If Shelter Island has been on your travel wishlist, there’s no better time than now to start planning your visit. While summer may be the peak season, smart travelers know that planning ahead means securing the perfect stay, snagging coveted reservations, and ensuring a stress-free getaway. We’ve got the insider scoop on why starting your plans now will make all the difference when you’re ready to unwind on our beautiful island.
Why Plan Now?
1. Secure Your Preferred Dates at Hotels and B&Bs
Shelter Island’s charming hotels and cozy bed and breakfasts fill up quickly as the warmer months approach. Planning your stay now means you’ll have better access to your preferred week, room type, and location. Don’t settle for what’s left—reserve the dates that work best for you while availability is wide open.
2. Coordinate the Ultimate Group Trip
Planning a trip with friends or family? Before the busy season arrives is the ideal time to sync calendars. Coordinating schedules can be tricky, but starting early gives everyone time to plan, request time off, and get excited together. Plus, with advanced notice, you can book larger accommodations or multiple rooms in the same property—making your group stay seamless and memorable.
3. Get First Dibs on Experiences and Services
Popular activities and services—like sailboat and fishing charters, bike rentals, and dining reservations—tend to book up fast. By planning now, you can lock in those special experiences that make your trip unforgettable. Imagine sailing at sunset or dining at that must-try waterfront restaurant—all because you planned ahead.
4. Plan Activities at Your Own Pace
From hiking the Mashomack Preserve to visiting local galleries, planning early lets you map out your ideal itinerary. You’ll have time to research events, like local farmers' markets or art fairs, and add them to your calendar before they’re fully booked.
How to Plan Your Shelter Island Trip
1. Start with Our Service Directory
Our Service Directory is your go-to guide for everything from transportation options to event planning services. Whether you’re looking for a reliable taxi service, bike rentals, or marina information, the directory connects you with trusted local businesses ready to make your trip smooth and enjoyable.
2. Check Out the Hotels Page
Not sure where to stay? Visit our hotel and bed & breakfast page for the best lodging options Shelter Island has to offer. From luxurious inns with waterfront views to quaint B&Bs full of character, you’ll find the perfect place to rest after a day of exploring.
3. Make Reservations Early
Whether it’s for dinner at a popular restaurant or tickets for a boat tour, booking in advance ensures you won’t miss out. Many services offer online reservations, making it easy to plan your perfect itinerary from the comfort of home.
4. Map Out Your Adventure
Shelter Island offers countless opportunities for adventure, from kayaking and paddleboarding to historical tours and nature walks. Planning ahead gives you time to create a balanced schedule—one that allows for both exploration and relaxation. And don’t forget to leave time for exploring some of the little-known historic places on Shelter Island using our interactive guide.
Insider Tip: Make It Yours
So, what are you waiting for? Your perfect Shelter Island getaway starts with a plan. And now is the best time to make it happen. Your friends at the Shelter Island Chamber of Commerce are here to help—start exploring today!