For the first installment of our new Getaway Guide series, T asked readers who hadn’t settled on their summer travel plans yet to describe their dream trip (but set a realistic budget, not including airfare). After consulting with a few travel experts, we came up with some suggestions. Below are answers to several of the most intriguing queries we received.

Grand Case Beach Club, St. Martin.Credit…Courtesy of Grand Case

A few of the summer offerings at Tickler’s, the restaurant at Wylder hotel on Tilghman Island, Md.Credit…Michael Carnevale
“I’m a federal contractor who recently got laid off, so I’m trying to find some budget travel options. I’d be traveling with my spouse and our 3-year-old and I’m hoping to take two or three weeks off — they could be different weeks — before preschool starts at the end of August. We enjoy swimming and water activities to stay cool during the summer. Any lodging options that offer separate sleeping areas and/or babysitting would be a huge bonus.” — Danielle, Washington, D.C.; budget: $2,500
Losing a job is stressful enough. Why add flying with a toddler to the mix? Lee Friedman,the founder of Mango Tree, a travel agency specializing in family vacations at boutique hotels, also lives in D.C., and she’s a big fan of the 50-room Wylder hotel on Tilghman Island, Md., about a two-hour drive east, in Chesapeake Bay. It offers a saltwater pool, paddle boards, kayaks, a crab shack and lawn games. “My husband and I have had some incredible long weekends there with our kids,” says Friedman, “Book one of the two suites if you want a separate living room. A week there would be more than $3,000, but you don’t need a full week to really feel unplugged.” (From about $375 a night for the suite in summer during the week; $700 a night on weekends.)
If the Eastern Shore of Maryland doesn’t feel like enough of an escape from the Beltway and you don’t mind a relatively short flight, you can find some great off-season deals in the Caribbean. Direct flights to St. Martin, for instance, which Friedman deems one of the most toddler-friendly islands (“It’s easy to navigate and the French influence is a delight,” she says) take about four hours and at press time cost under $600 a person from D.C. in August. Friedman’s especially fond of the island’s Grand Case Beach Club hotel, which juts out on a small peninsula and faces two quiet beaches. It has a seafront swimming pool, assorted water sports and split-level “loft” rooms with separate sleeping spaces and a balcony overlooking the ocean that run about $320 a night in summer. The hotel can also help arrange babysitting. You’ll find more bargains in Belize, but with fewer direct flights from D.C., it’s more logistically challenging. Although you’ll be rewarded for your effort at the Resort at Almond Beach — about a 90-minute drive south of Belize City — where you can book a one-bedroom beachfront suite for about $1,500 a week. “You can take drum lessons, rent a golf cart to explore the nearby town and go in search of howler monkeys,” says Friedman.

Tandem paragliding in the Swiss Alps near the ski resort of Verbier.Credit…Courtesy of Verbier Summits