A September Getaway – The Best Destinations in Europe & North America

There are quite a few perks when it comes to traveling in September. Cheaper flights, fewer crowds, and better weather make September the perfect time to book a trip. Let’s dive into the best destinations and hotels for this September. Whether you have a long weekend or a week off, we have destinations that are sure to suit you.

Calling Europe or North America home? As hotel experts, we know it isn’t always possible to book a flight and travel to the other side, so we’ve found destinations in both areas, as well as presenting our unique September destination.

Santorini– Summer in September? Thanks, Greece!

Santorini is a top destination no matter the season, but a hidden jewel is Santorini in September. A top September destination for a reason, this month still provides you with warm weather and beach excitement but with a bit of a breeze. So, you won’t be baking under the sun, but enjoying a fresh and breezy Santorini, but shh don’t tell, we don’t want the tourists finding out!

Coming in late September is when the crowds tend to die down, meaning you can photograph Instagram-worthy spots without the interruption of tourists. When booking restaurants, top hotels, and activities, the stress will fall off your shoulders, as you aren’t competing with the summer crowds.

Don’t want the beach? You’re in luck! This area has some of the best wineries in Greece. September is a huge month for the grape harvest, so whether you prefer whites or reds, there is something for you.

Divine Cave Experience

One of the most picturesque spots in Santorini, the hotel has wonderful views of Imerovigli and is tucked away in cave-like elements presenting you with a truly divine experience. Their wellness center is hidden in a cave that was previously used for wine production, so as you relax in this secluded oasis, your senses will come to life, as the subtle fruity scent drifts throughout the wellness-spa. 

Villa Arithera

A traditional Santorini escape, this is the place to be if a luxurious Greek experience is on your agenda. This beautiful villa was recently renovated in 2021 and 2022, preparing to give you the newest updates, of course. This villa is surrounded by vineyards and places you in the perfect area to take a stroll along the cobblestone paths to some of the quaint town’s best restaurants and cafes.

Mallorca, Spain – Meet Me in Mallorca

From limestone mountains, unique architecture (thanks to the Spaniards), and elegant beaches, Mallorca makes for an amazing destination. Mallorca may be known for its beach vacations, but September is a great time to enjoy hiking, mountain biking, and other outdoor activities as the weather begins to be a bit more adventure friendly. Toasty summers bring in a large influx of tourists to this Spanish region, but as September rolls around this wonderful island, you get to have a more personal experience. 

1902 townhouse

Very close to the city center, this townhouse hotel places you in the magic of Mallorca. From botanical gardens to fine dining, this hotel has the perfect location for it. With views of the mountains and Spanish paradise, this top hotel brings you the true experience of Mallorca. Relax, enjoy, and indulge in the finer things here at the 1902 townhouse.

Finca Ca’s Curial

An adult-only hotel, the perfect word to describe this space is charming. Perfectly set between the mountains and sea, you get the best of both worlds. Become one with this Spanish island as the hotel transports you to a romantic getaway, with no disturbance from the crowds, and grants you Majorcan-inspired architecture and elements.

Provence, France – Fly Me to France’s Finest #PleasedWithProvence

One of France’s most beloved regions, Provence brings the world a little village on a hillside with lavender fields, exquisite vineyards, and the pleasure of the Mediterranean Sea. This area will have you falling in love with its splendid views and making you wish your stay lasted just a bit longer.

Picturesque scenery and one of the most beautiful regions of France, Provence will surely become a core memory. Envision fields of endless lavender, sunflowers, and warm sunlight as the Mediterranean escape embraces you. Raising your glass, toasting to epic views, good wine, and a wonderful life, you realize you have truly made it home this September.

Les Lodges Sainte-Victoire & Spa

This top hotel features thirty-five suites, and four private villas, giving you an at-home feel. Although one could sip wine and enjoy the views daily, this hotel offers many activities. Some are hiking, tennis, and French bowling. Find yourself enjoying, The St Estève. The hotel’s fine-dining restaurant offers a wide variety of meals, and vegetarian options as well. The space looks out to the beautiful mountains and greenery that Provence has to offer.

