It's so easy to get FOMO (fear of missing out) these days, especially now that travel is picking up and it seems like everyone is going just about everywhere. Those photos of tropical islands might be calling your name, or medieval-era villages in Europe might be speaking to you on a deep-soul-type of level, and we get it. It's tough when you feel like you're strapped, destined to wait and plan out a future vacation like many others.

Related: Affordable Alternatives To Every Major European Destination (That Are Actually Worth A Vacation)


If you have only four days to spare, however, then there might just be hope yet for a vacation sooner rather than later. Not every international destination requires steady planning, months of research, and bookings a year or two in advance. Some destinations welcome last-minute plans, the sudden fulfillment of wanderlust, and a weekend full of adventure. It might mean immediately returning to your day job after the full four days are up but for those 96 hours, it'll be pure bliss.

All travel should be done in accordance with current CDC guidelines. Not every country is allowing international travel; any potential vacation destination should always be found on the CDC website. At the time of writing, not all of these countries are currently open. 

São Miguel, Portugal

One of the last places anyone would think to visit last-minute is the Azores but, as it turns out, São Miguel is surprisingly easy to get to from Boston. According to Thrillist, the red-eye will get travelers to this city in just under five hours, which is faster than a flight from one coast of the U.S. to the other. The airfare isn't cheap during peak season, though, and can run about $800 or slightly more round-trip. Going in the off-peak season (if you can wait that long) could potentially save a few hundred bucks which can be put back into the vacation.

São Miguel is absolutely breathtaking, with enough lush rainforests and crystal-clear waters for anyone to forget ever wanting to go back home. While you'll eventually need to board the plane to head back, the four days that are spent there will be done with incredible seafood, hikes that lead to spectacular views, and an appreciation for the ecosystem and Mother Nature.

Montreal, Quebec

While the border remains closed at the time of writing, a trip to Montreal isn't like any old city trip. There are both historic and modern parts of Quebec and it is possible to see them both in one weekend. A drive from any New England state is fairly quick crossing, and a plane from New York will take about three hours. The Adirondack train also takes travelers into the city and comes at a much lower cost; for less than $100, you'll be able to take in both the views along the way and leave the car behind - which is good news, since Montreal is a very walkable city.

The best times to visit Montreal are during the summer and fall months but it's equally as magical in the winter (especially if you're not driving). The city lights up for the holidays and feels as though you've been transported to a far-off European city without ever actually leaving North America. Of course, the poutine is divine but Montreal is home to a slew of food options, along with rooftop bars and unique dining that could give any U.S. city a run for its money.

Cayman Islands

The Cayman Islands offer plenty of options all on their own even without being an easy four-day destination. However, they're also super easy to get to for those who live in the southern half of the U.S., particularly near or in Florida. Flights from the sunshine state are less than two hours (about an hour and a half, to be exact) and flights from the northern midwest and East Coast states still clock in under four hours. Flights to the Cayman Islands aren't particularly expensive with off-season rates falling somewhere just under $500 round-trip. The other great thing about booking during the off-season is that hotel rates are also very affordable, so this might be a good option for a budget-friendly island getaway, as well.

There are several islands that make up the Cayman Islands, each of which offers its own unique itinerary. Grand Cayman is great for those who want a big island type of feel, complete with all the amenities, chic resorts, and plenty of nightlife. For those who prefer a quiet and secluded island vibe, Cayman Brac is the perfect place to get away, unwind, and enjoy the simpler things.

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