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The best places to fly to from Boston this fall

Shoulder season is the best season for far flung weekend getaways.

JQ Louise
Written by
JQ Louise
Former Editor of Time Out Boston
moskito island
Photograph: Courtesy Virgin Limited Edition
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We are lucky in Boston; we have an international airport just 10 minutes from downtown. So, while we all know that Boston is at its prime in the fall, if you are itching for a weekend away there are so many amazing destinations within reach. Here are a few of our top picks for international getaways from Boston that are worth booking this fall.

Barcelona

Why go: Thanks to a new affordable route from LEVEL, Barcelona is even more accessible than it was in the past. With three weekly nonstop flights from Boston to Barcelona, LEVEL is a new way to access Spain, which is a fantastic shoulder season destination due to balmy weather and lack of crowds.

Grand Hotel Central barcelona
Photograph: Courtesy Grand Hotel Central

Where to stay: For a funky, luxurious place to stay, go for the Grand Hotel Central. Located near the Gothic Quarter’s sites and restaurants and with one of the best rooftop pools around, the Grand Hotel Central is a great choice. Can’t miss things include: dining on the rooftop at the SKYBAR for tapas and cocktails; enjoying the Unique Spa’s treatments by Natura Bissé, a sauna and a hammam; and exploring all the labyrinthine streets of the neighborhood of El Born that borders the hotel.

Monaco 

Why go: The South of France is a good choice any time of year, but for Bostonians, it is an especially smart destination this fall. The South of France enjoy warm weather through November, so if your dream to visit the Monte Carlo Casino didn’t happen this summer due to expensive flight prices out of Logan, this fall they are a lot more manageable.

Monte-Carlo Société des Bains de Mer
Photograph: Courtesy Monte-Carlo Société des Bains de Mer

Where to stay: The place to stay in Monaco is the Hotel de Paris. The quintessential hotel is one of the most luxurious hotels in the world and this summer the property was bursting with guests cooped up for the past few years due to the pandemic. However, the fall is always a lot quieter in Monaco, so now is the time to check off this dream destination while flights are affordable and there are rooms available. Several new dining concepts opened in Monaco this year including Em Sherif at the Hôtel de Paris. Founded by Mireille Hayek in 2011 in Beirut, Em Sherif offers elevated Lebanese cuisine. And at the nearby Hôtel Hermitage, Pavyllon Monte-Carlo by Yannick Alléno also opened this season. The restaurant was already awarded a Michelin Star, so be sure to book a table during your trip to Monaco. 

London

Why go: We all know that the pound is at an all-time low, so now is one of the best times in recent history for Americans to visit London, which is known for being quite pricey. So, hop across the pond this fall for a weekend getaway from Boston that will cost you a lot less than it used to.

mayfair townhouse london
Photograph: J.Q. Louise

Where to stay: The Mayfair Townhouse is a beautiful home away from home in the center of London. Located in the chic Mayfair neighborhood, the Mayfair Townhouse opened during the pandemic and consists of 15 historic townhouses that were combined into the beautiful property that it is today. The charming touches, combined with the luxurious finishes make for a sumptuous pace to stay while visiting London from Boston. 

Santorini

Why go: Santorini is another of those dream destinations that cost a pretty penny to get to this summer due to the high flight prices from Boston. However, this fall prices from Boston to Santorini have dropped to around $1000 RT in November.

Katikies
Photograph: Courtesy Katikies

Where to stay: The Katikies hotel group is the smart choice on the island. This Greek hospitality brand has properties in all of the major towns on the island, each with a different flavor. If you want the classic Oia experience, go for the Katikies Santorini and stay in a cave-style hotel. If you are a foodie, stay at the Katikies Garden hotel and dine at the island’s top restaurant, Selene. And if you want the ultimate Instagram shot, book a stay at the Katikies Chromata to enjoy their insane infinity pool.

Turks and Caicos 

Why go: Moving to the Caribbean, as most people shy away from the region during hurricane season, there is a sweet spot after hurricane season and before the holidays where the crowds and prices are ideal. This shoulder season look at the Turks and Caicos.

pine cay turks and caicos
Photograph: J.Q. Louise

Where to stay: Pine Cay is an 800-acre private island in the Turks and Caicos, and you will want to book your next family getaway here. With a Relais & Chateaux hotel and 40 houses to rent, this luxe island getaway is surprisingly affordable, while offering all the perks usually reserved for the ultra-rich. Considering the hotel has just 12 rooms, it feels like you have the whole place to yourself all the time. And if you rent one of the homes on the island, your group will really feel like castaways.

The British Virgin Islands

Why go: Once again, the Caribbean in the fall is such a hidden gem. Enjoy the warm waters of summer, with lesser risk of hurricanes and none of the crowds of the holiday season. And coming from Boston, couldn’t we all go for a little sunshine and sand right about now?

Virgin Limited Edition
Photograph: Courtesy Virgin Limited Edition

Where to stay: For the ultimate treat yourself moment, book your next special occasion trip on Moskito Island. Moskito is Richard Branson’s “newest” private island, and it offers all that Necker is known for and even more. With multiple estates available for booking the trip can be whatever you want it to be. And just last week the newest property just hit the market and is available for vacation rentals. The Village is a nine-bedroom estate inspired by the flavors of a Balinese garden. There is also a secret DJ performance stage that rises from the deck and overlooks the neighboring islands. And of course, there is a multi-level infinity pool and a cliffside cantilevered glass-bottom hot tub that all your friends are sure to enjoy. Pricing starts at $19,000/night, but remember you can bring 18 people with you and that price includes the cost of your own private chefs and all your meals!

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