Trip ideas · 8 cities ranked
Solo Travel Over 50: The Best US Cities to Go Alone
Travelling alone after 50 is a pleasure in the right city: one you can walk, with good guides to join, bar seats and communal tables where eating alone is normal, and evenings where you can sit and listen to music without a plan. These are the eight we'd choose.
Some links on this page go to booking partners. If we join their affiliate programmes we may earn a commission when you book, at no extra cost to you. It never decides what we recommend. How we make money.
Every pick below is built from venues we checked in September 2026. We looked for walkable centres, tours you can book as one, places to eat without a table for two and evenings that work solo.
How we ranked them
- Easy on foot: a walkable centre, so you don't need a car or a companion to navigate.
- Tours to join: a guided walk, cruise or visit that puts you among other travellers.
- Good for dining alone: walk-in counters, bars or communal tables where a party of one fits in.
- Solo-friendly evenings: listening rooms, late museums and short concerts you can drop into.
At a glance
| # | City | Best for | Best way to meet the city | Ideal stay |
|---|---|---|---|---|
| 1 | Boston | History on foot and late museums | A guided Freedom Trail walk | 3 nights, with a day in Concord or Salem |
| 2 | Chicago | Architecture and jazz | The architecture river cruise | 3 to 4 nights |
| 3 | Charleston | A walkable historic district | A carriage tour to get your bearings | 3 nights |
| 4 | Savannah | Squares, stories and a communal table | Lunch at Mrs. Wilkes' communal tables | 2 to 3 nights |
| 5 | New Orleans | Music you can drop into | A short Preservation Hall set | 3 nights |
| 6 | Portland | A small, friendly food city | A small-group food walk | 2 to 3 nights |
| 7 | Santa Barbara | Wine tasting on foot | Free docent tours at the courthouse | 3 nights, 4 with a day in wine country |
| 8 | Asheville | Mountains, a spa and a wine bar | 5 Walnut's nightly live music | 2 to 3 nights |
1. Boston, Massachusetts
Best for: History on foot and late museums. Best way to meet the city: A guided Freedom Trail walk.
Join a 90-minute guided walk on the Freedom Trail, eat at the bar at Neptune Oyster (walk-ins only, so a party of one is quick to seat), and visit the Gardner on a Thursday, when it stays open until 9 p.m. The centre is compact and you won't need a car.
Freedom Trail walking tour
Starts at the Boston Common visitor center
A 2.5-mile trail linking 16 historic sites from Boston Common through the North End to Charlestown. The Freedom Trail Foundation's costumed guides lead 90-minute Walk Into History tours daily at 10, 11, noon, 1 and 2, with extra summer departures.
Neptune Oyster
63 Salem St, North End
A tiny North End oyster bar known for its lobster roll, raw bar, fried clams and North End cioppino. Open daily from 11 a.m.; the kitchen runs to 9:30 p.m. on weekdays and 10:30 p.m. at weekends. No reservations: walk-ins only.
Isabella Stewart Gardner Museum
25 Evans Way, Fenway
A Venetian-style palace around a flowering courtyard, hung with Isabella Stewart Gardner's collection. Open 11 a.m. to 5 p.m. every day except Tuesday, and until 9 p.m. on Thursdays. Adults $25, seniors $22.
Plan it
- 3 Days in Boston: A Grown-Up Itinerary
- A Weekend in Boston for Grown-Ups
- Boston for Grown-Ups: Things to Do for Adults
- All of Boston for grown-ups
Boston hotels on Stay22Freedom Trail walking tour (Viator)Boston Harbor sunset cruise (Viator)
Suggested base: Back Bay, near Copley Square and Newbury Street, walkable to the Public Garden and a short ride to the museums. Fly into Boston Logan (BOS), about 15 minutes from downtown.
2. Chicago, Illinois
Best for: Architecture and jazz. Best way to meet the city: The architecture river cruise.
