In the dead of winter, the short daylight hours, bitter cold, and gray skies can become monotonous. But for those willing to travel, sunshine and balmy weather are always just a drive (or plane ride) away.
Whether you want to dip your toes in one of the world’s most popular black sand beaches, watch the manatees play in lagoon waters, or immerse yourself in a cultural center, we’ve found a warm, sunny spot for you.
Americans can pack their swimsuits and leave their passports at home while visiting these 5 beach destinations.
San Juan, Puerto Rico
San Juan was a fortified city 500 years ago, and today, it is Puerto Rico’s cultural center. This U.S. territory offers 270 miles of coastline, warm temperatures, and approximately 300 beaches to locals and tourists. Explore the coves, snorkel in San Juan’s clear water, or watch the manatees playing in Condado Lagoon.
After you dry off from a day spent at the beach, head into the city to enjoy the culture of the city. San Juan is the oldest European-founded city in the Americas and has preserved the historic architecture and cobblestone streets for that Old World feel.
The fort, Fuerte San Felipe del Morro, Saint Christopher’s Castle, and San Juan Baptista Cathedral are also worth a visit.
Foodies can sample traditional dishes such as mofongo, fried alcapurrias, Puerto Rican tamales or pasteles, or roast pork, and then finish a meal off with a pina colada.
Whether you are looking for a capital of culture, or just some winter fun in the sun, San Juan, Puerto Rico is worth putting on your travel map. This popular destination also gets the top spot on U.S.A Today’s10 Best Beach Destinations list.
Big Island, Hawaii
On Big Island, Hawaii, you can enjoy balmy outdoor weather even in the winter months. The temperatures here see highs of up to 80 degrees and rarely drop below the mid-60s.
Also, you get to skip the summer humidity–and crowds!
The Big Island is known for its stunning views and some of the best rainbows in Hawaii. Head around to Punaluu Beach and visit the turtles that live on its striking black sand.
Or, tour the famous Kona coffee farms and enjoy a gourmet cuppa as you take in the views.
The weather, year-round activities, and unique beauty make Big Island a perfect winter destination to escape the cold.
Since Hawaii is America’s 50th state, U.S. citizens don’t need a passport to enjoy this gorgeous beach destination.
St. Simons Island, Georgia
St. Simons Island is the largest barrier island in the Golden Isles.
This island is just an hour away from Savannah, Georgia so the winter months are often chillier than more tropical locations. However, from January to March, you still can expect to enjoy mild 60-degree weather.
In fact, the winter months are a perfect time to enjoy the island without the crowds. You can birdwatch at East Beach and Gould’s Inlet, rent a beach cruiser to tour the island, bike the trails, or play golf at the picturesque King and Prince Golf Course.
From Labor Day until Memorial Day the beaches are open to pets. So you can enjoy the waves and white sands of St Simons Island with your furry friend at your side.
St. Thomas, U.S. Virgin Islands
The winter months are the best for visiting the U.S. Virgin Island of St. Thomas. From December to May temperatures reach the 80s and humidity is low. Also, there is very little rain during this season to dampen your vacation plans.
On St. Thomas, you can observe endangered green sea turtles while snorkeling or relaxing on the sands on Honeymoon Beach. At the top of St. Peter Mountain, you can take in the sights from Magens Bay to Puerto Rico.
This winter beach destination is perfect for enjoying the waves, sand, and sunshine without the crowds. It is one of the best spots in the Caribbean for family fun.
Anna Maria Island, Florida
Anna Maria Island is a popular vacation spot for national and international tourists alike.
This sunny spot with its white Florida beaches offers tropical foliage and old-fashioned charm.
You can enjoy nature and watch the dolphins and manatees play without high-rise condos and fast-foods spoiling the views.
Anna Maria is still untouched by mass tourism and allows you to unwind in the winter sun and enjoy the unbeatable views in peace and quiet.
While many remote workers surely have dreams of globetrotting with their laptop in tow, maybe their work arrangement just doesn’t quite match up.
The remote work takeover has its set of controversies ranging from frustrated bosses to empty commercial real estate spaces.
Digital nomads tend to say, “that sounds like a personal problem!”, as they hop from place to place and getting paid to do so.
A new study by MBO Partners revealed the latest trend of tethered nomading, which basically means more remote workers are staying put in the U.S.
