Trip ideas · 8 cities ranked
The Best Weekend Getaways for Couples in the US
Two nights is enough for a very good weekend away together, as long as the city is compact, the dinners are special and the evenings end with music you can talk over. These are the eight we'd choose from the cities we've researched in depth.
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Every city below has a two-day plan on this site, a walkable base, at least one dinner worth dressing for and a sunset worth planning around. Each venue card shows where we checked it and when.
How we ranked them
- Walkable weekend base: dinner, drinks and music within walking distance or a short ride, so you don't spend the weekend in cars.
- A two-night plan that works: each pick has a weekend or two-day itinerary on this site.
- One romantic dinner and one sunset: a dining room worth booking and a view, sail or rooftop worth timing.
- Grown-up evenings: jazz, piano bars and listening rooms rather than clubs.
At a glance
| # | City | Best for | Signature moment | Ideal stay |
|---|---|---|---|---|
| 1 | Charleston | Candlelit dining and jazz | Schooner Pride sunset sail | 3 nights |
| 2 | Savannah | Slow, atmospheric evenings | Pianist in the Planters Tavern cellar | 2 to 3 nights |
| 3 | New Orleans | Music every night | Jazz brunch at Commander's Palace | 3 nights |
| 4 | Santa Barbara | Wine, coast and gardens | BYO-wine sunset sail | 3 nights, 4 with a day in wine country |
| 5 | Asheville | Mountains and a spa | The Grove Park Inn's underground spa | 2 to 3 nights |
| 6 | Portland | Seafood and the sea | The Casco Bay mailboat | 2 to 3 nights |
| 7 | Key West | Sunsets and island dinners | Wind & Wine sunset sail | 3 to 4 nights |
| 8 | San Diego | Ocean sunsets and views | Sunset at Sunset Cliffs | 3 to 4 nights |
1. Charleston, South Carolina
Best for: Candlelit dining and jazz. Signature moment: Schooner Pride sunset sail.
The historic district is walkable from end to end, Charleston Grill has live jazz with dinner seven nights a week, and the Schooner Pride sails past Fort Sumter and the Battery at sunset. For a special night, Peninsula Grill is the only Relais & Châteaux restaurant in town.
Schooner Pride sunset sail
Floating dock by the SC Aquarium, 360 Concord St
Two hours under sail on an 84-foot, three-masted schooner as the sun drops behind the steeples, past Fort Sumter and the Battery, often with dolphins. Not narrated; the crew answers questions.
Charleston Grill
Belmond Charleston Place, Meeting St
Half refined dining room, half jazz club: Executive Chef Michelle Weaver's kitchen, with live jazz, soul and Brazilian sets seven nights a week. Open 5:30 to 10 p.m. daily.
Peninsula Grill
Planters Inn, Market St
A romantic dining room in the 1844 Planters Inn, the only Relais & Châteaux restaurant in Charleston, and home of the 12-layer Ultimate Coconut Cake. Anniversary territory.
Plan it
- A Weekend in Charleston: 2 Days for Grown-Ups
- Things to Do in Charleston for Couples
- 3 Days in Charleston: A Grown-Up Itinerary
- 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).
2. Savannah, Georgia
Best for: Slow, atmospheric evenings. Signature moment: Pianist in the Planters Tavern cellar.
Savannah is made for walking between the squares, then dinner in an 18th-century mansion with the Planters Tavern pianist downstairs from 7:30 p.m. Jazz'd has live music most nights, and Peregrin is a rooftop conservatory bar for sunset.
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.
Jazz'd Tapas Bar
Off Ellis Square, Historic District
A moody, below-street tapas bar with live music most nights of the week: jazz, blues, swing, soul and Sinatra-style vocals, with small plates made for sharing.
Peregrin at Perry Lane Hotel
Perry Lane Hotel, 256 E Perry St
A rooftop conservatory bar, redesigned with SCAD in 2024, with skyline views, cocktails and street-food-style bites; open 11 a.m. to 11 p.m.
