Where to Go for a Last Minute September Vacation

Where to Go for a Last Minute September Vacation

Lose those back to school nerves with holidays that squeeze out the last rays of summer

Don’t put your suitcase away just yet, people. Once September comes, vacation prices lower dramatically and there’s still more than enough sun to spare. Run, don’t walk, to your nearest airport to eek out the last bit of adventure before winter starts to settle back in. Below, I’ve rounded up the best September destinations for some last minute jet-setting.

Milos, Greece

Any Greek island at this time of year is an excellent choice to make the most of the last rays of summer, but Milos is one of the most interesting islands to spend your money on. Beaches that run from your traditional sandy stretch to seaside expanses that look like you’re on the moon, Instagrammable fishing villages, and a thriving food scene that’s not pretentious, make the ideal combination for a relaxed vacation that doesn’t leave you bored either. Yours truly will be running straight there the moment the 1st of the month hits!

Stay: Captain Zeppos

Captain Zeppos is an oceanfront hideaway that looks like this and won’t make you bankrupt. Comprised of four self catering suites that start at 120 a night, you’re in walking distance of the restaurants and could not be closer to the beach.


Berlin is an impressive city. With an unquestionably fabulous (and vegan-friendly) food scene, containing some of the best vintage shops in Europe, and numerous beautiful museums – there’s a mix of high and low culture in this city that can’t be matched. Whatever your taste, you’re unlikely to be disappointed. That being said, Berlin can be incredibly austere and a tad too cold in the middle of winter. This means that spring, summer, and fall are the best times to go, especially considering the many open air bars and nightclubs that open up during this time. For the people who had the willpower to save their vacation days until September (we applaud you!) the summer crowds disperse to let you enjoy all of this without competing with herds of tourists. Plus, in September music festival Lollapalooza is on so there’ll be even more music than usual filling the city.

Stay: Soho House Berlin

Yes, it’s a members club – but you don’t have to be a member to stay there. And while not all Soho Houses are worth the hype, this one certainly is. If the quirky and cozy rooms don’t convince you, then the rooftop pool, spa, and hammam will.


The most gushy of romance movies are set here for a reason. What’s not so romantic? Sweating it out while trying to hold hands. Fortunately, come September, you’ll still be able to enjoy the warm weather without suffering through some less than sexy sweat stains. If you’re planning a romantic vacation, this is the perfect time and place for it. Stay in the countryside and bounce between the perfectly Italian cities of Sienna and Florence. Many people think it’s best to stay in the city, but the best experience of Tuscany comes when you give yourself the freedom to experience the rolling hills as they should be, from a villa, surveying your (temporary) kingdom with a glass of wine in hand.

Stay: Dimora Buonriposo

A historical villa near Siena with the ultimate view, pool, and private chef – this is where to go if you want some serious romance and an old school Italian experience. Starting at £167 per night, you won’t be finding anything more perfectly Tuscan than this.

Lisbon, Portugal

Oh Lisbon, you’re just so freaking cute! I love this city for an extremely easy city break with friends. Tons of fashionable bars, hotels, and cafes are interspersed throughout the cobblestoned streets. And then there’s the beach, easily reachable from the city that’ll still be warm enough to allow the ultimate beach day. This city, and the rest of the country, is bursting with culture. If you somehow run out of things to do, you can take the train out to UNSECO world heritage site Sintra, which will fulfill all of your fairy tale ambitions. Luxurious gardens and palaces roll down to the Atlantic. It’s basically Disneyland for the cultured grown up. Don’t forget to try pastel de nata and the local wines while you’re there, either.

Stay: Palacio Belmonte

So, genuine question, who doesn’t want to stay in a palace? In the historic area of Alfama, this is the place to stay if you’re coming to Lisbon for the art and history. Surrounded by priceless art, five star service, and the opportunity to sleep at the top of the tower with 260 degree views, it’s not an exaggeration to say that it does not get better than this.

Buenos Aires, Argentina

Perhaps a little farther afield than Europe, but I promise, it’s worth it. A potent mix of Latin American and European culture, this city has countless things to see and do. If you’re dreading facing down another winter at your desk, the adventure you’ll find in this passionate and visceral city will help keep you warm the rest of the year. Visit the La Boca neighborhood with it’s colorful houses, as the birth place of tango, it does not get more authentic than this. There are countless art museums and exhibitions to see too. And you can’t miss out on seeing a polo match. Take it from someone who has tried and failed at the sport, it is an intense feat to be able to do what those dudes do. Plus, they don’t look half bad in those tight pants… Round out the trip with some great shopping, red wine, and a night of dancing.

Stay: Hotel Pulitzer Buenos Aires

A rooftop pool, stylish rooms, and within blocks of the city’s best tango clubs make this the perfect hotel to experience the city authentically and indulgently. And from £61.82 a night, the price lets you party all night guilt free!


What to Do If You Can’t Afford Therapy

They say that the first step to recovery is accepting you need help. But while

By Elizabeth Sulis Kim
June 7, 2020


The Quarantine Graduate’s Guide to Getting a Job

Graduating during a global pandemic? Just as the world heads into a recession as a

By restlessmagazine
June 7, 2020


How to Support a Friend Who’s Experienced Sexual Assault

The #MeToo movement that caught fire in 2017 was built around survivors of sexual assault

By restlessmagazine
June 7, 2020


An Introvert’s Guide to Making the First Move

There are three things the modern world is built around: money, men and extroverts. As

By Restless Team
June 7, 2020