In fact, the study concluded that 53% of digital nomads in the U.S. plan to stay in the country year-round compared to just 10% who plan on jet-setting internationally.
Just about any U.S. city worth planting roots in is going to be costlier than traveling abroad, but that isn’t stopping remote workers from giving it a go.
These are 5 U.S. cities perfect for digital nomads as more remote workers stay closer to home:
Chicago, Illinois
The midwest’s only metropolis is a thriving megacity with so much to experience. Any type of traveler will love a trip to The Windy City.
But Chicago is well suited for digital nomads for a variety of reasons. First and foremost, remote workers will have no issue staying busy when they shut their laptops off for the day.
The city is so much more than a shiny bean statue and delicious deep-dish pizza. There are wonderful neighborhoods to explore where you will all but certainly find your niche.
There is a growing community of digital nomads here ready to welcome you, including regular Meetup groups.
With a plethora of trendy cafes, co-working spaces, and the most affordable metropolis in America, Chicago should highlight your list of digital nomad spots.
Denver, Colorado
Colorado’s hippest city is a happenin’ place. There always seems to be something fun going on and you simply can’t beat the city of the majestic mountains as your daily backdrop.
Denver is a haven for beer enthusiasts with many breweries offering wi-fi. Maybe just set the beer out of view for your Zoom calls.
You know, for professionalism’s sake.
If that’s too risky, then one of Denver’s lovely cafes or a variety of co-working spaces may be better suited for you.
According to Nomad List, Denver was ranked the #1 city to live in the U.S, and for good reason. Family fun, fast internet speeds, and a high quality of life are just a few samples of the city’s highlights.
Orlando, Florida
Florida is one of the most visited states in the country. Orlando is a key reason why. From a digital nomad perspective, this city is the best of both worlds.
You have the fun city life mixed with beaches a day trip away. Not to mention the greatest theme parks in the world when you have some downtime.
The best part of all may be you can live here for under $2000 per month! That is quite a rarity in the U.S.
Factor in cushy co-working spaces and a variety of charming cafes; you can work wherever you want. Plus, the weather is fantastic!
San Antonio, Texas
A cultural gem an hour south of the trendy city of Austin is the lovely city of San Antonio. This vibrant city will allow you to immerse yourself in a buzzing cultural community full of history and amazing food.
San Antonio is very welcoming to all types of travelers and another rare place where digital nomads can live off a $2000 per month budget or less.
San Antone, as locals call it, is branching out with more thriving cultural neighborhoods ready to embrace more visitors.
There are multiple co-working offices throughout the city and trendy cafes serving local favorites with a Mexican twist.
El Paso, Texas
Another Texas gem is the often-overlooked city of El Paso. Set in the corner of Texas between Mexico and New Mexico is a city that will shock you with how much you love the culture and stunning nature.
Digital nomads may just love it the most, as this cocktail of cultures is perfectly suited for short and long-term stays at a very affordable cost.
We’re talking a monthly budget of $1500 or less! Airbnb’s are super affordable, and there is also a new capsule hotel downtown if you’re flying solo.
Fall and winter may be the best time to visit the safest city in Texas as the scorching desert heat dissipates.
Working from one of the many modern, tasty cafes or centrally located co-working spaces is much more enjoyable on the patio this time of year.
When most Americans think of jetting off to a tropical paradise, they probably think of places like Jamaica, Cancun, or The Bahamas. But did you know there is a stunning tropical destination close to home that you don’t need to pack your passport for?
For Americans itching to get a taste of the tropics without leaving the country, they don’t have to look far, as the perfect destination lies within easy reach — The Florida Keys 🌴.
Combining several incredible destinations in one, The Florida Keys deserves a top spot on your travel bucket list.
From the snorkellable Key Largo to the quirky Key West, there are endless opportunities to make your tropical dreams come true in The Florida Keys.
The Perfect Florida Keys Itinerary
There are so many incredible places to stay when visiting the Keys it can be difficult to pick one. The easy solution to this is, of course, to pick them all! There is something in The Keys for everyone, and every Key is worth checking out.
It’s also incredibly easy to see everything The Florida Keys has to offer without breaking the bank.
For the ultimate Keys trip, we highly suggest flying into Miami, renting a car, and road-tripping through The Keys. Best of all, there’s no need to make the trek back to Miami when the vacation sadly comes to an end. Simply drop your rental car off at Key West International Airport and fly home from there!