Plan it
- 2 Days in Savannah: A Grown-Up Weekend
- Things to Do in Savannah for Couples
- 3 Days in Savannah: A Grown-Up Itinerary
- 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).
3. New Orleans, Louisiana
Best for: Music every night. Signature moment: Jazz brunch at Commander's Palace.
Nowhere packs more live music into a weekend. Hear traditional jazz at Preservation Hall, take the Steamboat Natchez evening jazz cruise at sunset, and book the weekend jazz brunch at Commander's Palace, the classic grown-up New Orleans meal.
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
- 2 Days in New Orleans: A Weekend for Grown-Ups
- Romantic Things to Do in New Orleans for Couples
- 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).
4. Santa Barbara, California
Best for: Wine, coast and gardens. Signature moment: BYO-wine sunset sail.
Stay downtown or on the waterfront and you can walk to State Street and the Funk Zone's Urban Wine Trail. The Sunset Kidd sail takes no more than 16 passengers (bring your own wine), and El Encanto's garden terrace looks down to the coast.
Sunset Kidd Sunset Sail
Santa Barbara Harbor, 125 Harbor Way
A 41-foot ketch that takes no more than 16 passengers, and says plainly it's "not a narrated tourist ride". Bring your own wine and picnic in a soft cooler; there's no bar on board.
El Encanto Dining Room & Terrace
800 Alvarado Pl, the Riviera
The hilltop hotel restaurant of El Encanto, with alfresco tables in the gardens and views down to the coast. It serves breakfast, lunch and dinner and takes outside reservations on OpenTable and Resy; ask for the terrace.
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.
Plan it
- A Weekend in Santa Barbara for Grown-Ups
- Things to Do in Santa Barbara for Couples
- 3 Days in Santa Barbara: A Grown-Up Itinerary
- 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).
5. Asheville, North Carolina
Best for: Mountains and a spa. Signature moment: The Grove Park Inn's underground spa.
Pair a day at Biltmore with the Omni Grove Park Inn's underground spa of stone arches and waterfall pools. In the evening, 5 Walnut Wine Bar has live jazz seven nights a week, usually with no cover.
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.
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.
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
- A Weekend in Asheville for Grown-Ups
- Things to Do in Asheville for Couples
- 3 Days in Asheville: A Grown-Up Itinerary
- 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).
6. Portland, Maine
Best for: Seafood and the sea. Signature moment: The Casco Bay mailboat.
The Old Port is small enough to walk everywhere. Ride the working Mailboat Run to five Casco Bay islands, eat at Fore Street around its wood-fired oven, and end at Top of the East, a 15th-floor lounge over the bay. Some seasonal places close from mid-October.
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.
Fore Street
288 Fore St
Portland's landmark since 1996: a big old warehouse room around a wood-fired oven, grill and turnspit, with a menu that changes daily with what farmers and fishermen bring in. Open nightly from 4:30 p.m.; reservations by phone.
Top of the East
Westin Portland Harborview, 157 High St, 15th floor
A 15th-floor lounge with views over the city to Casco Bay, cocktails and small plates. Opens at 4 p.m. daily, until midnight on Fridays and Saturdays; reservations on OpenTable.
Plan it
- A Weekend in Portland, Maine for Grown-Ups
- Things to Do in Portland, Maine for Couples
- 3 Days in Portland, Maine: A Grown-Up Itinerary
- 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. Key West, Florida
Best for: Sunsets and island dinners. Signature moment: Wind & Wine sunset sail.
Old Town is small and flat, so leave the car. Watch the nightly Sunset Celebration at Mallory Square once, then book the calmer Wind & Wine schooner sail and a boat ride to dinner at Latitudes on Sunset Key. Winter and spring are high season.
Danger Charters Wind & Wine Sunset Sail
Old Town waterfront (departure point on booking)
A two-hour sunset sail on a classic schooner for up to 26 guests (ages 13+), with eight wines including champagne, craft beer and a spread of cheese, charcuterie and chocolate. Calmer and smaller than the party boats.
