Speaking of music, two kiddie rock heavyweights are playing this weekend: Laurie Berkner and Dan Zanes. Other indoor fun includes screenings of the classic French short The Red Balloon and a free performance by the Paper Bag Players.

All of our best bets for the weekend are below. Remember, there are even more options in our Event Calendar and our Spring Fun Guide.

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While 30,000 points round trip between NYC and London sounds like a steal, it is less of a steal when you include the $656 in taxes and fees on top of that. World Traveller Plus is 45,000 miles plus $750 on that route.

They’re also offering 25% off redemptions to Tokyo, Shanghai, Beijing, Bangalore, Mumbai, Delhi, and Dubai. That JFK-NRT flight will be 75,000 miles + $1,028, please. In coach.

It’s a terrible deal, but that doesn’t mean I shouldn’t share it.

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The first place I take a visitor from out of town is Piazza dei Salimbeni. Not just a beautiful square but also HQ of the world’s oldest bank: Monte dei Paschi di Siena has been rocking it big time (at least so far) since 1472. You thought the world used to be a better place? Forget it. Renaissance art and banking have always been intrinsically linked.

When I crave healthy ice-cream I always go to Grom’s. No way around the calories, but at least no nasty additives thanks to carefully selected ingredients. There’s a small children’s play area at the back and the thoughtful recycling of spoons, cups, and napkins makes my Swiss heart beat faster.

The sun sets on Piazza del Campo. (Photo by Adamo Banelli, My Shot)

To escape the crowds I head down Siena’s backstreets. There are no tour groups around (I guess they don’t fit through the medieval alleyways).

If I want to have a good time with my friends I go to Piazza del Campo and let the kids loose. No need for slides and swings if you can play hide-and-seek on one of the world’s most celebrated squares.

For complete quiet, I can hide away in front of Duccio di Buoninsegna’s masterpiece of a painting, the “Maestà.” It has a room dedicated to it on the second floor of the OPA museum. During high season, tour groups flock in and out, but nobody stays on to actually LOOK at the painting. Take half an hour, sit down, and understand why they didn’t invent TVs in the 14th century.

If you come to my city, get your picture taken with your mate on Piazza del Campo. Italy has beautiful squares all over the place, but don’t make up your top ten before you’ve had your Campari on Siena’s Piazza del Campo.

Libreria Senese (via di Città 64) is my one-stop shop for great books. There is a small children’s book section in English. If your kids are tired of playing around with your smart phone, you can always try reading to them. Mine still enjoy it.

Scooters line one of Siena's fabulous back streets. (Photo by Chris Parker, My Shot)

Locals know to skip Piazza del Campo’s over-prized eateries and check out the restaurants on the backstreets instead. Stick to coffee and Campari during your breaks on the square.

When I’m feeling cash-strapped I go to Il Grattacielo (via Pontani, 8), a little osteria (restaurant) the size of your average cupboard. Which explains its name (grattacielo = skyscraper) and makes for a good introduction to the Tuscan sense of humour.

For a splurge I go to Le Logge for plenty of ambiance and Tuscan cuisine at its best.

Photo ops in my city are literally everywhere. If you don’t have an issue with heights and claustrophobia, climb the stairs of the OPA museum to get a bird’s view of Siena’s impressive cathedral, then repeat the climb at the Mangia tower on Piazza del Campo.

If my city were a celebrity it’d be Katharine Hepburn. Rather reserved, of a certain age, but still incredibly elegant and beautiful.

The most random thing about my city is the relentless influx of badly dressed tourists. Do what you want, but no socks and sandals. Never!

My city has the most reserved and slightly arrogant men and women. Did I mention Siena’s banking history?

Birds scatter over Monte Oliveto Maggiore abbey. (Photo by Loredana Becchi, My Shot)

My city has the most mouth-watering choice of local food delicacies. Skip the touristy shops and go straight to the Consorzio Agrario’s main store (via Pianigiani, 9). Fill up your basket with the famous Cinta Senese Prosciutto or taste your way through the superb Pecorino cheeses. Throw in a bottle of Tuscan red and your picnic is ready to go.

In my city, an active day outdoors involves walking up and down our hills (leave your new Italian high-heels behind — we’re talking cobble stones only).

