Trip ideas · 8 cities ranked
Anniversary Trip Ideas in the USA for Grown-Ups
An anniversary trip should have one moment you'll still talk about in ten years: a dining room with a view, a sail, a balloon at sunrise. These eight cities each have one, and we've checked every place we name.
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Whether it's a first anniversary or a fortieth, the pattern that works is the same: one splurge dinner, one shared experience and a base where you can walk home. The ranking below weighs all three.
How we ranked them
- A special-occasion dinner: a room people plan anniversaries around, bookable ahead.
- One shared experience: a sail, a spa, a show or a view that makes the trip.
- An easy base: a walkable neighbourhood or a resort, so the evening doesn't end in a car park.
- Checked details: every place below carries its source and the month we checked it.
At a glance
| # | City | Best for | The anniversary dinner | Ideal stay |
|---|---|---|---|---|
| 1 | Santa Barbara | A quiet, luxurious escape | Stonehouse at San Ysidro Ranch | 3 nights, 4 with a day in wine country |
| 2 | Charleston | Old-school Southern romance | Peninsula Grill and its coconut cake | 3 nights |
| 3 | Las Vegas | A big night out | Eiffel Tower Restaurant | 3 to 4 nights |
| 4 | Scottsdale | Desert resorts and spas | elements at sunset | 3 nights, 4 with a Sedona day |
| 5 | New Orleans | Food, jazz and history | Galatoire's or Commander's Palace | 3 nights |
| 6 | San Diego | A splurge tasting menu | Addison (three Michelin stars) | 3 to 4 nights |
| 7 | Chicago | Culture and skyline views | Cindy's over Millennium Park | 3 to 4 nights |
| 8 | Key West | Island time | Latitudes on Sunset Key | 3 to 4 nights |
1. Santa Barbara, California
Best for: A quiet, luxurious escape. The anniversary dinner: Stonehouse at San Ysidro Ranch.
Dinner at Stonehouse, a Michelin-recognised room in a 19th-century citrus packing house with fireplaces and a creek-side terrace, then live music in the ranch's Speakeasy bar. Add a morning at Lotusland (open until October 31 in 2026) or a day in wine country.
Stonehouse at San Ysidro Ranch
900 San Ysidro Ln, Montecito
A Michelin-recognised restaurant in a 19th-century citrus packing house, with fireplaces, a creek-side terrace and produce from the ranch garden. Dinner nightly 5 to 9 p.m.; the ranch's Speakeasy bar has live music from 7 p.m.
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.
Ganna Walska Lotusland
Montecito (address given on booking)
Heads-up: Open for the 2026 season until October 31; reopens February 17, 2027.
Ganna Walska's celebrated Montecito garden, seen on a two-hour self-guided or docent-led visit. Visits are Wednesday to Saturday at 9:30 a.m. or 1:30 p.m., by advance reservation only; book about three weeks ahead.
Plan it
- Things to Do in Santa Barbara for Couples
- 3 Days in Santa Barbara: A Grown-Up Itinerary
- A Weekend in Santa Barbara for Grown-Ups
- 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).
2. Charleston, South Carolina
Best for: Old-school Southern romance. The anniversary dinner: Peninsula Grill and its coconut cake.
Peninsula Grill in the 1844 Planters Inn is anniversary territory, with its 12-layer coconut cake. Spend the sunset on the Schooner Pride or the Pavilion Bar terrace, and keep a night for jazz with dinner at Charleston Grill.
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.
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.
Pavilion Bar
Market Pavilion Hotel, 225 E Bay St
A fifth-floor terrace with a cascading pool and harbour views, known for sunsets, mojitos and martinis. It gets livelier later, with DJs on some nights.
Plan it
- Things to Do in Charleston for Couples
- 3 Days in Charleston: A Grown-Up Itinerary
- A Weekend in Charleston: 2 Days for Grown-Ups
- 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).
3. Las Vegas, Nevada
Best for: A big night out. The anniversary dinner: Eiffel Tower Restaurant.
