Sir Francis Drake Rating: 3.5 Pearls

Union Square, San Francisco, California

Bar Drake

One of downtown's best-known and largest hotels, the Sir Francis Drake is a San Francisco icon (known locally as simply "the Drake") due to its red-coated Beefeater doormen and Harry Denton's Starlight Room on the 21st floor, where nightly jazz and sultry cocktail waitresses attract a crowd of locals and visitors. Built in 1928, this Kimpton-run hotel (previously run by Hilton) was long one of the city's most opulent hotels, with a glamourous clientele. Today it's more of a facsimile of its previous self, with a heavy 1920s and '30s theme and a grand motto: "Experience the Legend." An Italian restaurant helmed by a former Top Chef contestant, drag-show brunches, and stylish rooms renovated in 2012 are lovely, but can border on gimmicky at times.

Beefeater doormen

The Sir Francis Drake's service signature is its uniformed Beefeater doormen -- particularly the city's most famed doorman, Tom Sweeney, who has been posted on Powell Street for over 30 years and, according to local legend, holds the honor of being the most photographed person in San Francisco. The service goes beyond the photo-friendly façade, however: Helpful front desk staff, bell staff, and room service are all up to standard. There aren't any major perks or surprises at the Drake (you'll have to move hotels and shell out more dough for things like turndown service, butler service, or a 24 hour-concierge), but it's as good as you'd expect for a large, midrange hotel in a big city.

• Beefeater doormen are a San Francisco icon.
• Concierge staff can help with city information, transportation, and reservations.
• Room service not available 24-hours, but close to it

View on a Larger Map

The Sir Francis Drake is one block north of Union Square, which is famous for its couture shops. Home to enormous outposts of Niketown, Saks Fifth Avenue, Tiffany, Macy's, Louis Vuitton, and Neiman Marcus, among others, Union Square is to San Francisco what Fifth Avenue is to New York. Locals don't hang out here much, but the square is great for people-watching nonetheless, and occasionally plays host to concerts, small festivals, and demonstrations. If shopping isn't your priority, you might prefer a hotel in a neighborhood closer to some of the biggest tourists attractions, like the Huntington in Nob Hill or the Argonaut Hotel Fisherman's Wharf.

• Three blocks from the Powell-Mason and Powell-Hyde cable-car lines, which run to Lombard Street and Ghirardelli Square or to Fisherman's Wharf, near Pier 39; a 20-minute ride
• Far from the Golden Gate Bridge, Golden Gate Park, the Presidio, and Haight-Ashbury
• Discount day-of theater seats available at the Union Square ticket kiosk
• Plenty of dining nearby, but if you want to avoid high-end hotel food and chain restaurants like the Cheesecake Factory, walk towards Nob Hill, where there's an abundance of small, locally owned restaurants.
• 30-minute taxi from San Francisco International Airport
• While Union Square is a safe area, be careful of wandering into the neighboring Tenderloin district (southwest of the square), an area with a reputation for drugs, prostitution, and other crime.

Petite Queen Room

The hotel capitalizes on its historic charm and prohibition-era roots, with "vintage" design in the Starlight lounge and 2011-renovated lobby and rooms. Rooms can be small and sound insulation is an issue (this is an older building), but all 416 rooms were renovated in 2011 with stylish, upscale decor, new furniture and solid amenities. Frette linens, eco-friendly toiletries (the hotel no longer offers Aveda products), and updated flat-screen TVs come with every room. The redesign features a jewel-toned color palette and a boutique-chic aesthetic: no two side-tables are alike in the bedrooms, lamps are unique to each room, and pops of color keep the spaces feeling fresh. The details strive for opulence, but the over-the-top design might not be for everyone.

Because the Drake is an older building, two rooms of the same type can have different square footage and have different bathroom configurations (some are cramped, with only a standing shower, and some are more generous, with a full bathtub/shower combo). This can be frustrating, particularly the smaller bathrooms.

• Rooms are on the small side for San Francisco -- 240 to 472 square feet; most are on the smaller end of that range.
• Poor sound insulation means you can get stuck listening to noisy neighbors and busy hallways (request a room on the top floors or beware street noise).
• Comfortable pillow-top beds have down comforters and Frette linens.
• Flat-screen TVs, DVD players, and iHome alarm clocks and docking stations in all rooms
• Mostly small bathrooms with either standing showers or bathtub/shower combos (varies per room).
• Eco-friendly toiletries
• Animal-print robes, camisoles, boxer shorts, and fuzzy socks available for purchase.
• Wi-Fi is charged per day, or free if you sign up for Kimpton InTouch Rewards.
• Laptop-sized safes in every room
• Tower Rooms, on floors 16 through 20, have the best views in the hotel.
• Five suites, including the Presidential Suite, offer separate living room and bedroom spaces but otherwise have the same amenities and decor as regular rooms.

