Your Essential Transportation Guide

Don't let transportation troubles dim your Stroll sparkle. Here's everything you need to know about navigating Nantucket during the island's busiest winter weekend.

The Transportation Reality Check

Let's be direct: Christmas Stroll weekend (December 5-7, 2025) brings summer-level crowds to Nantucket's winter infrastructure. Downtown parking vanishes. Streets designed for horses now host thousands of pedestrians. The Stop & Shop parking lot—usually your backup option—hosts the Christmas Marketplace with two rows completely closed.

If you're imagining casually driving downtown and finding a spot near the festivities, it's time to adjust those expectations. But don't worry—with smart planning and the right transportation strategy, you'll glide through the weekend while others circle endlessly for parking.

Why Taxis Become Your Stroll Secret Weapon

Consider this scenario: It's Saturday evening. You've been shopping all day. Your arms are full of packages, your feet hurt, and the temperature has dropped 10 degrees since noon. The walk back to your rental house in Tom Nevers suddenly seems impossible.

This is when having taxi numbers saved in your phone transforms from convenience to necessity.

Your Hour-by-Hour Transportation Timeline

Friday, December 5

3:00-6:00 PM: Ferries arrive with weekend visitors

• Steamship Authority and Hy-Line ferries are packed
• Taxis queue for 60+ minutes
• Airport sees steady arrivals
• Parking at ferry lots fills completely

Strategy: Pre-book your ferry/airport transfer. Cash tips are appreciated by drivers navigating chaos.

Saturday, December 6 (Stroll Saturday)

9:00 AM - Noon: The Rush

• Downtown fills with early shoppers and event-goers
• Street parking fills completely
• Taxi wait times: 15-30 minutes
• Multiple ride requests create high demand

Strategy: Walk from your accommodation to downtown if within 15-20 minutes. If not, book taxi in advance.

12:00 PM - 3:00 PM: The Peak

• Santa's arrival creates mass convergence on Main Street
• No street parking available downtown
• Taxi demand reaches maximum
• Estimated wait: 20-40 minutes for immediate requests
• The Marketplace (Stop & Shop lot) fills to capacity

Strategy: Plan to be wherever you want to be by noon. Moving around downtown is fine on foot, but arriving from outside downtown isn't practical.

3:00 PM - 6:00 PM: The Lull

• Early departures create temporary parking/taxi relief
• Downtown clears slightly as people head back to rest/change
• Dinner preparation begins; reservations start at 6:00 PM
• Taxi wait times: 10-20 minutes

Strategy: Ideal time for taxis to outlying attractions (lighthouses, galleries outside downtown) or to return to accommodation.

6:00 PM - 11:00 PM: The Evening Rush

• Post-shopping/coffee time, everyone heads to dinner
• Restaurant arrivals concentrate between 6:00-7:30 PM
• Second wave of arrivals from retail therapy naps
• Taxi demand spikes again
• Estimate: 15-30 minute wait times

Strategy: Book taxi when making dinner reservation (dinner at 7:00 PM = call taxi at 6:35 PM). Most drivers know all major restaurants and parking logistics.

Sunday, December 7

Morning & Early Afternoon: Gentle Recovery

• Day-trippers from Saturday departing
• Remaining visitors enjoying final brunches
• Significantly fewer cars downtown
• Taxi availability: Good to excellent

Strategy: This is the relaxed day. Explore, brunch, revisit favorites without rush.

3:00 PM - 5:00 PM: Final Push (Skating with Santa)

• Final organized events draw crowds again
• Families with young children focusing on remaining events
• Moderate taxi demand
• Wait times: 10-20 minutes

Strategy: If attending Skate with Santa, book taxi in advance. Pickup lines around the rink get congested.

Evening: The Exodus

• Sunday evening ferry departures begin
• Airport runs increase
• Dramatic demand surge 4:30-7:00 PM
• Taxi wait times: 20-45 minutes
• Many drivers prioritize ferry runs (higher fares, time-sensitive)

Strategy: If departing Sunday evening, book ferry taxi the night before. Don't wait until day-of. Confirm 3 hours before ferry departure.

Parking Reality & Strategies

Where to Even Try Parking

The Downtown Lots (Usually Full):

• Old South Wharf: Primary lot—fills by 10:00 AM
• Atlantic Avenue lot: Secondary lot—fills by 10:30 AM
• Folger Fish/Chamber parking: Tertiary—fills by 11:00 AM

The Backup Lots (Rarely Full But Inconvenient):

• Steamship Authority lot: 10-minute walk to downtown
• Miacomet Golf Club lot: Farther walk, but available
• Your accommodation: If staying at a hotel/house downtown, park once and don't move your car

The "Smart" Strategy

The smartest move? Park your rental car at your accommodation on Friday and don't move it until departure. This sounds extreme until you realize:

• You save 60+ minutes of parking searches across the weekend
• You eliminate stress of fearing boot/tow situations
• You pay roughly $30-60 parking across the weekend vs. $40+ in just the first hour
• You're free to enjoy Stroll without "parking meter anxiety"

Alternative Transportation Options

Walking

Pros: Free, scenic, you discover charming alleys

Cons: December weather, package weight, distance limitations, fatigue by evening

Best For: Staying downtown at hotel/inn within walking distance to Main Street activities

Bike Rentals

Pros: Fun, moderate speed, you're still outside atmosphere

Cons: December wind, slippery cobblestones, carrying packages awkward, bike parking becomes scarce

Best For: Short trips from nearby accommodations on calm days

Ride-Share Apps (Uber/Lyft)

Availability: Limited on Nantucket; service is spotty

Better Option: Stick with local taxis (phone calls) rather than app-based services for reliability during peak Stroll times

The Pro Taxi Strategy

Finding Licensed Taxis

Multiple licensed taxi services operate on Nantucket. Check nantucket-taxi.com for complete, current listings and phone numbers.

