Where to go for a romantic anniversary getaway

An anniversary getaway is a chance to reminisce and remember why you fell in love in the first place. But choosing the right destination, whether it be sipping cocktails under New York’s skyline or unwinding on the French Riviera’s sun-drenched beaches, is easier said than done.

Let these eight cities and coastlines serve as a picture-perfect backdrop for your love story. To plan the ultimate romantic getaway, a travel advisor can guide you to the locations, events, and activities that will bring your dream anniversary celebration to life.

8 dream anniversary getaways for couples

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Here are eight anniversary trip ideas for romantics, from wine tastings in Northern California to luxury resort stays in Santorini.

1. Napa Valley: Vineyard strolls and Michelin restaurants

Napa Valley is a haven of gently rolling hills blanketed in vineyards. The area’s endless spas and scenic outlooks invite you to slow down and spend quality time with your partner.

Couples who go on a romantic getaway to California’s Napa Valley will enjoy winding paths between grapevines, wine tastings in historic cellars, and gourmet dinners under starlit skies. Creating a cherished memory here can be as simple as taking a scenic train ride through the countryside, capped by a sunset toast with a glass of local wine.

For a truly romantic stay, work with a travel advisor to get VIP treatment at one of the area’s many private villas and boutique hotels with vineyard views. Book a quiet place to unwind after a day of wine tastings — or enjoy a few more.

2. Charleston: Southern charm and centuries of history

As South Carolina’s crown jewel, Charleston seamlessly blends Southern charm, rich history, and five-star experiences. 

Stroll arm-in-arm down historic King Street, where gas lamps line the sidewalks and moonlight dances off the shop windows. The aroma of crispy fried green tomatoes drifts through the air, hinting at more decadent Lowcountry flavors awaiting in Charleston’s many cozy bistros. In the evening, relax on a sunset sail along Charleston Harbor, champagne in hand and the city glowing behind you. Then, check out one of the acclaimed walking tours to learn more about Charleston’s history — haunted ghost tours are especially popular for the bravehearted.

Travel advisors recommend Charleston’s historic district, just steps from acclaimed restaurants like Magnolias’ elevated southern cuisine and landmarks like Rainbow Row’s multicolored waterfront. Many of the city’s most romantic hotels are housed in restored 19th-century mansions, featuring grand columns, antique furnishings, and rooms with original fireplaces and soaring ceilings. 

A travel advisor can make your anniversary even more magical by securing dinner reservations at Charleston’s best eateries (hint: Circa 1886) and unlocking exclusive access to historic home and garden tours. Tapping into their expertise means your romantic getaway is filled with thoughtful details designed just for the two of you.

3. Santorini: Sun-drenched cliffs and candlelit dinners

With its breathtaking architecture and ocean views, Santorini attracts couples worldwide. Lose yourselves as you wander narrow cobblestone streets that burst with bright flowers and quaint cafés. Spend lazy afternoons stretched out side by side on some of Greece’s most beautiful beaches as a warm breeze carries the scent of the sea. 

As evening falls, watch the deep-blue caldera shimmer in twilight. Admire Santorini’s picturesque windmills etched against a fiery sunset while you clink glasses of local wine with your partner.

Advisors find the best couples resorts perched on Santorini’s caldera cliffs where you can watch the sun melt into the Aegean from a private balcony, slip into a plunge pool overlooking the sea, and savor a candlelit dinner on a secluded terrace. It doesn’t get much more romantic than that.

4. Los Cabos: Golden sands and swaying palms

In Los Cabos, the desert meets the sea, forming a landscape of jagged cliffs, golden sand, and impossibly blue water. Few places blend rich marine ecosystems and arid dunes so seamlessly. 

You’ll find endless ways to celebrate your anniversary in Los Cabos, both indulgent and intimate. Lounge by the infinity pool at an all-inclusive resort, where cabana bookings and attentive service let you forget the world and focus entirely on your partner. Or swim in the Sea of Cortez’s crystal-clear waters and enjoy gourmet meals under swaying palms. 

