10 Bucket-List Trips That Are Perfect to Dream About for Retirement Travel

See recent posts by Kyle Valenta

The world may currently be on pause but that doesn't mean that your travel dreams have to stop. We think that all of this home time is the perfect occasion for working on our bucket lists. Whether you're on the verge of retiring, have recently retired, or are well into retirement, there are countless amazing travel opportunities out there to explore. All 10 spots on this list are perfect for retirement travel for a variety of reasons, from tourist-friendliness and ease of navigating to destinations that require a bit more time than we have when we're limited by jobs and vacation days. Read on and start dreaming about your bucket-list retirement trip for when it's safe to travel again.

Getting antsy to hit the road? Do it virtually with our favorite bucket-list destinations that are streaming

Road Trip in Portugal — from Lisbon to the Algarve

The Algarve, Portugal
The Algarve, Portugal/Oyster

For the perfect dose of vibrant city life, history, and stunning coastal scenery, Portugal is a no-brainer. By flying into Lisbon, you’ll give yourself a few days to explore the cafes, restaurants, and inimitable Lisbon scenery (as well as plenty of time to sample delicious sweets like pasteis de nata). Just note that Lisbon is full of street and cobblestone sidewalks, so you’ll need to be steady on your feet to make the most of it.

Once you’ve had your city fill, rent a car and head three hours south to the Algarve. Here, a collection of coastal towns stretches from west to east. Start in Sagres, where little development and dramatic coastal cliffs are the perfect retirement reward. Making your way east, allow for a few days in charming Lagos before continuing on to other quaint towns like Taveira.

Safari in the Masai Mara, Kenya

Elephants in Masai Mara, Kenya
Masai Mara, Kenya; Jessica Pamp/Unsplash

Retirees with a healthy sense of adventure will be handsomely rewarded with a trip to Kenya to experience the great migration across the Masai Mara. You’ve likely seen photographs of the dramatic crossings of wildebeest and other hoofed animals as thousands of them make their way across the crocodile-infested Mara River. And that’s only a fraction of the majestic natural spectacle.

There are plenty of ways to experience a Kenyan safari, from budget overland Jeeps to fly-in luxury tented camps. No options are cheap, but for an up-close-and-personal encounter with the big five and other species, it’s worth the investment. You’ll like have to take your pick between parks and national reserves like Aberdare, Masai Mara, Tsavo, and Amboseli — or a combination of several. If you’re after a truly exclusive experience, you’ll want to check out the private conservancies, like the Mara North Conservancy, which offers all night game rides and limits the amount of other safaris within their boundaries at a given time.

First time on safari? Here are 11 top tips for planning an African safari.

Drive the Pacific Coast Highway

Ocean Meadow at the Ventana Big Sur, an Alila Resort
Ocean Meadow at the Ventana Big Sur, an Alila Resort/Oyster

You don’t need to leave the United States to have an amazing bucket-list trip after you’ve retired. In fact, the U.S. is blessed with its own share of amazing cities and beautiful landscapes. For an easy-to-plan and easy-to-execute journey, hop in a car and drive (nearly) the entire coast of California.

Also known as California 1, the Pacific Coast Highway runs for over 650 miles — from Dana Point north to Leggett. While those names might not be familiar, the cities and towns in between include Los Angeles, San Francisco, Monterey, Big Sur, Santa Cruz, and Santa Barbara. And while exploring those cities is certainly part of the fun of this epic road trip, it’s the natural scenery that’s especially spectacular.

Beaches, mountains, vineyards, cliffs, forests, fog banks, and epic sunsets are all on the menu along the Pacific Coast Highway. Definitely make time for some day hikes in the many state parks and forests along the way. If you’re feeling ambitious, take a turn inland and hit up the Sonoma Wine Region to the north of San Francisco. Or opt to start your journey in San Diego and head all the way north in California to the wilderness of Redwood National Park.

Don’t miss a thing. Here are 11 stops to make along the Pacific Coast Highway.

Japan During Cherry Blossom Season

Odaiba, Tokyo tree blossoms
Odaiba, Tokyo/Oyster

To distill all of the reasons that Japan is a travelers’ dream down to one thing would be hard. There’s the dazzling cities, incredibly food, efficient transportation, quirky boutiques, and gorgeous landscapes across this nation. However, if you’re after a truly special only-in-Japan experience, you’ll need to visit during cherry blossom season (called sakura in Japan).

