Itineraries

The country’s smallest state is big on charm. Rhode Island is more than just historic mansions and sailing – although there are plenty of both to go around. Fun for every age awaits, checking much more than just the boxes on each of the four critical summer vacation “S” factors – sun, sand, sea and scene.

Easier to access than many New England summer destinations and no less inviting, both Watch Hill and Newport boast fine dining restaurants, championship golf and high-end hotels, as well as the small-town charm that makes both destinations feel like a break from city living. Pick a single spot or combine the two on a weekend or week-long escape with something for everyone in your vacation party.

Start Here

We’d begin our trip in Watch Hill, a resort-style escape that offers one plenty of time to sink into vacation mode.

When selecting a place to bunk down, there’s no better spot than the daffodil-colored Ocean House, which boasts more awards than one can begin to name – a Forbes Five Star designation, membership in Relais & Chateaux, and a reputation as arguably the Northeast’s finest seaside resort. The resort has been hosting well-heeled sun-seekers since 1896, boasting 49 rooms and 15 signature suites that feature luxe touches such as deep-soaking tubs, gratis in-room snacks and afternoon refreshments (we like the malted milk balls). Oh, and did we mention its famous neighbor? Taylor Swift owns the $17 million mansion next door. Ideal for adults seeking a romantic escape but also for families with children of all ages, this hotel fits the bill for nearly any type of traveler.

Lily Pond Luxury Client Perks:

Breakfast for two
$100 one time credit
Upgrade if available
Early check-in and late check out as available

Sister property Weekapaug Inn reminds one of family camps of yore. Slightly more rustic (and definitely a bit less pricey) it offers a more secluded marshland location and amenities like an outdoor pool and an in-house naturalist.

Lily Pond Luxury Client Perks:

Breakfast for two
$100 one time credit
Upgrade if available
Early check-in and late check out as available

For extended stays, choose Watch Hill Inn, just down the hill from Ocean House proper. Perfect for families or groups traveling together, its condo-style layout offers perks like full kitchens in every room, as well as complimentary continental breakfast, evening wine hours, and reserved parking (a premium in downtown). All properties in the portfolio enjoy reciprocal access, meaning you can stay at one, and dine or use facilities at any. There’s even a fleet of Mercedes house cars happy to shuttle you in-between at your leisure.

How You’ll Spend Your Days

The sleepy town of Watch Hill doesn’t boast overmuch in the way of shopping; the two-street downtown offers a variety of small shops worth browsing for names like Lilly Pulitzer and Vineyard Vines, as well as your usual assortment of tee shirt shops and trinkets. However, a stop at St. Clair Annex for ice cream is a must, as is a visit to the famed Flying Horse Carousel, so dubbed because its ponies fly outward when the carousel is in motion rather than simply bobbing up and down.

Don’t tax yourself too much, though. Relax on the beach, let the hotel arrange a round of golf, play a game on the championship croquet lawn, or, if the weather doesn’t cooperate, take in a leisurely massage at the hotel’s pampering OH! Spa— the aromatherapy massage with Melissa is among our all-time favorite ways to spend an afternoon.

Come dinnertime, linger over a farm-to-table meal at COAST, the Ocean House’s fine dining restaurant. Be sure to start with a lemon drop martini on the Verandah. Up for a drive? Head into town to try Ella’s Fine Food and Drinks, a local favorite, or The Cooked Goose for breakfast and casual fare.

The morning of your departure, linger over breakfast. The lemon scones in the pastry basket are to die for, and the jazz brunch on Sundays is heavenly. Then, ready yourself for the easy 45-minute jaunt over to Newport.

Newport Adventure Awaits

Spend your first day in Newport in the Bellevue Avenue Historic District for a look at some of the country’s grandest summer “cottages.” These visits are ideal for adults, but the tours are also suitable for children able to walk and operate a small audio device on their own. We’d suggest at least a three-house pass; you won’t want to stop at just one. Start at The Breakers, the grandest of all residences and former home to the Vanderbilt family. Self-guided audio tours offer interesting tidbits based on personal diaries, oral histories and architectural information. Each of the homes is lovely in its own way, but we’re partial to Rosecliff, which has played a part in movies like the original Great Gatsby and True Lies, as well as The Elms, which boasts a fascinating special tour dedicated just to servant’s life.