For romantic stays, advisors point to all-inclusive resorts that pair five-star service with peaceful surroundings. The best options sit right on the sand, with ocean views, private plunge pools, and a mix of intimate dining spots. These stays are designed for connection, making it easier to unplug and unwind.

5. Amsterdam: Iconic canals and fields full of tulips

With its golden canals, storybook streets, and art tucked into every corner, Amsterdam is a quietly romantic city, especially when explored at a slower pace.

Wander hand in hand through the Bollenstreek’s tulip fields (mid-April usually has the best blooms), then explore art masterpieces at the Van Gogh Museum. Evenings are best spent strolling along the city’s waterways, stopping for a cozy canal-side dinner as lights shimmer across the table.

After a day of sightseeing, unwind in one of Amsterdam’s boutique hotels. The centuries-old canal houses are narrow, elegant, and full of character. Inside, you’ll find warm lighting, oversized soaking tubs, and just enough modern polish to keep things feeling indulgent.

6. French Riviera: Seaside glamour and high-end shopping 

With high-end boutiques in Saint-Tropez and yacht-filled harbors in Monaco, the French Riviera often feels straight out of a romantic movie scene. Imagine reclining together on the sun-kissed beaches of Cannes, strolling the medieval alleys of Èze, or dressing up for a night out at the legendary Casino de Monte-Carlo. 

The region’s storied hotels hug the coastline, offering terraces high above the sea and private beach clubs where rosé appears before you ask. For a quieter escape, private villas tucked into the cliffs offer uninterrupted views and the kind of stillness that makes time slip by.

A travel advisor can make this dreamy escape even more memorable by arranging private yacht charters, exclusive shopping appointments, and exquisite dinners overlooking the Mediterranean. They handle everything to the smallest detail so you can bask in the good life.

7. New York City: Broadway shows and Michelin-star meals

Late-night harbor cruises, rooftop bars with glittering city views, and world-class opera shows await you in the city that never sleeps.

Spend the morning roaming the grand halls of The Met, admiring masterpieces that spark thoughtful conversations. Later, walk along Fifth Avenue, window shopping at artisanal storefronts, and savor a Michelin-star meal at Eleven Madison Park. Finish the night with a Broadway show or catch live jazz at an intimate downtown club — and that’s just one potential day.

For a classic stay, look to the Theater District, just steps from Broadway’s bright lights, and the Upper West Side, an upscale neighborhood with quick access to Central Park and world-renowned museums.

8. Amalfi Coast: Coastal charms and Mediterranean sun

With its cliffside villages and cinematic views, the Amalfi Coast turns a great trip into one of the best vacations you’ll ever take together. Its pastel-painted villages and sprawling coastline are an incredible draw for those wanting a unique, cultural experience.

Positano’s winding streets are full of tiny cafés where you can sip on an espresso or a limoncello before exploring the sunlit piazzas of Ravello or setting off on a private boat cruise through the lemon groves. 

Travel advisors point to the Amalfi Coast's steep cliffside for the best luxury stays, where hydrotherapy pools and Mediterranean tasting menus await your arrival. If the oceanside is more your vibe, the Bay of Naples features historic seaside retreats boasting large, luxurious rooms and scenic beaches.

Beyond the ordinary: Let advisors on TravelJoy design your getaway

Want a romantic getaway designed just for you? Advisors on TravelJoy can make it happen, crafting custom itineraries that match your style and preferences.

From uncovering hidden restaurants in Charleston to securing exclusive diving experiences in Los Cabos, travel advisors take the stress out of planning so you can get swept up in the magic of every moment. With their expert touch, planning your anniversary trip becomes effortless — letting you focus on the gift of simply being together.

If you’re ready for the ultimate getaway, let TravelJoy connect you with a trusted advisor. They’ll plan a romantic vacation that celebrates your love and adds a new chapter to your story.