To put it mildly: Japan goes nuts for cherry blossoms. The parks of Tokyo fill up — literally — with merrymakers having boozy brunches on blankets. All around people snap photos of themselves with an astonishing array of cherry tree varieties. But it’s not just Tokyo. Cities and towns and national parks across the land draw crowds with the spectacle as spring dawns from south to north across Japan.

That makes Japan a no-brainer for retired travelers looking to explore a good cross-section of Japan. Trains run fast and efficiently, and connect almost every corner of the country, making navigating Japan relatively easy. And while English isn’t spoken as widely as you might expect, everyone involved with the tourist industry will be able to get you to where you need to be easily. Don’t miss a hot soak in the world famous onsen.

Here’s a month-by-month breakdown on the best time to visit Japan.

Florence and Tuscany’s Wine Regions

Garden at the Aia Mattonata Relais
Garden at the Aia Mattonata Relais/Oyster

While you can make a tour of Italy a dreamy bucket-list trip in its own right, there’s something special about devoting a nice chunk of time to exploring one of Italy’s most iconic regions: Tuscany. Florence is the nerve center and is famous for its art, architecture, and food. You’ll find major Renaissance landmarks like the Duomo, the Uffizi Gallery, and the Galleria dell’Accademia here. Michelangelo’s “David” can be found at the latter.

Outside of Florence (and equally historic Siena), Tuscany is famous for its wine and truffles — all found in the beautiful rolling hills and forests of the region. Some of the most famous wines in the world bear names of Tuscan towns, including Chianti, Montalcino, and Montepulciano. But trust us when we say that there are almost too many charming towns and villages to explore. You’d also do well to bed down in one of the many agritourism properties, like Aia Mattonata Relais.

Utah’s National Parks and the Grand Canyon

The View Hotel
The View Hotel/Oyster

While the United States has some of the most beautiful national parks in the world, some parks are more accessible for seniors than others. There are also few places in the U.S. where you’ll find so many stunning natural parks packed into a relatively small region as you will in Utah and Northern Arizona. Whether you’re looking to explore vertigo-inducing hikes like the notoriously dangerous Angel’s Landing, take a multi-day trek into the desert landscapes, or simply enjoy some easy sight-seeing on short, simple walks, there’s plenty here to in Utah.

The major parks in Utah — Grand Canyon, Bryce Canyon, and Zion — all offer a range of trails and experiences for visitors. You’ll also find that Zion and the Grand Canyon in particular are well suited to travelers who have any mobility issues. Zion offers a tram through the center of its majestic valley with clear views of the major summits and cliffs all around. Along the South Rim of the Grand Canyon, the four main viewpoints (Yaki, Moran, Grandview, and Desert View) are all accessible. While Bryce Canyon is the least accessible of the major parks, though Sunrise Point and Sunset Point can easily be reached for some spectacular views.

Explore Ireland by Rail and Road

Kylemore Abbey
Kylemore Abbey/Oyster

Talk to anyone who has been to Ireland and chances are you’ll hear something close to rapture. Ireland is one of those destinations that absolutely lives up to the hype. And with over 33 million Americans claiming some level of Irish ancestry, it’s remained a favorite for travelers young and old seeking to find the roots of their family trees.

Whether you’re visiting Ireland because you’re researching ancestry or because you want to experience the mix of quaint towns, cool cities, and jaw-dropping emerald green landscapes, you won’t be disappointed. It’s a fast and easy train ride from buzzing Dublin’s historic sites to Galway’s funky foodie scene and artsy vibe. From there, you only need to grab a car rental to explore other amazing towns like Killarney (next to the stunning Killarney National Park), the stunning Cliffs of Moher (in County Clare), and the scenic Ring of Kerry. Just remember, you’ll drive on the left-hand side (a bucket-list experience in our opinion).

All around Ireland, you’re likely to stumble upon castles and abbeys, unexpected coastal vistas, and towns that are postcard-perfect. And while Irish is certainly still spoken — and you’ll hear signs in the language — English is officially used everywhere. That, combined with a well-oiled tourism industry — helps make navigating this country safe and easy for retirees and everyone else.

