Nantucket Guys' Weekend

Why Nantucket for a Guys' Trip?

Let's be honest - when your buddy suggests Nantucket, some of the guys might picture preppy polo shirts and overpriced brunch spots. But this island has serious adventure credentials that fly under the radar:

• Legendary fishing waters: Striped bass, bluefish, and false albacore that draw anglers from around the world
• Links-style golf: Ocean views and challenging winds at Miacomet make for memorable rounds
• Cisco Brewers: A brewery, winery, and distillery compound with live music and food trucks
• No car needed: Bikes and shuttles mean everyone can partake without a designated driver
• Incredible food: From raw bars to BBQ joints with bourbon flights
• Island atmosphere: Small-town feel with no chain restaurants or big-box stores

Plus, there's something about being 30 miles out at sea that makes a trip feel like a real escape. When the fast ferry pulls away from Hyannis, the stress of the mainland fades fast.

Fishing Charters: The Main Event

For many guys' trips, a day on the water is the centerpiece of the weekend. Nantucket's waters are legendary, and booking a charter is the best way to experience them - especially if you're not bringing your own gear.

What You'll Catch

The season runs roughly May through October, with different fish peaking at different times:

• Striped Bass: The marquee catch. June and September-October are prime time for trophy-sized stripers
• Bluefish: Aggressive fighters that put up a great battle. Late May through fall
• Bonito & False Albacore: August-October brings these speed demons that'll test your tackle
• Offshore (Tuna, Sharks): Full-day trips can target bigger game further out

Top Charters to Book

Albacore Charters - Voted Nantucket's Best Charter Boat. Captain runs trips for stripers, blues, fluke, sea bass, and offshore for sharks and tuna. They offer a fish guarantee - if you don't catch, you don't pay full price. Half-day and full-day options. Book at (508) 228-5074.

Capt. Tom's Charters - Serving Nantucket since 1973, this outfit has over 50 years of local knowledge. They offer inshore, offshore, night fishing, flats fishing, and even fly fishing trips. The experience here is unmatched. Call (508) 228-4225.

What to Expect

• Half-day trips (4 hours): $600-900 for the boat
• Full-day trips (8 hours): $1,000-1,500 for the boat
• All tackle and gear provided
• Massachusetts saltwater fishing license required (get it online at mass.gov)
• Bring sunscreen, snacks, drinks, and seasickness meds if anyone needs them
• Tip the mate 15-20% on top of charter fee

Pro tip: Book well in advance for summer weekends. The best captains fill up months out. A morning trip works well - you'll be back by lunch with time to clean up before hitting the bars.

Golf at Miacomet

Nantucket has several private clubs that require membership or reciprocal arrangements, but the good news is the island's premier public course is legitimately excellent.

Miacomet Golf Course

The Details: 18 holes, par 72, 6,831 yards from the championship tees. Classic links-style layout with rolling fairways, ocean views, and challenging winds that'll humble even solid players.

• Green fees: $150-200+ in peak season, less in spring/fall
• Address: 12 West Miacomet Road
• Phone: (508) 325-0333
• Full pro shop with club rentals
• Practice range and putting green
• Restaurant and bar on-site (more on that below)

The back nine has the best views, but the whole course delivers that Scottish links feel without the transatlantic flight. Book tee times in advance for summer - weekday afternoons tend to be less crowded and sometimes cheaper.

Quick 9 Option: Siasconset Golf Course

If someone in the group just wants a casual round, the 9-hole course in Sconset dates back to 1894 and offers a charming, low-pressure experience. Green fees run $60-80, and it's a great way to squeeze in some golf without committing to a full round.

Golf Day Strategy

Here's what works: book an early-ish tee time at Miacomet (9 or 10 AM), play 18, grab lunch and beers at The Restaurant at Miacomet, then head to Cisco Brewers for the afternoon. You don't need to golf to eat at Miacomet's restaurant - it's open to the public and serves solid food with a relaxed atmosphere.

Cisco Brewers: Essential Stop

If there's one must-do on a Nantucket guys' trip, it's an afternoon at Cisco Brewers. This isn't some cramped tasting room - it's a sprawling compound where you can spend hours sampling beers, wines, and spirits while lounging at picnic tables with live music playing.

