Nantucket for Groups: How to Plan a Weekend for a Large Group

Few places bring people together quite like Nantucket. Days are filled with beach walks, bike rides, and time spent exploring the island, while evenings are reserved for great meals, good conversation, and making memories you'll talk about long after the ferry ride home.

A Nantucket group trip takes a bit of planning, but that's part of the fun. No matter if you're celebrating a milestone birthday, hosting a family reunion, planning a bachelor or bachelorette weekend, or bringing colleagues together for a retreat, the right home base makes everything easier.

Here's how to create a group itinerary guests will love without spending the entire weekend managing logistics.

Start with the Right Home Base

The best group trips begin with choosing accommodations that make gathering feel effortless. When everyone is staying together (or just steps from one another), you spend less time coordinating and more time enjoying the island.

When searching for a Nantucket hotel for large groups, look for accommodations that offer:

• Flexible room types that can be reserved together
• Outdoor spaces where everyone can gather between adventures
• Walkable access to Nantucket's beaches and downtown
• An experienced team that understands group travel and room blocks

The Beachside Hotel was designed with togetherness in mind. Our collection of guestrooms can be reserved as room blocks, while the heated outdoor pool, spacious lawn, fire pits, and inviting common spaces naturally become gathering places throughout the weekend. Better yet, you're just a short walk or bike ride from both Jetties Beach and historic downtown Nantucket, making it easy for everyone to explore at their own pace.

Planning for ten or more guests? The Beachside team can assist with everything from coordinating room blocks to recommending restaurants and activities for your group.

Book Earlier Than You Think

Nantucket's popularity means summer weekends, and even many spring and fall dates, fill quickly. Larger groups benefit from planning ahead.

Once you have an approximate guest count:

• Reserve your room block as early as possible.
• Book ferry reservations well in advance, especially for Friday arrivals and Sunday departures.
• Make restaurant reservations for larger parties early, as many restaurants have limited seating for groups.
• Reserve activities like bike rentals, sailing excursions, or fishing charters several weeks before arrival.

Build a Group Itinerary Nantucket Travelers Will Enjoy

The best group itineraries include just enough structure to bring everyone together, with plenty of room for spontaneous island moments.

Friday: Arrive and Ease Into Island Time

After check-in, settle into your rooms before gathering around the pool or on the lawn for welcome drinks and conversation.

From there, stroll into town for dinner or enjoy cocktails before your reservation. The goal is simple: let everyone unwind after traveling and start the weekend together.

Saturday: Beach Time, Bikes & Island Exploring

Start the morning with coffee before heading to nearby Jetties Beach, one of Nantucket's most accessible and family-friendly stretches of shoreline.

Guests can borrow complimentary bikes from The Beachside Hotel and explore the island at their own pace. Some guests may want to browse boutiques downtown, while others linger by the water or relax back at the hotel pool. Giving everyone flexibility keeps the day feeling like a vacation rather than a schedule.

Come evening, gather again for a memorable group dinner. It's often the highlight of any Nantucket weekend, so reserve your table well ahead of time.

Sunday: One Last Island Morning

Slow mornings feel especially rewarding on Nantucket.

Grab coffee, enjoy breakfast outdoors, take one final walk to the beach, or browse downtown shops for a few last souvenirs before heading to the ferry. If your group has different departure times, the hotel's central location makes it easy for everyone to enjoy a little more island time before saying goodbye.

Make Dining Simple

Coordinating meals for a larger group doesn't have to be complicated.

A few tips:

• Reserve larger dinner tables well in advance.
• Balance planned dinners with casual breakfasts and lunches.
• Consider a private or semi-private dining experience for one evening.
• Keep drinks and snacks available back at the hotel for relaxed afternoons between activities.

Giving guests a mix of planned gatherings and independent meals allows everyone to enjoy the weekend their own way.

Pack with Group Travel in Mind

Along with comfortable layers, sunscreen, and supportive shoes for Nantucket's cobblestone streets, a few shared essentials can make the weekend even smoother.

• Beach games 
• A portable speaker for the beach
• Reusable water bottles to stay hydrated while exploring the island
• A beach tote or cooler for snacks, drinks, and towels
• A shared group chat with reservations and ferry details

Little touches like these help everyone stay connected without overplanning every moment.

Why The Beachside Hotel Is Ideal for a Nantucket Group Stay

A memorable group trip starts with accommodations designed for gathering.

The Beachside Hotel combines flexible room blocks, welcoming outdoor spaces, complimentary bike rentals, and an unbeatable location near both Jetties Beach and downtown Nantucket. From family reunions and birthday celebrations to wedding weekends, bachelor and bachelorette getaways, and corporate retreats, we help take the stress out of planning, so your group can focus on enjoying the island.

Ready to gather on the island? Let our team help you reserve your group stay, coordinate the details, and create a Nantucket group itinerary that leaves everyone looking forward to the next trip back.

‍