Annual fee: $175 (first year free)
This American Express ( AXP) card gets the nod primarily because of a generous 25,000 Membership Rewards points you can earn right off the bat by spending just $2,000 in your first three months of membership. You'll also get an extra 15,000 points if you charge $30,000 on the card in your first calendar year. And that's on top of 1 point for every dollar you spend on most purchases, plus 2 points per dollar for gas and grocery bills and 3 points for airfare. Other perks include free baggage insurance when you travel, free extended warranties and return protection on purchases and access to special Gold Card concerts, shows and sporting events.
Annual fee: $95 (first year free)
Woolsey gives this Visa ( V) card a thumbs up because it provides big bonuses for usage at Hilton hotels, a brand popular with businesspeople and upscale travelers. "Hilton is a chain that business travelers often have clearance from their companies to stay in, so they can leverage their corporate travel for their personal benefit in terms of earning rewards," he says. HHonors Reserve Cards carry a $95 annual fee, but consumers get two free weekend nights at select Hiltons if they charge just $2,500 of eligible purchases within four months of opening an account. You'll also earn an unusually high 3 bonus points for every dollar charged on the card, as well as 10 points every time you spent $1 at a Hilton, Embassy Suites hotel, Hampton Inn or other Hilton property. Additionally, the HHonors Reserve Visa offers 5 points for every dollar that goes toward eligible airfares or car rentals. The card also includes automatic membership in Hilton's HHonors Gold club, which provides free room upgrades, high-speed Internet access, soft drinks and other perks at select Hilton properties. Citi Platinum Select AAdvantage Visa Signature Card
Annual fee: $95 (first year free)
Woolsey carries this American Airlines ( AAMRQ) affinity card himself, partly because the carrier flies to a lot of destinations he goes to. The expert also likes the card's unusually large initial bonus, though -- 30,000 American Airlines frequent-flier miles when you spend just $1,000 within three months of opening an account. You'll also get a $100 discount on one American Airlines flight per year if you charge $30,000 over 12 months on your card. That's more than enough to cover your $95 annual fee. Additionally, the card offers consumers priority boarding, one free checked bag and twice the usual frequent-flier miles whenever they fly American. "Other airlines offer cards that are similar, but American's upfront bonus is unusually strong -- and very useful for vacations because the airline is such a large carrier," Woolsey say. Starwood Preferred Guest American Express Card
Annual fee: $65 (free in first year)
Like the Hilton HHonors Visa, this card offers special perks to consumers who frequent one specific hospitality company -- in this case Starwood Hotels & Resorts ( HOT), the parent company of Sheraton, Westin and other upscale brands. Benefits include 10,000 bonus points to start, plus 20,000 more if you charge $5,000 on the card within the first six months. Those are enough points for a free weekend at San Francisco's Westin St. Francis, Boston's W Hotel or other top-of-the-line Starwood properties. You can also use your bonus points as frequent-flier miles on some 350 airlines -- an unusually high number for a credit-card program, Woolsey says. "Many hotel-related credit cards typically have partnerships with just one airline and a few rental-car companies," he says. Visa Black Card
Annual fee: $495
The Visa Black Card is one of several ultra-high-end credit cards that charge hefty annual fees, but include free access to hundreds of airport VIP lounges around the world. The card also provides users with lots of other free travel-related services, from 24-hour worldwide concierge service to up to $300 for food and lodging if your flight is delayed more than 12 hours. You can also use your bonus points to buy tickets on virtually any airline around -- all with no blackout dates.