I love traveling in May – its starting to warm up in most parts of the United States, and the crowds are not as bad as you’ll find from late June to mid-August, once school is out of session.  Most of all – people become happier in May, especially up North, where they can feel summer sunshine and smell backyard barbeques right around the corner. So, this week, I’ve decided to share with you my picks for where you should visit this late Spring – if you don’t already subscribe to Jetblue or Southwest airlines, you should, as they regularly have spring and summer deals from major airports.  Last year, we flew from Fort Lauderdale to Grand Cayman for $59 each way via Southwest! Ok, I’ve digressed… Here are my top 5 picks:


San Diego, CA – It’s no secret, that I love California.  Who doesn’t love a state that offers the beach, city life, mountain hiking, and skiing?!  San Diego is leading as my favorite city in California as it has gorgeous landscapes (La Jolla I’m thinking about you), chill vibes, and great food.  Seriously, there are hundreds of restaurants that offer great Italian (and not only in the Little Italy area), seafood, Mexican, and of course, bakeries!!  May is great as you don’t have to contend with crazy summer crowds, but the temperature is still between 60 and 70 degrees, on average. The bad thing – it rains more in May than in most months, so you may have to deal with cloudy skies, and short bursts of rain, so it’s less likely you’ll be chilling at the beach.  However, that does mean more time to take in the sites of La Jolla (or go kayaking through the bay to sea the seals – I was HORRIBLE at it, but everyone else was great), or visiting the San Diego Zoo, or going on a cool bar crawl through the Gaslamp district. I can only imagine celebrating Cinco de Mayo in Old Town, or enjoying a delicious Memorial Day brunch by the bay side <- wait, I actually did do that once, and it was pretty darn fantastic!!


Boston, MA – maybe not so much in May, but come June/July, this city’s aura becomes infectious.  Boston is an amazingly walkable city, teeming with history. For starters, you have the Freedom Trail, which is about a 2.5 mile route that covers several historical sites, including Paul Revere’s house, and the site of the Boston massacre.  And you guessed it, these sites are better seen on foot, so its best to visit with warm weather. I also fell in love with Faneuil Hall – not only is it also part of our nation’s history (i don’t think any part of this City isn’t full of history, LOL), but today, it consists of tons of restaurants and shops, and even a museum.  It’s also cool to check out the Boston Harbor (take an amphibious tour to truly see everything), maybe go see the Red Sox (though I can’t vouch for the team, as an avid Yankees fan, though their stadium is historic!), Harvard University (Cambridge is a fun town full of restaurants like my personal fave Wagamama’s, and shops), and eat in Little Italy, which as you guessed it is home to quite a few delicious restaurants.  Boston brings to life all of those history tidbits you may have forgotten (or ignored) from high school history class.


New Orleans, LA – no, its not during Mardi Gras, but for me, that’s why I like visiting this time of year!  New Orleans was built on top of and surrounding a swamp, so you don’t really want to visit in June or July where the temperatures soar above anything comfortable, haha.  But in May, you have warm weather during the day, and cooler temperatures at night, which is absolute perfection. Then you have the cuisine in New Orleans (are you seeing a trend in the cities I’ve chosen thus far?!)…who doesn’t love great cajun food + beignets?! In fact, my last trip to New Orleans affected my brain and taste buds so much that I went looking for beignets while in NYC (and I found them…but that’s another story)!  There’s a lot to do in New Orleans aside from partaking in the awesome drink scene – you must try the Hurricane from Pat O’Briens and the Hand Grenade from Tropical Isle (get it frozen), and I’m still on the search for more options! For starters, I thoroughly enjoyed my trip to the Whitney plantation. It’s the only plantation in New Orleans that centers on what actually occurred there – slavery, as opposed to the balls that may have occurred in the Manor.  Their tour includes a visit to the slave quarters, the holding cell they kept slaves in awaiting auction, the kitchen used by the slaves to make dinner, and tons of real slave accounts from their time in bondage. This plantation prides itself on capturing the true stories as told by the slaves themselves, rather than a historian or writer’s account of what they may have seen or been told. If you want to truly see and feel what really occurred on a plantation, then this is the place for you.  I also took a bike tour through New Orleans and a Voodoo walking tour. I learned a lot on both tours from the history of the French and Spanish occupation(s), as well as how the Africans helped to shape the city’s future. So, for those who love history and great cuisine – this city, who is currently celebrating its 300 year anniversary, is the one for you to visit this spring.


Lisbon, Portugal – the first city on the list that I haven’t been to yet, but it doesn’t mean that its not on my radar.  Lisbon’s weather is perfect in May, and you don’t have the crazy summer tourists quite yet. Lisbon is somehow still staying under the radar as it loses folks to the flashier and more popular European cities like Barcelona, Madrid, Paris, and London.  Why is it on my list? From what I see, it’s gorgeous, calm, full of history and great seafood, and is a gateway to some other awesome sites like the Azores and Algarve regions, respectively. I also hear that a great majority of folks speak English (which is a plus for tourists like me who only learned one foreign language in high school, lol).  I do plan on visiting Portugal, hopefully in the next year, and when I do, expect a nice long write-up.


Bali, Indonesia – ok, I know this one first hand, because I recently booked my first trip to Indonesia for this upcoming June.  Why is it awesome this time of year? Well, for starters, its not monsoon season, haha. Another theme you may have noticed during my posts – I am not a lover of rain…I respect the need for it, but when I travel, I want non-stop sunshine.  Malaysia, Indonesia, the Philippines, etc., all enjoy pretty warm weather year-round, so they characterize their weather around rain. May in Indonesia is dry season, but its prior to when the throngs of tourists visit, so expect cheaper flights and hotel pricing.  What got my attention? 5 star resorts for as low as $80/night. And you know those awesome over-water bungalows that you see in Bora Bora? Those will cost upwards of $900/night, but in Malaysia you can stay at one for only $300/night. The most expensive part is the flight (subscribe to Qatar Airways and Emirates for deals), but once you arrive, you’ll be met with gracious folks, cheap but delicious food, and great scenery. I literally can’t wait, and you shouldn’t either!