Gurney's Star Island Resort & Marina

The historic Montauk Yacht Club Resort & Marina evokes another time. Originally built in 1928 by entrepreneur Carl Fisher (the man credited with turning Miami from a sleepy backwater town to a thriving resort metropolis), the resort quickly became the local go-to vacation destination for the wealthy (original members of the club include J.P. Morgan, Vincent Astor, and Harold S. Vanderbilt). Charles Lindbergh is said to have often flown his seaplane into the harbor to dock at the club's marina. And according to local legend, the Island Club (which was located next door to the original resort and would eventually become part of the resort as it stands today) was the most popular speakeasy and gambling casino around town during Prohibition. To avoid trouble, the club posted watchmen at the stone stanchions at the end of the island's causeway -- when the police stopped by, the guards would radio the club for management to hide the liquor and gambling equipment.Today, the resort maintains some of that storied appeal (the towering white lighthouse is what beaconed guests to the resort from its inception). Yet there are plenty of modernized amenities to keep today's guest happy -- though the two outdoor pools and small private beach are popular with kids, so if you’re looking for some celebrity-style peace and quiet, head to the ocean. Despite updates and upgrades, one original trait has remained consistent through the years: The resort, as a whole, attracts a wealthy set, and guests shouldn't be surprised to see the occasional celebrity roaming its grounds.

At the easternmost tip of Long Island, the Montauk Yacht Club’s lakeside location is kitty corner from Montauk Harbor -- an area with restaurants, shops, and plenty of harborside sightseeing. In addition to downtown Montauk (a nine-minute drive from the hotel), there are many nearby towns to explore, and, of course, miles of sandy beaches to enjoy. The drive to East Hampton takes about 25 minutes, and driving to Sag Harbor and Southampton takes about 40 and 55 minutes, respectively.

Montauk Yacht Club Resort isn't right on the Atlantic, but it offers many on-site amenities to redress the non-oceanfront location. There are two outdoor heated pools, both surrounded by brick patios and overlooking the marina. A small sandy beach with loungers and umbrellas (free; cabanas also available for a fee) overlooks the lake, but both it and the outdoor pools can feel crowded with kids. The oval-shaped indoor pool, also heated, provides a nice alternative; it's set in a skylit space with vintage pinstripe wooden surfboards hanging on the white wood walls. The full-service Spa MYC offers massages, body treatments, facials, waxing, and nail work, as well as spa packages and the option of in-room service. A fitness center provides all the necessary equipment (free weights, ellipticals, treadmills, machinery), plus cedar saunas, and there are four outdoor tennis courts, with racquets and balls free to use. Paddleboards, cruiser bikes, and kayaks are all free to borrow, and there is a playground for kids. The resort grounds include areas for volleyball, bocce ball, and horseshoes, plus outdoor seating areas and fire pits (the resort holds bonfires with s’mores in the warmer months). Private, semi-private, or group surf lessons and paddleboard sessions or tours can be arranged, and a Kids' Surf Academy is held on the weekdays. Excursions are available from charter boats in the marina. The hotel offers free shuttle service to Montauk Harbor, downtown, and beaches. Parking and resort-wide Wi-Fi are both free.

Montauk Yacht Club offers a good mix of dining options that appeal to both families and couples seeking romance. The upscale Coast Kitchen is a New American restaurant focusing on local ingredients (the menu features a daily fresh catch), while the casual The Alley & The Deck has a Florida feel and offers both indoor and outdoor seating. B-Bar is an indoor nautical-style lounge offering specialty cocktails and small bites, and the seasonal Sunset Pier allows for dockside eating, drinking, and watching the sunset.