Key Largo & Islamorada
The first stop on your adventure will be Key Largo, one of the best places to call home for a few nights on a journey through the Keys.
For a perfect spot to call home base, you can’t go wrong by checking into the Reefhouse Resort & Marina.
The resort is central to Key Largo’s top attractions, like John Pennekamp Coral Reef State Park, and it has plenty to do on the property, with an amazing pool, a private beach, and delicious food. Plus, you’re only a few minutes away from Islamorada, meaning you can experience 2 Keys in one during a stay at the Reefhouse Resort.
One of the top things to do in Key Largo (and the rest of the Keys for that matter) is to go diving or snorkeling. Don’t worry if you forgot your mask; the Reefhouse Resort & Marina has a dive shop right on site!
Get Underwater
Speaking of diving, don’t let yourself pass on the opportunity to get underwater while in Key Largo. This area is home to some of the best scuba diving and snorkeling spots in the U.S. and is not to be missed!
If you have never tried scuba diving and want to learn, there is no place better. If you are already certified, you will love getting to explore the unique underwater landscape the Keys provides.
The average depth when diving in the keys doesn’t typically go beyond 30 feet or so, meaning you’ll be able to spend plenty of time on the bottom saying hello to sting rays and turtles.
If you’re wondering where to try diving, give Horizon Divers a call and tell them what you are looking for. You can easily get yourself on a morning 2-tank dive to explore the shallow reefs and shipwrecks in the Upper Keys National Sanctuary, and you’re guaranteed to have a good time.
You will not go hungry in the Keys. There are so many incredible places to grab a bite to eat that we could write a novel listing them all out. However, there are a few that you definitely shouldn’t miss! Key Largo has one of the best places to grab a bite, the famous Fish House.
The Fish House has locally sourced seafood that is to die for, all served in a quirky “keys-style” restaurant. Just give them a visit and you’ll see what we mean. This is the perfect spot to grab lunch after a morning dive and it should definitely be on your list of must-dos.
Plus, there are plenty of opportunities to grab some photos with friends and family.
If you are staying at the Reefhouse or somewhere nearby, be sure to schedule an afternoon/evening to visit Islamorada. This is the Key directly below Key Largo and is close enough that you can check it out without having to swap hotels.
There are 2 things you definitely need to add to your list of must-dos in Islamorada, and both are delicious.
Firstly, no visit to the Keys is complete without spending some time at The Florida Keys Brewing Company. As you can imagine, space is a prized commodity in the Keys, which is part of what makes this brewery so special.
The Florida Keys Brewing Company brews all of their beer right on-site and is one of the only local breweries that can truly say their beer is made right in the Keys.
Aside from how incredible the beer is, the property itself is eclectic and inviting. Everyone you meet will be friendly and nice, and you’ll be surrounded by incredible artwork, amazing beer, and a welcoming vibe.
After a beer or two, you’ll feel like a regular and probably start contemplating a move to the Keys 😅.
After a tour of the brewery, head right across the street for an amazing sunset dinner at Morada Bay Beach Café. This was one of our favorite dinners in the Keys. Not only was the food incredible, it was beautiful. Even your water comes out dressed to the nines!
Morada Bay Beach Café sunset dinner
And not only was the food delicious and beautiful, the scenery was gorgeous as well. We found ourselves pulling out the camera to try to capture the sunset as it would paint a different picture of the evening for you every few minutes.
If you want to feel like you are eating dinner in a beautiful painting, this is the place to do it.
Heading South
The upper Keys are beautiful, and we already can’t wait to go back, but you are missing out on some of the most iconic sights in the Keys if you end your adventure there.
After spending some time checking out Key Largo and Islamorada, be sure to pencil in a few days to head down the most beautiful stretch of highway in the U.S. to Key West.
Overseas Highway in The Florida Keys
And there’s no need to rush; there are great places to stop off for a bite to eat or take in the scenery along the way.
We left right at around lunchtime, so we made a stop in Islamorada for a delicious meal at the Oceanside Safari Restaurant and Lounge — be sure to try their special Mojito with fresh mint!
It’s the perfect way to cap off your lunch and will leave you feeling refreshed and relaxed.
Oceanside Safari Restaurant and Lounge Mojito
On your way down to Key West, you may find yourself staring out of the window at the ocean around you.