Book a window table at the Eiffel Tower Restaurant over the Bellagio fountains, or make dinner the show at The Mayfair Supper Club. By day, Qua Baths & Spa has private rooms for couples' treatments. We've written a whole Las Vegas anniversary trip.
Eiffel Tower Restaurant
Paris Las Vegas, Center Strip
French fine dining on the 11th floor of the Paris hotel's tower, with window tables looking straight down on the Bellagio fountains. A dependable anniversary pick.
The Mayfair Supper Club
Bellagio, Center Strip
A theatrical supper club facing the Bellagio fountains, with a 360-degree stage that rises and lowers during dinner. Performers move through the room as the courses arrive, so it is dinner and a show in one seat.
Qua Baths & Spa
Caesars Palace, Center Strip
A large spa built around Roman baths of different temperatures, a laconium, a tea lounge and the Arctic Ice Room, where flakes fall from the ceiling. There are private rooms for couples' treatments.
Plan it
- A Las Vegas Anniversary Trip: Two Perfect Nights
- Things to Do in Las Vegas for Couples (Who Are Past the Club Phase)
- 3 Days in Las Vegas: A Grown-Up Itinerary
- All of Las Vegas for grown-ups
Las Vegas hotels on Stay22Red Rock Canyon tours from Las Vegas (GetYourGuide)
Suggested base: Center Strip (Bellagio, Cosmopolitan, Aria, Paris, Caesars). Fly into Harry Reid International (LAS).
4. Scottsdale, Arizona
Best for: Desert resorts and spas. The anniversary dinner: elements at sunset.
Time dinner at elements, on the slope of Camelback Mountain, for sunset. Float over the desert at sunrise with Rainbow Ryders and a champagne toast, then spend the afternoon at Joya Spa. The season is October to May.
elements at Sanctuary Camelback Mountain
Sanctuary resort, Paradise Valley
Chef Beau MacMillan's seasonal restaurant on the slope of Camelback Mountain, with a wall of windows and a deck over Paradise Valley. It is at its best at sunset.
Rainbow Ryders hot air balloon
Meets in Glendale; flies over the Sonoran Desert
About an hour aloft over the north Scottsdale desert, finished with a traditional champagne toast. Sunrise flights run year-round; sunset flights November to March.
Joya Spa at Omni Montelucia
Omni Scottsdale Resort at Montelucia, Paradise Valley
A 31,000 sq ft Andalusian and Moroccan-inspired spa with a hammam ritual, 20 treatment rooms and a private rooftop pool looking at Camelback Mountain.
Plan it
- Things to Do in Scottsdale for Couples
- 3 Days in Scottsdale: A Grown-Up Itinerary
- Day Trips from Scottsdale for Grown-Ups
- All of Scottsdale for grown-ups
Scottsdale hotels on Stay22Sedona day trip from Scottsdale (Viator)Phoenix hot air balloon ride (Viator)
Suggested base: Old Town Scottsdale, or a resort at the foot of Camelback Mountain. Fly into Phoenix Sky Harbor (PHX).
5. New Orleans, Louisiana
Best for: Food, jazz and history. The anniversary dinner: Galatoire's or Commander's Palace.
Take the weekend jazz brunch at Commander's Palace, a long lunch or calmer dinner at Galatoire's (jackets for gentlemen after 5 p.m.), and the Steamboat Natchez jazz cruise 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.
Galatoire's
209 Bourbon St, French Quarter
French Creole cooking in a mirrored, paddle-fanned dining room that has barely changed in a century. Friday lunch is a long, lively local ritual; dinner is calmer.
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.
Plan it
- Romantic Things to Do in New Orleans for Couples
- 3 Days in New Orleans: A Grown-Up Itinerary
- 2 Days in New Orleans: A Weekend for Grown-Ups
- 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. San Diego, California
Best for: A splurge tasting menu. The anniversary dinner: Addison (three Michelin stars).
Addison was Southern California's first three-Michelin-star dining room. For something less formal, George's at the Cove faces the Pacific sunset from three levels, or book a harbor dinner cruise with Champagne.