Take the Chicago Architecture Center River Cruise, 90 minutes with a docent, spend a day at the Art Institute, then drop into the Green Mill: no reservations, cash only, and a serious listening room where going alone is normal.
Chicago Architecture Center River Cruise
112 E. Wacker Dr (riverfront)
A 90-minute cruise aboard First Lady down all three branches of the river, with a docent covering 50-plus buildings and the bascule bridges. The single best introduction to the city. The 2026 season runs mid-March to late November.
Art Institute of Chicago
Michigan Ave at Millennium Park
One of the great art museums in the world, strongest in Impressionism and American art. Pick a wing or two and pace yourselves.
The Green Mill
Broadway, Uptown
The legendary jazz lounge (Al Capone's booth is still there), with live music seven nights a week. Cash only, no reservations, and a serious listening room.
Plan it
- 3 Days in Chicago: A Grown-Up Itinerary
- 2 Days in Chicago: A Weekend for Grown-Ups
- Chicago Jazz and Blues for Grown-Ups
- All of Chicago for grown-ups
Chicago hotels on Stay22Chicago Architecture Center River Cruise (GetYourGuide)
Suggested base: River North or the Loop near Michigan Avenue. Fly into O'Hare (ORD) or Midway (MDW).
3. Charleston, South Carolina
Best for: A walkable historic district. Best way to meet the city: A carriage tour to get your bearings.
Start with a one-hour Old South Carriage tour of the historic district, spend an afternoon at the Gibbes Museum of Art, and end at Forte Jazz Lounge, a candlelit listening room patterned on New York's.
Old South Carriage Company
14 Anson St
A one-hour, 2.5-mile carriage ride through about 30 blocks of the historic district, pulled by Percherons or Belgians with a Palmetto Guild-certified guide. The easiest way to get your bearings.
Gibbes Museum of Art
135 Meeting St
American art with a Charleston view, in a Beaux-Arts building in the historic district. Closed Tuesdays; open until 8 p.m. on Wednesdays.
Forte Jazz Lounge
475 King St
Charleston's only strictly jazz venue, patterned on New York listening rooms: candlelit tables and two sets a night Thursday to Saturday (7 and 9:30 p.m.). Open Wednesday to Saturday.
Plan it
- 3 Days in Charleston: A Grown-Up Itinerary
- A Weekend in Charleston: 2 Days for Grown-Ups
- Charleston for Grown-Ups: Things to Do for Adults
- All of Charleston for grown-ups
Charleston hotels on Stay22Fort Sumter ferry and tour (Viator)Schooner Pride sunset sail (GetYourGuide)
Suggested base: The historic district, between the Market and King Street. Fly into Charleston International (CHS).
4. Savannah, Georgia
Best for: Squares, stories and a communal table. Best way to meet the city: Lunch at Mrs. Wilkes' communal tables.
Join a Genteel & Bard walking tour of the squares, sit at the communal tables at Mrs. Wilkes' Dining Room for a weekday lunch passed family style, and end the day in the Planters Tavern cellar with the pianist from 7:30 p.m.
Genteel & Bard walking tours
Historic District squares
Audio-enhanced walking tours (you hear the guide through a headset) covering the squares, Jones Street and the Mercer Williams House, with history tours at 10 a.m. and 1:30 p.m. and ghost walks after dark.
Mrs. Wilkes' Dining Room
107 W Jones St
A Savannah institution: Southern dishes passed around communal tables, family style, at lunch on weekdays only (11 a.m. to 2 p.m.). About $40 a person.
The Olde Pink House & Planters Tavern
23 Abercorn St, Reynolds Square
Southern dining in an 18th-century mansion. Downstairs, the Planters Tavern cellar bar has fireplaces, the same menu and a pianist from 7:30 p.m.
Plan it
- 3 Days in Savannah: A Grown-Up Itinerary
- 2 Days in Savannah: A Grown-Up Weekend
- One Day in Savannah: The Grown-Up Version
- All of Savannah for grown-ups
Savannah hotels on Stay22Savannah history walking tour (Viator)Bonaventure Cemetery guided tour (Viator)
Suggested base: The Historic District, between the river and Forsyth Park. Fly into Savannah/Hilton Head International (SAV).