Eastern Australia

Bondi Beach
Bondi Beach/Oyster

Spotting a kangaroo; snorkeling the Great Barrier Reef; a tour of the Outback; seeing the Sydney Opera House; trying Vegemite — everyone has a reason for wanting to visit Australia (well, the last one might be a stretch). Even better? Australia makes an excellent destination for retirees for three reasons: it’s safe, it’s traveler friendly, and getting around is easy (but much like Ireland, you’ll be driving on the left-hand side of the road).

As one of the most urbanized nations on the planet, Australia’s cities are big, but by no means chaotic. Sydney is home to world-famous landmarks like the Sydney Opera House and Sydney Harbour Bridge, and has some of the coolest neighborhoods and best urban beaches in the world. Melbourne is the artsier alternative to Sydney, with charming boutique and cafes in spades and easy access to five different wine regions.

For a nature-made respite from all of the city style, Eastern Australia is flush with beautiful natural scenery. That ranges from rugged mountains in the southern interior to rolling hills near the coasts to stunning beaches to the tropical north of Queensland. Towns like Cairns and Townsville are a jumping-off point for catamaran trips across the Great Barrier Reef. Though if you want to unwind amid some of the most stunning island scenery in the world, we recommend a trip to the resorts of the Whitsunday Islands.

Tour India’s Golden Triangle by Train

The Pool at the Tree of Life Resort & Spa Jaipur
The Pool at the Tree of Life Resort & Spa Jaipur/Oyster

No one would describe a trip to India as a simple, easy thing. The moment you leave the modern airport in Delhi, it’s clear that you are very far from anything you’re used to — and that’s precisely the point. You’ve worked hard and played by the rules your entire life, and your golden years are the perfect time to explore something a little outside of your comfort zone: India’s Golden Triangle. With plenty of time to check off this bucket list trip, you’re also free to explore at your own pace, which is helpful in India.

So what is the Golden Triangle? It’s one of the most popular tourist circuits in India, connecting three major destinations by rail in the rough approximation of a triangle. It also happens to combine some of India’s most famous monuments and destinations in one itinerary, making it incredibly popular and relatively easy to plan. You’d do well to work with a private tour company if you’d like to guarantee your comfort and make securing train tickets easy. It can help take out some of the unavoidable stress you’re likely to feel once you’ve set foot on the ground in India.

The Golden Triangle starts in Delhi, where you’ll find old and new India side by side in startling contrasts. There are the frenetic markets and Mughal-era landmarks of Old Delhi, beautiful qawwali ceremonies at Hazrat Nizamuddin, and the ruins of Qutub Minar all harkening back in time while luxury malls pepper the wealthy districts and hip cafes pack charming Hauz Khas Village. From there, a fast train to Agra puts you at the foot of the iconic Taj Mahal — one of the most famous monuments in the world. Once you’ve had your fill, it’s off to the Pink City of Jaipur in Rajasthan to soak of its charms.

Here’s how to get an India visa online — it can be complicated.

Live on Island Time in Hawaii

Waikiki Beach at sunset
Waikiki Beach; Laura Hinely/Oyster

For many travelers, Hawaii is the kind of place you dream about. Jungle-clad volcanos, stunning beaches, dramatic seaside cliffs, luxury hotels, perfect weather, and amazing local food all put it high on the list of most people. However, long flights from much of the world mean that this is the kind of place best experienced when you have plenty of time.

Depending on your personality, Hawaii has plenty of sides to enjoy. History buffs and beach lovers will do well to stick to Oahu, where Honolulu and the famous Waikiki neighborhood sit right along one of the most famous beaches in the world. If you’re after untouched natural beauty, we suggest heading to Maui or Kauai, where development has been kept to a relative minimum. If you’re looking for an up-close-and-personal volcano experience, Hawaii Volcanos National Park is found right on the Big Island.

Since you’re retired, though, you can live on island time. By giving yourself 14 days or more, you have plenty of time to explore several of the islands at a leisurely pace. And when you’re not island-hopping or soaking up the sun on the beach, you’ll find restaurants of all types catering to everyone’s taste buds, which is always a comfort when you’re far from home.

Still not sure where to visit in Hawaii? Here’s a cheat sheet to all the Hawaiian islands.

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