Latitudes on Sunset Key
Sunset Key; launch from 245 Front St
A beachfront restaurant on the small private island of Sunset Key, reached by a short boat ride from the Front Street marina. Dinner nightly from 5 p.m.; OpenTable named it one of the 100 most romantic restaurants in the US in 2025.
Sunset Celebration at Mallory Square
Mallory Square, 400 Wall St
Key West's nightly ritual since the late 1960s: jugglers, magicians, musicians, artists and food stalls on the square while the sun drops into the Gulf. Free.
Plan it
- A Weekend in Key West for Grown-Ups
- Things to Do in Key West for Couples
- 3 Days in Key West: A Grown-Up Itinerary
- All of Key West for grown-ups
Key West hotels on Stay22Sunset sail on a schooner (Viator)Dry Tortugas ferry day trip (Viator)
Suggested base: Old Town, on a quiet street off Duval, or a waterfront resort near Mallory Square. Fly into Key West International (EYW).
8. San Diego, California
Best for: Ocean sunsets and views. Signature moment: Sunset at Sunset Cliffs.
Base yourselves in Little Italy or the Gaslamp for dinner at Mister A's, a penthouse dining room since 1965, then give one evening to the Pacific: the Sunset Cliffs or the fire pits by the Hotel del Coronado, with live music Thursday to Saturday.
Mister A's
2550 Fifth Ave, 12th floor, Bankers Hill
A penthouse dining room on top of the Manchester building since 1965, with views over the skyline, the bay and the Pacific, and planes gliding past at eye level on their approach. Recently renovated, with a bigger bar and rooftop patio lounge.
Sunset Cliffs Natural Park
Sunset Cliffs Blvd, Point Loma
A mile and a half of sandstone cliffs, arches and caves on Point Loma's ocean side, and San Diego's favourite place to watch the sun go down (and look for the green flash).
Hotel del Coronado: Babcock & Story Bar and Sun Deck
1500 Orange Ave, Coronado
The 1888 beachfront hotel's restored mahogany bar opens onto a big patio facing the Pacific, with live music Thursday to Saturday from 6 to 10 p.m.; next door, the Sun Deck has fire pits for the sunset.
Plan it
- A Weekend in San Diego for Grown-Ups
- Things to Do in San Diego for Couples
- 3 Days in San Diego: A Grown-Up Itinerary
- All of San Diego for grown-ups
San Diego hotels on Stay22San Diego harbor dinner cruise (Viator)USS Midway Museum tickets (Viator)
Suggested base: Little Italy or the Gaslamp Quarter, or Coronado for the beach. Fly into San Diego International (SAN).
Just missed the list
- Chicago is a superb weekend from May to October, with the architecture river cruise and the Green Mill. See the 2-day Chicago itinerary.
- Las Vegas works as a couples' weekend if you stay Center Strip and book one supper club. See Las Vegas for couples.
- Nashville away from Broadway: songwriters at the Bluebird, jazz at Skull's Rainbow Room. See the 2-day Nashville 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 weekend getaway for couples in the US?
For a grown-up couple, Charleston is our first pick: a walkable historic district, jazz with dinner at Charleston Grill every night, a sunset sail on the Schooner Pride and some of the South's best dining rooms. Savannah and New Orleans are close behind.
Is two nights enough for a romantic city break?
Yes, in a compact city. Charleston, Savannah, Santa Barbara, Portland (Maine) and Key West all fit a good weekend on foot. Book the one dinner and the one sunset experience you care about first.
Which weekend getaway is best for live music?
New Orleans, with Preservation Hall, Frenchmen Street and the Steamboat Natchez jazz cruise. Charleston (Charleston Grill and Forte Jazz Lounge) and Asheville (5 Walnut Wine Bar) are quieter options.
Where should couples stay for a weekend away?
In the walkable centre: Charleston's historic district, Savannah's Historic District, Santa Barbara's downtown or waterfront, Portland's Old Port, Key West's Old Town, or Little Italy and the Gaslamp in San Diego.