There is no other highway in the U.S. that gives quite the same feeling as the Overseas highway, and you’ll be glad you decided to drive through the Keys.
Be sure to stop off at the end of a bridge or two to take it all in and grab some photos.
Before you make it all the way to Key West, consider stopping at Bahia Honda State Park for a beach break. There are award-winning beaches and gorgeous stretches of sand to set up camp for a few hours. If you have snorkeling gear, definitely be sure to explore what’s in the water as well!
Pick The Perfect Hotel For You
After catching some sun and sand, you’ll be ready to head into Key West to your hotel (of which there are plenty!).
Depending on what you are looking for during your stay in Key West, there are tons of hotel options to suit your needs. Much of Key West’s action is centered around Duval Street, so if you are coming for the nightlife that may be where you want to look.
However, we wanted to be close enough to the action to enjoy all Key West has to offer without being right in the thick of it. We wanted to enjoy Key West but stay somewhere that felt like its own secluded area away from the rest of the island.
The Capitana Key West was the perfect place to call home that achieved exactly what we were looking for.
From the second you check in you can feel the calm and relaxing energy of The Capitana.
If you are staying in the main hotel building, you’ll have incredible views of the pool and beach from your room, but for a more intimate experience, we opted for the Two Bedroom Cottage.
Many people who come to Key West dream of packing up and moving there after visiting. Staying in a cottage allows you to feel like you already do!
The Capitana Key West Cottage Canal View
The property is a great escape that you could spend your whole trip enjoying if you wanted to, and it is great for every type of traveler and party size.
Spend the afternoon sipping cocktails by the pool or get active and try your hand at some badminton. Either way, you’ll love your stay at The Capitana.
Key West Is Endless Fun
You’ll have trouble deciding what to do with yourself because there are endless opportunities to have an amazing time in Key West, but let us help you out by sharing some can’t-miss experiences:
Sunset Sail
There are plenty of companies offering sunset sails, and if you walk to the Marina, you’ll see signs for all of them. We decided to head out with Sebago Key West and would absolutely do it again!
You’ll head out to the beat of a live musician while the (included) drinks start to flow, and the breeze from the ocean will cool you down before taking in a gorgeous sunset from a unique perspective.
Keep an eye out for dolphins and turtles. If you are patient, you’ll likely spot a few.
Speaking of dolphins, if you’ve never seen them up close and personal, then you should definitely go out on a dolphin watch. We went with Honest Eco, and cannot recommend them enough.
They explained so much about Key West’s dolphin population and you could tell they cared a great deal about the dolphins and making sure the experience was a great one for both humans and dolphins.
We were lucky enough to have some dolphins come right up to our boat to say hello, and it was a bucket list item of mine. I’m a bit of a sucker for animals, and this experience was surreal. I’ve always loved dolphins and been amazed at their intelligence; I’m not ashamed to say I teared up having them so close — there’s no experience quite like it.
If you are on the fence about a dolphin watch, go ahead and book it, especially if heading out with Honest Eco.
The Hemingway House is a classic tourist attraction in Key West, but there’s a good reason for it. The house itself is gorgeous, and the history behind it is fascinating.
Most people know it as Ernest Hemingway’s former home, but before Hemingway owned it, it once belonged to Asa Tift, one of the richest people to ever live in Key West and the most famous wrecker in the area.
Even if the history of the home isn’t your thing, it’s fun to see how many kitties you can spot around the property, all of whom are UNESCO world-heritage protected and allowed to roam the property at will.
Many of the best things to do in Key West are in or on the water, and a kayak tour is one of them.
You’ll see all sorts of wildlife from nurse sharks to starfish, and get to learn about the importance of the mangroves and their significance in the ocean ecosystem.
Kayaking through the mangroves makes you feel completely cut off from the world in the most beautiful way and is an experience you should try at least once. For a one of a kind experience, we went with Lazy Dog Charters.
I can’t stop going on food tours! Seriously, they are the best way to learn about a new destination and a great way to get the lay of the land at the beginning of your trip.
Not only do you learn about the area geographically, but you will also leave with a huge list of all the best places to eat and drink. Aside from the food, you’ll also learn about the culture and history of the area.
In Key West’s case, you’ll never be short on history, culture, or food to sample. Around every corner, there is another story waiting to be told and a new one ready to unfold. There is so much fascinating history in Key West, and it is certainly one of the most unique places in the U.S.
