Memorial Day Weekend on Nantucket

What to Expect

Memorial Day weekend marks the unofficial start of summer on Nantucket, and there's no better way to experience it than during this electric three-day stretch. The island transforms from its quiet spring slumber into a celebration of everything that makes Nantucket special: sailing traditions, exceptional dining, pristine beaches, and a community that knows how to welcome the warm season in style.

But here's what you need to understand: Memorial Day weekend on Nantucket isn't just any holiday getaway. This is Figawi weekend, one of the most storied sailing events on the East Coast, and the energy is palpable. Hundreds of sailors descend on the island after racing across Nantucket Sound from Hyannis, and the celebration spills into every restaurant, bar, and cobblestone street in town. Whether you're a sailing enthusiast or simply someone who appreciates a good party atmosphere, this weekend delivers.

The timing is interesting from a practical standpoint. You're catching Nantucket in transition. Not every shop has opened for the season. Some restaurants are still shaking off winter cobwebs. The water is cold enough to make even the hardiest New Englanders think twice about swimming. But that's part of the charm. You get the celebration atmosphere without the peak summer crowds and prices, and you'll find that the establishments that are open are genuinely thrilled to see visitors after a long off-season.

The Figawi Race Weekend

You cannot discuss Memorial Day weekend on Nantucket without talking about Figawi. This legendary regatta has been the centerpiece of the holiday weekend since 1972, when a group of friends at Baxter's Boathouse in Hyannis challenged each other to see who could sail to Nantucket the fastest. What started as a friendly bet has evolved into one of New England's most celebrated sailing events and charity fundraisers.

The Legend Behind the Name

The name itself is part of Nantucket lore. According to legend, during that first race in 1972, a thick fog blanketed Nantucket Sound, leaving confused sailors squinting through the mist and asking each other "Where the f**k are we?" Say that in a thick Boston accent, and you get "Where the Figawi" - or simply "Figawi." The name stuck, and so did the tradition of spirited celebration that accompanies the race.

The Race Itself

The approximately 25-mile race begins in Hyannis with staggered starts based on boat handicaps, typically between 10:00 AM and noon on Saturday. The boats make their way across Nantucket Sound and finish at the entrance to Nantucket Harbor, then parade into the Nantucket Boat Basin in a procession that draws spectators to the waterfront. Watching the fleet arrive, sails catching the late afternoon light, is one of those quintessential Nantucket moments.

The race has grown considerably from its humble origins. By the 1980s, prominent names like Kennedy and Koch were competing, drawing national attention. Today, the event attracts over 200 boats and raises significant funds for youth sailing programs, maritime education, veteran support, and local charities throughout Cape Cod and the Islands.

The Figawi Tent Party

The tent parties near the Boat Basin have achieved almost mythical status. Once the boats arrive, sailors and supporters gather under the Figawi tent for Goombay Smashes, Dark 'N' Stormys, and live music. The atmosphere is pure celebration - sailors who just conquered the Sound, supporters who drove or flew in, and locals who mark this weekend as the true start of their summer.

Keep an eye out for the coveted Figawi hats. These Mount Gay-embroidered caps, given only to sailors who complete the race (no more than three per team), have become prized possessions and badges of honor. They also serve as the "key" to enter the Figawi tent. The tradition of island teenagers devising elaborate schemes to steal these hats from unsuspecting sailors has become its own Nantucket legend.

Sunday brings the continuation of festivities with a joke-telling ceremony (a Figawi tradition), followed by a lobster clambake, the awards ceremony, and more live music. The race back to Hyannis takes place Monday morning, giving sailors one last competition before the long weekend ends.

Where to Eat

Memorial Day weekend catches Nantucket's restaurant scene in transition. Not every establishment has opened for the season, but you'll find plenty of excellent options, and the restaurants that are operating are fully staffed and ready for the rush. Reservations are essential - this is one of the busiest weekends of the spring season.

