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Looking to plan the trip of a lifetime to celebrate a big 50th birthday? Celebration trips are one of our favorite excuses to travel and a 50th birthday is certainly worth celebrating.

Want to enjoy incredible restaurants and pristine wilderness? Head to Vancouver for a city-meets-nature escape. Prefer to keep it laidback? Spend some time on a quiet island in Greece.

These 50th birthday trip ideas were hand-picked to offer a combination of gorgeous destinations and one-of-a-kind experiences to make you feel like a kid again. We’ve even included a handy guide to the best months for each destination so you can narrow the list down based on your birth month.

50th birthday trip ideas include:

  1. Kickback in Southwest Florida
  2. Live the Meditteranean life in Greece
  3. See the Northern Lights in Iceland
  4. Enjoy summer in Vancouver
  5. Indulge in New York City

Ready to plan your 50th birthday trip adventure? Head over to Troupe to let your fellow travelers share flight information, vote on their favorite destination, and more.

The best 50th birthday trip ideas

1. Kickback in Southwest Florida

If your 50th birthday falls during the winter months, you can count on a trip to Florida to brighten your spirits with its ample amounts of sunshine and beautiful Floridian nature.

Located in the south of the state, about 2 hours from Miami, you have your choice between Marco Island, Naples, and Sanibel Island. All three offer an array of things to do, both on land and also at sea.

Naples is the more posh choice for a 50th birthday trip. With incredible restaurants set along its trendy 5th Avenue, you’ll be spoilt for choice when it comes to good food and drinks. In addition, there are plenty of golf courses (both regular and mini) nearby and Naples’ beaches are perfect for a laidback day by the water.

Marco Island and Sanibel Island are two of the most beautiful beach destinations in the United States. Both have an ultra-relaxed Caribbean island feel. You’ll find everything from casual seafood restaurants to upscale dining. Celebrate your 50s by enjoying time kayaking, paddle boarding, or enjoying a luxury sunset dinner cruise on the Gulf of Mexico.

Best for birthdays in: November-April

50th Birthday Trip Ideas: Florida. Man spinning fire on the beach at sunset with tourists watching in the background

What to pack for a Florida vacation.

2. Live the Meditteranean Life in Greece

Whether or not you’ve made it to Greece already during your 50 years of life, this country will always have more for you to explore. Our favorite 50th birthday trip ideas for Greece are visits to Thessaloniki and Skopelos Island.

Thessaloniki is Greece’s second-largest city, located in the north of the country, about five hours by car from Athens. Thessaloniki is full of both ancient ruins and hip, modern eateries and bars. Visit the White Tower and Hagios Demetrios before grabbing dinner in Ladadika.

Now that you’re in your 50s, it’s high time for some relaxation. And no one knows how to relax like the Greeks. Skopelos is one of the quiet Greek islands we love the most. You can either fly from Thessaloniki to Skiathos (neighbor island to Skopelos) or take the Train to Velos and from there take the ferry to Skopelos.

Best for birthdays in: April-September

50th Birthday Trip Ideas: Greece. View from an ancient tower overlooking Thessaloniki.

3. See the Northern Lights in Iceland

You’ve made it half a century– how’s your bucket list looking?

If you still need to experience one of Earth’s greatest spectacles, now’s the perfect time for a trip to Iceland to see the Northern Lights. Pay a visit in the winter months when the sun sets around 4 p.m. and you have peak darkness in order to see the light shows at night.

Start your journey in Reykjavik where you can visit the Blue Lagoon and take a Northern Lights boat tour. Sail out away from the city lights and let the experienced guides tell you more about the science and folklore behind the Aurora Borealis. Many boat tours have warm blankets and overalls on board. In addition, if conditions aren’t favorable for viewing the lights, most companies offer to take you out a different night or refund your ticket.

Next, rent a car and spend a few days exploring the waterfalls, geysers, and other incredible nature along The Golden Circle.

Best for birthdays in: September-March

50th birthday trip ideas: Iceland. Northern Lights behind a waterfall

4. Enjoy summer in Vancouver

Looking for 50th birthday trip ideas for summer birthdays? Head north of the border while the weather is nice to enjoy summer in Vancouver. City lovers will enjoy spending their 50th birthday exploring Canada’s most western Metropolis. Vancouver is full of specialty bars, incredible nature, and plenty of fun events during the summer like the Jazz Festival.

Wander through neighborhoods like Yaletown, Gastown, and Chinatown. Head to Stanley Park and walk or cycle between the water and the redwood trees. Spend an afternoon on adorable Granville Island.

Visitors are pleasantly surprised to discover how much of Vancouver is focused around the water. We highly suggest renting a kayak and exploring the beautiful British Colombia nature surrounding the city.

Best for birthdays in: May-September

50th birthday trip ideas Vancouver: Image of Stanley Park with trees and water and skyscrapers int he background at sunset

5. Indulge in New York City

You’ve worked hard to get to where you’re at in life. Now that you’re in your 50s, it’s time to indulge in the finer things. Head to New York City where you can enjoy some of the best restaurants and entertainment in the world.

Splurge on front row seats to your favorite Broadway show. Haven’t been to the theatre in a while? You can’t go wrong with classics like Wicked or the Phantom of the Opera or you can try ultra-popular newbies like Hamilton and The Book of Mormon.

Ready to enjoy the very best food New York City has to offer? Pay a visit to Peter Luger’s Steakhouse as your big 50th birthday celebration dinner in NYC. Enjoy brunch at The Fulton with incredible views of the Brooklyn Bridge and East River. Try the 5-course tasting menu at the always beloved Gramercy Tavern.

Best for birthdays in: NYC is great any time of the year, but April/May and September/October are nicest.

NYC Itineraries for Every Type of Group Trip.

50th birthday trip ideas- New York City street corner with people city outside at a cafe

All set with 50th birthday trip ideas? It’s time to start planning your adventure.

To make it easy, head over to Troupe where you can collaborate with your fellow travelers all in one place. Vote on accommodations and share flight info, reservations, and more.

Still need more birthday trip ideas? Check out places to go for a 21st birthday, 30th birthday trip ideas, or ideas for a 40th birthday trip.

Is your birthday the same month as Halloween? Check out the 10 best countries to visit in October.