Boston stands out in the Northeast as a prime destination for shopping enthusiasts. With its mix of historic districts, modern malls, and extensive outlet centers, it offers a wide variety of retail experiences. Whether you’re hunting for high-end designer brands, seeking bargains at outlet malls, or exploring unique local stores, Boston’s shopping scene is worth exploring beyond its famous historic sites. Market tours here give you a chance to enjoy curated shopping trips, often with transportation included, saving you the hassle of figuring out logistics while providing insider tips and comfort.
If you’re planning your shopping adventure, you’ll want options that combine convenience, variety, and value. The two tours below provide a fantastic way to explore outlet malls outside the city—perfect for hunting down deals or discovering new brands. They also showcase different regional shopping districts, making them suitable for various tastes and budgets. To help you decide, we’ve included detailed descriptions of each, with honest insights on what makes each one special.
Quick Overview
In this guide, you’ll find two private shopping tours from Boston that focus on outlet shopping — one to Wrentham Village Premium Outlets and the other to Kittery Premium Outlets. Both tours include roundtrip transportation, multiple hours at the outlets, and a comfortable, stress-free experience. For more details on each, check out Private Shopping Tour from Boston to Wrentham Village Outlets and Private Shopping Tour from Boston to Kittery Premium Outlets.
1. Private Shopping Tour from Boston to Wrentham Village Outlets
At number one, this Private Shopping Tour from Boston to Wrentham Village Outlets offers a full day of bargain hunting in Massachusetts’ largest outdoor outlet center. The tour begins with a friendly driver picking you up from your Boston hotel, whisking you away in a private, air-conditioned vehicle. The journey takes about an hour, giving you some time to relax before hitting the stores.
Wrentham Village Outlets boasts over 160 brands, including Gucci, Jimmy Choo, Tory Burch, lululemon, and Saks OFF 5TH. Known for its discounted prices—up to 65% off retail—this shopping destination is ideal for finding designer labels at a fraction of the cost. The stores are spread out in a scenic outdoor setting, with many offering exclusive outlet deals that you won’t find elsewhere.
You’ll have approximately four hours to explore at your own pace. The outlet’s layout encourages browsing and discovering hidden gems, and there’s a good mix of luxury boutiques, sportswear stores, and accessories shops. The tour includes stops for lunch or coffee at some of the trendy cafes on-site, making it a relaxed experience. After a day of shopping, your driver will return you to Boston, leaving you free to enjoy your evening.
Bottom line: This tour is perfect for those wanting access to prestigious brands at outlet prices, with the convenience of door-to-door service. It’s especially suited for shoppers eager to maximize their retail therapy without the hassle of driving or parking.
2. Private Shopping Tour from Boston to Kittery Premium Outlets
Coming in at number two, the Private Shopping Tour from Boston to Kittery Premium Outlets offers a visit to Maine’s famous outlet district. The tour kicks off from your Boston hotel in a private, air-conditioned vehicle, with a scenic one-hour drive to the outlet center, located in the town of Kittery.
This outlet mall features over 60 stores, including Coach, Nike, Columbia Sportswear, Kate Spade, and Levi’s Outlet. Known for daily savings of 25% to 65%, Kittery is a favorite for those who want a good mix of fashion, outdoor gear, and accessories. The shopping area is compact but packed with well-known brands, making it easy to browse and find deals without feeling overwhelmed.
You’ll spend about four hours at Kittery, which is enough time to explore the stores thoroughly. The outlet offers a relaxed shopping environment, with some shops already offering significant discounts. The trip also includes time for a quick lunch or coffee at the outlets’ cafes and restaurants, so you can recharge before heading back.
The driver will return you to Boston after your shopping spree, with the option to customize your departure time. This tour is suited for those who prefer a shorter drive outside Boston but still want access to a variety of excellent outlet stores.
Bottom line: This tour offers a more localized experience in Maine, perfect for shoppers who enjoy outdoor shopping atmospheres and want great deals on popular brands. It’s ideal for a half-day trip with a focus on convenience.
How to Choose
When selecting between these shopping tours, consider your budget, shopping priorities, and how far you want to go. If you’re after luxury brands and don’t mind a longer drive, the Wrentham outing (more details here) provides a wide selection of designer labels with significant discounts. For a slightly shorter trip with a focus on mainstream brands and a more regional experience, Kittery (see more here) is a great choice.
Both tours are private, meaning you can tailor the time spent at each store and enjoy a relaxed, personalized experience. Keep in mind that prices are approximately $416 for Wrentham and $492 for Kittery per person; compare based on your shopping goals and group size. Booking early will ensure availability, especially during peak shopping seasons like Black Friday or holiday sales.
Final Thoughts
Boston offers exceptional outlet shopping options just outside the city. Whether you prefer the luxury brands at Wrentham, with its sprawling outdoor layout and top-tier boutiques, or the more compact, Maine-based Kittery Outlets, both tours provide convenient, well-organized ways to score great deals.
For those looking to make the most of a day trip, the Wrentham tour offers a broad selection of high-end labels, perfect for serious bargain hunters. Meanwhile, the Kittery trip suits shoppers who want a quick getaway with a focus on popular brands and outdoor shopping.
No matter your choice, booking in advance will help you avoid missing out—especially during busy shopping seasons. With these options, you can enjoy stress-free transportation and plenty of retail therapy, making your Boston visit even more memorable for all the right reasons.