Top 10 American Cities to Travel to in the Go Go Years of Retirement

The Go Go Years are your time to travel, explore, and enjoy all the experiences you’ve been waiting for, starting with these top U.S. cities.

Wondering what to do in retirement? Put travel at the top of your list

Retirement isn’t what it used to be. Today’s retirees are more active, adventurous, and ready to explore than any generation before. This is especially true during what we call the “Go Go Years,” the golden period right after retirement when your health is good, your energy is high, and your schedule is finally your own.

The Go-Go Years are a prime opportunity for travel and new experiences. After working hard for decades and saving diligently, you now deserve to enjoy the fruits of your labor. Many of our clients tell us that travel is at the top of their retirement wish list.

Where you choose to travel matters – both for your enjoyment and your retirement budget.

Some destinations offer better value, senior discounts, or seasonal pricing that can make your retirement dollars stretch further. Careful planning means you can see more places without compromising your long-term financial security.

Understanding the Go Go Years

Retirement isn’t a single continuous experience. Financial planners often break it into three distinct phases:

1. The Go Go Years
2. The Slow Go Years
3. The No Go Years

Each phase brings different lifestyle needs, activity levels, and spending patterns.

The Go Go Years typically span the first decade of retirement. During this active phase, you’re generally healthy, energetic, and eager to do all the things you couldn’t while working full-time.

This phase is ideal for travel adventures. Your health and mobility are usually at their retirement peak, allowing you to explore cities on foot, handle longer flights, and participate in various activities.

The Go Go Years often see higher spending than pre-retirement.

This surprises many retirees who assumed their expenses would immediately decrease. Travel, leisure activities, and pursuing new interests can temporarily increase your budget needs during this phase.

For a deeper look at retirement expenses, watch our video “4 Most Important Things to Consider When Estimating Retirement Expenses.”

Financial planning for Go Go Years travel requires balance. You want to enjoy these active years fully without compromising your long-term financial security. Setting a dedicated travel budget separate from your essential expenses can help maintain this balance.

Click to see all the latest retirement videos for your Retirement Planning research.

 

Consider creating a “retirement travel fund” before you retire. Many retirees set aside a specific amount solely for their adventure plans during the Go Go Years, allowing them to enjoy travel without worrying about depleting their core retirement savings.

Timing matters, too, because the Go Go Years won’t last forever.

Eventually, most retirees move into the Slow Go Years, a time when energy levels decrease and health considerations may limit certain activities. This natural progression makes early retirement travel particularly worthwhile, as these experiences are best enjoyed while you’re still mobile and active.

Tax planning for travel can stretch your retirement dollars further. Strategically withdrawing funds from different retirement accounts can minimize your tax burden while funding your adventures.

Want to be sure you’re making the right decisions for you? An Oak Harvest Financial Group financial advisor would be happy to help you figure out how to fund your travels.

Understanding this phase of retirement helps you make the most of it. The Go Go Years are your opportunity to check items off your bucket list, explore new places, and create lasting memories that will sustain you through the later, less active phases of retirement.

 

Now, where should you start? Our top 10 cities to explore in retirement

America offers incredible diversity for retirees looking to explore. There’s something for everyone, from coastal towns to mountain retreats to bustling cities to cultural hubs. The beauty of domestic travel is that it can be more affordable and accessible than international adventures while still providing rich, varied experiences.

We’ve selected 10 outstanding American cities that offer exceptional experiences during your Go Go Years.

Each location provides unique attractions, reasonable costs, and plenty of things to do in retirement. Whether you’re looking for outdoor activities, cultural immersion, historical exploration, or culinary adventures, these destinations deliver experiences worth adding to your retirement travel list.

Let’s explore these 10 noteworthy cities that should be on every retiree’s radar during those active early retirement years.

 

Asheville, North Carolina

Asheville offers the perfect blend of mountain living and cultural richness in the beautiful Blue Ridge Mountains. It ranks among the top retirement destinations for its moderate climate, natural beauty, and vibrant arts. The city combines Art Deco buildings with Victorian homes, while the Biltmore Estate, arts district, and craft breweries showcase its creative energy.

Asheville’s manageable size makes it easy to navigate while offering diverse experiences. The elevation provides cooler summers than most Southern cities, making outdoor activities comfortable year-round.

Activities and sites to see

• Tour the historic 8,000-acre Biltmore Estate and its award-winning winery
• Explore the vibrant River Arts District with over 200 working artists
• Drive the scenic Blue Ridge Parkway for breathtaking mountain vistas

Cost considerations

Asheville is moderately priced compared to major cities, though tourism has increased costs in recent years. Consider visiting during the shoulder seasons (April-May or September-October) for pleasant weather with fewer crowds, and stay in nearby towns like Black Mountain for lower accommodation costs.

Boston, Massachusetts

Boston combines American history, world-class cultural institutions, and walkability. As one of America’s oldest cities, Boston preserves its historic character through the 2.5-mile Freedom Trail while embracing innovation across its distinct neighborhoods. The city’s passion for sports, education, and seafood creates a vibrant cultural identity.