The Setup

Cisco is actually three operations in one location:

• Cisco Brewers: Craft beer including Whale's Tale Pale Ale and rotating seasonals
• Nantucket Vineyard: Local wines including the popular Nantucket Red
• Triple Eight Distillery: Vodka, gin, bourbon, and the excellent Notch Single Malt Whisky

What to Order

• Start with a flight of beers to find your favorite
• Triple Eight vodka is smooth and locally famous
• The Notch whisky is aged in barrels that previously held their beer - unique and worth trying
• Food trucks on-site serve everything from tacos to lobster rolls

Getting There (No Driver Needed)

Free Cisco Van: The shuttle departs from East Chestnut and Federal Streets downtown. Summer schedule runs Monday-Saturday 12-6pm, Sunday 12-5pm. No designated driver required - this is the move.

You can also bike (about 4 miles from downtown) or Uber, but the free van is the play. The compound is at 5 Bartlett Farm Road with free parking if you do drive.

The Vibe

Gloriously casual. Cornhole, giant Jenga, dogs everywhere, and live music most summer afternoons. The crowd spans families to bachelor parties. Pro tip: arrive early on weekends to snag a picnic table - they fill up. Open year-round, hours roughly 12-7pm daily.

Best Sports Bars & Casual Eats

After a day of fishing or golf, you need the right kind of spot - good food, cold beer, maybe a game on TV, and zero pretension. Nantucket delivers.

B-ACK Yard BBQ

This is the spot for the crew. Full-service BBQ restaurant on Straight Wharf featuring regional styles from across America. They've got 9 flat-screen TVs, Kentucky bourbons, Tennessee whiskeys, and live entertainment. The brisket is legit, and the bourbon selection will keep everyone happy.

• Address: 20 Straight Wharf
• Phone: (508) 228-0227
• Vibe: Casual, TVs, BBQ, bourbon

Brotherhood of Thieves

A Nantucket institution since 1972. American pub fare in a historic setting with three distinct dining areas. Known for burgers, seafood, and live music nightly. Part of the Cisco Brewers family, so expect good local beer. Walk-ins welcome.

• Address: 23 Broad Street
• Phone: (508) 228-2551
• Vibe: Classic pub, live music, casual

Kitty Murtagh's

Nantucket's only Irish pub. Two-storey restaurant with dining downstairs and a proper pub upstairs decorated with Irish antiques. Perfect for a pint and some craic. Year-round.

• Address: 4 West Creek Road
• Phone: (508) 325-0781
• Vibe: Irish pub, cozy, authentic

Tap Room

Upscale casual spot in the basement of the historic Jared Coffin House (1845). Craft beer selection, creative cocktails, and solid American fare in an atmospheric cellar setting with exposed brick. Good for when you want something a notch above pub grub.

• Address: 29 Broad Street
• Phone: (508) 228-2117

Slip 14

Dockside seafood spot on Old South Wharf with harbor views. Raw bar, local oysters, innovative cocktails, and late-night hours (open until 1 AM). This is where you end up for drinks after dinner.

• Address: 14 Old South Wharf
• Phone: (508) 228-2033

The SeaGrille

Local favorite for 35+ years. "Where the locals go" for seafood and eclectic American fare. Slightly off the downtown strip, which means fewer tourists. Great for a group dinner that won't break the bank.

• Address: 45 Sparks Avenue
• Phone: (508) 325-5700

Surfing & Water Sports

If someone in the crew wants to try surfing, Nantucket has legitimate waves - especially at Cisco Beach on the south shore.

Nantucket Island Surf School

Operating since 1999, they offer lessons for all skill levels right at Cisco Beach where the waves are most consistent. Private and group lessons available, plus board and wetsuit rentals if you already know what you're doing.

• Location: Cisco Beach
• Phone: (508) 560-1020
• Price range: $$-$$$

The combo play: surf lesson in the morning, lunch at Cisco Brewers (right down the road), beers all afternoon.