To get the most out of this experience, we went with Key West Food Tours, and the tour did not disappoint.
We said above that you wouldn’t go hungry in the Upper Keys, and the same holds true in Key West. There are a million food options that are all incredible, each with their own unique Key West flair. Certainly don’t restrict yourself to our list, but some of our favorites include:
Half Shell Raw Bar – If you love oysters, this is your spot! Right in the Marina, you can enjoy your meal knowing you are eating some of the freshest seafood money can buy.
Milagro – Chef Kevin has worked with Michelin Star chefs for most of his career and took that experience to create a restaurant with 5-star cuisine in a casual, bistro environment. The food is deliciously decadent in a more laid-back setting — in true Key West fashion.
Blue Heaven Key West – The most iconic brunch spot in Key West and a definite must. Not only is the food delicious, but you’ll feel like you stepped into another world the second you cross the threshold of the entrance.
No Keys Experience Is The Same
It’s an unfortunate fact of life that every vacation must eventually come to an end, but some destinations are worth endlessly repeating. The Florida Keys is definitely one of them.
There is a reason so many travelers come here time and time again, and every visit to The Keys will reveal something new and exciting.
We loved our time in The Keys and, like so many others, will be coming back the first chance we get!
**Travel Off Path was a guest of The Florida Keys, who helped with the creation of this itinerary by hosting some of our accommodations and attractions. Our opinions, recommendations, and suggestions remain our own.**
Mexico, in general, is becoming extremely popular amongst expats and digital nomads. Its mild weather, affordability, and diverse natural beauty make it ideal for a laid-back and easygoing lifestyle. In recent years, Mexico City has become a major hub for digital nomads, and Tulum has been attracting beachgoing crowds for a while.
However, there’s one small town on the Pacific Coast that is relatively unknown outside of the backpacker and digital nomad community.
Puerto Escondido, literally meaning “hidden port,” is an up-and-coming beach town on Oaxaca’s Pacific coastline known for its surf spots, relaxed atmosphere, and vibrant nightlife. Its beautiful beaches are lined with boutique hotels, surf schools, and seafood restaurants.
Visitors express that they like how calm and uncrowded it is. Many who plan to visit for a short time end up staying for much longer. Although it has flown relatively under the radar to the masses, Puerto Escondido is starting to appear more and more on social media and in travel publications.
Here are some of the reasons Puerto Escondido is one of the favorite spots amongst digital nomads in Mexico:
Laid-back Atmosphere
Digital nomads love Puerto Escondido because of its laid-back beach vibe, excellent surf opportunities, and incredible natural beauty. Aside from its gorgeous beaches and lush jungles, visitors mention friendly locals and a lack of pushy vendors.
Accommodations are usually smaller boutique hotels, coliving spaces, and surf hostels. Big resort hotels have not yet invaded the beaches, although this is a worry for those who fear that Puerto Escondido will become the next Tulum.
Being that the crowd is mostly backpackers and digital nomads, it’s not bringing in tourists on a short holiday. Even during busy times, it is said that it is far less crowded than other popular beach towns in Mexico.
Puerto Escondido has plenty of things to do when you close your laptop for the day. Of course, surfing is the number one activity, but if you’re not a surfer, you can relax on one of the many beautiful beaches, take a boat tour, or take a jungle hike to find waterfalls.
One popular event that happens every evening is the baby turtle release. Volunteers can participate in this unique opportunity and learn about the conservation of turtles in the area.
Nightlife
Although the relaxed beach atmosphere is one of its draws, Puerto Escondido also has a vibrant nightlife. There are plenty of bars, clubs, and restaurants to choose from.
There are lively beach bars, great music, and delicious food. You can find activities such as live music and karaoke, or just sit back and relax, enjoying a cocktail and the stunning sunset.
Affordability
Compared to many other popular beach towns, Puerto Escondido is considered much more affordable. It is smaller, a little off the beaten path, and brings in far fewer visitors than, for example, Tulum.
Accommodations and restaurants have a more local feel, rather than the big resorts and franchises elsewhere. With the cost of living relatively low, it is an ideal place to live and work remotely.
Great Base For Day Trips
Nomads and slow travelers often have a “home base” that they will then make shorter trips from during weekends or days off. Puerto Escondido is a perfect place for this, as there are so many amazing locations nearby.