Restaurants Typically Open Memorial Day Weekend

While specific openings vary year to year, these establishments are generally operational by Memorial Day:

Fine Dining

• Topper's at The Wauwinet - Their season typically begins in May, offering refined New American cuisine
• The Boarding House - A downtown favorite with excellent wine program
• Company of the Cauldron - Intimate dining with set menus (reservations essential)

Casual Dining

• Brotherhood of Thieves - Year-round pub with live music, perfect for the Figawi crowd
• The Nautilus - Shared plates and craft cocktails in a lively atmosphere
• CRU - Waterfront dining with oyster bar and excellent lobster rolls
• Slip 14 - Popular waterfront spot that fills with sailors all weekend
• Straight Wharf Restaurant - Classic Nantucket dining on the harbor
• The Lobster Trap - Casual seafood on the water

Breakfast and Lunch

• Black-Eyed Susan's - A beloved breakfast spot (expect lines)
• Something Natural - Famous sandwiches on homemade bread
• Provisions - Perfect for gourmet picnic provisions
• Island Kitchen - Mid-island favorite for all-day dining

Bars and Nightlife

• The Chicken Box - The island's legendary live music venue, packed all weekend
• The Gazebo - Expect long lines at this downtown bar during Figawi
• Cisco Brewers - The perfect afternoon destination for craft beer, wine, and spirits

Reservation Strategy

Book dinner reservations at least 2-3 weeks in advance for popular restaurants. For Figawi weekend specifically, consider making reservations when you book your accommodations. If you arrive without reservations, your best bets are early dining (5:00-5:30 PM) or the bar scene at places like Brotherhood of Thieves.

Beach Conditions

Memorial Day weekend beach conditions require honest expectations. The beaches are beautiful - arguably more peaceful than you'll find them all summer - but the water is not for the faint of heart.

Water Temperature

Expect water temperatures around 50-54 degrees Fahrenheit. This is cold. Dedicated swimmers might take a quick plunge, and you'll see some brave souls wading in, but this isn't beach swimming weather for most people. If you're serious about getting in the water, consider bringing a wetsuit.

Air Temperature

Late May air temperatures typically range from the mid-50s to low 60s, though sunny days can push into the upper 60s or even low 70s. The beaches are perfect for walking, picnicking, and enjoying the scenery - just don't plan on working on your tan or spending hours in the surf.

Lifeguards

Lifeguard coverage typically begins Memorial Day weekend at main beaches including Jetties Beach, Children's Beach, and Surfside Beach, though hours may be limited compared to peak summer. Confirm current coverage with the Town of Nantucket before your visit.

Best Memorial Day Weekend Beach Activities

• Beach walks - Miles of pristine coastline with fewer crowds than summer
• Sunset watching - Madaket Beach offers spectacular westward views
• Birdwatching - Spring migration brings diverse species to island beaches
• Cycling - Ride the bike paths to various beaches
• Photography - Early morning beach light is extraordinary

What's Open (And What's Not)

Memorial Day weekend represents the island in transition. Here's what to expect:

Generally Open

• Most downtown restaurants and bars - The core dining scene is operational
• The Whaling Museum - Opens for season around this time
• Cisco Brewers - The brewery, winery, and distillery complex is open
• Bartlett's Farm - Fresh produce and prepared foods
• Major hotels and inns - Most accommodations are fully operational
• Bike rental shops - Ready for the season
• The First Farmers and Artisans Market - Often opens for the season Memorial Day weekend

Possibly Limited

• Some boutique shops - A few may still be closed or have limited hours
• 'Sconset restaurants - Some don't open until June
• Beach concessions - May have limited offerings
• Water sports rentals - Kayak and paddleboard rentals may have reduced availability

Pro Tip

The Town of Nantucket's official website maintains a weekly updated list of open restaurants during shoulder season. Check before your trip for the most accurate information.

Other Memorial Day Weekend Events

Beyond Figawi, the weekend offers plenty of activities:

Memorial Day Parade

Nantucket honors its veterans with a heartfelt Memorial Day Parade on Sunday. The parade proceeds through downtown, featuring local veterans, the high school band, scouts, and community organizations. It's a touching reminder of the holiday's true meaning amid the celebrations.

New Moon Fest

The 'Sconset Casino often hosts the New Moon Fest on Saturday evening, featuring live music, food, and a festive atmosphere in one of the island's most charming villages.

Farmers and Artisans Market Opening

Sustainable Nantucket's First Farmers and Artisans Market typically opens for the season Memorial Day weekend. Browse local produce, artisan goods, and handcrafted items from island vendors.

