Where to Travel in 2019

January 16, 2019 Jeffrey Olinghouse

As we turn the page of the calendar and venture into 2019, planning travel for the upcoming year is often at the top of my clients’ list. While some trips can be enjoyed spontaneously, the best trips are planned ahead of time with great attention to detail. Like a beautiful wedding, a memorable trip is carefully chosen, mapped out, and scheduled in advance. Failure to plan carefully can often lead to high ticket prices, costly exchanges, sold out venues, and a host of other headaches. Therefore, as your knowledgeable travel advisor, I encourage you to sit down with your family early on in the year and discuss your travel plans, create a realistic budget, and make arrangements as soon as possible. Being proactive in your travel planning will serve you well in the long run, allowing you to enjoy the journey while minimizing stress.

During the initial planning stages, one of the most important things to consider is destination options. At the beginning of the year, my wife and I sit down and talk about where we would like to travel, what would be the most beneficial locations for gaining knowledge for my clients, how much we want to spend on travel, and when would be the best time for specific trips. We also consider what we’re willing to sacrifice for what we’re willing to gain. For example, Europe is one of our favorite destinations, but it’s also an expensive place for tourists in the summer. However, if we truly want to see a specific city in Europe, we’re willing to compromise and settle for less optimal weather in exchange for low-season prices. Discussing the pros and cons of each trip and the benefits thereof help us stay on track with both our vision and our budget.

After considering our options, we begin formulating a plan and a general budget for the trip. We factor in costs for air travel, on the ground transportation, accommodations, food, entertainment, and shopping. We’ve also discovered ways to cut back on our food budget like eating one larger meal a day, sharing meals, or purchasing snacks and sandwiches from a local grocery store. While these are small exchanges, they add up over the year and help us stay in agreement with our original plan. By the end of the year, we can look back and enjoy all the wonderful adventures and around-the-world memories we made together as husband and wife.

Of course, after having traveled to so many cool places, it can be challenging to narrow down my recommendations of the best 2019 destinations to my clients. Because travel is deeply personal and based on a customized experience, I endeavor to work with my clients to discover their particular interests and desires before planning a particular itinerary for them. As a result, I’ve had an amazing time creating and executing unique trips based on the client’s particular preferences. My concierge experience includes arranging an exclusive birthday party at a 5-star property in London, customizing private theme tours, setting up safaris in Africa, and designing packages for the Olypmics including front row seating to the events. Each trip has been like no other, and my clients come back from their experience with memories to last a lifetime.

In addition to catering to my clients’ individual travel aspirations, I also serve as an experienced resource for travel suggestions. Often, I find that unexperienced travelers can become easily overwhelmed with all the destination options available to them. Afterall, it is a big, big world out there! Thankfully, due to my 20-year tenure in the industry and my personal experience on the field, I can confidently suggest all-time winners that would please just about anyone and everyone regardless of their age or background.

With that being said, I’d like to share three specific destination options for 2019. I have personally experienced each of these destinations myself and have sent several clients to these places as well. None of us were disappointed, as the destinations on this list are both classic and customizable. If you’re at a loss as to where to experience your adventure this year, here’s my list of all-time winning destinations.

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ITALY

This southern European country is a traveler’s dream. Rich in culture, art, and history, Italy is alive with adventure and personal connection. Travelers can select from among the country’s diverse offerings including romantic Venetian gondola rides, art tours in Florence, historical ventures in Rome, sunbathing in the Almafi Coast, or spa treatments in Tuscany. Visitors can ski in the snow-capped mountains near Milan, drive a car through the winding vineyard countryside, or dine al fresco in posh resorts. Italy truly has something to cater to everyone.

My wife and I recently took a three-week tour of Italy and scouted the country from Venice to Sorrento. There was not one thing we didn’t absolutely enjoy about that trip—each stop on our itinerary was as magical as the next. We enjoyed meandering through the mysterious labyrinths of Venice, taking walking tours of Rome, visiting the Uffizi with an art history guide, and exploring off-the-beaten-path villages in the country. We had our fill of authentic pasta dishes, savored every gelato, and shopped for Italian made leather goods. The entire trip was full of romance, intrigue, and adventure—the perfect dynamic for any fun-loving couple.