Mazunte and Zipolite are two such places where you can find even more pristine and secluded beaches.
You can also head to the Punta Cometa viewpoint to get some amazing views of the Pacific Ocean.
Another popular option is to visit the Manialtepec Lagoon to see bioluminescent plankton or the Chacahua Lagoon for mangroves, wildlife, and the crocodile hatchery.
It’s important to note that while many cafes and coworking spaces are popping up throughout the little town, it is somewhat rural, and the internet can be slow and unreliable compared to what most digital nomads are used to. If you plan to spend some time here, be sure to familiarize yourself with coworking space options and have a backup internet source like a data plan or portable hotspot.
Have you been dreaming of leaving it all behind and jetting off to the Caribbean but keep putting off that passport renewal? Luckily, Americans can experience the beauty and charm of the Caribbean without a passport!
In fact, Americans can experience the best of the Caribbean without a passport, without exchanging money, without a long-haul flight, and without dealing with the hassle of international cell service limitations.
Take It From Me, Puerto Rico Is The Most Accessible Caribbean Destination
When the opportunity to travel to Puerto Rico this fall presented itself, I jumped on it immediately. Having lived elsewhere in the Caribbean since July, I was interested to see how different things were in San Juan. As an American, I knew I could travel to Puerto Rico without a passport. However, it didn’t register how truly easy it was to visit until I flew to San Juan.
The flight was a breeze! A lovely 2.5 hours from Miami with gorgeous weather, so the view from above turned the world below into a painting.
Having never been to Puerto Rico, I still felt like I was traveling to another country outside of the States. With Puerto Rico being a U.S. territory however, flying into San Juan was like any other domestic flight. When I landed and took my phone off airplane mode, I had fantastic cell service. Once deplaned, a small part of me felt like I needed to go through customs.
Instead, I was outside the airport and waiting for my ground transport in about 5 minutes! The drive to my hotel, The Sheraton, was smooth and short, which felt out of the norm for the Caribbean. If you’ve frequented much of the Caribbean, you probably know how rough the roads can get!
As we all know, the media often tends to exaggerate. As my departure date inched closer, I watched two hurricanes make landfall in Puerto Rico. First Fiona, and then Ian. Friends and family kept asking me if I planned to cancel my trip. I never had any intention of doing so, but did wonder what things would be like when I arrived.
Hurricane Fiona Approaching Puerto Rico Credit: Zoom.Earth
By no means am I discounting the impact Hurricane Fiona and Hurricane Ian had on residents of Puerto Rico, particularly those in the south. Still, while exploring San Juan, I saw no evidence of storm damage and no areas without power, save the occasional traffic light. Everything seemed to be operating business as usual.
Speaking with my driver on the way to the hotel, he recounted his experiences throughout various hurricanes. He told me how much his life changed during Hurricane Maria, one of the worst to ever hit the island. Fiona and Ian were no comparison, at least for him.
Brad Dean, CEO of Discover Puerto Rico, later informed us at a press conference that Hurricane Fiona barely impacted travelers’ plans to come to the island for vacation. Less than 10% canceled their trip, and in Dean’s words, Hurricane Fiona was “a setback, not a reset.” Indeed, most of Puerto Rico was and still is completely open and safe for travel.
One Of The Best Ways To Give Back
It may seem counterintuitive, but one of the best ways to help the local economy of Puerto Rico, even after a hurricane, is through travel and tourism. Even something as simple as grabbing a quick bite at a local brewery adds up and supports the locals who work there.
During my stay, I had the pleasure of talking to numerous locals working in the tourism sector. Each of them echoed this sentiment, traveling to Puerto Rico and enjoying local activities is one of the best ways you can help.
An Immense Cultural Experience
Since it was my first time in Puerto Rico, I didn’t know what to expect. My typical go-to destinations are mostly European, and I have a deep-rooted love for the old. Marveling at the beauty of St. Paul’s Cathedral in London, walking among ancient Viking burial mounds in Mølen, and exploring Blarney castle in Ireland are memories solidified in my brain. Not because of their visual appeal, but because of the connection I felt to the history and culture of those experiences.
