Chic Destinations a Hop From Your Doorstep


At this point, most of us have planned our summer travel, but there’s no reason our journeys have to end when the air starts to chill.

We’ve rounded up the best upcoming chic destinations for you, depending on your part of the country—because travel expenses aren’t just about where you’re going, they’re also about where you’re coming from. A quick and inexpensive trip for some might require hours in the air and thousands of dollars for others (Hawaii and London come to mind as quick jaunts for the West and East Coast respectively, not so much for the reverse coasts).

We’ve divided our favorite chic and inexpensive getaways by region, so you can spend less time and money in the air, and more where you want to—on the ground.

If you’re traveling from the Northeast:


A hot new destination, it’s close to the Northeastern United States and affordable compared to the rest of Western Europe. Iceland Air has a great stopover option which allows travelers to explore Iceland en route to (or on their way back from) more than 20 destinations served by the airline, for the cost of a single flight. For example: Depart Boston on September 9th, hang out in Reykjavik for a few days, and then head on to London on the 12th, all for $439 including taxes and fees. Despite the economic crisis that nearly turned Iceland into a barter economy just a few years ago, hotel prices still haven’t dropped to what we’d call “cheap” levels. But deals are certainly available. At the Hótel Frón, rooms in September start at $139 per night.


Portugal is a great destination for lovers of food, culture, and history. With a ton of castles, museums, music venues, delicious eateries, and kind, English-speaking locals (all just a few hours from the U.S.), it’s the perfect long weekend. One way to score an inexpensive flight is to fly from the East Coast to a major hub like London or Madrid, which tends to be less expensive than flying to Portugal directly. From there, try out a low-cost European airline like EasyJet for the short intra-European leg. In October, you can get from London to Lisbon for as little as 14 British pounds each way. (To play with the numbers, try out Skyscanner)

In Lisbon, the Hotel Vip Executive Diplomático is located in a quiet neighborhood near the incredible Castelo Sao Jorge and Parque Eduardo VII. For about $120 per night in October, you get a sizable room with a plentiful breakfast. For just $10 more, upgrade to luxury at the Tiara Park Atlantic Hotel, just a few blocks away. A short drive north from Lisbon along the coast leads to Porto, a beautiful city in the Douro River Valley that is a UNESCO World Heritage Site. Here, prices dip even lower than in the capital. October rates at the centrally-located, four-star Mercure Porto Centro start at just $72.

If you’re traveling from the Southeast:


From its friendly locals to its beautiful beaches, fascinating colonial history, glorious seafood, and wide range of lodging options, the tiny archipelago has a ton to offer (beyond those fabulous shorts).

The downside of Bermuda is its high GDP, which means that visiting the island can be a pricey undertaking—but not if you know where to go. Instead of staying at one of the big name resorts (Fairmont or Mandarin Oriental) where the cheapest rooms can run you upwards of $400 per night, check into a smaller guesthouse or B&B. These are tiny enclaves of British colonial hospitality where the proprietors treat guests like long lost cousins. The cozy Greenbank Guesthouse & Cottages is a short ferry ride from the city of Hamilton. A gardenview room with a kitchenette is $175 per night. An apartment with room for four is just $320 per night (that’s $80 per person).

Another option is the Oxford House, just across the water in Hamilton. This stately townhouse feels like a step back in time when people dressed up in morning coats and prim hats for luncheon.  A double here is $246 per night, but like Greenbank, it pays to bring friends—a quad room is $346, or $86 per person. Both properties include breakfast in the room rate.

If you’re traveling from the West Coast:

Baja Peninsula (but not where you’re thinking)

That long strip of land stretching from southern California down alongside the Sea of Cortez has come to be defined by the spring break party town that is Cabo San Lucas. But if you’re looking for something more authentic (and less “daiquiri in a foot-long plastic glass”), stay in the quiet artsy town of Todos Santos, 75 miles north of Cabo. The later fall months are shoulder season (the time between high and low tourist season), which means cheaper flights (around $400 roundtrip from Los Angeles and $600 from Seattle) and fewer tourist throngs.

Rancho Pescadero is the hidden gem of Baja. This incredible 27-room hotel combines luxurious amenities and top-notch service with a casual, shoes-optional vibe, and is located right on the Pacific Ocean where sightings of surfers and whales are the norm. There are no TVs or phones (though free WiFi is available for addicts), and activities include yoga, kayaking, stargazing, laying around, and eating homegrown organic food. Rooms are large, with balconies, and start at $185.

Image Credit: grahamwell on Flickr

If you’re traveling from the Midwest:

Toronto, Canada

Foodies and architecture buffs flock to Toronto for its diverse selection of cuisine (from Azerbaijani to Laotian) and eye-popping buildings (Frank Gehry’s Art Gallery of Ontario, Will Alsop’s Sharp Centre for Design, and Daniel Libeskind’s Michael Lee-Chin Crystal wing of the Royal Ontario Museum).

Canada’s new low-cost carrier Porter Airlines has direct daily flights from Chicago for around $400, including complimentary snacks, wine, and beer (you read that right—free booze on a flight!). The Novotel Toronto Centre is a grand property and a great value in downtown, with rates starting at around $150 per night. For something a bit trendier, check into the Drake Hotel in the artist-filled Queen West neighborhood. This 19-room property has performance art installations in the lobby and a crush of partiers waiting to get into its unspeakably cool bar on the weekends. Rooms here start at about $200 per night.

Travel More!