Maison Du Collectionneur

A luxury September vacation at a cozy bed & breakfast just minutes away from the city’s congress center you are truly in a beautiful part of Provence. Many rooms come equipped with a garden view and balcony, and some even have a grand view of the cathedral. In an intimate experience in your own getaway, you will fall in love with both the city and the hotel. Each room has been created through the inspiration of paintings, bringing to life different elements such as vivid color, furniture, and lighting.

Tuscany, Italy – An Italian Favorite, Let’s Talk Tuscany

Tuscany is home to beautiful landscapes, artistic expression, and a welcoming culture. Being one of Italy’s top vacation and must-see destinations, it’s definitely worth a trip. Now that heat of the summer months have passed, you'll find that September is a beautiful time in Tuscany, as most tourists head back to work, and leave this Italian oasis and relaxing atmosphere just for you. If you are in for a vacation filled with peace, serenity, and comfortable temperatures, Tuscany is for you.

Imagine gazing out into a majestic field as sunshine and warm breezes glide against you, reminding you that September truly is the best time to be in Tuscany. With wine tasting galore, food festivals, and beach access, you will have found your little Italian oasis.

AdAstra Suites

Reviewed by Condé Nast Traveler, Vogue, and Harper’s Bazaar this hotel will not disappoint. AdAstra brings you to the heart of Florence with fourteen unique rooms, each given their own personal style and atmosphere, you will be staying with true Italian art & talent. Wake up to a farm-fresh breakfast with a wonderful spread of local cheeses, farm-fresh eggs, pastries, and hand-selected meats. Sip your coffee as you sit on the terrace, taking in the beauty of Italy, and falling in love with your stay.

Riva Lofts Florence

A hidden gem tucked away in Florence’s historical center, Riva Lofts gives you a space far from the hustle and bustle of the city, presenting you with a tranquil environment where you can focus on the finer things in life. Whether you find yourself strolling through the historical district or biking through the region, there is always something to do. From beautiful views, to clean breezes, Riva Lofts and Florence alike will take care of you dearly.

Cornwall, England – Stay with Me at The Sea & Be Cozy in Cornwall

A lovely area of England, especially in September that gives you a mix of weather, smaller crowds, festivals, and hiking, Cornwall gives you a bit of everything. With bigger crowds than Tuscany, Provence, and Santorini, you can get more of a summer crowd feel if that's what you’re into. A beautiful place to head and attend festivals whether it be music or food, Cornwall has you covered. Hiking is also quite a hit – check out the South West Coast path to see some incredible views and wildlife viewing with cooler weather, you can enjoy comfortable hiking trails through the English hills. While sunlight still has its summer hours, September offers you longer days than October or November.

The Idle Rocks

Enjoy the Idle, your new seaside escape, and personal Cornwall dream. This quaint hotel offers eighteen bedrooms, each designed to bring the seaside Cornwall experience closer to you. Every detail, from art to window views, the Idle is dedicated to making your experience one of a kind, bringing you the best of England. One of the best, English hospitality brings you genuine and proper care, creating a visit you won’t forget. As a seaside breeze sneaks in your window, crisp air fills your breath, and the English seaside brings a smile to your face, you’ll know you picked the right stay.


This cozy bed & breakfast offers you three different luxury suites. From elegant linens to products from St. Kitts, Nearwater has you covered. In a garden with a cozy atmosphere, crispy air, and bright flowers, you are reminded of childhood. Worriless wandering and exploration, Nearwater awakens your inner adventure and excitement. Make yourself at home with access to the grand selection of herbal teas, homemade lemon shortbread, books, and hand-selected magazines.