My city’s best museum is the magnificent OPA; with a grand entrance hall on the ground floor, a meditative room on the first floor dedicated to Duccio’s above mentioned “Maestà,” and a breath-taking view over the whole city from what was supposed to become the new facade of the never finished cathedral.

My favorite jogging/walking route is… jogging? You must be kidding. After a day spent walking up and down those hills? If you still feel like jogging in the evening it’s because you’ve spent the day drinking too many cappuccinos.

For a night of dancing, go somewhere else. A fervent night life is not one of Siena’s strong points. The Sienese will hate me for it, but Florence and Rome are much better options for a few funky moves. I wonder whether it has anything to do with the Palio horse race. All that frenzy from June to August – there’s probably just no energy left for the rest of the year. If you don’t believe me, watch this.

For live music, come in the summer when Siena is hosting the Estate Musicale Chigiana, a famous classical music festival. To mix up things, they usually throw in a couple of pop or rock concerts, too.

Naples is the spot for late-night eats. See “For a night of dancing…”

You can tell a lot about my city from what happens to its population during the months before and after Palio. Definitely not your average horse race!

You can tell if someone is from my city if they start gesticulating wildly whenever somebody pronounces the word Palio.

Southern Tuscany's famous rolling hills, near Asciano. (Photo by Angiolo Manetti, My Shot)

In the spring you should make time to venture into the surrounding countryside to see the explosion of colours. Head towards Asciano, move on to the stunning Monte Oliveto Maggiore abbey and then get a sugar and culture fix in off-the-beaten-path Buonconvento.

In the summer you should visit Siena in the early morning or late afternoon. Between 10:00 a.m. and  5:00 p.m., tour buses unload hoards of tourists into Siena’s main streets, but most don’t stay overnight. Once you’ve had your share of heat, crowds, and medieval art, head down to Southern Tuscany’s coast, build your own beach hut, and enjoy the pristine natural surroundings.

In the fall you should soak up the warm autumn sun on Piazza del Campo. The light is fantastic for all the photographers out there. And remember to leave the city alone for an afternoon to pop into a winery in the Chianti region or in Montalcino. You’re in the Sangiovese grape’s home territory, so you’d best bring a glass.

In the winter you should keep coming back. Fell in love with Siena and want it all to yourself? This is the time of the year when it’s just you and the locals. Bring warm clothes — temperatures aren’t too bad outside, but those medieval stone buildings tend to be a little heating-challenged.

A hidden gem in my city is Siena’s small botanical garden. Admire a few lemon trees whilst looking out for Renaissance painter Il Sodoma’s ghost, who is said to haunt the gardens.

For a great breakfast joint try one of the several Nannini bars in town. Do it the Italian way: no sitting down, just lean on the counter for a quick espresso or cappuccino to get your day started. The Nannini bars are also great places to stock up on some of Siena’s famous sweets (Panforte, Ricciarelli, etc.) to take back home.

A vineyard in the Chianti region. (Photo by Holly Farless, My Shot)

Don’t miss the PALIO Festival! And if you do, just watch the films of past races (which is how the Sienese spend the rest of the year), or check out James Bond’s version of the event.

Just outside my city, you can get your lifetime fix of undulating Tuscan hills and cypress trees.

The best way to see my city is on foot. In the 1960s Siena was one of the first cities in Europe to close off its expansive historic centre to traffic.

If my city were a pet it would be a horse. Obviously!

If I didn’t live in my city, I’d live exactly where I live: in the marvelous Tuscan countryside. I love you dearly, Siena, but your housing prices are way over the moon.

The best book about my city is Explore and Discover Siena by Bartoli and Latini, which can be bought in most book shops and museums in Siena. It’s a children’s guide to the city and that’s exactly why adults will love it, too. It can turn football-crazy teenage sons and husbands into ardent art lovers. I’ve seen it happen!

When I think about my city, the song that comes to mind is ”Meravigliosa Creatura” (Marvelous Creature) by Gianna Nannini.  The Siena-born rock star is one of a kind. An outspoken lesbian, she is a far cry from ex-president Berlusconi’s female ideal. We can only thank Siena for providing Italy with such a different female role model! To be honest I can’t quite get the hang of her music, but my Tuscan native adores her, as does the rest of Italy.