5. New Orleans, Louisiana
Best for: Music you can drop into. Best way to meet the city: A short Preservation Hall set.
Preservation Hall runs several short concerts each evening, easy to catch on your own. Take the Steamboat Natchez evening jazz cruise, and treat yourself to the weekend jazz brunch at Commander's Palace.
Preservation Hall
726 St. Peter St, French Quarter
The small, plain room that has kept traditional New Orleans jazz alive since the 1960s. Several short concerts run each evening with a rotating line-up of the Preservation All Stars and other house bands.
Steamboat Natchez evening jazz cruise
Toulouse Street Wharf, French Quarter
A two-hour evening cruise on a paddle-wheeler, with live jazz from the Dukes of Dixieland and an optional Creole buffet dinner. Corny in the best way, and lovely at sunset.
Commander's Palace
1403 Washington Ave, Garden District
The turquoise Victorian landmark of Creole fine dining. The weekend jazz brunch, with a trio strolling between tables, is the classic grown-up New Orleans meal.
Plan it
- 3 Days in New Orleans: A Grown-Up Itinerary
- 2 Days in New Orleans: A Weekend for Grown-Ups
- Where to Hear Jazz in New Orleans (Without the Bourbon Street Crowds)
- All of New Orleans for grown-ups
New Orleans hotels on Stay22Steamboat Natchez evening jazz cruise (Viator)Garden District walking tour (GetYourGuide)
Suggested base: French Quarter edge or the CBD / Warehouse District. Fly into Louis Armstrong New Orleans International (MSY).
6. Portland, Maine
Best for: A small, friendly food city. Best way to meet the city: A small-group food walk.
The Old Port is small enough to walk everywhere. Join the three-hour, small-group Old Port Culinary Walking Tour, ride the working Mailboat Run to five Casco Bay islands, and visit the Portland Museum of Art, free on Friday evenings from 4 p.m.
Old Port Culinary Walking Tour
Meets at 10 Moulton St
A three-hour, small-group walk through the Old Port's food and drink scene with local history along the way, run year-round by Maine Day Ventures.
Casco Bay Lines Mailboat Run
Ferry terminal, 56 Commercial St
Ride along on the working ferry that delivers mail and freight to five Casco Bay islands, including Great Diamond, Long and Chebeague. Two and a half to three and a half hours, year-round, departing 10 a.m., noon and 3:15 p.m.
Portland Museum of Art
7 Congress Square
The city's art museum, in the Arts District on Congress Square. Open daily 10 a.m. to 6 p.m., until 8 p.m. on Fridays, when entry is free from 4 p.m.
Plan it
- 3 Days in Portland, Maine: A Grown-Up Itinerary
- A Weekend in Portland, Maine for Grown-Ups
- Portland, Maine for Grown-Ups: Things to Do for Adults
- All of Portland for grown-ups
Portland hotels on Stay22Old Port food tour (Viator)Lighthouse tour from Portland (Viator)
Suggested base: The Old Port, walkable to the restaurants, bars and ferry. Fly into Portland International Jetport (PWM).
7. Santa Barbara, California
Best for: Wine tasting on foot. Best way to meet the city: Free docent tours at the courthouse.
Take a free docent tour of the Santa Barbara County Courthouse and climb its clock tower, walk the Funk Zone's Urban Wine Trail, where a tasting room counter is a natural place to be one, and catch a free First Thursday evening at the Santa Barbara Museum of Art.
Santa Barbara County Courthouse
1100 Anacapa St
A working courthouse and Spanish Colonial Revival showpiece, with the painted Mural Room and a clock-tower observation deck looking over red roofs to the sea. Free, including hour-long docent tours daily at 2 p.m. (and 10:30 a.m. on weekdays).