Austin, Texas – Barbeque & Live Music, We Like To #KeepAustinWeird

The live music capital of the world, Austin definitely brings the jams to the U.S. With splendid blue skies, and endless sunshine, Austin makes the perfect place for kayaking, sports, swimming, and trendy dining. September is a beautiful time to enjoy boating on Lake Austin or exploring the many parks this city has to offer. The saying “keep Austin weird” reminds us of how wonderful musical and artistic expression is. A city that embraces individuality, creativity, and rocking with what you love, Austin is the perfect spot to vacation. Just be who you are, and you will fit right in. So, make September your time to enjoy cooler Texas temperatures, calmer lakes, parks, and dining scenes. Enjoy some of the best barbeque the U.S. has to offer and don’t forget to pack your boots for dancing!

The Carpenter Hotel

Welcome to the Carpenter, where the hotel is a unique combination of the city and the outdoors, bringing you the best of both worlds. With private terraces, and access to one of Austin's top parks, Zilker Park, there will be a plethora of options at your fingertips. Enjoy the best of Texas, with Carpenters Hall. Find yourself indulging in Chicken Schnitzel or Tex Mex, both pulling from international inspiration, a restaurant inspired by Texan history and the global scene that created the state. The hotel offers events such as pool parties and fitness classes, so check out what this September vacation has in store for you!

Heywood Hotel

Featured on Condé Nast Traveler’s Hot List and selected as a Traveler’s Choice 2020 winner, you know you’ve come across trendy architecture and top-tier accommodations. Placed in East Austin, you will have access to the best restaurants and the excitement of downtown. From cocktail lounges to barbeque stops, you will get to enjoy the true Austin culture. This hotel celebrates Austin in every capacity, by featuring artists and designers from the area to encapsulate the city’s vibe.

Vancouver, Canada – Stay Cool with Canada’s Trendiest Escape

One of Canada’s most vibrant cities, Vancouver is both a trendy city and a wonderful outdoor experience. Surrounded by both mountains and water, September in Vancouver offers you a plethora of outdoor activities. One of the best times to visit this city just so happens to be September, when the weather is a bit cooler with temperatures ranging from 65 to 53 degrees Fahrenheit. Perfect weather for biking, exploration, hiking, and a refreshing dip in the water.

Soak up the last of the city’s sunshine and let Vancouver be the perfect beginning to a wonderful fall. Hiking along Baden Powell Trail or through the trails located in Stanley Wall, you can really get your Canada on. Close distances to the city, ranging from one hour to two, the city brings you close to some of Canada’s most beautiful lakes. Only an hour away check out Lake Alice, which is surrounded by luscious greenery and towering mountains. Here you can fish, enjoy a calm stroll, and dip in for a refreshing swim.

Wedgewood Hotel & Spa – Relais & Chateaux

Located in downtown Vancouver, the Relais & Chateaux gives you a distinct feeling of comfort and elegance. This hotel places you in a great location to enjoy the area through fine cuisine, easily accessible activities, and outdoor adventures. For instance, the theatre, art gallery, symphony, wine tasting options, and of course, rafting, sailing, mountain biking, and a plethora of hiking.  

Shangri-La Vancouver

Producing a feeling of Zen and serenity, this hotel is tucked between both the sea and the mountainous escape of Vancouver. This hotel is located by exquisite shopping while also offering views of the beautiful nature Canada has to offer. With 119 suites, a wonderful bar and restaurant, and spa services, this is the perfect getaway for relaxation and adventure. Unwind with British Columbia’s finest natural beauty products at Chi, The Spa. Find a luxurious safe haven here at Shangri-La Vancouver.

Charleston, SC – Southern Charm & Beach Side Escape

Let’s cheers to Charleston for becoming one of the top destinations to live in the United States. With its cobblestone streets, colorful buildings, and palm tree outlined beaches, it’s no wonder everyone wants to come. September brings cooler temperatures as the South Carolina heat leaves for the Fall. The southern charm in Charleston is not something to miss. Enjoy fine dining, boutique hotels, small markets, carriage rides, and beach time.

This city has some seriously rich history, and with museums, and antique buildings everywhere, you’re sure to learn something new. Enjoy southern hospitality and charm, by staying in one of the South’s most beloved towns.

