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For a luxury trip to Boston, stay at one of the Back Bay's Forbes Five-Star hotels, such as Mandarin Oriental or either Four Seasons; book the counter at 311 Omakase in the South End, which holds the only Michelin star in the guide's first Boston selection; charter a traditional schooner on the harbor between May and October; and spend an afternoon among Newbury Street's jewelers and Copley Place's designer houses.
Boston's high end is compact: almost everything below is in the Back Bay, Beacon Hill, the South End or the Seaport, a short cab ride apart. Details are as of September 2026.
Where to stay
- Mandarin Oriental, Boston: 136 rooms and 12 suites on Boylston Street, a Forbes Five-Star rating, a 16,000-square-foot spa and a direct connection to the Prudential Center for shopping in any weather.
- Four Seasons Hotel Boston: Forbes Five-Star, facing the Public Garden, with an eighth-floor pool that looks over the park.
- Four Seasons Hotel One Dalton Street: the contemporary Five-Star option, on floors 8 to 21 of a 61-story tower, with a full wellness floor.
- XV Beacon: 61 rooms in a Beaux Arts building on Beacon Hill, with fireplaces in the rooms, for travelers who prefer privacy to a long list of facilities.
- The Newbury Boston: at the head of Newbury Street, across from the Public Garden, with the rooftop restaurant Contessa.
Tasting menus and fine dining
311 Omakase, a chef's counter at 605 Tremont Street in the South End, received one Michelin star in the MICHELIN Guide's first Boston selection, the only star awarded in the city. Chef Wei Fa Chen serves a nigiri-led omakase built on fish largely imported from Japan. It is closed Mondays, and bookings go through the restaurant directly. Michelin's next Boston selection may change the picture, so check the guide before you book around a star.
For a second splurge night, o ya in the Leather District serves a prepaid nightly tasting menu; chef Tim Cushman won the James Beard Award for Best Chef: Northeast in 2012 for it. Uni, Ken Oringer's sashimi and small-plates restaurant in The Eliot Hotel, offers a daily tasting menu. Grill 23 and Bar has a wine list of more than 2,600 selections with a Wine Spectator Grand Award. Menton, which older guides still recommend, has closed.
A glass of wine downtown
haley.henry at 45 Province Street in Downtown Crossing is a small natural-wine bar that also serves tinned fish. It opens Tuesday to Thursday 3 to 11 p.m., Friday 3 p.m. to midnight and Saturday noon to midnight, and takes reservations on Resy. For a view with your drink, Stratus, the bar at View Boston at the top of the Prudential Tower, is open from 3 to 10 p.m. with an observatory ticket.
A private sail on the harbor
Liberty Fleet of Tall Ships charters traditionally rigged wooden schooners from Fan Pier Marina in the Seaport from May through October, for up to 49 guests with a minimum of 1.5 hours in the afternoon or 2 hours in the evening, and bar packages available. A sunset charter shows the skyline from the water with no other passengers aboard.
Shopping Newbury Street and Copley Place
Start at the Public Garden end of Newbury Street, where Shreve, Crump and Low, the family-owned jeweler that dates itself to 1796, fills a three-story flagship at 39 Newbury with diamonds, estate pieces and a watch salon. Then walk to Copley Place, where Louis Vuitton, Dior, Tiffany and Co., Gucci and Saks Fifth Avenue Men's share two indoor levels.
Culture: the BSO, the MFA and the Gardner
The Boston Symphony Orchestra's 2026 to 2027 season at Symphony Hall, 301 Massachusetts Avenue, opened on September 30, 2026; weekend concerts sell first, so book ahead. By day, the Museum of Fine Arts and the Isabella Stewart Gardner Museum are neighbors in the Fenway; the Gardner runs on timed tickets and is closed on Tuesdays.
Related reading: more luxury ideas for a Boston vacation, a Boston date night and Boston's oldest restaurants.
Sources: MICHELIN Guide Boston 2025 and 311 Omakase page, haley.henry, Liberty Fleet, Boston Symphony Orchestra; hotel, restaurant and shop facts from our linked listings. Checked September 30, 2026.