The Palio is held twice a year -- on July 2 and August 16. (Photo by Ronald Hayden, My Shot)

If you have kids, you won’t want to miss Siena. Full stop. Why go to Disneyland if you can visit the real thing? We’re talking scary door knobs and fairy tale creatures hanging off marble window sills. And if that’s not enough try the Santa Maria della Scala Museum’s interactive children section.

The Palio could only happen in my city. The Palio, again?! Sorry guys, but do you know of any other festival out there that has been going strong for 500 years and is still as fascinating as it was on the first day?

My city should be featured on your cover or website because you’ll never ever forget that cappuccino on Piazza del Campo. A square is a square is a square definitely doesn’t apply to Siena.

Related [National Geographic's Guide to Italy]

Eat

In 2009 a nationally-syndicated food magazine named Portland the “Foodiest Small Town in America”, and for good reason. The state of Maine has a long-running dedication to fresh, local ingredients. Of course, the fact that the city is located so close to the ocean is used to its fullest advantage; it is easy to access some of the freshest and least-expensive seafood in the country. Everything from oysters, mussels, clams, and the world-famous Maine lobster.

Just one of the tasty snacks available

In addition to the delicious seafood, Maine also utilizes its resources in fresh produce: sweetcorn, potatoes, and fiddleheads run rampant, and most restaurants proudly display signs indicating that all food is Maine-made. But apart from the delicious ingredients, Portland’s restaurant scene is famous for using these foods to create highly original dishes. Alongside the classic diners are Mexican and Asian-fusion restaurants that take creative liberties with traditional ingredients in order to make highly unique dishes.

Drink beer

There's a lot of beer on offer

American beer has developed a bad reputation worldwide, but that’s probably because most international travellers don’t make the pilgrimage up to Maine. The state of Maine has more breweries than almost any other state in the US; and the majority of Portland’s breweries are small and do not distribute very far. However, most of them are very friendly and happy to show people around in order to show off their brewing techniques and unique recipes.

If sampling local American beer is not your thing, there is also an incredible amount of imported beer shipped from all around the world. Novare Res Bier Cafe serves beer from that has been tracked down from some of the best locations in the world including Belgium, Germany, Spain, Italy, and England.

Watch a game

Maine is dubbed “Vacationland” for its nearly-perfect summer atmosphere, so it shouldn’t surprise anyone that the number-one sport to watch is the classic summer pastime: baseball. The Portland Sea Dogs, a minor-league team associated with the Boston Red Sox, play all summer long. Because of the relaxed atmosphere and a stadium which is large for the size of the city, tickets to a baseball game do not need to be reserved in advance and can run fairly cheap.

Portland Museum of Art

Even after the summer has ended it’s still easy to take in a professional sports match; the Portland Pirates (Maine’s local minor league hockey team), and the Maine Red Claws (the local basketball team), play games throughout the winter.

Take in the art scene

Like all other major sites in Maine, the Portland Art Museum places special emphasis on locally-produced works. However, the Museum also houses works by Picasso, Renoir, Winslow Homer and Rockwell Kent. If you don’t want to pay an entrance fee you can wander down to the Arts District which is full of great galleries and quirky antique shops.

Take a ferry to one of the local islands

Take advantage of the famous Maine coastline and catch a ferry to one of the local islands. Once you’ve arrived, talk a walk or a bike ride around to see some beautiful scenery and even more local art. Bring a picnic to eat on the beach, explore some of the tide pools, or just swim around in the Atlantic Ocean. There’s really no wrong way to spend a day on an island in Maine. 

Tips

Maine is one of the more remote areas of the United States, so public transportation is an option but not an easy one. The best idea is to rent a car, especially if you want to explore more of Maine’s natural landscape.

Maine weather is notoriously fickle, so bring a sweater with you wherever you go just in case.

If you’re ever lost or need advice don’t be afraid to talk to the locals. Maine is a notoriously friendly place!

Top five things to do in my hometown of Portland, ME, USA by Danielle May Steinman was originally published on Indie Travel Podcast (find in iTunes). They also have travel books and guides to Asia, Europe, Oceania, South America, and more.