Since getting married and living in the United States Virgin Islands on St. John, Kristin quickly became the go-to Caribbean expert for friends and family. Phone calls to share advice and insider tips quickly turned into hands-on assistance with bookings and before she knew it, Kristin naturally transitioned to launching and growing her side hustle into a full-fledged travel consultancy.
Looking back on those earlier days, Kristin has found that her approach with clients has become much more personal over time; each client is individually looked after so she can make sure she’s tailoring each trip to their specific needs. Kristin shares, “Travel preferences are extremely subjective, so I make sure to work with each client to ensure their specific requests are fulfilled every time they book with me.”
How has your love for travel translated into the way you work with your clients?
Kristin Diehl: I have always been drawn to tropical destinations, from sailing on catamarans as a kid to now being able to bring my own children to the islands; it’s really special to watch them fall in love with crystal clear water and tropical vegetation the same way I did at an early age. Not every island offers the same experiences which is exactly where a Caribbean expert comes into play. By understanding my clients’ interests and purpose for a trip, I use my in-depth knowledge of the region to best advise clients on where their ideal trip should take place.
Tell us more about what you take into consideration when pairing a client with an island or beach spot.
KD: With any trip, the first questions are always who, why, when? Having an honest conversation about the “who” and “why” will dictate the style, flow, and purpose of the trip. Knowing what the client really wants out of their time on vacation is essential to finding the perfect pairing, as some want action and adventure, while others prefer ease and relaxation. For a resort with local experiences off-property, Sugar Beach in St. Lucia is ideal for both family vacations and romantic getaways. Opposite that for travelers needing R&R–especially honeymooners–we love Secret Bay in Dominica or Viceroy Riviera Maya in Mexico.
“I apply a balance of travel time and difficulty of access with the duration of stay, placing value on every minute of the trip.”
This is what leads me to the most important question in the planning process: when. The timing is all about striking a balance between dates and duration of stay as certain destinations are more complex to reach than others, while some may be truly seasonal. I apply a balance of travel time and difficulty of access with the duration of stay, placing value on every minute of the trip. For example, a weekend getaway is much better suited for the quick flight to the Bahamas or Turks and Caicos (especially if connecting in Miami), but if you have more time, the options can expand way beyond those countries! For a destination that’s worth the extra puddle jumper, look at Islas Secas in Panama.
You have two little ones–do you take them with you when you’re traveling for beach and sun? Where do you stay as a family?
KD: Since my girls are still young, I want easy travel days, kid’s clubs for when we need a break, and adventure when we are ready to go. Dorado Beach, a Ritz-Carlton Reserve, Rosewood Mayakoba, and Four Seasons Resort Costa Rica at Peninsula Papagayo are always on the top of my list. All of these locations have unique kid’s clubs, but Dorado’s Jean-Michel Cousteau’s Ambassadors of the Environment is beyond amazing. Located on the beach, with panoramic views of the beach, this indoor/outdoor club offers all the entertainment your kids need, while still reminding them of their stunning surroundings.
Easy travel days are important with kids, so getting to these destinations can be painless, especially when Rosewood Mayakoba is not only assisting with your easy arrival but pre-stocking the rooms with your Rose Buds amenities (skincare products, wireless monitors, etc.) in a pre-baby-proofed room. Last, we all want to have fun with our kids therefore adventure is key, like at Four Seasons Papagayo; from guided hikes and scavenger hunts to ziplining in the rainforest, some days are best with pura vida!
When you’re not traveling with little ones, where are your favorite places to stay as a Caribbean expert? What are some of your top beach picks for romance?
KD: Easily, my personal favorite for adult-only time is Hermitage Bay in Antigua. This resort is laid-back, private, and has a strong customer service focus. This property is perfect for rest, relaxation, and getting that idyllic island atmosphere you imagine when you think: toes in the sand and cocktail-in-hand. Alternatively, if you’d like to stay stateside for a quick weekend getaway, the sexy Faena Miami Beach’s electricity is exactly what every couple needs. Their restaurant, Pao will reawaken your palate and then guests can just head downstairs to the Faena Theater for a show for a perfect ending to your date night.
Tell us about your favorite spa experiences.
KD: I have two words: COMO. SHAMBHALA. Immediately you are blown away at COMO Parrot Cay by the spa views, overlooking the North Caicos Channel and the surrounding wetlands–and this just the entrance. The spa services are exceptional, and the facility offers ample space to rest and recharge via pools, steam, and lounges. I suggest starting your day with a private session with Natalie. Her Structural Alignment Pilates Program, inclusive of a full-body alignment screening and alignment-focused Pilates session, is the best way to kick off a spa day.
My specialization as a Caribbean expert bleeds into Mexico and a bit of Central America as well when it comes to sand and sun destinations. On a recent scouting trip to Cabo, I spent a day at Waldorf Astoria Los Cabos Pedregal’s spa. I started the day with sunrise yoga and meditation (I am admittedly bad at meditating, but it was worth it!) to slow my mind for my spa time. Once in the spa, I was welcomed with a Mexican foot cleansing ritual then set off to enjoy the steam rooms, saunas, ice rooms, and whirlpools for my pre and post-treatment time. I attempted more time in the salt-water meditation pool, but in the end, my time was better spent poolside, with a quiet lunch…as they say, it’s a tough job sometimes, but someone’s got to do it!
Best islands to enjoy local living? Tell us more about how you ensure guests get a taste of the local flair!
KD: St. Kitts and Nevis are more than Alexander Hamilton’s birthplace, but islands rooted in history and heritage. You can arrange an island tour with a local historian or self-tour this easy-to-navigate island. Dine at Indian Summer, about a 10-minute drive from Four Seasons Nevis, or go to Salt Plage on St. Kitts for a sundowner or… if you’re lucky, one of their full moon parties!
Best islands for nightlife and off-property experiences?
KD: Caribbean expert or not, it’s hard to argue that the best nightlife could be anywhere but St. Barths. You’ll definitely want to stay in St. Jean Bay, perhaps at the iconic Eden Rock – St Barths, but don’t spend all your time here! Once you’re on the island, you’ll quickly get drawn in the nightlife scene and will want to make sure you have the hottest reservations. For energetic lunches turned into sundowner scenes, check out Le Pearl (ideally Bikini Brunch on Saturday) or try Nikki Beach and Shellona and see what the DJs are spinning. For dinner, try Le Baz Bar for sushi and shows, La Case for a true Caribbean culinary experience, Isola for a romantic retreat, and Bagatelle for the harbor view terrace and more dancing.
For true island life and off-property experiences, I love St. Kitts and Nevis. Either Four Seasons Resort Nevis or Park Hyatt St. Kitts offer experiences like exploring rainforests complete with waterfalls and volcanoes. For history buffs, spend time with the island’s historians, and learning even more about Alexander Hamilton’s birthplace. These islands are on my 2022 bucket list, with or without my kids. I personally want to explore some of these local dives for Caribbean eats and drinks, after lots of adventure exploring past the blue waters.
As a Caribbean expert, do you have a favorite island or beach destination and if so, why? What spot remains at the top of your bucket list?
KD: The ultimate Caribbean vacation, in my opinion, will always be a crewed catamaran in the British Virgin Island. I am drawn to laid-back travel and heavy on customer service. Being on a boat with an intimate group, having all your meals, drinks, and activities arranged for you on the fly is heaven. But in terms of up-and-coming Mexico, a trip to One&Only Mandarina remains on my bucket list; this newly opened property has been a hit for couples and families alike. I have only the best feedback from clients and agents who have been lucky enough to visit recently, and I am actively trying to schedule!
Kristin Songy Diehl 