Boston’s excellent public transportation and pedestrian-friendly design make it easy to explore without a car. The city’s compact layout allows visitors to experience numerous attractions within a small area.

Activities and sites to see

• Walk the historic Freedom Trail past Revolutionary War sites
• Visit the Museum of Fine Arts and Isabella Stewart Gardner Museum
• Take in a Red Sox game at iconic Fenway Park

Cost considerations

Boston ranks among the more expensive U.S. cities, but the MBTA subway system provides affordable transportation with senior discounts. Consider staying in nearby Cambridge or Brookline for more affordable accommodations with easy subway access to downtown attractions.

Chicago, Illinois

Chicago offers world-class amenities combined with Midwestern friendliness and better value than coastal cities. The city’s stunning architectural skyline is complemented by 26 miles of lakefront parks, beaches, and walking paths along Lake Michigan. Each distinct neighborhood reflects its own culture and history, all connected by a comprehensive public transportation system that enables car-free exploration.

Active retirees appreciate Chicago’s flat terrain for walking and biking, along with excellent public transportation options. The city offers cultural activities for every interest from Broadway shows to blues clubs, world-class museums to neighborhood festivals. Lake Michigan provides opportunities for cruises, beach visits, and waterfront dining during the summer months.

Activities and sites to see

• Take an architectural boat tour on the Chicago River
• Visit Millennium Park and snap a photo at Cloud Gate, better known as “The Bean”
• Explore world-class museums like the Art Institute and Field Museum

Cost considerations

Chicago offers greater value than other major U.S. cities while still offering world-class attractions. For more affordable rates, look into accommodations in neighborhoods like Lincoln Park or Wicker Park, and take advantage of free admission days at major museums.

Charleston, South Carolina

Charleston’s well-preserved historic district features hundreds of meticulously maintained 18th and 19th-century buildings along charming cobblestone streets. The city’s distinctive architecture features colorful Rainbow Row townhomes and elegant antebellum mansions. Charleston’s intricate history as a colonial and Civil War site adds rich cultural context to a sophisticated dining scene that highlights fresh seafood and Lowcountry cuisine.

The city’s flat terrain and compact historical district make it easily walkable. Charleston’s mild winters attract retirees looking to escape the northern cold while enjoying outdoor activities year-round. The city’s cultural events and proximity to beaches offer diverse experiences within a manageable area that’s perfect for leisurely exploration.

Activities and sites to see

• Tour historic homes and gardens in the downtown historic district
• Shop and dine at Charleston City Market and along King Street
• Visit Fort Sumter, where the Civil War began

Cost considerations

Charleston commands premium prices, particularly in the historic district and during spring and fall peak seasons. Consider visiting during winter months for lower rates and comfortable temperatures in the 60s or look for accommodations in neighboring communities like Mount Pleasant for better values.

Denver, Colorado

Denver boasts more than 300 days of sunshine a year and a stunning location at the foot of the Rocky Mountains. The “Mile High City” blends historic Western character with modern urban development, featuring over 200 parks within city limits and an extensive trail system. Denver’s cultural scene includes world-class museums, seven professional sports teams, and a thriving arts district while serving as a gateway to mountain adventures.

Denver’s climate encourages year-round outdoor activity with low humidity and moderate temperatures. The city serves as an excellent hub for day trips to mountain towns, national parks, and scenic drives. Denver’s walkable downtown, reliable public transportation, and bike-sharing program make exploration easy for those seeking both urban amenities and natural beauty.

Activities and sites to see

• Explore the Denver Art Museum and the nearby Golden Triangle Cultural District
• Visit Red Rocks Amphitheatre for concerts or morning fitness classes
• Take day trips to nearby Rocky Mountain National Park or mountain towns

Cost considerations

Denver offers good value compared to coastal cities, though tourism has increased prices in recent years. The RTD light rail provides convenient transportation from suburban areas with lower accommodation costs, while free attractions like State Capitol tours and the 16th Street Mall shuttle help stretch your travel budget.

Portland, Maine

Portland offers New England coastal charm in a manageable, walkable city that combines a historic Old Port district of cobblestone streets and brick buildings with a working waterfront where fishing boats still bring in the day’s catch. The city’s food scene extends beyond lobster to include award-winning restaurants and breweries. An active artistic community thrives in the Arts District, while the surrounding region offers lighthouse-dotted coastlines.

The compact downtown area allows for easy exploration on foot, with most attractions within a 20-minute walk. Portland’s coastal location provides opportunities for boat tours, lighthouse visits, and beach excursions. The city serves as an excellent base for exploring Maine’s scenic coastline and mountain regions.

Activities and sites to see

• Explore the historic Old Port district’s shops and restaurants
• Tour the iconic Portland Head Light and other historic lighthouses
• Take a ferry to nearby Casco Bay islands for hiking and coastal views

Cost considerations

Portland experiences a surge in tourism during the summer months, leading to higher prices. Consider visiting in late spring or early fall when the weather is pleasant and rates are lower. Look for accommodations just outside downtown in neighborhoods like Munjoy Hill for better value.