Key Points:

• Not all taxis appear in online directories equally
• Phone direct is more reliable than apps during Stroll
• Multiple numbers = better odds of reaching available driver
• Ask your hotel concierge for their preferred numbers

Booking Tactics

• Two weeks before: Call and ask which company they prefer—some offer better response times during peak events
• Upon arrival: Get card from your airport/ferry driver; save their direct number
• Friday evening: Scout 2-3 taxi companies, call each, introduce yourself, ask for recommendations for next day
• Build relationships: Using the same driver all weekend improves reliability and service quality

Special Transportation Circumstances

Accessibility Needs

• Several companies offer wheelchair-accessible vehicles
• Must reserve in advance
• Specify needs when booking
• Consider staying downtown to minimize transfers

Traveling with Young Children

• Some companies have car seats (advance notice required)
• Alternative: Bring travel car seat
• Consider one parent staying with kids while other shops
• Book taxis during nap times to avoid meltdowns

Pet-Friendly Options

• Many drivers accommodate pets
• Mention when booking
• Bring towel for wet/sandy paws
• Consider pet carrier for small dogs
• Tip extra for pet accommodation

Weather Contingency Planning

If Snow is Forecast

• Book transportation immediately upon arrival
• Assume 50% longer travel times
• Have backup numbers for multiple companies
• Consider canceling outlying restaurant reservations

During Rain

• Taxi demand triples
• Downtown becomes slippery
• Allow extra time for pickup
• Keep shopping bags waterproof

Wind Chill Warning

• Don't attempt long walks
• Pre-book all transportation
• Consider afternoon hotel break to warm up

Cost Comparison: The Real Numbers

Taxi Budget for Typical Stroll Weekend:

• Airport/ferry round trip: $40-60
• Daily downtown round trips (x3): $60-90
• Dinner transportation: $30-40
• Miscellaneous trips: $40-60
• Total: $170-250

Versus Rental Car:

• Three-day rental: $400-600
• Gas: $40
• Parking frustration: Priceless
• Total: $440-640 plus stress

The Winner: Taxis, both economically and practically

Booking Your Stroll Transportation

Two Weeks Before Arrival

• Save multiple taxi numbers in your phone
• Pre-book airport/ferry transfers
• Coordinate with your accommodation for recommendations

Upon Arrival

• Confirm return ferry transfer
• Get business cards from your airport/ferry driver
• Ask hotel concierge for backup numbers

Each Morning of Stroll

• Book evening dinner transportation
• Arrange any special trips (lighthouse photos, etc.)
• Confirm next day's ferry transfer (if departing)

Taxi Etiquette During Stroll

Do:

• Call 15-20 minutes before needed
• Have cash ready (not all take cards)
• Share rides when possible
• Tip generously (20% during Stroll)
• Be patient—everyone's doing their best

Don't:

• Assume immediate availability
• Leave shopping bags in taxis
• Forget to get driver's card for return trips
• Wait until last minute for ferry transfers

Red Flags to Avoid

• ❌ "I'll just drive around until I find parking" → ✅ Park once at your accommodation and taxi thereafter
• ❌ "We'll walk back after dinner" (in December, after wine) → ✅ Book return taxi when making dinner reservations
• ❌ "Ferry's at 3 PM, we'll call a taxi at 2:30" → ✅ Book ferry transfer the night before
• ❌ "The rental car gives us flexibility" → ✅ Taxis provide flexibility without parking nightmares

The Local's Secret

Here's what Nantucket residents do: They book their favorite driver directly for specific times, treating them like a car service rather than on-demand taxi. Build a relationship Friday, use them all weekend.

Your Stroll Transportation Checklist

Pre-Arrival:

• ☐ Save 3-5 taxi numbers in phone
• ☐ Book ferry/airport transfers
• ☐ Coordinate with travel group
• ☐ Check weather forecast

Daily During Stroll:

• ☐ Book evening transport in morning
• ☐ Confirm return trips when dropped off
• ☐ Keep cash available
• ☐ Allow extra time for everything

Departure Day:

• ☐ Confirm ferry/airport transfer night before
• ☐ Allow 30 minutes extra for ferry
• ☐ Keep one taxi number for emergencies

The Bottom Line

Christmas Stroll is magical precisely because downtown becomes a pedestrian wonderland. Embrace this by planning transportation that keeps you mobile without the driving stress. Whether you're hopping between events, escaping weather, or simply saving your energy for more shopping, Nantucket's taxi services are your ticket to a stress-free Stroll.

The visitors who enjoy Stroll most aren't the ones who brought their cars—they're the ones who saved taxi numbers, booked ahead, and spent zero minutes searching for parking. This year, that can be you.

Visit nantucket-taxi.com to browse all licensed taxi services and save multiple numbers before you arrive. Your future Stroll-enjoying self will thank you.