Stay Here

After an afternoon of house tours, it’s time to check into your hotel. Your choices are numerous. The city boasts dozens of great bed and breakfasts, perfect for a less expensive weekend escape. We love the Lark group of hotels for these, as well as Mill Street Inn.

Boutique lovers will enjoy the more contemporary vibes at the waterfront Forty 1° North, with its quirky amenities like a giant outdoor chess set, or the intimate Vanderbilt, an Auberge Resorts Collection property, with its well-regarded Dining Room or the gorgeous views from its roof deck bar.

Lily Pond Luxury Client Perks:

Upgrade on arrival, subject to availability
Full Breakfast daily for two per bedroom
$100 USD Resort or Hotel credit to be utilized during stay (not combinable, not valid on room rate, no cash value if not redeemed in full)
Early check-in/late checkout, subject to availability
Complimentary Wi-Fi

But when it comes to luxury, only two hotels are on the list. Downtown’s The Chanler at Cliff Walk is perfectly positioned, as its name suggests, at the start of the three-and-a-half mile long Cliff Walk, a public access walkway that gives you a scenic view of the New England coastline as well as many of the mansions and lavish private homes of Newport. A 19th-century mansion turned hotel, this posh escape feels almost exactly like living in one of the Gilded Age homes it neighbors. Its Cara restaurant is one of our all-time favorite “date night” spots.

Lily Pond Luxury Client Perks:

Upgrade on arrival, subject to availability
Continental breakfast for two daily, served in restaurant
$100 USD Resort/Hotel credit to be utilized during stay (not combinable, not valid on room rate, no cash value if not redeemed in full)
Early check-in/late check-out subject to availability
Complimentary Wi-Fi

Should you prefer more resort-style accommodations, Castle Hill Inn, a Relais & Chateaux property, is another historic home turned hotel. The property offers some of the area’s best views, including panoramic vistas of Narragansett Bay from nearly every room in the house.

We’d opt for privacy in one of the luxe beach cottages about 250 yards from the main house. Sunbathe on “Grace Kelly Beach,” named after the movie star who spent many a weekend in the secluded spot, ride the water taxi into town, or just enjoy cocktails on “The Lawn,” a top destination for guests and locals alike.

On your second full day in Newport, your opportunities are limited only by your passions. Water lovers won’t want to miss a cruise on 12 Meter Charters’ Heritage, a boat that raced in the 1970 America’s Cup trials. Shoppers can peruse downtown’s many small boutiques, stocking up on everything from preppy essentials to local art, while culture seekers can tour the International Tennis Hall of Fame on Bellevue or play a match at one of the grass courts onsite.

Getting Here & There

It’s easy to get to Rhode Island from virtually any spot in the Mid-Atlantic, with many cities offering direct flights into Providence, or connect via train from Boston or New York. While both towns are mostly walkable, if you’re visiting for longer than a weekend, we’d suggest renting a car. It makes getting between the mansions and downtown much faster. If you’d prefer to take your chances with cabs, Newport does have a small Uber presence.

When to Visit

As with most seaside towns, high season runs from Memorial Day through Labor Day. Expect high volumes of tourists, particularly during holiday weekends and big events like late July’s Newport Antiques Show. Of course, you’ll also get the best weather. We are partial to mid to late June, when days can be crisp and clear in the 70s, and nights require a light jacket or sweater—the water isn’t yet warm enough for swimming, and so crowds are slightly smaller than in July or August. Westerley, where Ocean House is located, basically shutters before and after the holidays, so expect your trip to be limited to just the resort and its amenities if you plan a fall visit, although we do enjoy the off-season for fewer crowds and better than average rates.

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