Dance class. Bomba was created in Puerto Rico by West Africans and their descendants who worked the colonial sugar plantations at the end of the 17th century. It has since become Puerto Rico’s most popular genre of dance.
At sundown, enjoy a floating champagne golden hour deck on the Condado Lagoon booked by your SmartFlyer travel advisor. This guided tour starts with either a paddleboard or kayak excursion on the lagoon. You’ll be provided a picnic basket filled with Prosecco and your choice of a fruit or cheese board atop a floating platform as you watch the sun descend below the water for a picturesque end to your adventure-filled day.
After five nights in beautiful San Juan, it’s time to head to your next Caribbean island hopping oasis. Enjoy one final breakfast at Condado Vanderbilt before being picked up to go to the airport for your morning flight to St. Kitts. After touching down an hour later, you’ll be guided straight to Fisherman’s Village at the Park Hyatt St. Kitts Christophe Harbour. Here, you can begin the second leg of your Caribbean escape with some world-famous St. Kitts’s lobster.
This half of your trip is all pampering yourself and enjoying the tranquility of the sea. So, it’s only appropriate that you enjoy dinner at SALT Plage on the shores of Whitehouse Bay. After arriving by private car or boat, order a cocktail and lounge in a hammock just in time for the spectacular sunsets. Stick around for live music or perhaps a full moon party if the lunar calendar aligns with your stay.
Today begins with a half-day guided tour of St. Kitts’s many historical sites. Your first stop will bring you to The Circus, a roundabout anchored by a green clock tower and inspired by London’s Piccadilly Circus. The Victorian-style Berkeley Memorial Clock is the perfect place to get some unique island memorabilia.
Down the street, you’ll find Independence Square and The Immaculate Conception Cathedral. The square’s historical significance dates back to the 1790s when slaves were transported from ships off the coast of St. Kitts through underground tunnels. Today, the square serves as a place for locals to catch up and pass through on their way to and from town. A drive down Old Road Town will have you passing St. Thomas Anglican Church, the oldest Anglican Church in the Caribbean. Here, you can visit the Wingfield Estate’s excavated relics and learn more about the sugar plantation.
Return back to Park Hyatt St. Kitts in time to spend the afternoon learning the secrets to Caribbean cooking during a chef-led cooking class. If you’re craving more adventure, take a private guided hike up Mount Liamuiga, a 3,792-foot stratovolcano that last erupted over 300 years ago. For this evening’s dinner, visit Rock Lobster St. Kitts for a seafood-focused casual dining experience. If dining on a Sunday, be sure to enjoy a traditional English Roast Beef dinner with all of the trimmings including Yorkshire pudding.
After breakfast at the hotel, choose how you want to spend your final day on your Caribbean island hopping escape. The St. Kitts Scenic Railway is a three-hour guided tour along tracks originally built to transport sugar cane to the capital’s sugar factory. We recommend working with your SmartFlyer advisor to book a seat on the top deck for spectacular vistas of oceans, cliffs, and lush sugar cane.
If you’re looking for more seaborne exploration, the Maxi-Cat will transport you to Nevis, the birthplace of Alexander Hamilton. First, take the opportunity to snorkel at a protected cliffside cove. Then, sail across the Narrows, a two-mile channel to the lush neighboring island. Or, if you prefer to stay closer to the hotel, order a Park Hyatt St. Kitts picnic lunch and dine on the beautiful resort grounds. Spend the last evening of your trip dining privately at the Rampart Pool, built to mimic the UNESCO World Heritage Site Brimstone Hill Fortress.
As the saying goes, all good things must come to an end. As you board your homeward-bound flight, recount all the sights and sounds of the Caribbean as the islands sink below the clouds.
Contact your SmartFlyer travel advisor to begin planning your Caribbean getaway.
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