The gym

A business center and fitness center are the only real on-site facilities aside from Scala's Bistro and Harry Denton's Starlight Room lounge. For a hotel of this size, price, and location, that's not surprising; few non-luxury hotels in San Francisco have more. Because the Drake is a Kimpton property, there are a few extras that are less obvious: pet-friendly services, in-room spa services, and an eco program that allows guests to forgo daily linen washings for a discount on their bill.

• Unstaffed 24-hour business center
• The fitness center (called the "Vigorous Lounge") was added to the hotel in 2007 in a former meeting room. It has nine Precor cardio machines -- bikes, ellipticals, and treadmills -- and weight machines that are in good condition.
• Wi-Fi throughout the hotel is charged per day. Or use it free if you sign up for the Kimpton InTouch Rewards program.
• Free bike rentals available
• Pet-friendly policy allows any type of pet under 200 pounds, and doesn't require a deposit (just a waiver form). Free pet bowls, pet beds, and leashes are provided for guests on arrival. Pet sitting and grooming services can be arranged through the concierge.
• "Relax and Rejuvenate" program arranges in-room spa services.
• "Earthcare" program allows guests to forgo daily linen washings for a discount on their room rate.

A cocktail in the Starlight Room

On the 21st floor, the famous Harry Denton's Starlight Room has nightly jazz performances set against a backdrop of skyline views. Waitresses in slinky dresses and a classic cocktail menu give the bar a kind of 1930s jazz-lounge glamour on most nights. On weekends, Harry's fills with a rowdier dance-club crowd that stays until closing time at 2 p.m., when an overflow of revelers stops up the elevators. (Luckily, guests don't have to sleep next to the Starlight Room.)

• Cocktails organized on the menu by categories like "sophisticated," "tall," "rocks," "bubbles," and "Harry's Favorites."
• Small bites available.
• "Million dollar cocktails" made from vintage spirits and specialty champagnes mostly range in $100s; the most expensive, "Drinking the Stars," is made of Chateau de Ravignon 1979 armagnac infused with Madagascar Vanilla, served with a bottle of Dom Perignon.
• "Sunday's a Drag," the weekly Starlight Room brunch buffet, includes a drag-show performance.

As a brand, Kimpton makes an effort to be family friendly, but this isn't their best hotel for kids. The rooms are on the small side, and the old building's poor sound insulation isn't great for nap time or a sound night's sleep. The hotel is better known for a busy lobby bar and Harry Denton's Starlight lounge than it is for a family vibe. Other Kimpton hotels in San Francisco, like the Hotel Monaco and the Argonaut Hotel, offer the same services but with better rooms and atmosphere.

• Kimpton's standard set of family-minded amenities includes a special room-service menu for kids, Kimpton drawstring backpacks, and special treats served in the lobby during busy seasons (free ice cream pops in the summer, for instance).
• Daily fee for rollaway beds
• Cribs are free.
• Child care services can be arranged through concierge with 24 hours notice.
• Located on a steep hill in a busy part of downtown; somewhat inconvenient for families with small children.

A $21 million renovation was completed in 2009, and another $30 million one in 2011. Furniture, carpeting, paint, and decor were all updated. Daily housekeeping keeps sheets and towels fresh.

Ravioli at Scala's

Scala's Bistro, a modern Italian restaurant, serves three meals a day, and is most notable for its semicelebrity chef, Jennifer Biesty, a former contestant on the reality show Top Chef. Consistently good standard Italian fare (made with local, fresh ingredients, of course) is far from San Francisco's most exciting dining option, but it's a good one for Union Square, and the service and atmosphere are pleasant.

• Scala's Bistro, with executive chef Jennifer Biesty, serves modern Italian food (a pizza- and pasta-heavy menu).
• Well-designed dining room and attentive service.
• Bar Drake, located in the 2011-renovated lobby, claims to be a throwback to the old-school gin joints of the Prohibition era. While the sleek design might not fit that bill, the cocktails are authentic and the liquor is top-shelf.
• Room service for lunch and dinner.
• "Sunday's a Drag," the weekly Starlight Room brunch buffet, includes a drag-show performance.