San Diego, California

San Diego offers ideal retirement travel with what many consider America’s best climate – mild temperatures year-round with minimal rain and low humidity. The city’s 70 miles of coastline include busy beaches and secluded coves, while Balboa Park houses 17 museums and the renowned San Diego Zoo. The city’s proximity to Mexico adds cultural diversity, particularly evident in its Old Town district and excellent Mexican cuisine.

San Diego’s climate allows outdoor activities every month of the year, from beach walks to desert hikes. The city’s varied terrain, from coastal flat areas to inland hills, accommodates different fitness levels. Transportation options include an efficient trolley system connecting major attractions such as museums and botanical gardens.

Activities and sites to see

• Explore diverse beaches from lively Mission Beach to serene Torrey Pines
• Visit world-class attractions like the San Diego Zoo and Balboa Park
• Experience the historic Gaslamp Quarter and Old Town San Diego

Cost considerations

San Diego’s desirability comes with higher prices, especially in beach communities and during the summer. Consider visiting during the shoulder seasons (April-May or September-October) when the weather remains excellent but crowds thin, and stay in neighborhoods like Mission Valley for lower accommodation costs with good access to attractions.

Santa Fe, New Mexico

Santa Fe offers a unique cultural experience as America’s oldest capital city (founded in 1610), preserving its historical character through strict building codes that maintain its distinctive adobe architectural style. The city has over 250 galleries and art museums, making it the third-largest art market in the country, while its blend of Native American, Spanish, and Anglo influences creates a cultural tapestry unlike anywhere else in America.

Santa Fe’s walkable downtown plaza features museums, restaurants, and shops. The city’s focus on wellness and spirituality attracts those seeking rejuvenation through spa treatments, meditation retreats, or natural hot springs. Cultural experiences abound through cooking classes, art workshops, and guided historical tours, while the surrounding mountains and desert provide outdoor activities at varying levels of exertion.

Activities and sites to see

• Explore historic Santa Fe Plaza and surrounding adobe buildings
• Visit world-class museums, including the Georgia O’Keeffe Museum and the Museum of International Folk Art
• Shop for authentic Native American art under the portal at the Palace of the Governors

Cost considerations

Santa Fe provides better value than many other destinations while offering unique experiences. Consider visiting during shoulder seasons for ideal weather and fewer tourists, and look for accommodations in the midtown or southside areas for better values than the historic downtown.

Savannah, Georgia

Savannah enchants visitors with its Historic District, which features 22 park-like squares surrounded by historic homes and churches preserved according to the original 1733 town plan. Live oak trees draped with Spanish moss create a romantic atmosphere throughout downtown, while the city’s strategic location near the Atlantic coast provides access to barrier islands and beaches. The city blends architectural beauty, excellent cuisine, and storytelling traditions that bring history to life.

Savannah’s flat terrain and organized grid of streets make it remarkably walkable. The moderate winter climate allows year-round outdoor exploration without extreme temperatures. Savannah’s historical significance offers intellectual engagement through diverse tours and museums, while the city’s laid-back pace encourages leisurely experiences.

Activities and sites to see

• Stroll through the historic squares and Forsyth Park
• Take a riverboat cruise on the Savannah River
• Tour historic homes like the Mercer-Williams House or Owens-Thomas House

Cost considerations

Savannah offers good value compared to larger cities, though its popularity has increased prices in the historic district. Consider visiting during January-February for lower rates and take advantage of the free DOT shuttle that provides transportation throughout the historic district.

Seattle, Washington

Seattle combines stunning natural beauty with sophisticated urban amenities, set dramatically between Puget Sound and Lake Washington with mountain views of the Olympic and Cascade ranges. Seattle’s coffee culture, farm-to-table dining, and vibrant music scene create distinctive local experiences, while the surrounding region offers island exploration, mountain hiking, and cultural diversity.

Seattle’s excellent public transportation and walking paths make exploration accessible for active seniors. The city’s mild summers provide pleasant conditions for outdoor activities without extreme heat. Cultural offerings include world-class museums, theater productions, and music venues, while its central location serves as an ideal base for day trips to national parks, wine country, and coastal communities.

Activities and sites to see

• Visit the iconic Space Needle and Seattle Center campus
• Explore Pike Place Market and the original Starbucks location
• Take a ferry to nearby Bainbridge Island or San Juan Islands

Cost considerations

Seattle ranks among the more expensive U.S. cities, but it offers several economical ways to visit. Many museums offer free admission days each month, and neighborhoods like Queen Anne or Fremont provide better accommodation values while maintaining good transit access to major attractions.

Your Go Go Years adventure awaits

Traveling during the Go Go Years offers a perfect opportunity to explore America’s diverse cities while you’re most active. Each destination provides unique experiences, from mountain adventures to coastal charm.

For more travel planning advice, check out our blog “6 Tips on Saving and Planning Extended Travel When Retired.”

The financial advisors at Oak Harvest Financial Group understand that travel is about creating meaningful experiences during your Go Go Years. Schedule a consultation with one of our experienced advisors who can help create a personalized plan that supports your travel dreams while ensuring your retirement remains secure.

 

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