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Writer's pictureJenya Veselova

6 Travel Trip Ideas for Couples From Boston

One of my favorite trips to plan, are for couples in the Boston area to find time to reconnect, celebrate, and relax. As a mom of two young kids, I know how important it is to find time not just for the family vacation but also to live, love, laugh with your significant other. Being a travel advisor, I have helped dozens of couples in the Boston area (and beyond!); from newlyweds looking for that perfect honeymoon to couples looking to celebrate an anniversary or dare I say escape the kids to reconnect. So I thought, why not share some of the more popular ideas I have helped plan for my clients with you?


Couple Vacationing
Time to Live, Love, Laugh

Before we get going, I just want to point out that no solution fits every couple. One of the most important reasons for why you should work with a seasoned travel professional is to actually get the vacation for the budget you have in mind. Some couples want a thrilling action packed adventure, others want to explore the cultural wonders of the best cities in the world, while others want to find themselves on a pristine beach with a nice cocktail in their hand. There is no right answer except the one that suits your desire. Before you get going planning, think about contacting a well reviewed agent that will ask you the right questions and provide honest advice.


Now lets get to exploring!


The Winning Formula


While the result will differ for each couple, the formula for a successful decision tends to be the same.


Best vacation = vacation style + convenience + budget optimization


Let's break it down


Vacation style is essentially whether you want your trip to be focused on active/adventure, exploring cities/culture/nightlife, or relaxing at a resort destination. Of course its not a zero sum game, and many couples choose to find a blend and there are specific destinations I will get to below that are best suited for a blend.


Convenience is all about maximizing your vacation time by choosing destinations with optimal flight schedules and ideally direct flights. Traveling can be hectic with air travel surpassing pre-Covid era, so while it may be trivial to think about what destinations have direct connections but let's face it you get more time at your destination and less chance of an airline issue by going direct. Of course this does not mean you should never do connections, but in Boston we are actually blessed with dozens of direct international connections to Europe, South America, and Asia so this is not as much of a limiting factor as it may seem to fly direct.


Budget optimization is all about getting the best for whatever your budget may be. Hotels often provide deeper discounts to travel agents and hacking flight dates/times in combination can provide very significant savings for you. A lot of my clients are surprised to find that they can get so much from their budget.


The Pick 6 Travel Destinations for Couples in Boston


Riviera Maya, Mexico: Beaches + Mayan Ruins


With a direct flight year round from Boston to Cancun, you can be relaxing at an immaculate resort in about 4 hours. For couples, I recommend to go away from Cancun and head to the nearby Playa del Carmen region (just 45 minutes away). Some of the best resorts in the Caribbean are found nestled between the mangroves in this stretch of pristine beaches.


Why do I prefer Riviera Maya? There are a lot of amazing resorts to choose from that provide the best luxury experience for any budget. There are also a ton of activities to choose from beyond watersports, golf, and scuba. You can go on day trips to see the famous Mayan ruins in Chichen Itza or Tulum and finish the day jumping into a refreshing cenote.


I often get asked if its safe to go to Riviera Maya. As with any destination, or frankly even Boston, nobody can reliably guarantee someone's safety however I can tell you that I have personally gone to this region every winter with both my kids as well as on couples getaways with my husband. Hundreds of my clients visit this region every year and in general this is one of the most popular destinations for US and Canadian travelers every year.


My favorite resort picks for couples?


Fairmont Mayakoba



Secrets Maroma



Paradisus La Perla




Lisbon and Beyond in Portugal: European Charm + Gastronomical Wonder


One of the easiest destinations to get to from Boston, Portugal has so much to offer all year round. From amazing cultural cities like Lisbon and Porto, to the wineries of Douro Valley, and the beaches and landscapes of Algarve...Portugal punches the highest satisfaction among my clients vacationing as couples. You can really mix and match the type of vacation you want with a destination like Portugal because getting around is extremely easy and your budget goes further than most other European destinations.


My favorite itinerary takes you through the magical streets of Lisbon featuring a gastronomical adventure that is sure to please any foodie. In nearby Cascais you can relax with a great cup of coffee right on the coast surrounded by exquisite 'old world' mansions while in Sintra you will see some of the grandest palaces of Europe. Porto brings its distinct architectural marvels to life in a city filled with nightlife and music. To top it off, just an hour away you will be in one of the most famous wine regions in Europe relaxing at a winery boutique hotel.


People often ask me how easy it is to get around Portugal particularly because you will be driving. Let's just say that if you can handle Boston drivers and traffic, then Portugal will be incredibly stress free. The road networks are pristine and fellow drivers are respectful of the rules. One thing to note though is unlike other European countries, using trains is not particularly effective in Portugal especially if you want to see more than just Lisbon and Porto.


Final thought....Not only are there daily direct flights to Lisbon from Boston but its also one of the quickest flights to mainland Europe with the least amount of jet lag. Ok one more thoughts...Portugal is very affordable especially when comparing to France, England etc.