The Dewberry Charleston

Bringing back the old Charleston elegance, John Dewberry has certainly brought the city modern elegance and charm. Enjoy your time at The Living Room, designed to be a sophisticated Charleston living room, where you can enjoy a morning coffee or evening cocktails at the brass bar. Relax after shopping or a day at the beach with a Lowcountry spa treatment from The Dewberry’s very own spa services.

The Spectator Hotel

Stay in the center of Charleston’s historic district by booking with The Spectator. Bringing to life the era of Jazz and the chic environment of Charleston’s history, there is no question as to why this hotel constantly ranks as one of the city’s top hotels. Indulge in gourmet dining services, lovely views, and an experience created just for you. Ride on the complimentary bikes as you breathe in the sunshine-filled air, palmettos, and ocean views, you get to truly experience southern living.

Moab, Utah – Utah’s Hidden Gem, The Breathtaking Desert Oasis

Check out Arches National Park, Canyonlands National Park, and more as you enter this desert wonderland. For some of the most sensational views in the U.S., Moab is a must-see destination as it is filled with adventure and an atmosphere that cannot be replicated. Imagine a vast wonderland of orange desert, warm breezes, cacti, hiking, off-roading, and adventure opportunities, and did I mention the sunsets? Sunsets in Moab are breathtaking as the sun falls behind this rocky oasis, and colors light up the sky creating a work of art. With wonderful weather and fewer tourists, September is the perfect time to check out this amazing city. Moab’s national parks have some of the most iconic destinations and must-see stops. With epic mountain biking and unforgettable views, Moab doesn’t disappoint.

Moab Springs Ranch

Welcome to Moab Springs Ranch, where the unique hotel is tucked underneath Moab’s iconic red rock. Here you will find chic accommodations, a cool atmosphere, and get to view an entirely new side of the desert. Whether you want a luxury bungalow or a multi-bedroom townhouse, you’ll have it here at the Ranch.

There aren’t just amazing living accommodations, but this resort also offers a plethora of amenities. Some of those are ponds, hammocks, a campfire area, a large park, and trails that lead you right to the scenic views of Moab.

Radcliffe Moab

Moab’s boutique escape, Radcliffe offers an epic view of both the East and West. From modern design to a cozy environment it doesn’t seem like it can get much better but…it does. The hotel’s restaurant Il Posto Rosso serves food inspired by the region. Using ingredients from local producers, Radcliffe’s love for Moab comes full circle. Enjoy the pool while you absorb the true beauty of Moab. Want to bring a furry friend to hike with? Good news – your pup can come too!

Colorado Springs, CO - Let's Go Glamping This September!

An adventure-filled area where nature meets luxury. Colorado Springs is an amazing area if you’re into outdoor adventures, but love staying in elegance. It's truly a historic experience in which you can enjoy one of the only cog railways left in the United States, explore the mountains and take in the fresh air and picture-perfect views.

The Lodge at Flying Horse

Let’s give a round of applause to one of Colorado’s top boutique hotels. The resort amenities include but are not limited to lap swimming, 18-hole golf, tennis & pickleball, steakhouse dining, spa services, and a fitness area. Looking to enjoy Colorado Springs from the hotel? This is the best place to do it!

Kinship Landing

A hotel that takes pride in giving you the best experience and helping you find the wonders of their home, Colorado Springs. This hotel offers trendy design, and Colorado style, and uses elements inspired by nature. Enjoy the food scene here at Kinship where you can enjoy with the locals as well, as it is a restaurant and bar loved by many.

Hermanus, South Africa – A September Vacation's Unique Destination

Listed as the best place to experience land-based whale watching across the globe, Hermanus is an amazing and unique choice. September is the perfect time to whale watch and experience all the sunshine that South Africa has to offer. So why not plan this September vacation in Hermanus?

Birkenhead House

Check out Birkenhead House, one of the best hotels in the area for a luxurious seaside escape. An intimate setting where you are set in the town of Hermanus, overlooking Walker Bay. Unique activities such as mussel picking, shark cage diving, and horseback riding on the beach, are just some of the few interesting options this hotel offers.

Sloan Koester

By Sloan Koester in Getaway , Adventure , By month