Puerto Rico now has a place among this special set of memories, and I can’t wait to go back. Walking through the historic district of Old San Juan showed me that Americans don’t have to travel far to see a unique blend of history. Old San Juan is the oldest city in the U.S. and its territories. Visitors can see gorgeous buildings displaying Baroque, Neoclassical, Gothic, and Spanish Colonial architecture — all within walking distance of each other. On the western side of Old San Juan, some buildings date back to the 1500s — the history lover in me felt right at home.
A Unique Take On History
I explored Old San Juan in a unique way that I highly recommend to anyone visiting the area. Rather than simply walking around and exploring independently, I went on the Old San Juan Walk & Taste Tour with The Spoon Experience. This tour wasn’t just a guided walk among beautiful buildings and experiencing local food and drinks. While that was certainly part of it, what made the tour unforgettable was the vast amount of history eloquently expressed by our incredible guide.
In just a few hours, I sampled the most authentic local foods available while learning each meal’s historical and cultural significance. In between our food stops, our guide talked about Old San Juan’s rich history. From the obvious details like its strategically defensible position, to the not-so-obvious fact that the endless shade offered by San Juan’s architecture only exists due to a poor compass reading during the city’s planning. There was so much incredible history shared, and I can’t wait to go back and do it again to learn more!
Top 6 Reasons I’ll Be Going Back To Puerto Rico
It’s So Easy – Visiting Puerto Rico was like taking everything great about the Caribbean and packaging it with easy domestic flying. My flight from Miami was only 2.5 hours, and getting through the airport and to my hotel was a breeze. If I lived in Miami, I’d visit Puerto Rico on every available long weekend.
For More Of Old San Juan – I fell in love with Old San Juan the moment I saw it. The architecture, the charming little shops, and the immense cultural experience have cemented this beautiful city in my mind.
For The Adventure – My trip was spent in San Juan, but next time I head to Puerto Rico, I plan to check out more off-the-beaten-path sights. Some that I have in mind include El Yunque National Forest and Laguna Grande, a bio bay where visitors can experience the beauty of bioluminescence in the water.
For More BeachTime – I didn’t spend much time at the beaches, but definitely will in the future! From the gorgeous El Escambrón in San Juan to the stunning Pelícano Beach in Ponce, I’ll be scoping out Puerto Rico’s beaches during my future trips.
For The Art – I had the pleasure of taking part in a walking art tour in Santurce, a municipality in San Juan known for its vibrant art scene and exciting nightlife. Just like the culinary tour, it was a history lesson in disguise. I learned more about Puerto Rico and its people during the tour than I ever had in school. This was entirely due to our incredible guide from theartwalkpr.
For The Food – The food, I miss it so much! Aside from the Old San Juan Walk & Taste tour, I had the pleasure of taking a cooking class with Mesa Redonda at the lovely Cocina Abierta. My group was responsible for making the Sofrito, a staple base for many Puerto Rican dishes. Everything was incredible, and I left convinced that every meal should start with Alcapurrias and end with Tembleque.
Best Times To Visit Puerto Rico
I’m of the opinion that anytime is the best time to visit. However, depending on your preferences, there are months of the year that may best suit your needs.
To avoid crowds, stick to the shoulder seasons of September to mid-December and mid-April to May.
To save money, June through September is generally more affordable, as it is hurricane season. Just keep an eye on the weather and be sure to purchase suitable travel insurance, and you’ll be all set.
To avoid rainy days, shoot for February, as it is one of the driest months of the year.
How To Get There
While you may stop and see Old San Juan for a day during a cruise, if you want to stay in Puerto Rico for a while, you’ll have to fly. This is where Puerto Rico shines when compared to many other Caribbean destinations. San Juan has over 25 direct routes from the U.S. mainland, and flying in is incredibly easy.
Americans will not need a passport, and there is no lengthy customs line waiting for you upon landing. Not only that, it’s typically quite affordable. For instance, a direct flight from New York City to San Juan can be found for around $300 with JetBlue this November, carry-on included. Puerto Rico is undoubtedly one of the most accessible destinations in the Caribbean.
The Number One Reason I’ll Be Back
I arrived in Puerto Rico not knowing what to expect. I left with a newfound love and respect for the culture and people that made this island come alive. While the experiences themselves were incredible, the people behind them were the true magic. And they, more than anything else, are the reason I’ll be coming back.
**Travel Off Path was a guest of Discover Puerto Rico who helped with the creation of this itinerary by hosting some of our accommodations and attractions. Our opinions, recommendations, and suggestions remain our own.**