Here are some day trip activities in and around Lisbon (I would recommend the ones that include Sintra as its easier to do as a tour)



Costa Rica: Eco Adventures Abound


One of my favorite destinations---and also that of my clients---is the amazing country of Costa Rica. It would be hard for me to recommend another destination that provides so much eco diversity and adventure as Costa Rica. Zip line through the jungle? Check. Hangout at a surfer beach while monkeys jump around looking for a snack? Check. Explore a cloud rainforest with waterfalls, beautiful flowers, and flora/fauna? Check. Visit a volcano and hang out at the spas? Check.


Simply put Costa Rica is so rich in activities that I could write a book on what you can do. While its geared more for the adventure style vacation, Costa Rica also provides an amazing coast line that is mostly free from large resorts and crowds where you can unwind.


The go-to region is Guanacaste but there are multiple micro regions within this province that provides a drastically different look and feel. You can reach Costa Rica easily with a direct flight to Liberia in about 5 hours




For Costa Rice adventure activities you may consider booking a tour especially if you are interested in adventure activities like ziplining, ATV, and boat tours through the jungle


Switzerland: Simply Magical


While many think Switzerland is mostly a winter skiing destinations, its actually one of the best countries to visit in Europe during the summer months as well. Let's face it summer in Europe is extremely busy especially in cities like Paris, London, and Barcelona and frankly can be quite uncomfortably hot. Meanwhile Switzerland is like stepping into a magical land with pristine natural wonders and old world Europe charm cities. During the summer months, Switzerland provides a respite from the heat and opens up to great hiking, rock climbing, and boating. The country is quite compact and allows you to see multiple cities and small towns along the way with much of where you want to go being accessible by train.


Some of my clients prefer the more adventure and nature side of Switzerland and select to base their stays in and around Interlaken in the Bernese Oberland region. While others prefer to mix in more the cities of Zurich, Lucerne, and Geneva. My preference? I would do both! You can easily start in Zurich with a direct flight from Boston and after a few days head out to the lakes and mountains of the Alps that surround the city


One thing to keep in mind is that Switzerland can be quite expensive especially relative to other European options. However, as I mentioned before even with more expensive destinations there are still plenty of options for different budgets.




Italy: Food, History, and Plenty of Wine


Italy feels like a country that does not require any introduction; after all its one of the most popular destinations in the world. While there are many options of where and what to explore in Italy, I will focus on some of the more popular itineraries that my clients enjoy.


Starting off in Rome, the eternal city, you can soak in the rich culture that only Rome can provide. From the collections of the Vatican to touring the Colosseum, Rome takes you back in time with its absolutely massive collection of historical sites. Moving forward you can head north towards Tuscany with a base of stay in San Gimignano which looks like a gothic version of Manhattan with its towers. Tuscany provides the romantic retreat that couples are sure to love with its cute little towns, bountiful collection of wineries, and world renowned restaurants. After visiting Siena, you will find yourself in Florence less than an hour away. Florence with its grand Duomo and palaces is sure to delight any art lover with its rich collection. Finally you can end the trip in Venice a city known for its grand views and romantic strolls.


One thing I have to say is that I personally would not recommend this trip during the summer months. If summer is your only available time and you are set on Italy I would suggest cutting out Venice and in general focusing more time on Tuscany or perhaps venturing further north to Como. In the summer months, cities in Italy are overwhelmed with tourists and places like Venice (and to be fair Florence as well) simply cant handle the crowds.





Whether you want to take a vespa together through the rolling hills of Tuscany or take a pasta cooking class together, there are some great options for Tuscany to consider


Norway: The Fjords are Calling


While not a direct flight from Boston, Norway is worth the connection to visit and is a great hit with couples. This trip is all about taking in the natural beauty that Norway provides with its beautiful fjords and natural scenery. In the late fall through winter time, Norway is also a great way to enjoy an arctic adventure to see the northern lights in Tromso. Just imagine taking a sled ride out into the crisp snow to see this winter marvel while also enjoying a cozy fire back at your hotel.


However, Norway is not just about the winter experience. In the summer you can find amazing hiking and cycling trips around beautiful fjords. You can take one of the most scenic train rides in the world to Bergen and then hop on a fjord cruise to explore the beautiful surroundings. Norway provides a great respite from the heat and crowds of summer travel while also giving couples a good blend of both cultural and natural beauty.


Norway is rated as one of the happiest places on earth and is a fantastic destinations for couples looking for something different than what they are use to in a European getaway.




If you are visiting during the northern lights period in Tromso getting an organized tour is a must have in order to get the best view


For the best Fjord experience I would highly recommend booking a cruise with many great options departing Bergen


Summing it Up


Whether its your honeymoon, anniversary, or just because...make it a point to travel with your significant other. Choose the experience you want by thinking about whether you are more in the mood for a beach vacation or a city escape. Whatever your passion, there is always a destination that will open your eyes to new cultures, good food, amazing people, and natural beauty.


As with any "top" list there are many places that could have made the list. I have planned cycling adventures for couples to Tucson as well as Patagonia. I have clients who have loved exploring Japan as well as southeast Asia. There is no real top because that really depends on what you are in the mood for so here I tried to give you a glimpse of what are some of the favorite destinations that my clients choose for their couples retreat.


If you would like guidance on what will work best for you then feel free to contact me and I will be sure to help you decide and insure you are getting the most out of you hard earned vacation.



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