The Funk Zone and the Urban Wine Trail
Funk Zone, between State St and the beach
More than 20 tasting rooms pouring Santa Barbara County wines, most of them in the converted warehouses, murals and galleries of the Funk Zone, with a second cluster on Anacapa Street and El Paseo downtown.
Santa Barbara Museum of Art
1130 State St
The city's art museum on State Street, a block from the courthouse. Open Tuesday to Sunday, 11 a.m. to 5 p.m.; closed Mondays. First Thursdays run to 8 p.m. with free entry from 5 p.m.
Plan it
- 3 Days in Santa Barbara: A Grown-Up Itinerary
- A Weekend in Santa Barbara for Grown-Ups
- Santa Barbara for Grown-Ups: Things to Do for Adults
- All of Santa Barbara for grown-ups
Santa Barbara hotels on Stay22Funk Zone wine walk (Viator)Santa Ynez wine tour (Viator)
Suggested base: Downtown or the waterfront, walkable to State Street, the Funk Zone and the beach. Fly into Santa Barbara Airport (SBA).
8. Asheville, North Carolina
Best for: Mountains, a spa and a wine bar. Best way to meet the city: 5 Walnut's nightly live music.
Tour Biltmore at your own pace with the audio guide, give an afternoon to the Omni Grove Park Inn's underground spa, and spend the evening at 5 Walnut Wine Bar, with live jazz seven nights a week and no cover most nights.
Biltmore Estate
Biltmore Village entrance, south of downtown
George Vanderbilt's French Renaissance chateau, with a self-guided audio tour of the house, formal gardens and a winery in Antler Hill Village where admission includes a free tasting (21+). Timed tickets; buying online is cheaper.
The Spa at The Omni Grove Park Inn
290 Macon Ave
A 43,000-square-foot underground spa of stone arches and tunnels, with waterfall pools, a lap pool under 6,500 fibre-optic stars, saunas and eucalyptus steam rooms.
5 Walnut Wine Bar
5 W Walnut St
A small wine bar and listening room with live music seven nights a week, mostly jazz, swing and gypsy jazz, and no cover most nights. Cheese and charcuterie boards to go with the wine.
Plan it
- 3 Days in Asheville: A Grown-Up Itinerary
- A Weekend in Asheville for Grown-Ups
- Asheville for Grown-Ups: Things to Do for Adults
- All of Asheville for grown-ups
Asheville hotels on Stay22Biltmore Estate tickets (Viator)LaZoom comedy bus tour (Viator)
Suggested base: Downtown, walkable to the restaurants and bars, or the Grove Park Inn for a resort stay. Fly into Asheville Regional (AVL).
Just missed the list
- Palm Springs is lovely alone in the cooler months, with ranger-led hikes at Tahquitz Canyon, but you'll want a car. See the 3-day Palm Springs itinerary.
- Las Vegas has piano bars and shows for one, if you stay Center Strip. See Las Vegas nightlife without the club scene.
- Sedona has astronomer-led stargazing tours to join. See the Sedona weekend itinerary.
Everything here was checked in September 2026. Hours, seasons and reservation rules change, so confirm with each venue before you go.
Questions people ask
What is the best US city for solo travel over 50?
Boston is our first pick: a compact, walkable centre, guided Freedom Trail walks, walk-in oyster bars and museums open late on Thursdays. Chicago and Charleston are close behind.
Where can I eat alone comfortably on a trip?
Look for walk-in counters and communal tables: Neptune Oyster in Boston, Mrs. Wilkes' Dining Room in Savannah and the tasting rooms of Santa Barbara's Urban Wine Trail all suit a party of one.
What are good evenings for a solo traveller?
Listening rooms where you sit and hear the music: the Green Mill in Chicago, Preservation Hall in New Orleans, Forte Jazz Lounge in Charleston and 5 Walnut Wine Bar in Asheville.
Do I need a car for these cities?
No. Every pick has a walkable centre, and the day trips can be done by tour or train. Palm Springs and Sedona are the exceptions, which is why they didn't make the list.