Addison
Fairmont Grand Del Mar, 5200 Grand Del Mar Way
Chef William Bradley's three-Michelin-star dining room, Southern California's first, serving a changing ten-course tasting menu. It marked its 20th year with a redesigned room and a new Champagne lounge.
George's at the Cove
1250 Prospect St, La Jolla
A La Jolla institution for more than 40 years, with three levels over the cove: the casual Ocean Terrace rooftop and the dressier dining room below, all facing the Pacific sunset.
Flagship harbor dinner cruise
Broadway Pier, 990 N Harbor Dr
A two-and-a-half to three-hour evening cruise on San Diego Bay: a three-course dinner, a glass of Champagne, skyline views past the Coronado Bridge and the Midway, and a DJ for dancing.
Plan it
- Things to Do in San Diego for Couples
- 3 Days in San Diego: A Grown-Up Itinerary
- A Weekend in San Diego for Grown-Ups
- 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).
7. Chicago, Illinois
Best for: Culture and skyline views. The anniversary dinner: Cindy's over Millennium Park.
Take the architecture river cruise (mid-March to late November), hear the Chicago Symphony Orchestra in its own hall, and toast at Cindy's, a glass-atrium terrace over Millennium Park and the lake.
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.
Chicago Symphony Orchestra at Symphony Center
220 S. Michigan Ave
One of the world's great orchestras in its own hall across from the Art Institute. Check the season calendar for your dates.
Cindy's
Chicago Athletic Association, 12 S. Michigan Ave
A 13th-floor glass-atrium restaurant and terrace looking over Millennium Park and the lake. Fire pits in winter, open-air seats in summer.
Plan it
- Things to Do in Chicago for Couples
- 3 Days in Chicago: A Grown-Up Itinerary
- 4 Days in Chicago: The Unhurried Grown-Up Version
- 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).
8. Key West, Florida
Best for: Island time. The anniversary dinner: Latitudes on Sunset Key.
A short boat ride takes you to dinner at Latitudes on Sunset Key. Before it, the two-hour Wind & Wine sail pours eight wines including champagne; the next evening, book a table at Café Marquesa.
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.
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.
Café Marquesa
The Marquesa Hotel, 600 Fleming St
An intimate hotel dining room a block off Duval, with a seasonal menu from chef Travis Lee and polished service. Dinner nightly from 5:30 p.m.
Plan it
- Things to Do in Key West for Couples
- 3 Days in Key West: A Grown-Up Itinerary
- A Weekend in Key West for Grown-Ups
- 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).
Planning tips for an anniversary trip
- Book the dinner first. Many of these rooms release tables weeks ahead; say it's an anniversary when you book.
- Pick one big experience per day, and leave the afternoon before a special dinner free.
- Want it built around your dates? The trip planner lays out a day-by-day plan in any of these cities.
Everything here was checked in September 2026. Hours, seasons and reservation rules change, so confirm with each venue before you go.
Questions people ask
Where should we go for our anniversary in the USA?
For a quiet, luxurious trip, Santa Barbara (Stonehouse at San Ysidro Ranch, El Encanto). For Southern romance, Charleston (Peninsula Grill). For a big night out, Las Vegas (the Eiffel Tower Restaurant or The Mayfair Supper Club). For a desert resort and spa, Scottsdale.
What is a good 10th, 20th or 25th anniversary trip in the US?
Choose a city with one unforgettable dinner and one shared experience: Addison in San Diego, Stonehouse in Santa Barbara, a sunrise balloon with champagne over Scottsdale, or a sunset sail in Charleston or Key West. The ranking above works for any milestone.
How many days should an anniversary trip be?
Three nights is the sweet spot in most of these cities. That fits one splurge dinner, one big experience and a slow day in between. Santa Barbara and Scottsdale reward a fourth day for wine country or Sedona.
What is the most romantic restaurant on this list?
It depends on the mood: Peninsula Grill in Charleston for classic candlelight, Latitudes on Sunset Key for a beach at sunset, the Eiffel Tower Restaurant in Las Vegas for the view, and Stonehouse at San Ysidro Ranch for a fireside dinner.