If you wish to visit Italy this year, I suggest planning a minimal 10-day trip. Once you arrive in the country, ease into your trip by resting on your first day. After sleeping off the jet-lag and orienting yourself to the new surroundings, take a morning walking tour of the city. Should you decide to book a multi-city tour, I recommend using the train system until you get further into the countryside. If resort style is your preference, be sure to visit the Almafi Coast, focusing your visit in Sorrento and Positano. Regardless of your personal taste, you’ll return from Italy with a cherished memory and a rich experience!

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THE CARIBBEAN

The warm turquoise waters of the Caribbean are hard to resist, even for those who enjoy the cooler Northern climates. Nothing is truly more relaxing than a day sitting out under the warm sun, listening to the flavorful beats of a steel drum, sipping a fruit smoothie, and absorbing the view of white sands, blue waters, and open sky. If travelers have the possibility in their schedules, I would suggest at least one Caribbean trip a year, just for the sake of the slow-paced style and tranquil scenery.

Some travelers have been hesitant to visit the Caribbean after the storm damage of Hurricane Irma in 2017. However, most islands now are almost completely operational and offering their pre-hurricane services. On occasion, a traveler might experience a delay in service or power blackouts, but for the most part, the Caribbean is repaired and back to working order.

If visiting the Caribbean this year, I recommend the Dominican Republic for family-friendly all-inclusive resorts and Aruba for high-end leisure and relaxing properties. On my radar as well is Turks and Caicos, Anguilla, and Barbados. My wife and I have visited Aruba twice in the past 2 years and couldn’t agree more with the country’s slogan—it is a happy island, and one that we’ll visit time and time again.

NON-CONTINENTAL US

American travelers are familiar with crisscrossing the country for business and pleasure, but far few Americans take time to venture farther into Alaska and Hawaii, our country’s two non-continental states. Visits to to these locations are an enriching experience, as they enlarge travelers’ understanding of the US as a whole and give them a much larger perspective of the beautiful diversity in our own home country.

As we have been traveling extensively over these past few years, my wife and I have had opportunities to visit both Alaska and Hawaii and profoundly loved each experience. Like many Alaska visitors, we traveled to the state on a summer cruise and stopped along the coast at various ports of call. Each port provided us an opportunity to experience the most popular tourist attractions of Alaska including whale watching and wildlife sighting. As we sailed through Glacier Bay, the sunrise over the artic icebergs stunned us with its violet hues and cold stillness. We ended the trip with a 3-hour train ride from the last port to Anchorage that gave us a huge window into the Alaskan interior with full views of majestic nature and exotic wildlife.

Our excursions to the South Pacific islands of Hawaii have been no less of an adventure. We’ve visited the state twice, focusing our tour on Oahu and Maui. Of all the places I’ve visited, Hawaii has a special draw in its vibrant culture and beautiful people. Here, we’ve tasted of all the wonderful flavors Hawaii has to offer including incredible fresh seafood and fruit. We’ve seen its gorgeous beaches, experienced its sunset luaus, driven its mountainous heart-racing roads, and even survived its most recent hurricane in August 2018. Hawaii is a state like no other, full of both crazy adventure and captivating beauty.

Any traveler visiting Hawaii will walk away from these islands with unforgettable experiences that will last for years to come. This is an excellent destination for old and young couples alike as well as families of all ages. Many of the hotels offer family-friendly services, while other properties cater more to adults and couples. Regardless of your needs and preferences, Hawaii has something memorable to offer you and your family.

As you plan your travels for 2019, I hope you’re able to visit one of these places listed above if you haven’t already. Each location is a treasure in the world of travel and will be places you’ll love for the rest of your life. Happy New Year and may your travels bring you closer to the ones you love!