Museum Openings

The Nantucket Historical Association's Whaling Museum and walking tours often begin their full season schedule around Memorial Day weekend. It's an excellent time to explore the island's rich history.

Booking Accommodations

Memorial Day weekend is one of the most popular times to visit Nantucket, and accommodations book quickly. Here's your strategy:

When to Book

• 3-4 months ahead - For best selection at hotels and inns
• 4-6 months ahead - For vacation rentals, especially larger properties
• As early as possible - If you're reading this close to Memorial Day, start calling immediately

What to Expect

• Minimum stays - Many properties require 2-3 night minimums
• Peak pricing - Rates are higher than typical spring weekends, though not quite summer peak
• Figawi packages - Some properties offer special sailing-themed packages

If You Can't Find Accommodations

• Day trip option - Stay in Hyannis and ferry over for the day
• Check cancellation lists - Call properties directly about last-minute openings
• Consider arriving Thursday - Extends your stay and may offer more options

Ferry Considerations

Getting to Nantucket requires advance planning, especially on holiday weekends.

Book Both Directions Early

Do not wait until you arrive to book your return ferry. Sunday and Monday departures fill up quickly as Figawi sailors and weekend visitors all head home. Book round-trip when you make your accommodation reservations.

Consider Skipping the Car

Car ferry reservations for Memorial Day weekend are extremely difficult to secure. The good news: you don't need a car on Nantucket. The island is easily navigated by bike, shuttle, taxi, or on foot. Save yourself the hassle and expense.

Options for Getting There

• Steamship Authority - Traditional and high-speed ferries from Hyannis
• Hy-Line Cruises - High-speed and standard ferries from Hyannis
• Flying - Cape Air and JetBlue (seasonal) offer flights to Nantucket

Ferry Tips

• Arrive at the terminal 45-60 minutes before departure
• The high-speed ferry takes about an hour; traditional ferry takes over two hours
• Consider mid-week travel if your schedule allows - less crowded than Friday arrivals

What to Pack

Memorial Day weekend weather on Nantucket can be unpredictable. The saying "if you don't like the weather, wait five minutes" applies here. Pack for versatility.

Clothing Essentials

• Layers - Mornings can be cool (50s), afternoons warmer (60s-70s)
• Light jacket or fleece - Essential for evening events and waterfront dining
• Rain gear - A packable rain jacket is non-negotiable
• Comfortable walking shoes - Cobblestones require sturdy footwear
• One nice outfit - For upscale dining or the Figawi tent
• Windbreaker - Harbor breezes can be brisk

Beach Gear (Adjusted Expectations)

• Beach blanket or chairs for sitting, not swimming
• Sunscreen - the sun is strong even when it's not hot
• Sunglasses
• Wetsuit if you're serious about swimming

Don't Forget

• Camera for capturing sailboats and scenery
• Binoculars for watching the Figawi fleet arrive
• Cash for some vendors and tips
• Confirmation numbers for all reservations

Sample Weekend Itinerary

Friday

• Afternoon: Arrive via ferry, check into accommodations
• Late Afternoon: Explore downtown, browse open shops
• Evening: Dinner at Brotherhood of Thieves or The Nautilus (reservations recommended)
• Night: Check out early Figawi festivities downtown or catch live music at The Chicken Box

Saturday

• Morning: Breakfast at Black-Eyed Susan's (arrive early to beat the line)
• Mid-Morning: Bike ride to Cisco Brewers via the bike path
• Afternoon: Head to the waterfront to watch the Figawi fleet arrive at the Boat Basin (typically mid-to-late afternoon)
• Late Afternoon: Soak up the Figawi tent atmosphere or grab drinks at Slip 14
• Evening: Dinner at CRU or Straight Wharf Restaurant
• Night: Join the celebration - downtown bars are lively, The Chicken Box has live music

Sunday

• Morning: Attend the Memorial Day Parade downtown
• Late Morning: Brunch at Island Kitchen or pick up sandwiches from Something Natural
• Afternoon: Beach walk at Surfside or explore the Whaling Museum
• Late Afternoon: Sunset at Madaket Beach
• Evening: Final dinner at a favorite spot from the weekend

Monday

• Morning: Leisurely breakfast, last stroll through town
• Midday: Depart via ferry (book early - return ferries fill up)