Long Weekend Wonders: 4 Last-Minute Memorial Day Trips


Summer is just around the corner, and there’s no better time to plan your last-minute Memorial Day weekend getaway. Though many travelers focus on taking trips later on in the season — August being a particularly high month for tourism — booking earlier in the season can have its advantages, as well. Namely: Fewer crowds, cheaper hotels, and cooler weather (helpful when visiting the tropics). From the sand dunes of New England to the coastline of Costa Rica, read on for the top five trips to book for Memorial Day weekend.

1. Bermuda

The coastline in Bermuda

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Though the ambiance of Bermuda feels very Caribbean, the island is located in the Atlantic (only 650 miles off the coast of North Carolina), making the island perfect for long weekend travel. Plus, Memorial Day weekend kicks off the high season in Bermuda — which is from May through September— when all of the events and festivities on the island take place. The first thing for visitors to add to their agenda? Bermuda Day, which is celebrated on the last Friday of May and falls this year on the long weekend — May 26th. Expect street parades, live music, drums, and Gombey troupes (Bermuda’s signature dance tradition, which dates back to the early 1800s). Bermuda fish soup and rum swizzles await. 

2. Cape Cod

A shipyard in Cape Cod

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The gorgeous, hook-shaped peninsula of Cape Cod has long been a favorite summer destination — not only for New England natives but travelers across the country. As such, there tends to be traffic — nothing good comes easily! — but if you travel in the shoulder seasons of peak summer (i.e., May or September), you tend to save time in transit. As such, Memorial Day is a safer bet for a long weekend trip than Labor Day in August. And, for those who want to minimize travel time, they can always fly into Hyannis and just navigate the roads once on the island. Regardless of when you arrive, be sure to make time for sunset cocktails at Chatham Bars Inn. And if you can’t make it for Memorial Day, consider a visit for later in the summer when the Inn’s White Shark Ecotourism programs are underway — if your dream is to see a Great White Shark in the wild, this should immediately be added to your bucket list. 

3. Costa Rica

A man admiring a waterfall in Costa Rica

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We’re flying down to Central America for a dose of Pura Vida for our next selection: the evergreen jungles and sandy beaches of Costa Rica. Though traveling to Costa Rica in May comes with a higher chance of rain than in the months prior, it’s nowhere near the heaviest month for rainfall (that award goes to September and October). Furthermore, a bit of liquid sunshine is the best way to offset the tropical heat. Additionally, May is the start of the off-season in Costa Rica, when prices for hotels and airfare are lower — and won’t dramatically increase until November. Plus, a long weekend is the perfect length of time to learn a new skill during your stay. We suggest the twice-daily private surf lesson at W Costa Rica, which is located in the Guanacaste Province along the nation’s northwest coast. Surrounded by tropical forests, there’s no more gorgeous place to stay and play (and attempt to hang ten). Surf’s up.

4. St. Maarten

A tourist walks the streets of St. Maarten

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You needn’t be a snowbird to fly south, and there’s no better place to kick off summertime revelry than in one of the most fun islands in the Caribbean: St. Maarten, also known as the “Friendly Island.” While the residents of St. Maarten are known all across the island for their warmth and hospitality, the destination is unique for being home to two nations — with two distinct cultures and ambiances. The southern part of the island is the Dutch side (Sint Maarten), where Dutch, English, and Creole are widely spoken, and the USD is the accepted currency. While the southern part of the island has a more Caribbean feel, the northern part is more European. Saint Martin, on the northern part of the island, has more opportunities to connect with nature and is slightly more remote. Either way, you can’t go wrong. Additionally, the rainy season doesn’t begin in earnest until later in the summertime, and the rates are low in May compared to the end of the year. So, what are you waiting for? Book your next tropical trip now.

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