Other Options

• Kayak fishing: Paddle out and fish the shallows
• SUP: Stand-up paddleboarding at calmer harbor beaches
• Sailing: Charter a boat for a sunset cruise (Endeavor Sailing offers group trips)

Where to Stay: Rental House Tips

For a guys' trip, forget the boutique hotel - you want a house where the crew can spread out, cook breakfast, play cards, and not worry about noise complaints.

What to Look For

• Multiple bedrooms: Minimum one bedroom per two guys (nobody wants to share beds)
• Outdoor space: Deck or patio for morning coffee and evening beers
• Grill: Essential for cooking your fishing catch
• Big table: For poker nights and group dinners
• Location: Mid-island is fine - you'll be biking or shuttling anyway

Book Through

Major rental agencies handle most inventory:

• VRBO and Airbnb for direct bookings
• Great Point Properties for curated selection
• Congdon & Coleman for established rentals
• Fisher Real Estate for premium options

Budget reality: Summer weekly rentals run $3,000-10,000+ depending on size and location. Split 6-8 ways, it's manageable. Shoulder season (May, September-October) offers significant savings.

Poker Night Setup

Bring your own chips and cards - the house probably won't have them. Folding poker table is optional but appreciated. Stock up on beer at the grocery store (Stop & Shop has the best selection) and you're set for late-night sessions after the bars close.

Sample Guys' Weekend Itinerary

Day 1 (Friday): Arrival & Settle In

• Afternoon: High-speed ferry from Hyannis (book in advance)
• 4:00 PM: Pick up rental bikes, head to house
• 5:30 PM: Beers on deck, unpack
• 7:30 PM: Dinner at B-ACK Yard BBQ - get the brisket and a bourbon flight
• 10:00 PM: Drinks at Brotherhood of Thieves (live music)
• Late: Poker at the house

Day 2 (Saturday): Fishing Day

• 5:30 AM: Coffee, light breakfast
• 6:00 AM: Meet captain at Straight Wharf for half-day charter
• 11:00 AM: Back at dock, hopefully with fish
• 12:00 PM: Lunch at Slip 14 (raw bar, harbor views)
• 2:00 PM: Free Cisco Van to Cisco Brewers
• 2:30-6:00 PM: Brewery, live music, lawn games
• 7:30 PM: Grill your catch at the house (or dinner at SeaGrille)
• 10:00 PM: Kitty Murtagh's for pints

Day 3 (Sunday): Golf & Departure

• 8:00 AM: Breakfast at the house
• 9:30 AM: Tee time at Miacomet
• 2:00 PM: Lunch at Restaurant at Miacomet
• 4:00 PM: Pack up, return bikes
• 5:30 PM: Ferry back to Hyannis

Extended 3-Day Option

If you have an extra day, add: morning surf lesson at Cisco Beach, afternoon at Jetties Beach (easy to reach, good for swimming), dinner at CRU Oyster Bar for a nicer meal, and drinks at Tap Room.

Budget Breakdown (Per Person, 6 Guys)

Here's a realistic look at what a guys' weekend costs, assuming 6 people splitting everything:

Transportation

• High-speed ferry round-trip: $100
• Bike rental (3 days): $75
• Subtotal: $175

Accommodations

• House rental (2 nights, summer): $4,000-6,000 total
• Per person: $700-1,000

Activities

• Fishing charter (split 6 ways): $100-150
• Golf at Miacomet: $175
• Cisco Brewers: $40-60
• Subtotal: $315-385

Food & Drinks

• Groceries (breakfast, snacks): $75
• Dinner Friday: $60-80
• Lunch Saturday: $40-50
• Dinner Saturday: $50-80
• Lunch Sunday: $40-50
• Bar tabs (2 nights): $100-150
• Subtotal: $365-485

Total Per Person

• Budget trip: $1,500-1,800
• Comfortable trip: $2,000-2,500
• No-holds-barred: $3,000+

Money-saving tips: Visit in shoulder season (May or September-October) to cut housing costs significantly. Bring groceries from the mainland for breakfast and snacks. Take the free Cisco Van instead of Ubers. Book early for better rates on everything.