4 Places You Should Travel As Soon As You Retire

Whether you have your retirement date marked on your calendar or you’ve just started this next chapter of your life, a trip has probably crossed your mind. But how do you choose the perfect destination? There are a lot of things to consider: cost, activities, language, transportation… the list goes on and on.

So we reached out to our Retirement Awaits Facebook group to get some pro tips. We asked: What is one trip you recommend others to take as soon as they retire? You answered! Here are some insights into the best places to travel when your retirement date arrives.

1. Italy

“Italy really has everything which includes so much history, beauty, the wonderful people and the food! I had the best pizza of my life in Naples as it is the birthplace of this wonderful concoction. The pasta was also exquisite, especially in Rome. So foodies and history buffs will really enjoy this country.”

After retiring, Janet Surwillo took a tour of Naples, Sorrento, and the Amalfi Coast, including the island of Capri. “Touring the Amalfi Coast and the Isle of Capri was probably my favorite activity. It is the most beautiful place I have seen to date, even beating out Hawaii — in my opinion, of course. The bus ride up the cliffs was a bit scary but was so worth it!”

Surwillo toured what is left of the ancient city of Pompei and what destroyed it, Mount Vesuvius. She took a boat ride on the Mediterranean — which she says is “the bluest of blues” — and saw the Colosseum and Trevi Fountain in Rome.

“In order to see as much as possible, there will be walking involved, so comfy shoes are a must. I visited in early fall in order to avoid the summer heat, which can be quite warm in the summer months. It is a great place to enjoy the Italian culture. Oh, and did I mention the food?”

Since she was traveling from St. Louis, she says getting a direct flight to Naples was not possible, but suggests going through Rome, which is easier to reach from most large cities in the U.S.

2. Portugal

Tim Frank lived in Tavira in Portugal‘s Algarve region for 3 months from April to June. He says while it gets hot sometimes, the weather is fabulous and is perfect for its Blue Flag beaches — an award that means they’re some of the best in the world.

“I was on the beach every day! The availability of fresh seafood, especially clams just picked that morning… Yum! I enjoyed the local festivals, which seemed pretty plentiful. The architecture (Moorish influence) was fascinating. I loved listening to fado music. Had some of the best Sangria ever in Tavira. Great entertainment at local pubs.”

Frank says getting around is easy with fast, efficient, and affordable transportation. He took trains to Faro, Lisbon, Porto, and other stops in Algarve. English is widely spoken, but he says it does pay to learn some Portuguese, especially if you need to use municipal services or other services like the internet. Frank says grocery stores are well-stocked and people are friendly. 

His pro tip: “Do not get large Euro denominations. Try to stay away from any bills over 20 euros. Get used to using ATMs to get cash. They are all over.” 

If you’re looking for some relaxation on your first trip in retirement, Frank says he found Portugal to be laid back and slower-paced. “Many shops close down from lunchtime to mid-afternoon for their siesta. Restaurants generally don’t start serving dinner until 7 p.m.-ish, so plan accordingly. Enjoy the fresh seafood! And the nightly entertainment especially if you can catch a fado performance. Participate in the festivals. Live like a local. Enjoy the beaches. Ride the trains!”

3. Ireland 

Frank also spent a month in Dublin, Ireland, and another month in a little village about 70 kilometers (43 miles) away called Moynalty.

His favorite part about the country was meeting people. “Plan on making friends! Strangers are only strangers until you meet them. Give yourself time to explore Dublin but also make sure to get outside of Dublin and explore the countryside. I highly recommend Galway and Dingle. Take a tour with a local company. I went on one for 7 days and explored the Irish countryside. It was fantastic! Enjoy the pubs and entertainment! Take in a true Irish dance performance.”

While Dublin is very walkable, Frank recommends a car in Ireland but warns the roads can be narrow. He also says Ireland can be more expensive. 

With so much to see and do, Frank says he never got bored. “In Moynalty, I had perfect strangers invite me into their homes for dinner and family get-togethers. The food everywhere was fantastic (I love lamb). Even developed a taste for black pudding. Drink some Irish whiskey and beer (in moderation of course)! Visited Galway and Dingle. Loved both. The Irish dance performances were fantastic. Saw the 20th anniversary of Riverdance and a couple of Broadway plays.”

Never heard of black pudding? It’s an essential part of the English breakfast, originating in the United Kingdom and Ireland. It’s a kind of sausage made with blood and a kind of cereal, usually oatmeal. It’s a “love it or hate it” kind of food, but like Frank, you won’t know if you don’t try it!

4. Alaska

If you’re looking to stay stateside, Linda Scott says to take the trip to Alaska. She’s been six times and says she still hasn’t seen it all. “I recommend Alaska for its beautiful mountain ranges, the glaciers, the beautiful lakes and rivers, waterfalls, wildlife, diverse landscapes, large bustling cities and small charming towns, national parks, old mining towns, unspoiled nature, and the rich history of the last frontier.”

Scott’s first trip to Alaska was with her husband on a 7-day cruise of the Inside Passage. Ports of call included Seward, Juneau, Skagway, Ketchikan, and Sitka. She liked this option because passengers can explore port cities and take shore excursions.

If you have more time, like several weeks or longer, she suggests renting a car or motorhome. Or if you’re brave like they are, drive your own RV up the Alaska Highway. Scott and her husband’s next five trips were as RV ambassadors for an RV tour company. The starting point was Dawson Creek, British Columbia, which is the start of the Alaska Highway.

They then worked their way up through the beauty and history of the Yukon. City tours included Chicken, AK (first point of entry), Tok, Fairbanks, Denali, Anchorage, Homer, Seward, Palmer, Valdez, Haines, Skagway, and Juneau. After Haines, they started working their way back down through the Yukon and western B.C., ending their trip in Prince George.

Scott’s favorite activity? “For me, being a tourist. Taking it all in, photographing spectacular scenery. For those that like to fish, there are numerous fishing charters in Homer, Seward, and Valdez. You can take a helicopter ride to see Denali up close and personal, or the glaciers, or bears. There’s so much to see and do in Alaska!”

Pro Tip: Scott says pick up a copy of The Milepost. It’s a best-selling travel guide to Alaska. “It’s a must! It has everything, and I mean everything in it. We led the 48-day tour to Alaska and there was so much to see and do. Lots of optional tours for our guests to do also.”

These are a few of the most popular comments we got on our post. We’d love you to join our group, “Retirement Awaits,” and share some of your pro tips as well! It’s a private group where we can share retirement together. You can engage with others, ask and answer questions about your retirement experience and talk about things you want to know. 

We can say one thing for sure, a common theme in all of your Facebook comments: relax and enjoy, you’ve earned it!