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Even if you are one of the hip kids staying at the Drake, you must try a poutine in Toronto. Although it sounds harmless (charming, even), don’t be fooled. Poutine is a street snack made of french fries, gravy, and cheese curd. Heart valves beware!

Above and Beyond

Which travel sites are best to search for plane tickets? We made a comparison chart.

Say you’ve booked your trip. Should you get travel insurance? Read this.

If you’re looking for more ideas, check out these 3 other places where your dollar goes the distance. Click here.

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  • Cacarter85

    What about the SW? Texas, NM, AZ? Are we now part of the west?

    • Anonymous

      I was wondering the same thing! This article leaves out a huge chunk of the country! Disappointed…

  • Rochelle

     You’re saying $185 a night in Mexico is a bargain? You obviously haven’t had to travel on a real budget!

  • Alison

    I’ve been to Bermuda.  I’ll take any East Coast beach any day over pricey Bermuda.  Try North Myrtle Beach & Myrtle Beach, North Carolina; Virginia Beach, VA, Rehoboth Beach, MD, etc.  Very nice & areas and not too expensive.

    I’ve lived in southern Arizona for over 5 years and have never been to Mexico – it’s too dangerous. 

    I guess you don’t read the government’s travel advisories.  Tourists are discouraged from travelling to Mexico because of all the drug violence. 
    The following is part of the US Government’s travel advisory for Mexico:

    “Violence along Mexican roads and highways
    is a particular concern in the northern border region. As a result, effective
    July 15, 2010, the U.S. Mission in Mexico imposed restrictions on U.S.
    government employees’ travel. U.S. government employees and their families are
    not permitted to drive from the U.S.-Mexico border to or from the interior of
    Mexico or Central America. Travel by vehicle is permitted between Hermosillo and

    While violent incidents have occurred at
    all hours of the day and night on both modern toll (“cuotas”) highways and on
    secondary roads, they have occurred most frequently at night and on isolated
    roads. To reduce risk, you are strongly urged to travel only during daylight
    hours throughout Mexico, to avoid isolated roads, and to use toll roads whenever
    possible. For more information on road safety and crime along Mexico’s roadways,
    see the Department of State’s Country Specific Information.

    Due to ongoing violence and persistent
    security concerns, you are urged to defer non-essential travel to the states of
    Tamaulipas and Michoacán, and to parts of the states of Sonora, Chihuahua,
    Coahuila, Sinaloa, Durango, Zacatecas, San Luis Potosi and Jalisco. Details on
    these locations, and other areas in which travelers should exercise caution, are

    Violence along the U.S. – Mexico

    You should be especially aware of safety
    and security concerns when visiting the northern border states of Northern Baja
    California, Sonora, Chihuahua, Nuevo Leon, and Tamaulipas. Much of the country’s
    narcotics-related violence has occurred in the border region. More than a third
    of all U.S. citizens killed in Mexico in 2010 whose deaths were reported to the
    U.S. government were killed in the border cities of Ciudad Juarez and Tijuana.
    Narcotics-related homicide rates in the border states of Nuevo Leon and
    Tamaulipas have increased dramatically in the past two years.

    Carjacking and highway robbery are
    serious problems in many parts of the border region and U.S. citizens have been
    murdered in such incidents. Most victims who complied with carjackers at these
    checkpoints have reported that they were not physically harmed. Incidents have
    occurred during the day and at night, and carjackers have used a variety of
    techniques, including bumping moving vehicles to force them to stop and running
    vehicles off the road at high speed. There are some indications that criminals
    have particularly targeted newer and larger vehicles with U.S. license plates,
    especially dark-colored SUVs. However, victims’ vehicles have included those
    with both Mexican and American registration and vary in type from late model
    SUVs and pick-up trucks to old sedans.

    If you make frequent visits to border
    cities, you should vary your route and park in well-lighted, guarded and paid
    parking lots. Exercise caution when entering or exiting vehicles.

    Large firefights between rival TCOs or
    TCOs and Mexican authorities have taken place in towns and cities in many parts
    of Mexico, especially in the border region. Firefights have occurred in broad
    daylight on streets and in other public venues, such as restaurants and clubs.
    During some of these incidents, U.S. citizens have been trapped and temporarily
    prevented from leaving the area. The location and timing of future armed
    engagements cannot be predicted. You are urged to defer travel to those areas
    mentioned in this Travel Warning and to exercise extreme caution when traveling
    throughout the northern border region.

    Northern Baja
    California: Targeted TCO assassinations continue to take place in
    Northern Baja California, including the city of Tijuana. You should exercise
    caution in this area, particularly at night. In late 2010, turf battles between
    criminal groups proliferated and resulted in numerous assassinations in areas of
    Tijuana frequented by U.S. citizens. Shooting incidents, in which innocent
    bystanders have been injured, have occurred during daylight hours throughout the
    city. In one such incident, an American citizen was shot and seriously wounded.

    In this economy, why not save some of your hard-earned money and boost the US economy by vacationing within the US.  There are hundreds of places that are just as exotic if you’ve never been there.

    • Erin

      Certain parts of Mexico are dangerous, but that doesn’t mean you shouldn’t visit the country. It’s like saying violence in Los Angeles means you shouldn’t visit San Francisco.

  • Jaza Renee Montgomery

     Since when is Canada on the same page as Baja, Bermuda, Iceland or Portugal…this article basically says there is nowhere cool for midwesterners to travel cheaply