33 deals from our U.S. site*
* Taxes and fees may be additional.
Source: CheapCaribbean.com

Sun-drenched beaches and 4-star treatment are the perfect cure for winter blues.

February-June departures
Source: Sheraton Old San Juan

This hotel is in the heart of Old San Juan, with the cruise terminals right along the waterfront.

Select Sundays-Thursdays through March
Source: Sheraton Puerto Rico Hotel & Casino

Great for business or leisure, the hotel is near both the convention center and Condado Beach

Select weekdays through March
Source: Regent Seven Seas Cruises

This deal includes prepaid gratuities, unlimited shore excursions, unlimited drinks, transfers, a hotel stay & cruise through exotic Caribbean ports.

Depart March 8
Source: Virginia Wine Pass

Take in scenic Virginia wine country at more than 80 wineries and cideries with the Virginia Wine Pass for two people at half off.

Redeem by Sept. 25, 2015; pass good through 2015
Source: Madame Tussauds Washington D.C.

Brush elbows with the Founding Fathers and A-list celebrities like George Clooney and Angelina Jolie with 40%-off tickets to Madame Tussauds.

Through March 31, 2015
Source: Béarnaise Restaurant

Former "Top Chef" contestant and celebrity chef Spike Mendelsohn brings this "upscale" (Zagat) bistro to Capitol Hill, where two can dine for more than 40% off.

Through March 15, 2015; closed Mondays
Source: Uncork'd Art

Create your own masterpiece at Uncork'd Art, the 2014 City Paper readers' poll winner for Best Art Class.

Through March 31, 2015
Source: Meli Cafe

Praised on WTTW's "Check, Please!" for "a warm, welcoming atmosphere" where "attention is paid to every detail," Meli Cafe offers members up to 50% off.

Through March 23, 2015
Source: French Quarter Phantoms

Save 60% on a historic New Orleans cemetery tour from French Quarter Phantoms -- voted one of the top 10 ghost tours around the world by TripAdvisor.

Through March 31, 2015
Source: Skin Beauty Bar

Unwind at Skin Beauty Bar with your choice from massages or a facial at up to half off regular prices.

Through March 16, 2015
Source: Roofers Union

From the "talented chef at the arty Ripple" comes Roofers Union (Washington Post). Sit down for brunch at this Adams Morgan hot spot and save nearly 50%.

Saturday-Sunday through April 26, 2015
Source: South Coast Winery Resort & Spa

Save 55% on an exclusive winter escape to wine country at Temecula's "most luxurious resort ... surrounded by 38 acres of vineyards" (Fodor's).

Travel through Feb. 26
Source: Chic Clinique Spa Boutique

Treat yourself to a two and a half hour spa visit or a custom facial at Pacific Beach's Chic Clinque Spa Boutique while saving 50% on treatments.

Through March 15, 2015
Source: The Grill Room at Capella Washington, DC Georgetown

The Grill Room at Capella earns rave reviews for its "high-end" cuisine and "air of relaxed refinement" (Zagat). Enjoy a luxe lunch for two for nearly 50% off.

Monday-Friday through Feb. 27, 2015
Source: Bike & Roll Miami

Save nearly 50% on a segway tour from Bike & Roll Miami, which earns a 4.5 star rating from TripAdvisor users.

Through Feb. 28, 2015
Source: Bourbon DC - Glover Park

Try a variety of American whiskeys and scotches at a tasting class at Bourbon in Glover Park, one of best bourbon bars in America (Bourbon Review).

Feb. 21, 28 or March 7, 2015; Private tasting class through March 31, 2015
Source: Bourbon DC - Glover Park

Bourbon in Glover Park is listed as one of the best bourbon bars in America (Bourbon Review). Enjoy cocktails or dinner and drinks at up to 50% off.

Through March 31, 2015
Source: Downtown Culture Pass

Learn the storied history of Lower Manhattan with a three-day pass that includes admission to 10 museums and discounts on tours for up to 60% off.

Through June 30, 2015
Source: Le Mirch

Visit Dupont Circle for a top-rated Indian dinner with wine at 40% off regular prices.

Through April 30, 2015
Cheap Roundtrip Fares to San Juan from:
(Per person, including taxes and fees. Click a price to verify availability now.)
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Travelzoo Tips

Hilary Solan — Travel, Entertainment and Local Deal Expert
Hilary Solan
Deal Expert, Chicago
Several hotel chains, including Hilton and Choice Hotels, offer discounts for active More